dream yacht charters annapolis

Annapolis Bay Charters/Dream Yacht Charters

7080 Bembe Beach Road,Suite 211A, Annapolis MD 21403

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The Oldest & Most Respected Charter Company on the Chesapeake Bay. Annapolis Bay Charters is the original yacht rental business in the Chesapeake Bay area. Our agents help sailors explore the diverse area on water and ashore. Choose from catamarans or monohulls in our fleet of well-maintained yachts including motoryacht models to discover some of Chesapeake Bay’s hidden gems. We offer many extras, such as itinerary planning, Annapolis sailing instruction with our NauticEd Sailing School, provisioning, captain, and crew services.

The Marine Trades Association of Maryland (MTAM) is a non-profit dedicated to promoting the recreational marine industry and waterway preservation. Founded in 1972, MTAM now comprises nearly 400 marine related businesses.

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P.O. Box 3148 Port Annapolis Marina Annapolis, Maryland 21403 Phone: 410-269-0741

Marine Trades Association of Maryland | © Copyrights 2023

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Captained and Bareboat Charters in Annapolis, Maryland

The Chesapeake Bay is among the world’s top cruising and sailing destinations. A true American treasure, the Bay delivers a long enjoyable sailing season from early Spring to late Fall, with over 11,000 miles of shoreline to explore. From quiet, unspoiled anchorages, to historic seaside towns like St. Michaels and Oxford, to the vibrant ports of Baltimore and Annapolis, the Chesapeake Bay offers something for everyone.

Our docks in historic Eastport overlook the celebrated city of Annapolis and the Naval Academy. Take a short stroll or dinghy ride into town and enjoy the quaint shops and world-class restaurants before heading out on your Chesapeake Bay adventure.

Charter with Waypoints Annapolis to Experience:

• Daily, Weekend, and Week-Long Charters 
• Skippered, Bareboat, and ASA Certification Charters 
• New Luxuriously Appointed Fountaine Pajot Sailing and Motor Catamarans, Dufour Sailing Monohulls, Jeanneau Sailing Monohulls, and Jeanneau Powerboats
• Yachts Equipped with Air-Conditioning and Generators 
• Provisioning and Personal Concierge Services

An Insider’s Viewpoint

“How would we describe the perfect cruise from Annapolis to St Michaels? Talk to Susan and Traci at Waypoints and hire Mike to be your captain and chef extraordinaire! Booking was easy and Dark Star was the perfect venue for our sail on the Chesapeake. We were blessed with beautiful weather and we never lacked in getting the details we needed quickly when we asked questions and made requests. We launched the boat from their very accessible location on the Eastport side of Spa Creek. They helped us navigate parking and Waypoints had people help us with our luggage. We can’t say enough good things about our experience. They exceeded our expectations!” Julie M.

“If you are looking for a Five-Star full-service charter experience and marina, look no further than Waypoints Annapolis. The boat was in mint condition and the service at the Marina was exceptional. Annapolis is a beautiful historic city with great restaurants and a fun nightlife for those who want to spend an evening onshore.” Mike

“This may be the best charter company I have ever used. Fantastic customer service, wonderful, perfectly maintained boats, price competitive, perfect location right on the Severn next to Chart House, boat choice from small to large.” Sandy

“Phenomenal company, team, and experience, from start to finish! Waypoints Annapolis offers the finest yachts for charter and boat-as-business opportunity we’ve ever seen!” Karen

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• Annapolis Spring Sailboat Show

Dream Yacht Charter

Wherever you want to go in the world, and whatever type of yacht charter you’re looking for, we have your perfect sailing vacation.

With more choice of destinations than any other yacht charter company, we’re opening up a whole world of possibilities for adventure seekers and those who just want time to unwind at some of the most beautiful locations on the planet.

From bareboat and skippered to the exclusivity of fully-crewed yacht rentals, we have amazing charters for seasoned sailors and those with no experience at all.

Tickets are on sale now!

Elite Charters of Annapolis

Luxury yacht charter experiences.

Unique and Unforgettable Memories Await in Annapolis and on the Chesapeake Bay

Why Choose Elite Charters of Annapolis

Exclusive Yacht Charter Experiences

Let us host your next special occasion, cocktail cruise, relaxing weekend, or wedding cruise aboard one of our luxury yachts.  

