St Regis Guest, please email: [email protected]

Castillo Tours DMC

Castillo Tours

Adventure Tours in Puerto Rico

Choose Your Experience

Adventure tours.

Learn More »

Boat Tours & Charters

City tours & excursions, fishing charters, our most popular tours.

  • Most Popular
  • Hour Glass 5.5 hrs
  • Users Ages 4+
  • Tags Up to 44 People
  • Info Boat Tour

Catamaran Day Trip (Icacos Island)

Book our most popular adventure and enjoy a half-day charter full of leisure and white sand beaches as you sail on our catamaran and enjoy world-class snorkeling!

  • Hour Glass Half-Day
  • Tags Up to 12 People
  • Info Adventure Tour

El Yunque Rainforest Tour

El Yunque National Rainforest is a landmark not to miss when you visit Puerto Rico!

Castillo Tours is a full-service DMC with 45 years of experience. Water sports, cultural adventures, culinary experiences, adrenaline-filled tours, relaxing walks connecting with nature — we can provide it all. From family events to corporate groups, we can help you achieve an unforgettable experience in Puerto Rico.

More Great Experiences

  • Hour Glass 2 Hours
  • Users All Ages
  • Tags Up to 6 People

San Juan Harbor Sunset Cruise

Come aboard our 48-foot powerboat and enjoy a relaxing tour of beautiful Old San Juan Harbor! Bring along the whole family for this unforgettable experience!

Find a Tour by Date

Searching available tours for . . .

Showing Tours for -

Over 1,200 Excellent TripAdvisor Reviews

Castillo Tours DMC

Out of everything we did in PR this was by far my favorite. The guys are such great entertainers and servers as well! Our drinks were never empty and the food was so good. My boyfriend and I had so much fun snorkeling and the island they take you to is so beautiful!

My friends and I booked this Catamaran trip as part of our recent vacation in San Juan. The staff was professional and fun, and the trip went really smoothly. Would definitely book again!

Very enjoyable! Carlos, our guide, was excellent! He was so knowledgable, informative, nice, patient and loved sharing his culture. He was an excellent driver and very personable. He even stopped at a local place for lunch before leaving the forest that we didn't expect. What a treat!

This trip was amazing! The staff on the vessel are top notch, very caring and made you feel welcomed, safe and comfortable. Willy does a great job helping you learn how to snorkel. This is a must do if you visit Puerto Rico. Had so much fun!!

Logo

San Juan Sunset Sail

san juan catamaran sail

Description

Our most popular sail! A relaxing cruise around the calm waters of San Juan Bay to enjoy a beautiful sunset and a perfect start to your evening.

See Old San Juan as it changes from daytime to sunset colors and then city lights coming on at night as we are headed back to the marina.

Our two-hour sailing route stays within the calm, protected waters of San Juan Bay for a relaxing experience.

Complimentary refreshments include Prosecco or Cava sparkling wine, our special house rum punch, local Medalla beer, rum and cokes, orange and pineapple juice, soda, or water.

San Juan Bay Marina at Slip A72

Things to know

Cancellation policy.

We have a 48-hour cancellation notice policy for a full refund. 48 hours or fewer cancellations forfeit 50% fare. 24-hour cancellations forfeit the full fare.

Sail Start Times

Our Morning sail starts at 10:30 am, Afternoon Sail at 2:30 pm, and Sunset Sail at 5:00 pm.

Meeting Location

We are a convenient 5-10 minute drive from the major hotels in the San Juan, Condado and Isla Verde area. We are located in San Juan Bay Marina at Slip A72. If you are taking a cab, ask your driver to take you to San Juan Bay Marina and reference where the Sizzler Restaurant is located. Once at the Marina, walk through the boatyard towards the lower part of Sizzler Restaurant. Once at sea level, go past a jet ski rental kiosk towards the long dock with boats on either side. Our slip is on the left past the white gate that leads to the dock. Our boat is “Ohana.” Slip numbers are marked on the floor.

What to Wear

Sunset sails have usually calmer breezes and cooler temperatures so you may dress comfortably, however, we do recommend light clothing. If you choose to go out into the ocean, the possibilities of getting wet are more likely as we will be sailing in bigger seas. No shoes allowed on board.

Ask a question

Check availability, more experiences .accent-svg{fill:#f35726;}.

san juan catamaran sail

Morning Mimosas Sail

Enjoy a unique start to your morning, sailing on our spacious catamaran taking in the sights of Old San Juan from the bay.

Make yourself comfortable on the front net and take some sun in or sit back in the shaded cockpit area and sip your drink of choice as we narrate some historical facts along the way.

This one-hour and 30-minute sail includes bottomless mimosas, house rum punch, local Medalla beer, rum and cokes, orange and pineapple juice, soda, and water.

6 spaces are available per sail. To book privately for yourself or a group choose Private Charter.

san juan catamaran sail

San Juan Bay Afternoon Sail

Soak in the sun with a drink in hand while taking in the sights of Old San Juan and Cataño from a unique point of view.

While the sun is fully out during the time of this sail, the back cockpit area of our catamaran is shaded so you can also enjoy the sail without being subject to the sun.

Bring your lunch and enjoy it aboard; we provide the drinks! Choose from mimosas, house rum punch, local Medalla beer, rum and cokes, orange and pineapple juice, soda, or water.

Our hour and a half sailing route stays within the calm, protected waters of San Juan Bay. Open ocean sail available upon request dependent on weather.

6 spaces available per sail. To book privately for yourself or group choose the Private Charter.

Anacortes Yacht Charters

Escape the ordinary with a San Juan Islands yacht charter vacation.

Adventure awaits

The San Juan Islands and Gulf Islands are some of the most popular cruising areas in the world.

