Come Sail with us for an Authentic Cape Experience

Sailing Summer 2021!
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, Billingsgate Island & Jeremy Point. Do some beachcombing, seal watching 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. We sail daily from Wellfleet Town Pier.

Our sailboat provides plenty of space to stretch out on deck and 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

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

Day Charters (4 Hour)

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. Due to Covid19 we do not serve and food or drinks this year. 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. 

What People Are Saying

  • 5 star rating

    Perfect sunset cruise Enjoyed a beautiful sunset sail with captain Keith in his catamaran in wellfleet. Keith was very knowledgeable and also very accomplished as a sailor. It’s a perfect thing... read more


    We had a group of six and took the sunset cruise on 8/24. Wonderful experience. Captain Kieth was professional, knowledgeable, and fun. We had a beautiful sail... read more

    Stephen Logan
    4 star rating

    A fun afternoon outing with friends We had a very pleasant midday/early afternoon sail, exploring the waters off Wellfleet with friends. The skipper is very friendly and the boat has very nice interior spaces. ... read more

    5 star rating

    The best offshore trip that we’ve taken 👍🏻 We’ve been coming to the Cape for many years, and we’ve taken a lot of large and small boat trips from the Cape. The Cap Cod Catamaran trip today was... read more

  • 5 star rating

    Sunset Sail We would like to thank Keith for an awesome sail. He took us through the harbor, guided the boat to where the dolphins were playing. He anchored the boat so... read more

    5 star rating

    Sunset Sail We had a great time on our sunset sail. Keith is friendly and knowledgeable and the boat is comfortable and clean. We would go again!

    C M
    5 star rating

    Afternoon cruise We did the afternoon cruise with Cape Cod Catamaran. We had a great time! The boat is spacious and comfortable, the ride is beautiful, and captain Keith is friendly, knowledgeable,... read more


    Went out with Captain Keith Scott and had an awesome time! It is so beautiful out on the water and Capt. Scott is very friendly and knowledgeable! He has been... read more

    Taner Bertuna

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!