Category Sailing

Washington DC · SAILING

4 Sailing Trips in Washington DC Actually Worth Booking

4 tours compared

The best sailing trips in Washington DC fill up fast, especially in cherry-blossom season. These 4 are the standouts, each with its current price and the thing that sets it apart, so you can book before the calendar does.

Washington, DC: Potomac River Yacht Cruise with Open Bar

Washington, DC: Potomac River Yacht Cruise with Open Bar - Open Bar Value: Cocktails, Beer, Wine, and More

Sailboat Cruise on Chesapeake Bay

Sailboat Cruise on Chesapeake Bay - Calvert Cliffs, Shipping Channel, and the Main Bay Route

2.Sailboat Cruise on Chesapeake Bay

★★★★★★★★★★5.0 · 38 reviews · 2 hours 30 minutes (approx.) · from $102Top rated

Small-group Chesapeake Bay sailing on the 42-foot yacht Eternal Hope. Calvert Cliffs, wildlife, and time at the wheel.

“We could not have picked a more perfect day to go sailing with Captain Andy and First Mate Stephanie. My friends and I had a wonderful and memorable Sunday on the Chesapeake. Andy and Stephanie felt like they were part of our group and we had the best time talking about the history of the area, as my friends and I grew up in the DC/MD area. The winds were light and the waves were calm. It was the most perfect way to relax and enjoy some good company.”

Check availability →Read the full review

Private Yacht Tour along Washington DC Waterfront

Private Yacht Tour along Washington DC Waterfront - Georgetown waterfront, the Three Sisters, and Roosevelt Island

Party Yacht Cruise along Potomac River

Party Yacht Cruise along Potomac River - Watergate Complex: modern architecture with a headline history

4.Party Yacht Cruise along Potomac River

★★★★★★★★★★4.0 · 22 reviews · 2 hours (approx.) · from $74

A 2-hour Boomerang Boat party cruise on the Potomac with open bar, music, and big DC sights from Georgetown to Arlington.

“It was...fine. The 'booze' part was terrible, cheap wine, bad beer and way too sweet cocktails. It was nice simply because of the views, but it was only fine. Not worth the price.”

Check availability →Read the full review