sailboat cruises annapolis

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A Grand Experience for All

Custom built for sailing, comfort and fun. Our cruising grounds are some of the most beautiful and historic in the country

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Special occasions, adventure & entertainment.

Custom built for sailing, comfort and fun, the Liberte is a grand experience for all. Our cruising grounds are some of the most beautiful and historic in the country. The captain and crew are dedicated to your safety, comfort and enjoyment.

USCG certified for 49 passengers. Music. Full bar. Every Sail is Unique.

One Great boat, two great locations

About the boat.

The schooner, Liberté, is based on Spa Creek in Annapolis, Maryland. During the summer months, she’s docked at the Patriot Party Boats pier in Falmouth harbor in Cape Cod, Massachusetts. Captain Chris and Jane had this vessel built just for them.

The original hull design by Dudley Dix is a Hout Bay 70, a two-masted gaff-rigged schooner intended as a heavy but fast offshore cruiser. Many alterations were made to the design, including adding a spoon bow, scaling down the lines to meet U.S. Coast Guard parameters, redesigning the deck layout and adjusting the rig to a three-masted staysail design.

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Picture Perfect Sailing

• Meet your Skipper

Sail in Annapolis, Book a Sailing Cruise Today

Enjoy quality time with family and friends sailing out of Annapolis. You'll fall in love with the Chesapeake Bay. Your sailing charter awaits. 

CHOOSE YOUR SAILING ADVENTURE

Sailing options.

With Picture Perfect Sailing, the options are virtually endless!

Your skipper will take you for a day sail in Annapolis for a few hours towards St Thomas Point Lighthouse or the Chesapeake Bay Bridge, or perhaps around Annapolis harbor. For a longer sailing charter, choose our all-day sailing experience or overnight. You'll find yourself sailing to Baltimore or Saint Michaels. Book a sailing cruise now, make the memories of a lifetime with your family and friends!

Day Sail: come sailing for a few hours

Duration: 3 hours (leaves and returns to Annapolis)

Starting at $650 for 2 guests. Your sailing charter includes: skipper, snacks & beverages. Please check rates and book a sailing cruise by clicking the button below.

Sunset Sails: come sailing as the sun goes down

Duration: 2.5 hours (leaves and returns to Annapolis)

Starting at $650 weekdays for 2 guests. Your sailing charter includes: skipper, snacks & beverages. Please check rates and book a sailing cruise by clicking the button below.

All Day of Sailing: come sailing on the Chesapeake Bay all day!

Duration: 6 hours (leaves and returns to Annapolis)

Starting at $1,550 weekdays for 2 guests. Your sailing charter includes: skipper, crew member, snacks, lunch & beverages. Please check rates and book a sailing cruise by clicking the button below.

Overnight Sailing: experience sailing and sleeping aboard!

Choose one or two overnights: (leaves and returns to Annapolis)

Single (one) overnight: typically departs at 10am, one overnight in Baltimore or St Michaels, with disembarkation at 5pm the next day. Variations upon request. Starting at $2,450 weekdays for 2 guests. Your sailing charter includes: skipper, hostess, lunches x 2, snacks, breakfast x 1 & beverages. 

Double (two) overnights: typically departs at 9am,  one overnight in Baltimore or St Michaels, second overnight at the dock back in Annapolis and disembarkation at 9am the next morning. Starting at $3,900 for 2 guests.  Your sailing charter includes: skipper, hostess, snacks, breakfast, lunch x 2 & beverages.

The prices displayed in the booking schedule include yacht fuel, dock fees, water, propane for cooking, yacht insurance, cabin linens & bath towels. 

What’s not included: water activities off the boat (due to insurance limitations) such as swimming, paddle boarding or dinghy use; dinners (plan dinners on shore); crew gratuity.

How to book a sailing cruise with an overnight? Contact us for availability and custom pricing.

*Rates vary by season. Holiday rates upon request. Special pricing for Navy families, veterans, and first responders.  Contact Picture Perfect Sailing for more information and to book a sailing cruise today!

The Sailboat

You'll sail aboard a Beneteau Oceanis 45, with extensive cockpit protected by canvas and well-appointed to accommodate up to 3 couple for overnight sailing in maximum comfort; a head (bathroom) with shower, a full galley (kitchen) and comfortable salon. Arguably the nicest charter boat to sail in Annapolis. Let the sailing adventures begin, book a sailing cruise now.