Located in the heart of Annapolis, our professionally crewed charter yachts are easily accessible and create stunning and memorable experiences on the Chesapeake Bay. 

Our yachts are equipped with state-of-the-art amenities, including air conditioning, comfortable seating, and entertainment systems.

Professional Captains and Crew

Our crew members are experienced and knowledgeable about the Chesapeake Bay. They will ensure that you have a safe and memorable experience on your charter.

Muse - 87' Warren Yacht

• This sleek 87 ft sport yacht is available in Annapolis and the Chesapeake Bay.
• Invite up to 12 guests for half or full-day private yacht charters.
• She boasts beautiful teak decks, dual salons, and a spacious aft entertainment area.
• With a 5 ft draft, Muse can navigate secluded coves and anchorages.
• A 27-knot cruise speed ensures fast travel and exploration of multiple destinations.
• Overnight guest accommodations for six plus crew.

Shredder - 54' Eastbay

• Built by Grand Banks, the 54 ft Shredder is the quintessential Downeast-style cruiser.
• Accommodates up to 12 guests for half or full-day private yacht charters.
• Ideal for multi-day or week-long luxury Chesapeake Bay cruises for a couple in the spacious master stateroom.
• Perfect for day excursions to quaint Chesapeake Bay towns, romantic dinners, and water activities.

Firefly - 68' Azimut

• The Italian-designed and built Firefly turns heads with its sleek lines and lavish leather interiors.
• With a 6 ft draft, Firefly can access secluded Chesapeake Bay coves and shallow rivers.
• Features two spacious staterooms, making it an ideal overnight retreat for two couples or accommodating up to 12 guests on a day charter.
• Suitable for various experiences, from an elegant sunset cruise to a week-long excursion along the Chesapeake Bay, Annapolis, and Baltimore.
• Firefly ensures your private yacht charter is marked by style, comfort, and luxury.

Photo Gallery

The stunning yacht Muse at her winter home in Miami

Reserve Your Charter Today!

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326 1st Street, Suite 403, Annapolis, MD 21403

Mike Esposito / [email protected] 239-227-7879

Copyright © 2024 Elite Charters of Annapolis - All Rights Reserved.

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Rent the best Annapolis luxury yacht charters of 2024

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How to rent a luxury yacht charters in annapolis, find the perfect boat.

Enter your desired location and date to explore our fleet of luxury yacht charterss.

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Enjoy your day on the water with friends and family!

Why Boatsetter?

As the global leader in peer-to-peer boat rentals, Boatsetter offers an easy, safe and accessible way to experience on-the-water adventure. With boat rentals in 600+ locations, finding a boat is easy and with the option to tap into the largest network of USCG licensed captains, boating experience is not required.

Get out on the water worry-free, knowing our insurance covers every boating trip

Choosing the right boat rental platform is essential to your peace of mind while on the water. That's why we've gone the extra mile to focus on safety through our exclusive partnership with GEICO Marine and BoatUS. As the first and only boat rental marketplace to offer insurance on every peer-to-peer rental, you are protected during all rentals with insurance coverage and on-water assistance through TowBoatUS.

Got questions?

Frequently asked questions

What makes Boatsetter different from other boat rental platforms?

What makes Boatsetter different is peace of mind. Boatsetter is the first and only boat rental marketplace to offer insurance on every peer-to-peer boat rental. We know choosing the right boat rental platform is essential to your experience while on the water. That's why we've gone the extra mile to focus on safety through our exclusive partnership with GEICO Marine and BoatUS. As the first and only boat rental marketplace to offer insurance on every peer-to-peer rental, you are protected during all rentals with insurance coverage and on-water assistance through TowBoatUS.

How to rent a boat on Boatsetter?

At Boatsetter, our mission is to make getting out on the water as easy as possible. With our intuitive booking system, you can rent a boat as soon as today. -First, you must determine your budget and the type of boat you want to rent. -Next, decide where you would like to boat and the kind of boat you would like to spend the day on. -Finally, determine if you will be needing a boat captain and reach out to the boat owner. That’s it! You’re officially on your way to a fantastic day out on the water.