What is it that draws people to these islands? A big reason is because the islands are remote but accessible at the same time. A short drive from Seattle or Vancouver puts you in Anacortes, Washington, the “Gateway to the San Juan Islands.” From there, the San Juan Islands start a mere 15 miles away.

Your Cruise. Your Choice.

Once in the islands, you’ll find quaint both communities and hidden hideaway, all surrounded by a calm inland sea. Seemingly endless miles of coastline and over 100 islands give you plenty of options for exploring and relaxing. Drop anchor in a quiet cove, or tie up at one of the island marinas – it’s your choice when you charter!

Anacortes Yacht Charters has provided San Juan Islands yacht charters for 45 years. We have the largest selection of motor yachts and sailboats in the Northwest. Our experience and fleet mean we can match you with the perfect boat for a trip of lifetime.

To book a bareboat or skippered San Juan Islands yacht charter contact us at:

800-233-3004 or [email protected]

Big Boat Charter Sale

We are offering our biggest savings on the biggest boats in the fleet.

Class/Charter Bundle

Save $1,900 and launch or build your bareboat charter resume.

Our Guarantee

Should you have a breakdown during your charter, we will complete repairs within four hours of notification for any vessel within 20 miles of our charter base. View Guarantee

san juan catamaran sail

Yacht Charter

A private yacht charter is your ticket to a Pacific Northwest vacation of a lifetime. Choose to bareboat charter a powerboat or sailboat for a hands-on adventure. Or, hire a skipper for a more guided experience. A few of our larger boats require a crew and are shown on the crewed yacht page.

san juan catamaran sail

Yacht Ownership

If you own a boat, or are pondering a purchase, consider placing your boat into charter service. This a great option to help offset the cost of ownership and earn real tax advantages, Use our in-house service department for year-round care of your boat. Arrange time on your boat for yourself as desired.

News and Announcements

san juan catamaran sail

Featured Boat Weekly Special

Book 6 nights and get the 7th night free in red and gold seasons..

Special available for new 2024 bookings made through 8/20/2024. Insurance & Daily Damage must be paid for the free night. Cannot be combined with any other offer or discount. Other restrictions may apply. Contact us for additional details on this special offer. 1-800-233-3004

Charter Bundle Save 1,900

See Details >

Big Boat Charter

Book 3 — get 1 free.

san juan catamaran sail

We are proud to be celebrating our 45th Anniversary in 2024. Over the years providing San Juan Islands yacht charters, our crew has pioneered mini-fleet management. Along the way we have provided over 15,000 charter trips – illustrating our commitment to quality and customer service.

san juan catamaran sail

All of our charter vessels are clean, well-maintained, and include a breakdown guarantee. We take the risk out of chartering to better ensure the quality of your charter experience.

san juan catamaran sail

Our yacht charter fleet includes a variety of power yachts , sailing yachts and crewed yachts from 27’ to 70’.  Make your choice to host nearly any group of friends and family for a magical San Juan Islands yacht charter.

Toll Free: (800) 233-3004 | (360) 293-4555 | [email protected]

© 1979 - 2024 | All Rights Reserved, Anacortes Yacht Charters

  • Power Yachts
  • Sailing Yachts
  • Catamaran Yachts
  • Crewed Yachts
  • 7-night San Juan Islands
  • 7-night San Juan Islands and Taste of Gulf Islands
  • 7-night San Juan Islands and Gulf Islands
  • 7-night Perfect Sail or Trawler Cruise
  • 14-night Desolation Sound and Princess Louisa Inlet
  • 14-night Leisurely Sail or Trawler Cruise
  • 14-night San Juan Islands to Desolation Sound
  • How to Charter
  • How to Book
  • Boating Qualifications
  • Charter Details
  • Loyalty Programs
  • Travel Protection Insurance
  • AYC Power Cruising Classes
  • ASA Sailing Classes
  • Yacht Service
  • Anacortes Yacht Brokers
  • ROI Calculator
  • Privacy Policy
  • Email Sign Up
  • Owner Quarters

Header image

San Juan Catamaran Sunset Sail with Drinks Included

TICKET PRICES STARTING FROM

Taxes and fees will be calculated at checkout

Sit back, relax and take in the amazing sights of historic San Juan Bay with picturesque sunset lighting. This 2-hour sail aboard a 37ft catamaran sailboat completely powered by the wind is the perfect setting for a romantic moment with your loved one or a fun time with friends. Complimentary beer, rum & coke, rum punch, and sparkling wine will be available to celebrate that special occasion or just because you're on vacation. Your veteran captain will point out sights along the way as you enjoy the views and the company aboard.

Ticket Options

1 Option Available

Sunset Sail: $119

Ticket Information

  • Mobile or paper ticket accepted
  • One per booking

What's Included

  • Complimentary drinks included in moderation. Minimum drinking age is 18 years
  • Professional captain and guide

What's not Included

  • Hotel pickup and drop-off
  • Snacks and dinner not included but guests may bring their own

Cancellation Policy

  • For a full refund, cancel at least 24 hours before the scheduled departure time.

Additional Info

  • Not recommended for travelers with spinal injuries
  • Not recommended for travelers with poor cardiovascular health
  • Public transportation options are available nearby
  • Infants are required to sit on an adult’s lap
  • Suitable for all physical fitness levels
  • A minimum of 2 people per booking is required
  • A maximum of 6 people per booking
  • Guest are required to check-in at the boat AT LEAST 20min before departure time or will not be allowed to board.
  • Complimentary drinks included in moderation. This is not a booze cruise. Minimum drinking age is 18 years.
  • Departure times - 5pm from September 15th until April 30th 5:30pm from May 1st- September 14
  • No shoes allowed on board. You will be asked to take them off to board and they will be stored on the boat.
  • Minors must be accompanied by an adult.
  • Not recommended for travelers with walking and/or mobility issues

Travel Like an Expert with AAA and Trip Canvas

Get ideas from the pros.

