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

Weddings, Rehearsal Dinners and More!

Schooner Woodwind Weddings on the Chesapeake Bay
This couple chartered both boats for a terrific wedding! Call us to find out how this worked.

Schooner Woodwind & Woodwind II

Two identical 74-foot schooners that set sail daily from downtown, historic Annapolis.

Book a private charter for your wedding festivities. Or join us on a public sail for a pre-wedding celebration.

Small Weddings Aboard

Get married aboard the Woodwind with the gentle wind in your veil as you sail away into the sunset. Woodwind can accommodate up to 40 people comfortably for a small wedding aboard one boat. Add up to another 40 people, and charter both Woodwinds for a slightly bigger wedding or reception.

Have more than 80 people? Just invite your closest family and friends for your ceremony aboard and then have a larger reception somewhere else in downtown Annapolis after your sail.

Sailing on the Woodwind is a great way to show off Annapolis and the Chesapeake Bay to your friends and family.

  • Rehearsal Dinners
  • After Wedding Brunches
  • Bachelor/Bachelorette/Pre-Wedding Party Outings

CateringRehearsal Dinners: Enjoy a delicious meal underway with many catering menus available. Celebrate in style while sailing on the Chesapeake Bay. Fun for the whole family!

After Wedding Brunches: Don’t want the fun of having friends and family around to end after the wedding? Invite them in the morning to go sailing in Annapolis for a terrific brunch with great food and morning cocktails.

Bachelor/Bachelorette/Pre-Wedding Party Outings: Before heading out for your late night event, relax and enjoy a fun sail. Watch your friends sail the boat, raise the sails or just relax while enjoying champagne & local microbrewed beer.

Weddings on the Schooner Woodwind in Annapolis, MarylandIf you’re having your event in Annapolis, tell your friends & family about sailing the Woodwind!

Join us on one of our public cruises. We sail up to four times daily. If you have a group of 18 or more, book a group sail with us, or book the entire boat for a private charter.

Thank you to all of the happy couples that have allowed us to use their images. We are proud to be the perfect venue for about six wedding ceremonies per year, and many receptions aboard.

 Call 410-263-1981, or email us to obtain a quote for your special event!


Schooner Woodwind