Chesapeake Bay Catamaran Sail 2-Hour Harbor Tour in St. Michaels

A catamaran built for comfort, not just speed.

A 2-hour catamaran sail on the Chesapeake Bay from St. Michaels, Maryland, aboard the modern vessel Epiphany, with a harbor tour past the historic Hooper Strait Lighthouse. The boat carries binoculars, cushioned seating with pillows, beanbag and reclining captain's chairs, rain jackets, life jackets and bottled water. The crew is live and English-speaking. Infants must sit on an adult's lap, and moderate fitness is needed to board.

Step-by-step itinerary

2-hour catamaran sailing tour

• Board catamaran Epiphany
• Sail through Chesapeake Bay
• View Hooper Strait Lighthouse
• Enjoy panoramic water views
• Spot local wildlife
• Relax or learn sailing basics
• Disembark at St. Michaels

The experience

St. Michaels sits on the Chesapeake Bay's eastern shore, and the Epiphany launches from there into waters calm enough that the boat's wide catamaran hull lets you settle into cushioned seating or a beanbag chair without gripping the rail. The 2-hour loop glides past working watermen's boats, marsh grasses and the shoreline where the bay's maritime history lives, including the Hooper Strait Lighthouse, built in 1879 to guide ships through the strait and now preserved by the Chesapeake Bay Maritime Museum after being moved to St. Michaels. Binoculars come aboard, so you can spot herons, osprey and whatever else moves in the shallows.

The crew handles the sail while you choose your role: lean back and watch the water, or ask questions about what you're seeing and how the boat moves. Rain jackets and life jackets are there if weather turns, and bottled water keeps you hydrated across the afternoon. The boat's design means you're not crammed with dozens of others: the space and the shade work together to make the time feel unhurried.

What’s included

• Bottled water.
• binoculars.
• rain jackets and life jackets.
• beanbag and reclining captain's chairs.
• shaded cushioned seating with pillows.
• amusement tax and 20% gratuity.

Before you book

Days and timesEvery day5 departure times: the first at 09:00, the last at 14:00Last departure this season: 15 Nov

Book up to4h before

AgesAdult (19 to 64 years) · Senior (65 and older) · Youth (13 to 18 years) · Child (3 to 12 years) · Infant (under 3)

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.

Paid on siteUS$ 20

Prices and times updated 11 days ago

Good to know

Moderate physical effortPets welcomePublic transport nearbyInfants must sit on laps

Operated by St. Michaels Sailing Charters

Is this one for you?The boat leaves from St. Michaels' waterfront, and public transit reaches the area, so you don't need a car to get there. A straightforward option if you're staying in town or passing through without your own wheels.

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Top questions

Can children come?

Yes. Ticket types: Youth (13 to 18 years); Child (3 to 12 years); Infant (under 3).

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 is the Hooper Strait Lighthouse and why does it matter?

Hooper Strait Lighthouse was built in 1879 to guide ships through Hooper Strait and was later moved to St. Michaels, where the Chesapeake Bay Maritime Museum preserves it. You'll sail past it during the harbor tour, and it's a landmark of the bay's working maritime history.

What's included on the boat besides the sail itself?

Bottled water, binoculars, rain jackets and life jackets are provided. Seating includes cushioned chairs with pillows, beanbags and reclining captain's chairs in shaded areas. Amusement tax and a 20% gratuity are also included in the price.

How much space is there on the catamaran, and will it feel crowded?

The Epiphany is a modern catamaran designed for comfort with a spacious layout, cushioned seating and panoramic views. The wide hull and shaded areas mean you're not packed tightly with other passengers.

Does the tour leave from downtown St. Michaels, and how do I get there without a car?

The sail departs from St. Michaels, and public transportation options are available nearby if you're not driving. Check local transit routes to the waterfront before your sail time.