How much does it cost to rent a boat?

The cost to rent a boat depends on whether you are renting for a half-day or a full day, the boat features and the boat size can impact your boat rental price. Rental prices can range from $200 to $1,000 plus depending on the boat rental itself and the length of time of the rental.

How many people can fit on the boat rental?

The number of people who can fit on boat rental largely depends on the boat’s size and how many life jackets are on board. Currently the coast guard allows a maximum of 10-12 people on a Boatsetter boat rental.

How much does it cost to rent a yacht?

The cost of renting a yacht depends on the boat’s size and the amount of time you’ll use the yacht. The onboard amenities and luxurious accommodations also dictate the price. You can contact our yacht specialists for a custom quote by visiting https://www.boatsetter.com/luxury-yacht-charters .

How old do you have to be to rent a boat?

You must be 18 years old to rent a captained boat and 25 years old if you would like to rent a bareboat charter.

Do I need a boating license to rent a boat?

Boating license requirements vary from state to state. As a renter, you are responsible for understanding local state requirements.

Can you rent a yacht for the day?

Boatsetter allows you to rent a yacht for the day. Single-day yacht rentals are available for a select number of yachts. To chat with a yacht specialist please visit https://www.boatsetter.com/luxury-yacht-charters .

Can you rent a yacht for the week?

Boatsetter allows its customers to rent a yacht for the week. Renting a yacht for a week gives you more access to the wide range of yachts available on our platform. You can either book a rental directly through the site or connect with one of our charter specialists to plan your trip here: https://www.boatsetter.com/luxury-yacht-charters .

Can you rent a yacht for the month?

Booking a month-long yacht rental is a detailed and hands-off process when working with our team of yacht charter specialists. We tailor each yacht charter to our client's specific wants and needs. Our luxury yacht charter specialists can be reached at (954) 715-4114 or by visiting https://www.boatsetter.com/luxury-yacht-charters .

How to rent a private yacht?

Renting a private yacht is a very detailed experience that caters to your exact needs while onboard one of our luxury yachts. To plan your private yacht rentals experience please visit https://www.boatsetter.com/luxury-yacht-charters .

How much does it cost to rent a pontoon boat?

The cost of renting a pontoon boat depends on the size, location, and rental time of the boat. Prices can range anywhere from $200 for a half-day rental or just under a $1,000 for longer rentals.

How much does it cost to charter a yacht?

The cost to charter a yacht varies depending on the boat size and the length of the charter. Prices typically range from less than $1,000 to $5,000 plus if you’re wanting to charter the yacht overnight.

How much does it cost to rent a boat for the day?

The cost of renting a boat for the day on average ranges from $200 to $1200. The cost to rent a boat varies depending on the size of the boat and the length of time that you will be using the boat.

How does the boat insurance work?

Boat insurance typically covers loss caused by things such as fire, sinking, storms, and collisions. The extent of the coverage varies depending on the policy.

Do I need my own insurance to rent a boat?

You do not need boat insurance when renting with Boatsetter. Coverage is provided under the Peer-to-Peer Boat Rental Policy, which is underwritten by GEICO Marine Insurance Company. The policy was written from the ground up as a stand-alone recreational boat rental insurance policy covering the period of time that the boat is being rented and is available for all non-commercially insured boats.

Does Boatsetter screen renters?

Yes. We use a system called Cognito to ensure that payment information matches the renter's identity. We also require renters taking out a captained boat to be at least 18 years old and on a bareboat to be at least 25 years old.

Is listing my boat on Boatsetter free?

Yes! Listing a boat is completely free. We only take a commission when your boat is rented. We only make money when you do!

What if I'm not comfortable having a renter drive my boat?

If you are not comfortable having a renter drive your boat, we have an expansive network of licensed and experienced captains. Once your boat is listed, you can filter through our network of captains and favorite captains in your area that you would like to operate your boat.

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Top luxury yacht charters reviews in Annapolis, MD

Beautiful boat! Seats the max capacity easily!! It was absolutely great for cruising on the potomac and the fold out...

46' Catamaran...

We rented this boat for my sister's bachelorette party and had the BEST time! Seriously it was the highlight of the...

