Group Sailing

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.
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 18 people or more on a scheduled 2 hour public sail. 

If you are interested in 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 Appreciation
  • Vendor Gratitude
  • Team Bonding
  • Schmooze Cruises

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.
  • Crew Gratuity is included on Group Sails.
  • Guarantee the sail will not be booked for a private event.
  • Discounted Base Ticket Price

Group Sailing Rates:

Weekday Daytime
Adults:
$ 45.00
Seniors/Students:
$ 42.75

Children (under 12):
$ 29.75
($34.67 + 6.24 + 4.09)
(Ticket + Gratuity + Tax)
($32.94 + 5.93 + 3.88)
(Ticket + Gratuity + Tax)
($22.92 + 4.13 + 2.70)
(Ticket + Gratuity + Tax)

Sunset & Weekends
Adults:
$ 48.75
Seniors/Students:
$ 46.00

Children (under 12):
$ 29.75
($37.56 + 6.76 + 4.43)
(Ticket + Gratuity + Tax
($35.44 + 6.38 + 4.18)
(Ticket + Gratuity + Tax)
($22.92 + 4.13 + 2.70)
(Ticket + Gratuity + Tax)

All prices include a soft drink, snack, taxes and 18% gratuity.

Group Sailing Schedule

Italicized Times can only be booked by a Group Sail.

April 18 – 30

Tuesday – Sunday

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

May 1 – 8

Tuesday – Sunday

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 – Thursday we have different activities on our Sunset Sails- Check out our Schedule here.

May 9 – August 30

Seven Days a Week

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 – Thursday we have different activities on our Sunset Sails- Check out our Schedule here.

August 31 – September 27

Seven Days a Week

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 – Thursday we have different activities on our Sunset Sails- Check out our Schedule here.

September 28 – October 4

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

October 8- 12

Only Sailing for Private Events Only

October 21 – 31

Tuesday – Sunday

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

Italicized Times can only be booked by a Group Sail.

 

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.

A Family Reunion Celebrates on Woodwind.

Payment Schedule:

$300 deposit is due at time of booking to hold the date and the customer must sign an agreement to buy a minimum of 18 tickets. Balance is due 2 weeks prior to the cruise date along with the final head count.  All remaining spaces will be opened to the public six days prior to the date of the sail.  Boarding passes can be picked up at the dock office on the day of your cruise.

 

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, excluding any catering ordered.  All attempts will be made to reschedule the cruise if possible.

 

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

Call 410-263-1981 to arrange a cruise for your Group.

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