With Picture Perfect Sailing, your designated skipper (and mate, depending on your sailing option!) will lead the sailing charter: maneuver the boat, guide your visit of the Annapolis area on the water, and ensure the fun & safety of all! 

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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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Sailing Charters in Annapolis, MD

Classic Sail Charters offers Chesapeake Bay sailing adventures on our thoroughly refined sailing yacht, the Licentia. It is exquisitely appointed, safe, and ready for you to call home while you enjoy the mystique and allure of some of the best sailing grounds in the world.

Select A Time

1 - 6 people | 3-hour (am/pm) - 2.5-hour (sunset) sailing yacht cruise | 25% deposit, minimum age: 7 years., gratuity not included in pricing.

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• Hour Glass 2.5 Hours
• Users Up to 6 Passengers

Sunset Sail - Licentia

Come join us for an unforgettable cruise on one of our world-class sailing yachts and enjoy the beautiful sunsets in Chesapeake bay!

• Hour Glass 3 Hours

Morning Sail - Licentia

Classic Sail Charters offers Chesapeake Bay sailing adventures on a thoroughly refined sailing yacht Licentia, a 2008 Catalina 42 MKII.

Afternoon Sail - Licentia

Come sail with us on the Chesapeake Bay! As the largest estuary in the world, the Chesapeake Bay is stunningly beautiful!

Other Times

• Hour Glass 8 Hours

Full Day Sail - Licentia

Come sail with us on the Chesapeake Bay! As the largest estuary in the world, the Chesapeake Bay is stunningly beautiful, fed by countless navigable rivers and home to an abundance of wildlife.

Chesapeake Bay - Annapolis

Looking for a unique sailing experience on the Chesapeake Bay? Our charters are the perfect way to explore the Bay and its navigable rivers. As the largest estuary in the world, the Chesapeake Bay is a natural beauty filled with an abundance of wildlife. Create your own sailing adventure on the Chesapeake Bay as we work with you to define your perfect excursion and then you may leave the rest to us!

Annapolis, located less than an hour from Washington, D.C., is noted not only as the location of the US Naval Academy but as America’s ‘Sailing Capital.’ It is home to a rich history that includes the oldest working state capitol building in the U.S., noted as the location where General Washington resigned his commission, as well as dozens of first-class bed and breakfasts, hotels, and fantastic restaurants. As a sailing venue, it is second to none.

Annapolis Cruises

Annapolis is a beautiful historic seaport that’s great to explore by water.

Whether it’s a narrated sightseeing cruise or a day trip to St. Michaels, get out on the water with Watermark for an unforgettable journey. Our boats have a full bar service with light snacks available for purchase and restrooms on board. Most of our vessels are handicapped accessible and climate controlled.

Come on down and find us at Annapolis City Dock, 1 Dock Street and look for the red umbrella!

Annapolis Harbor & USNA

Hear the history of the U.S. Naval Academy, Annapolis’ role as a historic seaport, the region’s waterways, and catch a glimpse of the Bay Bridge.

Spa Creek Cruise

Step aboard our cozy launch for an intimate cruise up Spa Creek into the residential area of Old Annapolis, Eastport, and the banks of the U.S. Naval Academy.

See Schedule

Day on the Bay to St. Michaels

Cruise across the Chesapeake Bay to St. Michaels on the Eastern Shore.  Enjoy fresh seafood, boutique shopping, and historic sites all within walking distance.

Scenic Severn River Cruise

A spectacular 6-mile cruise on the beautiful Scenic Severn River and historic Annapolis Harbor; includes the banks of the United States Naval Academy

Chesapeake Bay Bridge Cruise

Cruise through Annapolis’ historic harbor, by the United States Naval Academy, and under the twin spans of the famous Chesapeake Bay Bridge.

Thomas Point Lighthouse Cruise

View this National historic landmark as you cruise the Chesapeake Bay on a narrated cruise.  Not just for lighthouse enthusiast; everyone loves it!

Annapolis Sunset Cruise

Enjoy a fun music playlist, the sun setting, and a cool beverage from our River Run Bar as you relax on this 60-minute cruise through the Annapolis Harbor.

Water Taxi Service

Hop on a taxi to visit your favorite restaurant or to get downtown from Eastport.  Taxi’s operate in the Annapolis Harbor, including Spa Creek and Back Creek

Special or Seasonal Cruises

From live music cruises to New Year’s Eve, Watermark offers a variety of special and seasonal cruises throughout the year.  Click below to learn more.

