Sail with us for an Authentic Cape Experience

Daytime Sailing Charters & Sunset Cruises from Wellfleet Cape Cod

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, Billingsgate Island & Jeremy Point. Do some beachcombing, birdwatching or just kick back and relax as our experienced captain navigates the local waters.

Our sunset cruise during the “Golden hour” at sea lets you bask in the romance & relaxation of a stunning Cape Cod sunset. We sail from Wellfleet Town Pier every Morning, Afternoon and Sunset.

Our boat tours have a maximum of 6 guests.

Daytime Cruises on Cape Cod Bay

Book a Seat or Charter the Boat

Outer Cape Sunset Sails

Cape Cod Catamaran Charters

Weather and tide permitting, Discovery sets sail from Wellfleet Town Pier (Wellfleet Town Pier, 255 Commercial St, Wellfleet, MA 02667) each morning and afternoon for two 4 hour day cruises. Each day is topped off with a beautiful 2 hour sunset cruise.

Morning & Afternoon Charters (4 Hour)

Depending on the tide we will either take you out to Billingsgate Island, Jeremy Point or the sheltered Herring Cove.

Billingsgate Island 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.

Or 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.

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.

We serve continental breakfast for the morning cruise. During afternoon and sunset cruises we provide a light snack and non-alcoholic beverages. BYOB

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 with a light snack or Wellfleet Oysters and a beverage. Feel free to pick up a to-go order and make it a dinner cruise.BYOB.

An experience you’ll never forget!


Private Charters:

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. 

      Spectacular way to see the sunset!!! Went with friends some snacks and Rose’. One of the loveliest evenings of the summer. So beautiful and peaceful. Will definitely do it again. I have been on other boats.......Captain Keith and Discovery are by far the best

    thumb Lisa S

      The moment you step aboard Discovery with Cap’n Keith, the adventure begins. My husband and I have had the opportunity to experience more than one of these adventures and each time we return to shore in awe of the sheer beauty surrounding Wellfleet and the...More

    thumb SheddyCapeCodMA

      What a wonderful way to spend a day on the water in Wellfleet! The catamaran, Discovery, was perfect for an outing with friends! Captain Keith was knowledgeable and friendly, the boat comfortable and well appointed!. I highly recommend you book a sail while on the...More

    thumb Jodi B

      We had an amazing relaxing glorious day with Captain Keith. We saw our hometown and waters through a whole new lens as Keith took us to Jeremy Point and around the bay. The boat is impeccably clean, comfortable and roomy and we can't wait for...More

    thumb jl02667

Ready to book your trip?

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!