My group had the best time with Windsong Charters. Everything was exactly as described and we had a wonderful day....

ESCAPE--Leopard...

We had a group of 8 to celebrate a birthday and Captain Jack was great! We had an amazing time and the catamaran was...

The boat was super spacious and filled with an array of water toys that were a crowd favorite at my sister’s...

VIP Yacht...

51 foot luxury...

Easily the BEST boat I’ve been on ever. Extremely clean boat captain and crew were amazing almost forgot I was in DC...

Boat was super big and undeniably beautiful. Plenty of space for the 11 of us

Dare to Dream is a Dream! This is a beautiful vessel (better in person). Steve and Colin are simply awesome. ...

Great crew, nice and clean boat!!

Sailing Charter -...

Audrey and Garrett were fun, friendly, knowledgable, and accommodating. Perfect first sailing experience. Highly...

Luxury Yacht Charters in Annapolis, MD

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Dream Yacht Sales

Location & Hours

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7080 Bembe Beach Rd

Annapolis, MD 21403

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About the business.

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Dream Yacht S.

Dream Yacht Sales offers expert yacht buying assistance that helps sailing enthusiasts own a luxury yacht. Our business specialists help you match our flexible yacht ownership programs to your personal lifestyle choices and financial situations. Your yacht buyer's broker assists you with understanding completely how you can own the yacht you want with lower expenses and reduced challenges and risks of traditional boat ownership. Plus most programs offer weeks of sailing our worldwide charter bases. We offer more choices of locations and sailboat models, more charter management locations, financing and cost reduction options and incomparable flexibility. …

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DONT. PLEASE DONT GIVE THIS AWFUL COMPANY ANY OF YOUR TIME OR MONEY. THEY WILL RUIN YOUR VACATION. It is evident that Dream Yacht Charters had no intention to fulfill its obligation to our reservation or booking contract from the beginning. Even if you are not a sailor the list below gives you a sense of their "double dipping" gaining monies from our booking and clearly booking the vessel to another party the minute we could not take any more lies or failed repairs. We left the unseaworthy boat and they quickly prepared it for a new client. Just about the most abhorent unsafe practice. No refund, No acknowledgement of their responsibility, no maintenance records. The pictures attached say it all. Anchor & Windlass Windlass broke on 2 occasions rending the boat inoperable and leaving crew in exposed unsafe conditions, without the ability to raise or lower the anchor manually. Anchoring - a 5:1 scope ratio is generally considered the minimum standard for anchoring; we were advised to put down a 3:1 scope and when doing so the boat dragged at night despite a good set on the sandy bottom requiring crew to attempt to sail back to safe moorage during the night. For the Indian ocean a 7:1 scope may be more appropriate. At best Dream Yacht Charters provided a 3.8:1 scope ratio for the anchor yet telling us to only use 45m which is 2.8 scope without any markings. Main sail No reef points on luffed main sail, making it impossible to reef the main as there is no reef 1 tack or reef 2 tack point thus there is no way to secure the foot of the sail while reefed. Reef points exist on the leech, however they are only lines through the reef points back to the winch which risks tearing of the main sail when downward pressure is applied, as usually a vessel of this size has a block system for reefing on the main sail. Defective main sail halyard unable to winch to the top due to underpowered winch size and inappropriate line sizes. Unable to sheet in Jib for proper sailing angle as lines slip through winch, due to inappropriate sized winch and lines. Genoa Main Sheet winch blew apart port side under sail Dingy Dingy under inflated and had leak in hull, outboard motor would not stay on for more than 2 mins, no oars provided - crew had to swim 0.5km to shore dragging dingy and then waited 6 hours for rescue. All crew members were injured during the swim with one suffering from deeply embedded sea urchin spines that required medical attention and caused inability to walk easily for 1 week. Additional Issues Refused to provide us with a tank key, despite us asking several times Freezer did not work Watermaker has not been serviced, it is "operational" but water quality is poor and monitoring dials not working - crew was unable to drink water from Watermaker without violent nausea Swim step ladder was unsafe - it was attached to rotted wood on Transom which gave way under any strain Auto pilot will not helm by wind angle