Baltimore Cruises

From live music cruises to New Year’s Eve, Watermark offers a variety of special and seasonl cruises throughout the year.  Click below to learn more.

Sailing Charters aboard the 'PINTITA' out of Annapolis & Baltimore

Make your next getaway a sailing adventure on the Chesapeake Bay!

Are you planning a birthday or anniversary celebration, planning a proposal, getting married or renewing your vows, or just want to enjoy the Annapolis or Baltimore skyline with a cold beverage while sailing?  Help raise and trim the sails, navigate, man the helm or simply take in the experience and sights while relaxing with a cold beverage. Come see what the allure of sailing is all about. The professional Captain and Crew of the ‘ PINTITA ’ can help make your next adventure a memorable one. 

We are currently booking private sailing charters for up to 20 passengers! 

We ask that you continue to support your local businesses and this Veteran owned small business needs your support and patronage.  Please book your private sailing charter soon for your next friends, family, and or corporate outings.  We are looking forward to harnessing the wind and creating memories with you.

Pla n to join us for the U.S. Navy Blue Angels in Annapolis during Commissioning Week in May, 2024

See our Charters page from the menu above

Call us now to book your getaway:

443-510-5756

The ‘PINTITA’ is perfect for:

Bachelor & Bachelorette Parties

Engagement Proposals

Anniversaries

Alumni Events

Company Events

Team Building

We offer many charters to meet your needs.

The 'PINTITA' Sailboat is licensed for groups of up to 20 persons! She has an all weather enclosed cockpit to keep you dry from passing showers! She is designed to make your outing as entertaining and comfortable as possible.

The PINTITA

Come sail the chesapeake bay..

Join us in Annapolis & Baltimore.  We hold a current USCG Certificate of Inspection for Private charters, meaning that she is inspected in her construction, equipment, and maintenance to rigorous federal standards.

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The Annapolis Maritime Museum & Park

A Maritime Museum and Park located in Annapolis Maryland

SKIPJACK TOURS

Annapolis sailing cruise, book your cruise & experience the chesapeake bay on the historic skipjack wilma lee, heritage cruise, specialty cruise - rum runners, education on the water, wednesday night races, sunset cruise, private charter, wilma lee history, history of wilma lee, weather cancellation policy.

We cruise rain or shine, but we will cancel two hours prior to departure for high winds or thunderstorms. We will contact you via text on the cell phone number provided. Cruises are subject to cancellation due to weather and unforeseen conditions and are fully refundable. No refunds for guest cancellations or no-shows.

Departure/Return Location

Refer to your ticket for departure point. Cruises are from the Annapolis Maritime Museum Campus, Annapolis Maritime Museum Park Campus, or Annapolis City Dock, please check the schedule before booking.  Boarding starts 15 minutes prior to departure time, please arrive 30 minutes prior to departure. We depart on time, please be prompt. 

Other Important Info

• Children must be accompanied by an adult. The U.S. Coast Guard considers all children, regardless of age and size, to be passengers, and as such, you need to purchase a ticket for each child.
• Please allow extra time for parking. We are unable to hold the boat past our scheduled departure time.
• Flat shoes are recommended, and heels will not be permitted.
• Please bring sunscreen, a water bottle, and a hat and wear comfortable clothing. There is very little shade on the boat. No outside food or drink is permitted.
• Not wheelchair accessible.
• If you do not receive an email confirmation after purchasing your ticket, please email  [email protected] . Every passenger is required to have a ticket.

Sailing Season is Here. Join Us for a Sail!

Buy Tickets for Today or This Week

• We sail rain or shine.
• There are no refunds or exchanges unless the captain cancels the cruise due to unsafe conditions.

* Everyone has loved having more room, so we are staying at just 30 people per cruise (instead of 48).

Online tickets go on sale at midnight 6 days before you want to sail.

Tickets may also be purchased, during office hours, in person or by phone (410-263-8994) beginning 6 days before the date you want to sail.

• The boat leaves on time, you will not be refunded if you miss the boat.
• We have a bar filled with local microbrews, wine and bubbly. You cannot bring your own alcohol.
• Pets are not allowed aboard, with the exception of “working” service dogs, which are permitted.