As one of the largest travel agencies in North America, we have a wealth of recommendations to share! Browse our articles and videos for inspiration, or dive right in with preplanned AAA Road Trips, cruises and vacation tours.

Build and Research Your Options

Save and organize every aspect of your trip including cruises, hotels, activities, transportation and more. Book hotels confidently using our AAA Diamond Designations and verified reviews.

Book Everything in One Place

From cruises to day tours, buy all parts of your vacation in one transaction, or work with our nationwide network of AAA Travel Agents to secure the trip of your dreams!

san juan catamaran sail

Check out our Most Popular Tour! Click Here and Book Today!

Salty Dog Catamaran

  • Most Popular!

DAY SAIL & SNORKEL

Quick details.

Hour Glass Duration:  5 hours while making 2 stops (beach and coral reef)

Users Ages:  All ages

Checkmark Inclusions: Snorkeling equipment, flotation belts, rum cocktails, soft drinks, and pre-packed lunch provided

Checkmark Available at Dock:  Beach essentials available for purchase at the dock (snorkeling equipment, towels, and sunscreen – call for availability)

Private charter

Welcome aboard The Salty Dog where you can experience and enjoy Puerto Rico’s best unspoiled islands off the eastern coast of Fajardo. Wander the white sandy beaches, slip on a pair of fins and discover a colorful world of tropical fish in the crystal clear caribbean waters with snorkeling belts, refreshments, and lunch provided by our friendly bilingual crew.  During our sail, we’ll be making two stops: one being the white sandy beach of the nearby natural reserves and the second at the coral reef where you will be able to snorkel in 15ft – 20ft depth of water. Enjoy tropical cocktails made with local Don Q rum from Puerto Rico and some music perfect for your day out on the water. We guarantee that our experience will be the highlight of your trip to Puerto Rico!

Transportation:

Roundtrip transportation is available from most locations in Metro San Juan and hotels at an additional cost of $50 per person. Transportation requires a minimum of 6 passengers in total in order to operate. MUST be arranged 48 hours prior to the scheduled trip or transportation is not guaranteed.

Islands That We Visit:

Destination will be determined by our captain on the day of the experience. The destination is determined based on the weather and water conditions of the day. 

Isla de Palominos

Located some 3.5 nautical miles east of Fajardo, it has a size of approximately 104 acres. It is one of a few private islands that exist throughout Puerto Rico. Part of the island is on lease to El Conquistador Hotel to be used as the hotel’s beach. About a quarter-mile south of Palominos island lies Cayo Palominitos, which is a one-acre sandy key with tropical vegetation perfect for swimming or snorkeling.

Isla de Lobos

Located some 1.5 nautical miles east of Cayo Icacos, it has a size of approximately five acres. It is also one of a few private islands throughout Puerto Rico. In the early ’60s, the island hosted a very exclusive hotel, which ran into financial difficulties and was abandoned for a great part of the ’70s and ’80s until it was bought by a local family and converted into a paradise vacation home. Surrounded by small keys and coral reefs, it is great for snorkeling.

Cayo Icacos

Located some four nautical miles northeast of Fajardo, it has a size of approximately 163 acres. It is part of a chain of small islands, keys, and coral reefs known as La Reserva Natural de la Cordillera. The island hosts a fairly large amount of marine life, coral reefs, birds, and land iguanas. It is the perfect setting for snorkeling, swimming, diving, and beachcombing. It gets its name from the large number of Icacos bushes on the island. The Icacos is a small sour fruit, which grows to about the size of a key lime. When ready to be picked, they are pale yellow in color and come off the bush quite easily. The best way to eat them is cooked in heavy syrup.

Cancellation Policy:

Customers will receive a full refund within 48 hours of notice of cancellation to scheduled reservation . Must call to make any changes. THIS CANCELLATION POLICY DOES NOT APPLY TO GROUPS, COUPONS, SPECIAL OFFERS, OR PRIVATE CHARTERS. Customers will also receive a full refund in case of operator cancellation due to weather or other unforeseen circumstances. All reservation changes must be made by phone. No-shows will be charged the full price.

san juan catamaran sail

Related Sails

  • Hour Glass 2 Hours
  • Users All Ages

AFTERNOON SAIL & SUNSET

Let the warm caribbean breeze and gentle waters wash your cares away as you lounge in complete relaxation on a catamaran sunset sail. We will stop for a relaxing time at a beach before setting sail to watch the sun go down. Sip a Painkiller cocktail and enjoy the view as the sun sets.

🌅The 6 Best Puerto Rico Sunset Sailing [2024 Reviews]

Enjoy sailing around puerto rico at sunset with one of these sailing cruises.

San Juan, Puerto Rico is one of the hottest vacation destinations for people around the world. Not only is it conveniently-located for those who live in North America, it’s full of rich culture, delicious food, colorful architecture, and beautiful  naturaleza. 

If you’re going to see all of the beauty San Juan has to offer, we have the perfect tours for you: the best sunset sailing tours! These take place out on the water, where the rich oranges and reds reflect perfectly – offering an unmatchable view that is best enjoyed on a sailboat.

We’ve done the “hard” part for you, making sure you are getting the best bang for your buck, and a sailing experience that you’ll want to take over and over again.

Be sure to see our reviews of Puerto Rico Kayaking Tours , El Yunque Rainforest Tours and Puerto Rico ATV Tours .

