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.
What People Are Saying
We had the best experience! We booked the sail for my friend’s bachelorette party and were blown away. The crew was so friendly and accommodating, and gave us the opportunity... read moreWe had the best experience! We booked the sail for my friend’s bachelorette party and were blown away. The crew was so friendly and accommodating, and gave us the opportunity to walk the beach which was beautiful. We saw a seal on the trip which was unexpected and amazing! Would recommend this company to anyone, such a lovely and relaxing experience. read less
Galina Pate7/15/2022We had such a great time with Cape Cod Catamaran on our Sunset Sail. The boat was very comfortable and clean. Keith and Paul were fun/informative and very... read moreWe had such a great time with Cape Cod Catamaran on our Sunset Sail. The boat was very comfortable and clean. Keith and Paul were fun/informative and very accommodating. We had the best weather and the water was like glass. We were able to see a couple of seals and a magnificent sunset. Would highly recommend to anyone with a small group!!! read less
Julie Leonard7/01/2022Our 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 moreOur 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. Keith's knowledge of fishing, sailing, sea life, and the Cape is extensive. He was happy to answer any questions. The weather was perfect as we sailed the bay and watched birds, seals, and the most glorious sunset while sipping champagne that we brought along. We thoroughly enjoyed the evening and can't wait to sail again. read less
Virginia Johnson9/07/2021We 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 moreWe 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, swim, fish). Would definitely recommend and go again. read less
Rob Hershfield9/01/2021
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!