For groups buying individual tickets, that would like to sail on the same boat, please use the comment section ONLINE to alert us of the group name so we can try to keep your group together.

All policies listed in link below including parking, smoking, check in, footwear and more.

• Wheelchairs and strollers cannot be accepted aboard. See FAQS

Contract of Carriage

Accessibility

I have a mobility issue, or i am traveling with someone who has a mobility issue, is this cruise suitable.

• The Woodwind boarding ramp is approx 22″ wide with rope handlines on one side (crew members will offer their arms and hands to help guests board). The current tide determines the angle of the ramp (higher tides mean a steeper slope to the ramp).  At the end of the ramp, guests must step down (approx -11″) onto the deck.
• The cockpit area provides bench seating with a non-cushioned backrest and an area where guests can brace their legs. This is the most suitable place for guests with mobility and/or stability issues to sit and feel the most secure.  In order to access this area, guests must step (or swing legs) over and down approx 13.5″ to the bench and then down to the cockpit floor (approx 16″ down).
• As Schooner Woodwind is a sailboat, she may at times, sail heeled over at an angle of 5-20 degrees from one side to the other. Guests with mobility issues will likely find it difficult to move around the boat and/or keep themselves seated comfortably when the boat is heeling.
• The restrooms (heads) are located below deck – accessed by means of a companionway ladder (about six steps).

Can I bring my mobility aid aboard?

• Most wheelchairs and walkers do not fit aboard the Woodwind without compromising the safety of the boat and/or other passengers aboard. Mobility aids can be left at our Dock Office and retrieved following the cruise.  The captain has the authority to determine if it is safe for the other passengers aboard to allow mobility aids aboard.

Are you ADA compliant?

• The vessel configuration does not violate the law. There are no vessel configuration regulations now in place with which to comply.

Please consider all of these factors before deciding to purchase a ticket for a cruise on the Schooner Woodwind.  The captain has the right to determine if a specific person with limited mobility will be a danger to other guests aboard due to the current conditions.  In such cases that a person is not able to sail, a refund will be provided to this person and one caregiver that stays behind.

All Cruises

I see that only 30 people is the capacity on public cruises, but i see that the boat is uscg certified for 48 which one will it be.

The company has decided that the experience aboard with just 30 people (who may not know each other) is a better experience than the USCG capacity of 48 people.  Before the COVID-19 pandemic, we would sell out the boat with 48 people aboard. We reduced how many tickets we sold and our crew and customers have loved it.  We will be operating this way all season.

When will the decision be made to cancel a trip due to bad weather?

Unless there’s a tropical storm heading our way, the decision is typically made just prior to departure time.

Are there life jackets for my infant?

Yes. When you check-in at the dock office, let us know that you have an infant and we will hand you a special infant life jacket.

What should I wear for the cruise?

Soft-soled shoes are required and the dress is very casual and comfortable. Depending on the season, layered clothes work best. We supply complimentary ponchos should there be rain during the cruise.

What about motion sickness?

Since we sail in relatively protected waters and we have a heavy ballasted keel, it is very rare for people to get seasick (less than 1%). We recommend getting “sea bands” for your wrists if you are concerned about this. You can purchase these wristbands from our ticket office prior to your cruise. Motion Sickness pills will work too, however, the side effect is they may make you drowsy. We do not sell medication to help with motion sickness; please bring anything you may need with you.

What about being caught out in a lightning storm?

During the summertime, lightning storm forecasts are a common occurrence. Most of these do not materialize, but if one does “pop up” while sailing and when possible, we will head for the dock as soon as we can. Our captains are excellent at reading these storms; where the storms are and where they are going.

What do you typically see? Where do you go?

All cruises are dependent on weather factors. Minimally, all cruises will sail past the Naval Academy, Annapolis Harbor area, and the “Scenic Severn River”. Most trips leave the harbor and head out to the Bay, passing by osprey nests and other sailboats & powerboats. While sailing you may get to see the 4.5 miles long, Chesapeake Bay Bridge and as the Woodwind sails back into the harbor, the historic, Annapolis skyline stands out quite prominently. If the wind is light, we often sail up the Severn River where the magnificent waterfront estates meet the shoreline. Some trips are just right for a cruise under the Bay Bridge, and on less frequent occasions, we can sail to Thomas Point Lighthouse. It’s very easy for us to say “each trip is unique”, which keeps frequent sailors coming back for a new adventure!

