Please browse the sections below for answers to frequently asked questions about our sailing cruises.


• I have a mobility issue or I am travelling with someone who has a mobility issue, is this cruise suitable?

  • The Woodwind boarding ramp is approx 22″ wide and there are no hand rails (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 go over a step (approx -11″) onto the deck.
  • The cockpit area provides bench seating with a non cushioned back rest 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 to the other passengers aboard to allow mobility aids aboard.
  • Are you ADA compliant?
    • The vessel configuration does not violate 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 1 caregiver that stays behind.

• 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 purchase an “infant” ticket, it will signal us to provide you with an infant life jacket for the duration of the cruise when you pick up your boarding ticket at the dock office.

• What should I wear for the cruise?

Soft-soled shoes are required and the dress is very casual and comfortable. Depending on season, layered clothes work best. We supply emergency 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 wrist bands 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 they 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 a to see the 4.5 mile 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 deck where you can truly experience sailing, however there is space below decks if you need to get out of the elements for awhile.

• Can I bring a bottle of wine onboard?

No. We have a liquor license and it does not allow any type of alcohol to be brought onboard. We do sell a variety of beer, wines and bubbly.

Public Cruises

• Why are there no refunds or exchanges on tickets?

To be fair to other passengers and to guarantee a place onboard to guests who purchase advance tickets, we must enforce this policy. It enables us to give the best customer service possible with a consistent policy.

• 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, only if you agree to purchase 18 or more tickets and sign a Group Sail contract. There have been many times that people have elected this choice to guarantee the boat will go out with their group and pay for a few extra people (that aren’t going) to ensure their date and time. Click here for group sail information.

• When do I need to show up?

We begin boarding 15 minutes prior to departure time. Allow plenty of time for traffic and parking and time to check in at our Dock Office to pick up your ticket(s). We cannot hold the boat if you will be late.

• What kind of snacks come with the cruise?

Assorted types of chips, pretzels or cookies.

• Can I smoke onboard?

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

• What about cigars?

No cigars are permitted on public cruises.

• Can I bring food onboard a public cruise?

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

Private Cruises

• Do you do teambuilding?

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 schooner. Visit our Teambuilding page here to learn more.

• Can I bring my own food?

We work with our exclusive caterer, Palate Pleasers, 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 bagged lunches to full lunch and dinner buffets. All food is prepared 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 charter contract.

• 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 Insurance” 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:

  1. On any charters contracted within 14 days of the Event Date.
  2. If the charter originates from a port other than Annapolis, MD.
  3. If both Woodwinds are chartered for the same cruise time.

Girl Scout Cruises

• What is the cruise like? What will they learn?

First the girls will learn how to ask for permission to board the schooner. Once aboard the captain will give a safety speech about the boat and have one of the girls demonstrate how to put on a lifejacket. After leaving the dock, the crew will ask for volunteers to help raise the sails. Then the Girl Scouts will be divided into smaller groups (depending on size of the group) where they will be taught the aspects of sailing by one or two of our professional and fun crewmembers. During this time they will learn about nautical terms, proper lookout, boating safety, Chesapeake Bay facts, weather and the basics of sailing. We do this in a question and answer manner. For example, the crew would ask “does anyone know how a sailboat can sail through the water” and when the girls start answering the questions, the crew keeps asking them more probing questions, so they are learning the whole time.See curriculum for each program.

After this learning period which length is determined by the girls attention span, they are then quizzed on everything they have learned by the captain in order to sail the boat. When the girl answers a question right, they get to steer the boat for a little while, and use their newly acquired skills. Depending on wind conditions and the attention of the girls, they may also be instructed how to work the sails. Everyone will get a chance to sail the boat. See curriculum for each program.

 • What do the adults do?

The adults (and siblings) can listen in on all the fun the girls are having, take pictures or simply relax and enjoy the sail. While the girls are in their learning stage, the adults can steer the boat.

 • What is a good age for the cruise?

Any age is great for these cruises. The captain and crew tailor the experience for the age group aboard. We have had every age group aboard, and they all love the experience!

Descriptions for each group are on these web pages:

Brownies, Juniors, Teens, All Ages

 • What are the times for a Girl Scout sail?

We sail from mid-April through the end of October. Click on Girl Scout Brochure for our exact times and dates we can sail.

 • How much are the tickets?

Weekday Daytime: $47 Adults, $45 Students (12 years old +), $32 Children (under 12)
Weekend trips: $51 Adults, $48 Students (12 years old +), $32 Children (under 12)
– Rates include soda, snack, tax and gratuity.
– Child & Student Tickets include Schooner Woodwind Participation Patch

 • Do they get a turn at the wheel (helm)?

Absolutely. They all participate in a sailing trivia contest and when they get the question right, they steer the boat. Everyone will get the chance.

 • How many people do we need in order to get the “Group Sail” Price and reserve further than 6 days out?

18 people is the minimum number of people. 48 is the maximum- unless you use both boats.

 • What happens to the extra tickets that we don’t purchase for the “Group Sail”?

We have a capacity of 48 passengers. Any remaining tickets you do not purchase will go on sale to the general public six days prior to that sail.

•  If we don’t have the minimum 18 people to get a “Group Sail” what are my choices?

You can still sail with us, but you would not be able to get your tickets until they went on sale to the general public six days prior to the date that you wanted to sail. Under certain circumstances, we may be able to group you with another Girl Scout group. You could also check with other groups to get your numbers up to 18 people, or open it to siblings, too.

• 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”. They come with each child or student ticket that you purchase. Additional patches are $4.25. Click here to see patches

 • Do you have merchandise so the girls 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 bought at the dock office. For large quantity orders, please let us know ahead of your visit, so we can make sure we have everything in stock.

 • What is the life jacket policy?

According to the Girl Scout USA Safety Checkpoints, they want all girl scouts, adults, and other children aboard a “Girl Scout” cruise to be outfitted in life jackets. We have purchased Type III lifejackets which are more comfortable for non-emergency use.

  • How many people can we fit on the boat?

The USCG limits us to 48 passengers. We take aboard one captain and three crew members. We do have two Woodwinds, so if you have an extremely large group (49 to 96), we can fit them aboard both boats.

What to Bring/Wear

• What should I wear for the cruise?

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

• What should I bring aboard?

Bring cash for bar items or for an extra soda (or water) or snack. Bring a real raincoat, if it is forecasted to rain, yours will far surpass our complimentary rain ponchos that we have aboard.

• Can I bring a bottle of wine onboard?

No. We have a liquor license and it does not allow any type of alcohol to be brought onboard. We do sell a variety of beer, wines and bubbly.

• Can I bring food onboard a public cruise?

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

• Should I bring a life jacket?

We have life jackets for everyone aboard.


• Where is the best place to park?

Great Question!

We have made up a very detailed page with an interactive map about the parking in Annapolis.

PRIVATE PARKING LOTS, CITY GARAGES AND EASTPORT STREET PARKING are the only ways to park without a 2-Hour Limit. All Woodwind cruises are 2-hours or longer.


• 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 tickets and 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 print out of your ticket confirmation page. If you have a smart phone you can bring up the confirmation email on your phone. If you bought your tickets over the phone then please have your confirmation number and a photo ID with you when you pick up your tickets. You will get a Boarding Ticket so that you know what boat you are boarding and where to line up.

• When should I arrive?

Please arrive at the dock no later than 15 minutes before the schedule 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.

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