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

    Outstanding private sailing with a great crew We had an outstanding trip with Keith and his crew. The sailing was beautiful. There's a lot of space on board for the whole family with all necessary facilities. There's... read more

    John T
    7/16/2021
    5 star rating

    Sunset Serenity on the Sea We took a sunset cruise with Captain Keith on the Discovery. We were a little nervous about being around too many folks while the country is still digging out from... read more

    Mr_and_Mrs_Cuddles
    6/27/2021

    If I could give Captain Richard and Cape Cod Catamaran 10 stars, they would get it! Had an excellent experience with my family on a morning ride out to Jeremy... read more

    Imran Oomer
    6/21/2021
    5 star rating

    Great Sunset Sail The Sunset Sail with Keith and Paul was a perfect end to an otherwise rainy day with spectacular colors and cloud formations. Calm waters in the bay provided opportunities to... read more

    Ellen D
    6/20/2021
  • 5 star rating

    Sunset Serenity on the Sea We took a sunset cruise with Captain Keith on the Discovery. We were a little nervous about being around too many folks while the country is still digging out from... read more

    Mr_and_Mrs_Cuddles
    6/01/2021
    5 star rating

    Great Sunset Sail The Sunset Sail with Keith and Paul was a perfect end to an otherwise rainy day with spectacular colors and cloud formations. Calm waters in the bay provided opportunities to... read more

    Ellen D
    6/01/2021
    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

    phufnag
    9/10/2019

    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
    9/06/2019

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!