Can we go below decks to get out of the rain and/or extreme heat?

We do encourage you to stay out on the deck where you can truly experience sailing, however, there is space below decks if you need to get out of the elements for a while.

Can I bring my own alcohol onboard?

We do sell a variety of beer, wines, and bubbly. We have a liquor license, and it does not allow for any type of alcohol to be brought on board.

Public Cruises

What if i need to cancel.

Our cruises do not allow for cancellations.  You can sell or give your ticket to someone else.  In the event that we need to cancel the cruise, all ticket monies will be refunded.

Must I buy a ticket for an infant or toddler?

Yes, they count as a passenger, according to the U.S. Coast Guard.

Can I buy tickets more than 6 days in advance?

Yes, you can. By purchasing a flat-fee Group Sail package (1-16 guests), you will be guaranteed the sail time that you want.  An added bonus, if you are checked in at the Dock Office 15 minutes prior to the sail, your group will board first to select the seating you like.  Click here for Group Sail information.

When do I need to show up?

We begin boarding 10 minutes prior to departure time. Allow plenty of time for traffic, parking, and time to check-in at our Dock Office. We cannot hold the boat if you will be late.

Can I smoke onboard?

There is no smoking of any kind or vaping permitted on any public or private cruises.

Can I bring food on board a public cruise?

If you wish to bring food on board, it must be individually packaged for each person. No spreads, buffets, and no cakes.

Private Cruises

Do you do team-building.

We have wonderful team-building programs for groups of 7-70 people, including our popular “Ultimate Team Challenge: Match Racing Program” with our two, identical schooners. Visit our Teambuilding page here to learn more.

Do you have merchandise so my guests can remember their adventure?

We have a wide variety of merchandise, from t-shirts to hooded sweatshirts, postcards to patches, we have it all. Check out our Ship’s Store for what we sell. All this merchandise can be purchased at the dock office or online in advance of the cruise. For large quantity orders, please let your sales agent know ahead of your visit, so we can make sure we have everything in stock.

Can I bring my own food?

We work with our exclusive caterer to provide your group with the best menu for your sailing event. All food is served chilled or at room temperature. Our menus include great appetizers, brunch, breakfast items, and gourmet lunch and dinner options. All food is pre-packaged for each guest and delivered to the boat and served by the extraordinary crew aboard. See our menus here.

Who takes care of gratuities and taxes?

All gratuities and taxes are included in your private cruise contract under Service Fees.

Can I have my wedding on the Woodwind?

Small weddings are ideal aboard the Woodwind. Rehearsal dinners while sailing or a cruise to entertain and show off Annapolis to your guests is also a treat aboard. A true taste of Maryland!

What if the weather is bad?

We typically sail rain or shine unless the captain cancels the cruise due to unsafe conditions. We do offer “Rain Protection” at an additional cost on some of our private charters. See below.

What is Rain Protection?

Schooner Woodwind offers “Rain Protection” at an additional cost. This insurance gives the charterer a time period of 24 hours prior to the charter until 2 hours before the scheduled departure to cancel if there is a greater than 30% chance of rain forecasted for the time of the charter.

Rain Protection is not available:

• On any charters contracted within 14 days of the Event Date.
• If the charter originates from a port other than Annapolis, MD.
• If both Woodwinds are chartered for the same cruise time.
• Special dates like Blue Angels Fly-Over, July 4th, and other Holidays.

Scout and Student Cruises

Is a private cruise the only option for a scout or student trip aboard the woodwind.

Yes. In order for our crew and captains to be able to offer interactive programming for the Scouts, we do need it to be a private event.

If we wanted to brush up on our nautical terms, where should we go?

Go to our Educational page where they can learn terms, names of the sails, and other great information.

Does Schooner Woodwind have Scout patches? If so, how much?

We have great Participation Patches that say “Annapolis Sailing Cruises”.  Each participating scout and student will receive a patch as part of the Private Cruise Pricing. Additional patches are $4.25. Click here to see patches

Do you have merchandise so the guests can remember their adventure?

What is the life jacket policy.

According to the Girl Scout USA and BSA safety procedures, they want all Scouts, adults, and other children aboard a cruise must be outfitted in life jackets. We have additional Type III life jackets that are more comfortable for non-emergency use.

How many people can we fit on the boat?

