Come Sail with us for an Authentic Cape Experience

Daytime Sailing Charters & Sunset Cruises from Wellfleet Harbor

Explore Billingsgate Island & Jeremy Point

Experience Cape Cod without the crowds, sail aboard the Wellfleet catamaran Discovery and enjoy the peace and beauty of the bay. Beachcomb Billingsgate Island or Jeremy Point, seal watch or just kick back and relax as our experienced captain navigates the local waters during your private charter.

Our sunset cruise during the “Golden hour” at sea lets you bask in the romance & relaxation of a stunning Cape Cod sunset. 

Our sailboat provides plenty of space to stretch out on deck and offers a stable, comfortable ride during your excursion in Wellfleet Harbor and Cape Cod Bay.

Sail Cape Cod Bay

Morning & Afternoon Day Charters

Cape Cod Sunset Sails

Cape Cod Catamaran Charters

Discovery sets sail daily from Wellfleet Town Pier (Wellfleet Town Pier, 255 Commercial St, Wellfleet, MA 02667) for a 3 hour morning and 4 hour afternoon trip. Each day is topped off with a beautiful 2 hour sunset cruise.

3 Hour Morning &
4 Hour Afternoon Charters

Enjoy a beautiful cruise out to Jeremy point and beachcomb on a secluded beach, go for a swim then come back on the boat for a bite to eat before we head back for a leisurely sail into Wellfleet harbor.

Or, we will sail to Billingsgate Island which is completely submerged at high tide but revealed at low. In the 1800 this was an island with homes and a thriving fishing and whaling community, shifting sands and changing oceans have left only a breakwater where the lighthouse once stood. Billingsgate is now above water only a few hours each day. We’ll anchor up and you can go for a swim or a stroll on this unique island.Depending on the tide and wind we will either take you out to Billingsgate Island, Jeremy Point or the sheltered Herring Cove.

Sailing with us is a perfect alternative to a fishing charter. During our voyage you can watch the seals and birds, do some sunbathing and take in the beauty and sounds of Wellfleet’s and Eastham’s salt water ecosystems.


Sunset Cruises (2 Hour)

Enjoy Cape Cod’s golden hour with the warm light that has brought so many artists and nature lovers to this area. Watch the sun go down over Great Island and Cape Cod Bay.

Depending on the tide we’ll anchor up to enjoy a relaxing sunset. Feel free to pick up a to-go order and make it a dinner cruise. BYOB. 

An experience you’ll never forget!


We are happy to work with you to customize your private charter for those special celebrations and people in your life. 

Up to 6 guests. 

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Getting Here

Wellfleet Marina (Wellfleet Town Pier, 255 Commercial St, Wellfleet, MA 02667), is located walking distance from downtown Wellfleet. We are a 25 minute drive from downtown Provincetown and about 40 minutes from downtown Chatham. Make sure to leave some extra time for Cape summer traffic!