Sailboat Cruise Chesapeake Bay: Wind-Powered 2.5-Hour Sail

Drift across the bay under sail, no engine noise

A 2.5-hour sailboat cruise on the Chesapeake Bay aboard the Eternal Hope, a 42-foot sailing yacht, departing at 9 am, noon or 3 pm Tuesday through Sunday (plus Mondays for Memorial Day and Labor Day). The boat is wind-powered only, and the route passes the historic Cliffs of Calvert with chances to see dolphins, ospreys and passing cargo ships. Snacks and water are included. A minimum of 4 passengers is required. You must call 24 hours before your departure time to confirm the cruise will run.

Step-by-step itinerary

Sailboat cruise on Chesapeake Bay

• Board 42' sailing yacht Eternal Hope
• Cruise Chesapeake Bay for 2.5 hours
• View Cliffs of Calvert and wildlife
• Possibly sail near opposite bay side

The experience

If you have a free afternoon and no car, the Eternal Hope departs from the bay itself, so you only need to reach the dock. The boat sails at three fixed times each day, which means you can fit the cruise around the rest of your plans without hunting for a departure window. Once aboard, there's nothing to do but settle in: the captain and first mate handle the sails while you watch the water and the shoreline pass.

The route follows the Chesapeake itself, so you'll see the Cliffs of Calvert rising from the water and the shipping channel where cargo vessels move through. Dolphins and ospreys show up often enough that the crew watches for them, though sightings are never guaranteed. If the wind is strong from the west, the boat may cross to the other side of the bay, which opens up different views. The whole thing runs on wind, not an engine, so the only sounds are the water and the rigging: the reason people come back to this boat.

Snacks and water come with the ticket. Life jackets are required for children 12 and under at all times, and for all passengers outside the cockpit while the sails are up. Soft-soled shoes are required. Black-soled shoes are not allowed on deck. The cruise lasts two and a half hours from start to finish.

What’s included

• Snacks and water.
• all fees and taxes.
• life jackets for children 12 and under and for passengers outside the cockpit under sail.

Before you book

Days and timesFriday and SaturdayDepartures at 09:00 and 12:00

Book up to15h before

AgesAdult (13 to 63 years) · Senior (64 and older) · Youth (7 to 12 years) · Child (3 to 6 years) · Infant (1 to 2 years)

GroupUp to 6

Live guideEnglish

Meeting point and pickupNo hotel pickup: you go to the meeting point. Ends back at the starting point.

Cancellation and refundsFree cancellation up to 24 h before the start. After that, no refund.It may be canceled due to bad weather or if the minimum number of travelers isn't reached. If that happens, you're offered another date or a refund.

Prices and times updated today

Good to know

Moderate physical effortNot recommended during pregnancyNot recommended with heart problemsNot recommended with back problemsInfants must sit on laps

Operated by Chesapeake Windsail Cruises Corporation

Is this one for you?The boat departs from the Chesapeake Bay itself, so you don't need a car or a ride to reach it. Just get to the dock. The three daily departure times (9 am, noon and 3 pm) mean you can book around your other plans without waiting for a specific window.

Traveler reviews

4.81★★★★★★★★★★

42 verified traveler reviews

5 ★39

4 ★1

3 ★0

2 ★1

1 ★1

Read all the reviews ›

Top questions

Can children come?

Yes. Ticket types: Youth (7 to 12 years); Child (3 to 6 years); Infant (1 to 2 years).

What happens if it rains?

It may be canceled due to bad weather. If that happens, you're offered another date or a refund. Free cancellation up to 24 h before the start.

What's the Cliffs of Calvert, and how close does the boat get to them?

The Cliffs of Calvert are a historic shoreline formation along the bay that the boat passes during the cruise. The exact distance depends on the wind and the route the captain chooses that day, but they're a landmark feature of the Chesapeake that you'll see from the water.

Can I bring my one-year-old on the cruise?

Yes, children are welcome from age 1. Infants must sit on an adult's lap during the cruise, and life jackets are required for all children 12 and under at all times.

Do I need to call ahead to confirm the cruise will actually run?

Yes. You must call 24 hours before your cruise time to confirm that the minimum of 4 passengers has been met. If the minimum is not reached, the cruise will not depart that day.

What should I wear on the boat?

Soft-soled shoes are required. Black-soled shoes are not permitted on deck. Wear layers if the weather is cool, since you'll be on the water for two and a half hours. Life jackets are required for children under 12 and for all passengers outside the cockpit while sailing.