The USCG limits us to 48 passengers, however, we are limiting the boat to 40 passengers.  We do have two Woodwinds, so if you have an extremely large group (40 to 80), we can fit them aboard both boats.

What to bring/Wear

Soft-soled shoes are required, and the dress is very casual and comfortable. Depending on the season, layered clothes work best. We supply complimentary ponchos should there be rain during the cruise.

What should I bring aboard?

Bring a smartphone to purchase bar items or an extra soda or water. Bring a real raincoat, if it is forecasted to rain, yours will far surpass the complimentary rain ponchos that we have aboard.

Can I bring a bottle of wine aboard?

No. We have a liquor license, and it does not allow any type of alcohol to be brought on board. We do sell a variety of beer, wine, and sparkling wine.

What do I do when I arrive at the Annapolis Waterfront Hotel Dock?

Check-in at our ticket office when you arrive at the dock for boarding instructions. Our ticket office staff will direct you to the boarding line for your cruise. If both Woodwind and Woodwind II are sailing, there will be two lines.

If you have not already purchased tickets, you can do so at our ticket office on the dock.

What do I need when I check in?

If you bought your tickets online, you should bring the printout of your ticket confirmation page. If you have a smartphone, you can bring up the confirmation email on your phone. If you bought your tickets over the phone, please have your confirmation number and a photo ID with you when you pick up your tickets. You will be told where to stand for which boat you are on.

When should I arrive?

Please arrive at the dock no later than 15 minutes before the scheduled departure time of the cruise. If you arrive early you can check in at any time, there is a great bar and restaurant located on the water at the Annapolis Waterfront Hotel. No alcohol may be brought aboard.

Click on the picture above to get a 360 degree view of the boat and where the Schooner Woodwind is docked.

General Policy

• Once tickets are purchased, there are no refunds or exchanges.
• We sail rain or shine, unless the captain cancels the cruise due to unsafe conditions.
• We begin boarding 10 minutes before the departure time. Please arrive early and check in at the Dock Office.
• Please wear rubber soled shoes.
• Smoking is prohibited on public cruises.
• Pets are not allowed aboard, with the exception of “working” service dogs, which are permitted.
• We have a bar with local microbrews, wine and bubbly. By law, no alcohol can be brought aboard or removed from the vessel.

In Addition to Above

For Weekday Sunset Sails:

If the scheduled entertainment cannot perform for any reason, we will continue to sail the scheduled public cruise. No adjustments will be made to the price since our crew will do our very best to make the cruise enjoyable without the scheduled entertainment.

For Wednesday Night Races (5:30 Departure Time):

Schooner Woodwind will depart promptly at 5:30 PM, however our starting time for the race is 6:45. We will be racing a fairly short course and there is a strong possibility that we will get back to the dock after 7:30 PM. This is bonus time so that we can finish the race. We will return to the dock no later than 8:00 PM. Schooner Woodwind will still depart even if the races have been cancelled by the yacht club, but the Captain has deemed the conditions safe to sail.

For Wednesday Night Races (6:25 Departure Time):

Schooner Woodwind will depart promptly at 6:25 PM, because our starting time for the race is 6:45. We must get to the starting line on time. Schooner Woodwind will still depart even if the races have been cancelled by the yacht club, but the Captain has deemed the conditions safe to sail.

For Public Special Event Cruises with catering:

The captain will wait up to one hour past the scheduled departure time to resolve any weather or mechanical issues before deciding if the event needs to be canceled. If the event is cancelled or shortened and food is able to be served or individually distributed, the food costs will not be refunded.

For Public Lighthouse Cruises:

We will make every attempt to see three lighthouses on this cruise, however, weather conditions, wind speed, and direction may impede our ability to do so. This is not a motor cruise to see the lighthouses. We hope it is breezy enough to sail the majority of the time. If the guest speaker is unable to perform for any reason, we will still sail the scheduled cruise. If the cruise is cancelled due to unsafe conditions, a refund will be issued for the cost of the sail but not the catering, the bagged lunch will be available for pick up.

For Public Wine in the Wind Cruises:

If the wine representative is unable to attend for any reason, we will still sail the scheduled cruise. Also, the captain will wait up to one hour past the scheduled departure time to resolve any weather or mechanical issues before deciding if the event needs to be cancelled. If the event is cancelled or shortened, a refund will be issued for the cost of the sail but not the catering, the food will be available for pick up.