Best Sunset Sailing Cruises From San Juan

Avenida Campo Rico ("Roberto Sanchez Vila Avenue"), Este Final, CarolinaPickup availableSan Juan, (point will be determined upon booking)
5:00 PMContact tour operator2:30 PM
2 hours1 hour7 hours
2-hour ATV adventure, basic ATV instructionsTransport from San Juan, 1-hour ATV adventureAir-conditioned vehicle, snacks, 3.5 hour ATV adventure

Quick Answer: The 6 Best Sunset Sailing Cruises in Puerto Rico

  • San Juan Catamaran Sunset Sail
  • SUNSET SAIL aboard PRIVATE SAIL YACHT in Fajardo
  • Janise Sailing Afternoon Charter in Fajardo, Puerto Rico
  • Sunset Sail by San Juan Historical Bay
  • Sunset Harbor Boat Ride in San Juan
  • Private Sunset Sail on the East Coast of Puerto Rico

San Juan Sunset Sailing Reviews

1. san juan catamaran sunset sail.

  • Duration: 2 hours
  • Departure:  482 Av. Manuel Fernández Juncos, San Juan, 00901
  • Departure Time: 5:00 PM
  • Includes:  Professional captain and guide, beverages

Let’s start things off with the beautiful San Juan Catamaran Sunset Sail . This 2-hour sail is the perfect way to lead you from the warm day into a refreshing evening.

While sailing on just about any bay will make for a picturesque moment, the San Juan Bay and port have a rich history and various landmarks that make this tour particularly special. You’ll meet up with the rest of your group/guides at Slip A72 on the main dock at San Juan Bay Marina.

The crew makes this process seamless, so everyone can get acquainted, go through safety information, and focus on the incredible view and having fun! The captain and crew are so warm and friendly, and really make the entire experience pleasant from the beginning.

Start off at La Puerta de San Juan, or “San Juan Port”. This landmark is very important in the history of the country. Founded all the way back in the early 1500’s by Ponce de Leon, it has become a major seaport for the country in culture, manufacturing, tourism, and more.

Expand To See More See Less

While a lot has changed in so many hundreds of years, a lot has stayed the same, which makes it such a tourist hot spot.

You’ll then spend the rest of the tour sailing around the bay, catching up-close views of the castle “Castillo San Felipe del Morro”, and the fort, “La Fortaleza – Palacio de Santa Catalina” from the water.

The captain and crew are very experienced and will tell you all about these crucial pieces of history that will only make the adventure that much more interesting!

Tour Information & Booking

100% refund for cancellations within 24 hours of tour experience, other puerto rico experiences you may enjoy:, 2. sunset sail aboard private sail yacht in fajardo.

  • Duration: 2.5 hours
  • Departure:  4900 State Road 3 Km. 51.4, Fajardo, 00738, Slip 1089
  • Departure Time: Contact tour operator
  • Includes:  Coffee and/or tea, bottled water, soda, alcoholic beverages, snacks

Are you looking for a captivating cruise in Puerto Rico, but one that offers style and luxury? If so, then look no further than the Sunset Sail Aboard Private Sail Yacht in Fajardo ! This 2.5-hour cruise simply offers the best seat in the house for appreciating all that this beautiful country and city has to naturally offer.

Start off by meeting with the captain and crew, and board the private yacht. Before you get to sailing around the sparkly azure seas, they’ll brief you on sailing basics and safety precautions to take so that all the fun is to be had.

Sit down on the ample seating aboard, and get ready to just relax and take it all in. According to the weather, the captain will take the best route possible so that you’ll comfortably get to see all around the islands and cays on the eastern coast of the country.

Meanwhile, enjoy some delicious fresh fruit platters and/or platters of cold cuts and cheeses! Wash it all down with up to 2 hard liquor drinks, sparkling wine, mojitos, or sangria!

Something else that really makes this tour stand out is the way that the staff makes an effort in ensuring you have the best experience possible. This isn’t a cookie-cutter tour. Nope, they will offer you planning assistance in your tour to make sure you (realistically) can see everything you want to on board.

While the tour is by default around 2.5 hours, you can add extra hours, photos, video edits, or even make special accommodations for occasions like birthdays, proposals, and more.

Search For San Juan Experiences You May Enjoy:

3. janise sailing afternoon charter in fajardo, puerto rico.

  • Duration: 3 hours
  • Departure: Puerto Del Rey Marina, 00735
  • Departure Time: 2:30 PM
  • Includes:  Romantic sailing with a beautiful sunset backdrop, alcoholic beverages, soft drinks

Are you looking for a tour that lasts a bit longer? Then check out the Janise Sailing Afternoon Charter in Fajardo, Puerto Rico . There are various start times to choose from, from the afternoon until the evening so you can choose what works best for you and the rest of your group!

Your tour will take place aboard the Janise Lagoon 380, which is a stunning charter that offers comfortable seating with excellent views of the island and surrounding seas.

No matter if you’re looking for a fun time with friends or a romantic evening with your significant other, this is sure to be one of the best ways to spend 3 hours in Fajardo.

Your voyage will go all around the shores and secluded islands of the eastern coastline, which feel almost like you have them all to yourself. This is definitely one of the top activities to take if you want something away from the hustle-and-bustle of crowds and touristy spots.

After sailing for a nice amount of time, the captain and crew will drop anchor on the coastline, where you’ll be able to select your next activity. You can either take a refreshing dip in the ocean, kick your feet up in the catamaran, or enjoy some mouth-watering snacks and beverages; all while watching the electric sunset.

There are all kinds of snack options on board, along with water, sodas, beer, wine, sangria, and more. If this sounds like a good time to you, then hurry and make your reservation for one of the top-rated San Juan sunset cruises around!

