Chesapeake Bay Itineraries

Sunset Cruise on the Bay

Half Day

For gorgeous views and a romantic escape, spend an evening on the Bay taking in the beautiful sunset.

So Maryland: Crab Feast + Sail

Full Day

Enjoy a scenic sail to the Eastern Shore where you’ll debark for a crab feast lunch at the famous Kentmoor Restaurant.

Overnight in Annapolis or Saint Michaels

Overnight

Waking up aboard a luxury catamaran can be absolutely magical!

Custom Itinerary

Full Day

Have something else in mind? We'll work with you to customize your day on the water.
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