Sunset Cruise Chesapeake Bay: 42-ft Sailing Yacht

Sail past Ospreys and Dolphins as the sun sets over twin beaches

A 2.5-hour sunset cruise on Chesapeake Bay in Maryland aboard the Eternal Hope, a 42-foot sailing yacht, where you watch the sun drop over the Western Shores while passing the Cliffs of Calvert. The boat carries a small group. You'll need to confirm at least four passengers 24 hours before departure. Snacks and water are onboard. A moderate level of fitness is required for the sailing conditions.

Step-by-step itinerary

Sunset cruise on Chesapeake Bay

• Board 42 ft. sailing yacht Eternal Hope
• Sail along Western Shores of Chesapeake Bay
• Watch Ospreys and Dolphins near Calvert Cliffs
• Enjoy sunset over twin beaches
• Take photos of the sunset

The experience

How do you close out a summer day on the water? You sail into the sunset on Chesapeake Bay. The Eternal Hope is a 42-foot sailing yacht that runs a 2.5-hour cruise timed to catch the sun dropping over the twin beaches of the Western Shores. Along the way, you pass the Cliffs of Calvert and have a real chance to spot Ospreys and Dolphins from the deck: the wildlife shows up often enough that it's worth keeping your camera ready.

The boat stays small by design: you need a minimum of four passengers to sail, and you'll confirm the group size by calling 24 hours before your departure time. That call matters because the cruise adjusts for the season. September sailings are shorter and run at a different time than the later fall dates, when the boat leaves at 3 pm to chase the later sunset. Snacks and water come aboard, and the Captain and First Mate appreciate tips.

Soft-soled shoes are required: no black-bottomed shoes allowed on deck. The boat moves with the wind and the water, so a moderate level of fitness helps. The operator notes that spinal injuries, pregnancy and poor cardiovascular health are reasons to sit this one out. Weight limit is 250 pounds per person. Children from age one are welcome, though infants must sit on an adult's lap.

What’s included

• 2.5-hour sunset cruise aboard the Eternal Hope, a 42-foot sailing yacht.
• opportunity to spot Ospreys and Dolphins.
• views of the Cliffs of Calvert and the Western Shores.
• snacks and water onboard.

Before you book

Days and timesNext departure: 12 May 2027

Book up to2d 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. If that happens, you're offered another date or a refund.

Prices and times updated 11 days ago

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?Small groups work best here. You need at least four passengers to sail, so this suits friends or a family booking together rather than solo travelers or pairs looking to join a larger crowd. The 2.5-hour sail and the moderate fitness requirement make it a good fit for people comfortable on the water and ready to stand on deck for the full sunset.

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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.

Can I bring alcohol or dinner on the cruise?

Alcoholic beverages and dinner are not included and not permitted onboard. Snacks and water are provided.

What if I'm not sure we'll have four people? Do I still need to book?

You book as usual, but you must call 24 hours before your cruise time to confirm the minimum of four passengers has been met. If the group doesn't reach that size, the cruise won't sail.

What's the best time to see wildlife on this cruise?

Ospreys and Dolphins are a real possibility on the Chesapeake Bay, and you'll have the best vantage point from the deck of the Eternal Hope as you pass the Cliffs of Calvert. There's no guarantee, but sightings happen often enough to keep binoculars or a camera handy.

How does the sunset timing change through the fall?

September 9 through 21, the cruise is shorter and runs at an earlier time because the sun sets earlier. September 23 through October 30, the boat departs at 3 pm to catch the later sunset, and the cruise may also be shorter depending on daylight.

Do I need sailing experience to enjoy this cruise?

No sailing experience is needed. You're a passenger aboard the Eternal Hope. The operator does ask for a moderate level of physical fitness because the boat moves with wind and water, and you'll be on deck for the full 2.5 hours.