4. Sunset Sail by San Juan Historical Bay

  • Departure: 480 Av. Manuel Fernández Juncos, San Juan, 00907
  • Includes: Refreshments, beverages, bottled water, snacks, unlimited beer, wine and soft drinks, alcoholic beverages

Are you on the hunt for a tour that combines sportsmanship, history, and exploration all into one adventure-packed activity? Then get yourself ready for the Sunset Sail by San Juan Historical Bay tour!

On this tour, you’ll not only get to see the natural beauty of San Juan, but also learn all about it and its iconic landmarks!

Meet up with the captain and crew to board the awesome 30-foot racing boat! This boat seats 6, which means it’s great for intimate groups, personalized attention, learning, and of course high speeds!

If you have a need for speed, then this is one of the best tours to take, but rest assured the captain will always make sure you’re okay with going that fast beforehand. With his clear competence, you can feel confident that you’re in good hands.

Of course, not everything is about getting the adrenaline pumping. You’ll sail very close to important landmarks such as the Castillo San Felipe del Morro, La Fortaleza – Palacio de Santa Catalina, and San Juan Bay.

El Castillo San Felipe del Morro has been around for hundreds of years, and currently is the governor’s mansion. “El Morro” is very impressive to look at, and was built on the orders of King Charles V of Spain. “La Fortaleza” has been around since 1846 and is the oldest executive mansion in continuous use in the New World.

San Juan Bay also has an interesting commercial history, with notoriously flat waters. While you learn, try to keep an eye out for dolphins playing around the boat while watching the sun set over the pristine Caribbean.

5. Sunset Harbor Boat Ride in San Juan

  • Duration: 1.5 hours
  • Departure:  482 Cll Guamani, San Juan, 00901
  • Includes:  Bottled water, local beers, sodas, appetizers

Say you’re tight on time or simply want to pack in as many activities as possible into your day, but still want to partake in a sunset tour. If so, then the Sunset Harbor Boat Ride in San Juan is just for you! This 1.5-hour tour may be a bit compact but it sure is full of fun!

With a pickup from select hotels, the entire experience is streamlined so you can make the most of your time and don’t have to worry about finding a meetup point or transportation

. As with the other tours, the captain and crew are very friendly and knowledgeable about the area, ensuring everyone has a great time.

Take a seat on the relaxing boat ride while enjoying some snacks, soft drinks, and alcoholic beverages. This makes for an excellent precursor to a full dinner on shore while also learning new things and enjoying some fresh air and breathtaking nature.

Partake in some grapes, cheese, chips, and other snacks and beverages. This tour will take you by all kinds of island highlights, such as the Paseo de La Princesa, La Fortaleza, the San Juan City Walls, El Morro, and more!

The excursion involves commentary by the onboard tour guide who knows all about the history of these landmarks, giving you a perspective into colonial times to present-day.

If that weren’t enough, with the sun setting it makes for an even more magical time, illuminating the centuries-old buildings and seas. It makes you feel almost like you’re transported back to “the olden days”.

6. Private Sunset Sail on the East Coast of Puerto Rico

  • Duration: 2.5 hrs
  • Departure:  Puerto Del Rey Marina, 00735
  • Departure Time: 4:30 PM
  • Includes: Snacks, alcoholic beverages, water, soft drinks

Are you looking for a perfectly romantic way to spend an evening with your special someone? Maybe you’re just looking for a relaxing tour to enjoy San Juan’s naturaleza ? If that sounds like something up your alley, take a good look at the Private Sunset Sail on The East Coast of Puerto Rico .

Lasting 2.5 hours, this tour is an excellent way to break up the common stress of scheduling in as much as possible or navigating crowds. Here, you’re going to relax and let any tension melt away while you sip on delicious cocktails, munch on some appetizers, and enjoy the picturesque Costa Rican sunset on the water.

You can choose to sit inside or outside on the deck – whatever you prefer. Seating up to just 6 people, the private sail is meant to be personal. This is also a great way to ask your onboard guide and crew any questions that you may have about the area, the sea, or anything else relating to San Juan.

They’re all very knowledgeable and will provide you with an educational commentary on the area on the landmarks.

Start out by sailing from the marina to the private islands on the eastern coast of Puerto Rico. Once the captain finds the perfect spot, they’ll drop anchor so you can just enjoy all kinds of cocktails and eats while watching the sun set.

This is also the ideal time to take some videos or photos, should you like. You may even see some dolphins or other sea critters, if you’re lucky!

Tour Guides

The San Juan Catamaran Sunset Sail is our Editor's Choice so the top sailing cruise in Puerto Rico

Robert Baker

Related articles, the 7 best el yunque rainforest tours [2024 reviews], the 7 best puerto rico ziplines [2024 reviews], the 6 best puerto rico atv tours [2024 reviews], the 4 best puerto rico bioluminescent kayak tours [2024 reviews].

Sail Getaways

Sail Getaways

Boat tours, private charters & snorkeling in fajardo, puerto rico, update: open for business, boat tours, private charters & snorkeling trips in fajardo, puerto rico.

a glass with a blue pool of water

  • Most Popular
  • Hour Glass 6 Hours
  • Scuba Mask Beach & Snorkel
  • Cruise Ship Power Boat

Culebra Power Boat Snorkeling & Beach Tour

Culebra Island in Puerto Rico offers a memorable experience for snorkeling and beach exploration. With its pristine white sand beaches and abundant tropical fishes, visitors are in for a treat. Whether you choose to relax on the shore or discover the wonders underwater, Culebra is just the place to be!

  • Hour Glass 5 Hours
  • Food Lunch included

Icacos Power Boat Beach & Snorkel Island Hopping Adventure

Embark on an enchanting island-hopping journey that begins with a visit to Palomino. Explore the stunning coral reefs of The Cordillera Reserve, immersing yourself in the vibrant underwater world. Conclude your adventure on Icacos island, where you can luxuriate on its pristine, powder-white beach.

