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 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.

Group Sailing Tour Includes:

  • Complimentary soft drink and a snack (bag of chips, pretzels or cookies)
  • Narration featuring the history & ecology of Annapolis and the Chesapeake Bay.
  • On weekday sunset sails, we offer special entertainment included in the price.
  • 18% Crew Gratuity
  • All taxes

Ideas for Group Sailing Trips on the Bay:

Social:

  • Birthdays
  • Reunions
  • Anniversary
  • Alumni Events
  • Meet- Up Groups

Corporate:

  • Staff Incentive
  • Client Appreciation
  • Vendor Gratitude
  • Company Picnic (on the water)
  • Schmooze Cruises

Group Sailing Rates:

Daytime
Adults:
$ 42.75
($32.94+5.93+3.88)
(Ticket + Gratuity + Tax)
Seniors/Students:
$ 40.75
($31.39+6.65+3.71)
(Ticket + Gratuity + Tax)
Children (under 12):
$ 29.75

($22.92+4.13+2.70)
(Ticket + Gratuity + Tax)
Sunset & Weekends
Adults:
$ 46.00
($35.44+6.38+4.18)
(Ticket + Gratuity + Tax)
Seniors/Students:
$ 43.75
($33.71+6.07+3.97)
(Ticket + Gratuity + Tax)
All prices include a soft drink, snack, taxes and 18% gratuity.

2014 Group Sailing Schedule:

April 19 – April 30
  • 10:00 – 12:00 noon
  • 12:30 – 2:30 pm
  • 3:00 – 5:00 pm
No Mondays.
May 1 – May 9
  • 10:00 – 12:00 noon
  • 12:30 – 2:30 pm
  • 3:00 – 5:00 pm
  • 5:30 – 7:30 pm (Sunset Sail)
No Mondays.
May 10 – September 1
  • 11:00 – 1:00 pm
  • 1:30 – 3:30 pm
  • 4:00 – 6:00 pm
  • 6:30 – 8:30 pm (Sunset Sail)
Seven Days A Week.
September 2 – 29
  • 10:00 – 12:00 noon
  • 12:30 – 2:30 pm
  • 3:00 – 5:00 pm
  • 5:30 – 7:30 pm (Sunset Sail)
Seven Days A Week.
Sept. 29 – October 5
October 22-26
  • 10:00 – 12:00 noon
  • 12:30 – 2:30 pm
  • 3:00 – 5:00 pm
No Mondays

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:

$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.

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