Loading Events

« All Events

Classic Wooden Boat Regatta

September 20 @ 11:00am

| $90.00
The Wooden Boat Regatta in Annapolis photo by Kate Gahs

Participate in the Classic Wooden Boat Regatta. The Woodwinds’ have been invited to participate in the race in the “Spirit of Tradition Class”.

The course is approximately 5.4 NM and takes place in the Severn River. It is a 3 lap race with pursuit style race. Each boat has a rating, and by the rating they will get a start time. The pursuit style race challenges the competitors to sail through the other race boats to win the regatta. This will be an amazing trip for photography (hint B&W or sepia tone) of these old, gorgeous boats.

This is going to be a fun, challenging race! Join the crew!

Departs Annapolis Waterfront Hotel Dock at 11:00 am and returns to Annapolis Waterfront Hotel Dock at 2:30pm. Ticket Price includes bagged lunch, soft drinks and bottled water and tax. Our cash bar includes a selection of Craft Beer, Wine & Bubbly!

The participating boats will be on display on Saturday (other than the Woodwinds).

Zoned Seating Pricing ~ Limited Capacity (24 person max):

  • 2 person zone ~ $180.00 (for 2 guests)
  • 4 person zone ~ $360.00 (for 4 guests)
  • 6 person zone ~ $540.00 (for 6 guests)

Gourmet Bagged Lunches

Bagged Lunches include dill potato salad, charred corn and fennel slaw & a Cowboy cookie.
Sandwiches (Choose 1 per person in zone)
Cranberry Pecan Chicken Salad Wrap
Honey Ham with Boursin cheese, rosemary mustard & arugula on a multigrain baguette
Vegetarian Hearts & Greens Wrap with artichoke hearts, power greens, almonds & tarragon mayo



Classic Wooden Boat Regatta
September 20 2020 11:00am
September 20, 2020 2:30pm
Event Categories:


Annapolis Waterfront Hotel
80 Compromise Street
Annapolis,MD21401United States



© Copyright 2020. Running Free, Inc. DBA Annapolis Sailing Cruises: Schooner Woodwind. Annapolis MD. All right reserved. Privacy Policy.

Site Designed by: Green Mountain Marketing & Advertising, Inc.

Woodwind Annapolis Sailing cruises logo

Be the FIRST to know!


Sign up to get the latest info on Specialty Cruises, Events, and Opening. 

Thank you for signing up for Schooner Woodwind News. 

Schooner Woodwind