All-Inclusive Vieques Excursion: Swim with Turtles and Enjoy Pristine Beaches

Embark on an extraordinary journey with Sail Getaways to the enchanting island of Vieques. Immerse yourself in the pristine waters during our All-Inclusive Snorkel and Beach Excursion, promising a perfect blend of adventure and relaxation.

  • Most Relaxing
  • Sailboat Sailboat

Sailing Catamaran Icacos Beach & Snorkel Tour

Explore the Cordillera Cays Nature Reserve aboard our 32-foot sailing catamaran, Getaway. Wade in knee-deep, crystal clear waters, sunbathe on stunning beaches and spot tropical marine life.

  • Hour Glass 4 Hours

Icacos Double Dip Power Catamaran Snorkel & Beach Tour

Runaway, tailored for day charters – perfect for both early birds or late risers. This boat embodies fun and speed, providing ample time for snorkeling and beach enjoyment.

an umbrella sitting on top of a table

  • Hour Glass 2 Hours
  • Sunset Private Charter

Private Catamaran Sunset Sail in Fajardo

Relax and let the warm Caribbean wind carry your cares away while you sit back and enjoy some great music or the soothing sound of the boat sailing through the waves on this sunset sail.

  • Hour Glass 3 Hours
  • Sunset Sunset Sail

2 in 1 Icacos Beach & Sunset Adventure

If your vacation days are running out and you want to experience all that our aquatic world has to offer, then the 2 in 1 Icacos Twilight Beach and Sunset Adventure is for you!

Come Getaway With Us

Explore Puerto Rico on a public sail or private charter in a more intimate atmosphere compared to other tour operators that carry larger amounts of passengers.

Enjoy the best of popular tourist destinations like Icacos Cay and Culebra Island on an unforgettable sailing, snorkeling, and beach adventure in Fajardo!

Our vessels are equipped with private restrooms, shaded and open deck space, comfortable cushioned seats, fresh water showers, and easy water access ladders for snorkeling and swimming in the pristine Caribbean waters.

Sail Getaways is a family business committed to excellence by creating lifelong memories through personalized service delivered with genuine Puerto Rican hospitality.

Photo Gallery

Top-Rated Charters & Snorkeling in Fajardo, PR!

icon

I did the tour to icacos island and palomino with the captain Jay, pablito and I forgot the tall guy name but three of them were great! We had a blast on our tour. Drinks were amazing. The crew was making sure we were safe and the most important part make sure we had fun and we enjoy the tour. Thanks for everything !! I will be back.

chart

The spot chosen for snorkeling was just amazing. Flamenco beach is definitely a must. But what made a difference is the awesome Sail Getaways crew. All of them were super attentive and nice with us. They went above and beyond to ensure our trip was perfect. Not once I had to order for a refill of my drink. 11 out of 10, 100% recommended, I'll definitely repeat.

logo

Was all of our first time and it was so beautiful and fun. We got to see a barracuda, big jellyfish and a bunch of other little fish. We enjoyed the guys explaining everything, Oscar was fun and kept us entertained since the music wasn't working haha. Loved that lunch and alcohol was included, was so worth the money!

We went with a friend to visit Culebra Island and everything was very nice, the trip was very pleasant, the guides were very attentive, VERY good music and food, I recommend them, 10/10!!

Wonderful experience. Clear turquoise water, white sandy beaches, lush green islands, and a remarkable crew. It was a perfect day of swimming, snorkeling, and positive vibes all around. Highly recommend these guys.

My friend and I took the tour to Tamarindo and Flamenco beach and it was amazing. The weather was perfect which made the ride super smooth. We were a fortunate group to enjoy a beautiful day. It was our first time experience and we loved it. We are beginner swimmers (to say the least) and the gentlemen were kind enough to get in the water with us so we wouldn’t miss the opportunity. Everyone on the boat was super friendly and made us feel like family! It’s definitely a must do activity when visiting the island. Looking forward to many more!!!

It was soo much fun. We took off on time went snorkeling not many fishes but still a great experience then we went to the flamingo island and got 2 hours to ourself to enjoy l. Crew was super friendly and kept the drinks coming. Would totally recommend

diagram, icon

Great quick getaway for our group of 13. Quick boat ride to snorkel, excellent fish viewing and lunch. Then a quick boat ride to Flamenco Beach to wander around. The staff was friendly, knowledgable, and patient.

icon

We took the three-in-one catamaran getaway on New Year's Day with Omar and Arturo. Our group was 2 adults a 9 year old and a 5 year old. All of us had an amazing time. Omar and Arturo were awesome sailors/hosts/guides making sure they got us to Icacos safely for snorkeling, answered all our questions, taught us about Puerto Rico and even served us delicious drinks and snacks. A really beautiful afternoon/evening with super friendly guides, Omar and Arturo.

Responsive image

Cruising Catamaran (ASA 114) "Liveaboard" 2 Day Class

This class includes a night at anchor and all meals, (9am saturday to 5pm sunday or 9am wednesday to 5pm thursday).

An advanced weekend course for those who want to learn the nuances of multihulls, but are limited on time. Bareboat Cruising/Charter certification (ASA 104) or equivalent experience is a prerequisite. The course is taught on one of our beautiful catamarans and is geared to the bareboat charter skipper who wants the added skills to charter multihulls between 30 and 50 feet. And, experience the cruising lifestyle with a night at anchor (weather-permitting)!

There will be both a written and a skills test to complete the course. Thorough study of the text, Cruising Catamarans Made Easy , will prepare you for your course and greatly enhance your learning experience. The Cruising Catamaran (ASA 114) curriculum (link below) is helpful to follow while reviewing the text and will streamline your studying.

