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

Loading Events

« All Events

  • This event has passed.

Schooner Race Watch

October 5, 2023 @ 11:00 am - 2:00 pm

2002 Great Chesapeake Bay Schooner Race Start

The Annual Great Chesapeake Bay Schooner Race Start Watch aboard the Schooner Woodwind II: Join in the excitement and watch the start of the race. There will be up to 25 plus schooners at the starting line. Seven of them are at least near 100+ feet. This is going to be incredible. Join the fun! They will be racing to the Norfolk area, we will cheer them on till it’s time to go in.

We will be under sail with the schooners (and yes you’ll be sailing on one too). We will not cross the starting line, but we will be sailing around them all as they come down from Baltimore.

Tickets are $125.35 per guest and include bagged lunch, bottled water, soft drinks, and snacks. Beer and wine are available for purchase.

Event departs from the Annapolis City Marina (410 Severn Ave, Annapolis, MD 21403) promptly at 11:00am. Boat cannot wait for late arrivals and no refunds will be given if you miss the boat.


  • Departs Annapolis City Marina at 11:00 am and returns to Annapolis at 2:00pm.
  • Includes Box Lunch with two sides and a cookie.
  • Includes Soft drinks and tax.
  • Our bar includes a selection of Craft Beer, Wine & Bubbly available for purchase!
  • $10 of each ticket purchased will be donated to the Great Chesapeake Bay Schooner Race, a non-profit organization that races to save the Bay with educational programs up and down the Chesapeake Bay.

Box Lunch includes:

Choice of Sandwich, Tomato & Cucumber Salad, Potato Salad, and Chocolate Chip Cookie Bar

Sandwich Choices:

Roast Beef & Boursin Roast Beef, Boursin cheese spread, tomato & arugula, served on a sesame seed roll
Southwest Chicken Wrap Grilled Chicken, corn & black bean salsa, lettuce, tomato, Colby Jack cheese & house Southwestern Ranch dressing
Vegetarian Falafel Wrap Chickpea Falafel, marinated cucumbers, tomatoes, red onion, & lemon garlic tahini dressing served on the side

Kid’s Box Lunch includes:

Choice of Sliders, fresh fruit, and chocolate chip cookie

2 Turkey & Cheese or 2 Peanut Butter & Jelly

2002 Great Chesapeake Bay Schooner Race Start


I am text block. Click edit button to change this text. Lorem ipsum dolor sit amet, consectetur adipiscing elit. Ut elit tellus, luctus nec ullamcorper mattis, pulvinar dapibus leo.


October 5, 2023
11:00 am - 2:00 pm
Event Category:


Schooner Woodwind
View Organizer Website


Annapolis Waterfront Hotel
80 Compromise Street
Annapolis, MD 21401 United States
+ Google Map
Schooner Woodwind