Come Sail with us for an Authentic Cape Experience

Daytime Sailing Charters & Sunset Cruises from Wellfleet Harbor

Explore Billingsgate Island & Jeremy Point

9/8/2021: Due to the dredging of Wellfleet Harbor, the docks are being removed early this year, bringing our season to a close. We hope to see you on the water next year!

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

  • Our 2-hour Sunset sail on the Discovery on August 31, 2021, was outstanding. Captain Keith gave us a warm welcome aboard and we set sail out of Wellfleet Harbor.... read more

    Virginia Johnson

    We had a great trip. Captain Keith was very friendly and knowledgeable. The boat is very comfortable, and there were lots of places to see and things to do (walk,... read more

    Rob Hershfield

    The employees of Cape Cod Catamaran Sailing Charts are courteous, kind, professional, and so much fun to be around! My girlfriend and I chartered a boat for 7:00 AM, and... read more

    Derek Felano
    5 star rating

    Terrific afternoon on the water We had an awesome afternoon sailing with Captain Keith and Paul. It was a four hour cruise with my husband and I and two friends who were visiting. We left... read more

    Howard K
  • I recently sailed on the Cape Cod Catamaran sunset cruise! The staff was pleasant and accommodating ! Keith & Paul were wonderful, highly recommend them!

    Frank Popolizio

    Thanks to Captain Keith and (1st Mate?) Paul this was honestly one of the highlights of our week. We had 6 people, one a 76-year old. The guys were very... read more

    Tyler Lane
    5 star rating

    Fantastic Sunset Cruise Thanks to Captain Keith and (1st Mate?) Paul this was honestly one of the highlights of our week. We had 6 people, one a 76-year old. The guys were very... read more

    Tyler L

    Our family had an incredible day on Wellfleet Bay with Keith and Paul from Cape Cod Catarmaran. Their hospitality, knowledge and humor made the day all the better.... read more

    Ross Campbell

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!