Based on boat size and cabin layout, this course can accommodate up to 5 students.

$1195 per person (private stateroom) $1045 per person (shared stateroom)* Spend 2 days/1 night living aboard and learning from an ASA certified USCG Captain/Instructor. Tuition includes your ASA 114 certification, linens, meal provisioning and fuel. *To receive the shared stateroom discount, you and the person you will be sharing a stateroom with must book your course together. We do not pair people who do not know each other.

This course covers ASA 114 (Cruising Catamaran). If you prefer to join the class to practice hands-on skills but not pursue ASA certifications, you are welcome to do so. Please let us know if you will not be pursuing ASA certifications and we will discount your tuition $20.

Bareboat Cruising/Charter Certification (ASA 104). If you don’t have the prerequisites, but do have equivalent experience, click here for information on challenging prerequisite certifications.

. The same date being listed more than once indicates multiple sessions of this class on that date.

If the course you are seeking is full, please contact us to be put on a waitlist.

Cruising Catamarans Made Easy , by American Sailing Association Order text online through the ASA Store , through Amazon or iBooks , or check out from your local library.

Click here for information on options to let you implement and enjoy what you have learned after graduation and to help you continue to build your sailing skills.

Please contact us by e-mail or at 360-671-8339 to register for your course and to confirm course date availability. This weekend courses require a minimum of 4 students, maximum of 5 students for course confirmation. This is a non-smoking, non-vaping course.

For our weeklong Cruising Catamaran Learn-n-Cruise option, which includes Basic Coastal Cruising (ASA 103) and Bareboat Cruising/Charter Certification (ASA 104) and Cruising Catamaran (ASA 114), click here .

Go to the following links for more information:

  • ASA 114 Curriculum
  • Packing List
  • Course Checklist

Special Opportunities

-->
Courses & Stateroom Bookings Summer Guided FlotillasSpring & Summer Guided Flotillas Fall Guided Flotillas

T. 360-671-4300 (charter) | T. 360-671-8339 (school) | T. 360-671-0829 (brokerage)

2615 South Harbor Loop, Suite 1, Bellingham, Washington 98225

Facebook

HOME       INSTRUCTION       CHARTERS       BROKERAGE       ABOUT US       CONTACT

©Copyright 2023 San Juan Sailing | All Rights Reserved | This Website was Handcrafted by the Staff at San Juan Sailing

View Our Sitemap

Site map

COMMENTS

  1. THE TOP 5 San Juan Catamaran Cruises (Prices from $99)

    1 hour 30 minutes. Free Cancellation. from. $99.00. Likely to Sell Out. Culebra Snorkeling Tour by Catamaran from Fajardo. 2,182. Cruise by high-speed catamaran to Culebra from Fajardo for a fun-filled day trip swimming, beach combing and sunbathing on this island paradise. Spend your morning exploring the fascinating undersea creatures that ...

  2. San Juan Catamaran Small-Group Sunset Sail with Drinks 2024

    What To Expect. Soak up views of San Juan from the water, and watch the sunset in style, on this sunset catamaran cruise, with drinks included and an intimate group of just six passengers on a 37-foot (11-meter) catamaran. Make your own way to the San Juan Bay Marina to board the catamaran from dock A72 before your scheduled departure time.

  3. Salty Dog Catamaran

    From $102. Take a fun-filled day sail around some of Puerto Rico's most amazing, unspoiled islands like Isla de Palominos, Isla de Lobos, and or Cayo Icacos. Learn More. All Ages. 5.5 Hours. Follow on Instagram.

  4. Castillo Tours

    Castillo Tours offers adventure tours in San Juan, Puerto Rico, including rainforest, city, boat, and fishing experiences. ... Book our most popular adventure and enjoy a half-day charter full of leisure and white sand beaches as you sail on our catamaran and enjoy world-class snorkeling! Book Now Learn More Half-Day Ages 4+ Up to 12 People ...

  5. San Juan Catamaran Sunset Sail with Drinks Included

    Hop aboard a catamaran sailboat and take in the sights of historic San Juan Bay on this picturesque sunset tour. Perfect for a romantic moment with your sweetheart or a fun time with a group of friends, this evening sail includes your choice of beverages including beer and wine. Plus learn about historical landmarks from the captain along the way.

  6. THE TOP 10 Puerto Rico Catamaran Cruises (Prices from $99)

    Along the way enjoy a lunch, with included bottled water, sodas & tropical drinks. 5 hours 30 minutes. Free Cancellation. from. $131.21. Likely to Sell Out. San Juan Catamaran Sunset Sail with Drinks Included. 497. Sail the calm, azure waters of San Juan Bay at sunset during a cocktail cruise.

  7. 3 Best Puerto Rico Sailing Tours & Charters

    Established in 2015, Sail PR is a young, modern experience provider. Our captain is a semi-pro racing sailor currently ranked #14th in the world sailing his specialty, Hobie Cat 16 sailboats. Our 37ft Lagoon Catamaran sailboat will take you sightseeing Old San Juan and San Juan Bay in a small group with complimentary drinks included!

  8. San Juan Sunset Sail

    Established in 2015, Sail PR is a young, modern experience provider. Our captain is a semi-pro racing sailor currently ranked #14th in the world sailing his specialty, Hobie Cat 16 sailboats. Our 37ft Lagoon Catamaran sailboat will take you sightseeing Old San Juan and San Juan Bay in a small group with complimentary drinks included!

  9. San Juan Catamaran Sunset Sail with Drinks Included

    Sit back, relax and take in the amazing sights of historic San Juan Bay with picturesque sunset lighting. This 2-hour sail aboard a 37ft catamaran sailboat completely powered by the wind is the perfect setting for a romantic moment with your loved one or a fun time with friends.