Dream Yacht Charters are truly the worst. In a tome when people should be looking out for each other, and trying to help, these guys literally refuse to refund my $6300 deposit for a trip planned for September. As the COO for a company that supports kids with special needs I was trying to facilitate a magical sailing trip for them. Covid hits, we legally cannot travel - no refund. How selfish can a company be, to steal #dyc #dreamyachtcharter #charters #scam #yachts #moneythieves @dreamyachtcharter Dream yacht charters, DO NOT USE! These schemers literally just took my $6000 for a trip that can't happen due to Covid. You've been warned! #thieves #dycharter #dreamyachtchartersfr #victim #bvi #warned #donotuse #theyshouldbeashamed #embarrassed

I promised my family a dream vacation and instead we got a broken boat, 6 days on a floating toilet smelling of sewage; the first 2 days spent in the marina standing on the dock watching the boat being repaired. I contracted for a boat, specific in the contract you must sign with these un-ethical people, and it simply wasn't delivered. Instead, we walked up to an old chartered-out MESS, surprised the boat was still afloat (big bash in the starboard bow, did it leak? No one seemed interested. Not sea-worthy? No one inspected, no one seemed to care). So much other things to worry about! Headsail in tatters, exposed wiring (on a 220v boat!!), port motor not running (!), moldy mattresses, port 2+ cabin water-logged smelled of mold and rot, backed-up sewage from the waste tanks spilling out the waste vent, no refrigerator, no contracted gen-set, no A/C, no water maker. All of it not compensated by the "Dream Yacht" non-existent "customer service" and their placating "one day voucher credit" on another Dream Yacht vacation! (They must believe their customers are crazy?) Once you sucker-up and sign the contract they have your MONEY, and you are now betting that money that you won't be SCREWED by these people waiting for them to deliver on their contractual promise. Good Luck. You might, randomly, get lucky, and get a boat that is newer and not a chartered-out and broken POS but good luck with that, don't count on it. Picture yourself standing in the hot sun at the marina with no place to stay, no provisions, no communication with them about the broken boat you've contracted, and you'll get the idea. They LITERALLY DON'T CARE. And don't think that your credit card will protect you, tried contesting the contracted charge for non-delivery and was denied because "the merchant is not liable for "the quality' of the rendered service." Can you believe it? I was SCREWED by DYC. Un service client horrible et une expérience horrible.

Dream Yacht Charter are scammers. We were in the midst of setting up a charter with them and then the pandemic came. We had not signed a contract with them as of yet but had given them thousands of hard earned dollars. When we told them that the airlines had canceled our flights and that it would be impossible to even get to the country we would be sailing from they essentially told us to pound salt and that they would be keeping our money. They are thieves. I can't believe these scumbags are still in business when there are so many reputable outfits out there. I wish I had read the reviews about them before giving them my money. Apparently, I am not the first that they have cheated. #sailing #catamaran #bareboat #Caribbean #BVI @BritishVirginIs @viycstt #ScrewedByDYC

#dreamyactcharter Dream Yacht Charter is an unscrupulous entity and you should not trust them. Prior to the onset of the COVID-19 we entered into a negotiation with DYC for the charter of two catamarans in Greece in Sept 2020. In anticipation of a successful negotiation surrounding the terms of the charter contract we provided them with a $6,300 deposit. The COVID19 pandemic hit which obviously makes it reckless to get into the tight quarters of two catamarans with 16 people. On top of that, Greece will not permit Americans to enter because the virus is not controlled here. This would obviously make it impossible for us to travel to the port of embarkation. Further, in the middle of the negotiation, DYC swapped out the contract on the table and replaced it with one that essentially makes us their pandemic insurance policy. The new contract would leave them with no risk and the right to keep our money. We advised them that we could not sign either contract nor could we pursue a charter with them in Sept or any other time. Their response was it is their policy not to return money. These people are thieves and stole our money. There are lots of trustworthy #charter companies out there. DO NOT USE DREAM YACHT CHARTER, THEY ARE SCAMMERS. #sailing #catamaran #bareboat #Caribbean #BVI #ScrewedByDYC

I highly recommend the folks at Dream Yacht Sales. They are professional and courteous, and the Dufour line of sailboats are nothing short of remarkable. I assure you, that you can trust DYS for a pleasurable experience.

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