2024 Sailing Season is coming! See you April 13, 2024!

Group Sailing

Having fun on Schooner Woodwind on Chesapeake
Sailing with friends

Schooner Woodwind, Annapolis Maryland Customer Testimonials Customer Reviews

“We had a wonderful time aboard the Woodwind. Our family truly enjoyed the sail. We loved the fact that you used the guests to raise the sails, let us steer the boat and had so much interesting information regarding sailing and the sea. The crew was so friendly and made the day feel like we were out sailing with just old friends.”

Cindy S.

“We had such a great time! We had beautiful weather, calm seas, and lots of fun with the Captain and the entertainment. They both were so funny! Thanks again.”

Cindy D.
MiddleBrook Pharmaceuticals

Schooner Woodwind offers Group Sailing for groups of up to 16 people on a scheduled 2-hour public sail.

If you are interested in the exclusive use of the Woodwind please visit our Private Cruises page.

Great Group Sail Ideas:

Social:

  • Birthdays
  • Reunions
  • Anniversary
  • Alumni Events

Corporate:

  • Staff Incentive
  • Client or Vendor Appreciation
  • Vendor Gratitude
  • Networking

Why Book A Group Sail vs Public Tickets?

  • Group Sails can purchase tickets further in advance. Public Tickets can only be purchased six days prior to the date you want to sail.
  • All Service Fees are included on Group Sails.
  • Guarantee the sail will not be booked for a private event.

 

2023 Group Sail Rate for up to 16 guests
Weekday Daytime 
$1295.03
Weekend, Sunset, and Holidays
$1368.84
2-Hour Sailing Cruise includes a Soft Drink, Tax, and Service Fees

 

Group Sailing Schedule

2023 Group Sailing Schedule

April 15 – April 25

10:00 am- 12:00 pm
12:30 pm – 2:30 pm
3:00 pm – 5:00 pm
5:30 pm – 7:30 pm


April 26 – May 12

10:00 am- 12:00 pm
12:30 pm – 2:30 pm
3:00 pm – 5:00 pm
5:30 pm – 7:30 pm (Sunset Sail*)
*Monday-Wednesday we have different activities on our Sunset Sails- Check out our Schedule here.


May 13 – August 27

11:00 am – 1:00 pm
1:30 pm – 3:30 pm
4:00 pm – 6:00 pm
6:30 pm – 8:30 pm (Sunset Sail*)
* Monday – Wednesday we have different activities on our Sunset Sails- Check out our Schedule here.


August 28 – September 24

10:00 am- 12:00 pm
12:30 pm – 2:30 pm
3:00 pm – 5:00 pm
5:30 pm – 7:30 pm (Sunset Sail*)
* Monday – Wednesday we have different activities on our Sunset Sails- Check out our Schedule here.


September 25 – October 1

11:00 am- 1:00 pm
1:30 pm – 3:30 pm
4:00 pm – 6:00 pm

October 2 – October 17

Only Sailing for Private Cruises Only


October 18 – 29

Private Charters available October 31st

11:00 am- 1:00 pm
1:30 pm – 3:30 pm
4:00 pm – 6:00 pm

 

The best way to experience the Chesapeake Bay is under sail on a 74-foot schooner. Plan your next authentic sailing experience; from family parties to reunions or corporate outings or a staff appreciation cruise aboard our fast and fun sailing vessels.

Payment Schedule:

A $500 deposit is due at the time of booking to hold the date. The balance is due 2 weeks prior to the cruise date.

Cancellations:

Our cruises do not allow for any cancellations.  Our weather policy: if the weather is stormy and the Captain feels it is not safe to depart, then all monies are refunded.  All attempts will be made to reschedule the cruise if possible.

If it is raining we will still sail!!
We offer complimentary rain ponchos.

Contact a Schooner Woodwind Sales Agent

Learn more about Group Sails and sailing aboard the Schooner Woodwind & Woodwind II

Call 410-263-1981, or fill out an inquiry form by clicking on the button below.

Schooner Woodwind
410-263-7837