  10. Blue Doubloon

    Book the yacht today and enjoy the views of Old San Juan from the water! Blue Doubloon is an all-inclusive crewed day sail experience in San Juan. For those of you who want to enjoy the luxury of sailing without leaving the city, we are here for you. We have a variety of experiences from Brunch and Sunset sails with picturesque Old San Juan in ...

  11. Anacortes Yacht Charters

    Our yacht charter fleet includes a variety of power yachts, sailing yachts and crewed yachts from 27' to 70'. Make your choice to host nearly any group of friends and family for a magical San Juan Islands yacht charter. A San Juan Islands yacht charter is your ticket for exploring the scenic San Juan Islands, Gulf Islands and Desolation Sound.

  12. Cruising Catamaran Weeklong Course

    You'll learn the skills essential to skippering a twin screw 38' - 41' catamaran aboard this comprehensive weeklong course. This course will cover sailing fundamentals for Basic Coastal Cruising (ASA 103) and Bareboat Cruising/Charter Certification (ASA 104), well as the nuances of multihull cruising for Cruising Catamaran (ASA 114).

  13. San Juan Catamaran Sunset Sail with Drinks Included

    Overview. Sit back, relax and take in the amazing sights of historic San Juan Bay with picturesque sunset lighting. This 2-hour sail aboard a 37ft catamaran sailboat completely powered by the wind is the perfect setting for a romantic moment with your loved one or a fun time with friends. Complimentary beer, rum & coke, rum punch, and sparkling ...

  14. Puerto Rico Sunset Sail

    Our sunset sail is a unique and enjoyable experience for everyone who visits us in sunny Puerto Rico! Reserve your sunset sail with Salty Dog Catamaran today! ... Roundtrip transportation is available from most locations in Metro San Juan and hotels at an additional cost of $50 per person. Transportation requires a minimum of 6 passengers in ...

  15. Puerto Ricos Best Sail & Snorkel Experience

    Embrace the warm tropical breeze while sailing to one of Puerto Rico's unspoiled islands off the coast of Fajardo. Reserve your day sail and snorkel today! ... Roundtrip transportation is available from most locations in Metro San Juan and hotels at an additional cost of $50 per person. Transportation requires a minimum of 6 passengers in ...

  16. San Juan Sailing Charter Listings

    4150. 3675. 70/day. 20/day. * NOTE: $20/day provides you and each member of your crew with a total of $1,000,000 personal liability coverage during your charter. Discounts available for multi-week (2+) and for multiboat (3+) charters. For details and off-pattern rates please visit our charter FAQs.

  17. Historical San Juan Bay Sunset Sailing Tour

    San Juan Catamaran Sunset Sail with Drinks Included. 249. Catamaran Cruises . from . $119.00. per adult. San Juan Bay Day Sail with Drinks Included. 149. Catamaran Cruises . from . $99.00. per adult. Sail Away: Private Scenic Excursion from San Juan. 23. Sailing. from . $595.00. per group (up to 6) San Juan Mini Boat Tour. 89. Extreme Sports.

  18. THE TOP San Juan Sunset Cruises (UPDATED 2024)

    San Juan Catamaran Sunset Sail with Drinks Included. 495. Sail the calm, azure waters of San Juan Bay at sunset during a cocktail cruise. Enjoy a warm welcome aboard from your friendly captain and crew, then settle in for a scenic ride. Watch the island coastline glide by as the sun sinks toward the horizon.

  19. The 6 Best Puerto Rico Sunset Sailing [2024 Reviews]

    Let's start things off with the beautiful San Juan Catamaran Sunset Sail.This 2-hour sail is the perfect way to lead you from the warm day into a refreshing evening. While sailing on just about any bay will make for a picturesque moment, the San Juan Bay and port have a rich history and various landmarks that make this tour particularly special.

  20. San Juan Sailing Courses

    San Juan Sailing offers monohull and catamaran sailing instruction, to prepare you for your first charter or transition to a larger yacht. ... in just one week. We limit course size to four students (up to 6 on our catamarans) and one instructor as you live aboard beautiful yachts between 30 and 45 feet. Basic to Bareboat Learn-n-Cruise (ASA ...

  21. Sail Getaways

    Sail Getaways will be open for business starting August 16, 2024. We look forward to continuing our adventures with you on the beautiful waters of Puerto Rico! Previous slide. Most Relaxing. From $130. Lunch included. Sailboat. Beach & Snorkel. 5 Hours.

  22. THE TOP 10 San Juan Boat Cruises, Sailing & Water Tours (w/Prices)

    1 hour 30 minutes. Free Cancellation. from. $59.00. San Juan Sunset Harbor Boat Ride. 993. Enjoy a new perspective on Old San Juan—and soak up Caribbean breezes and sunset views—aboard this evening boat tour. Following pickup at select local hotels, hop aboard the boat and find a comfortable seat on the deck.

  23. Coast Guard coordinates removal of grounded sailing vessel from reef

    SAN JUAN, Puerto Rico - The Coast Guard announced, Tuesday, a crane barge is headed to Culebra, Puerto Rico, for Resolve Marine contractors to remove the grounded sailing vessel Obsession from the reef just off Flamenco Beach. ... Friday, for the vessel Obsession, a 72-foot sailing catamaran that ran hard aground on a reef July 21, 2024. The ...

  24. Cruising Catamaran Weekend Course

    This weekend courses require a minimum of 4 students, maximum of 5 students for course confirmation. This is a non-smoking, non-vaping course. For our weeklong Cruising Catamaran Learn-n-Cruise option, which includes Basic Coastal Cruising (ASA 103) and Bareboat Cruising/Charter Certification (ASA 104) and Cruising Catamaran (ASA 114), click here.