Explore Billingsgate Island & Jeremy Point
Escape the crowds and immerse yourself in the serene beauty of Cape Cod on the Wellfleet catamaran Discovery. With a private daytime charter, you can explore the bay and nearby attractions such as Billingsgate Island or Jeremy Point, seal watching, or simply unwind and enjoy the tranquility of the local waters.
Experience the romance and magic of a Cape Cod sunset during our private sunset cruise, where you can soak in the mesmerizing views during the “Golden Hour” at sea.
Our spacious sailboat provides ample room to stretch out and relax on deck while our experienced captain ensures a smooth and comfortable ride as he navigates Wellfleet Harbor and Cape Cod Bay. Book your private charter today and make unforgettable memories on the water.
Please note that, in accordance with Coast Guard regulations, we cannot accommodate more than six passengers.


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
Discover the hidden treasures of Cape Cod with our private sailing charters. Cruise to Jeremy Point and relax on a secluded beach or take a refreshing swim.
Explore the unique submerged wonderland of Billingsgate Island, once a thriving fishing and whaling community in the 1800s, the island is now only visible during low tide. Depending on the tide and wind, we can also take you to Jeremy Point or the sheltered Herring Cove.
Sailing with us is a perfect alternative to a fishing charter. Observe playful seals and an array of bird species while soaking up the sun and immersing yourself in the natural beauty and sounds of Wellfleet’s and Eastham’s mesmerizing saltwater ecosystems.
As we leisurely sail back to Wellfleet harbor, take in the picturesque scenery along the way. What are you waiting for? Book now!
Sunset Cruises (2 Hour)
Experience the stunning beauty of Cape Cod at the magical “Golden Hour” with our private sunset sail aboard the Wellfleet catamaran Discovery.
As the warm light casts a golden glow over Great Island and Cape Cod Bay, you’ll witness a breathtaking sunset that has inspired artists and nature lovers for generations.
We’ll set sail and explore the local waters before anchoring up to provide the perfect backdrop for a relaxing evening on the water. You’re welcome to bring your own food and beverages and enjoy the sunset with your favorite drink in hand.
This unforgettable experience is perfect for any special celebration or occasion in your life. We are happy to work with you to customize your private charter and ensure it’s tailored to your unique needs and preferences.
Book your private sunset sail today and make unforgettable memories on the water!
What People Are Saying
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Telegram +44 7503 451223 read lessMichael S.11/02/2023A great morning! It was foggy the morning of our sail so we delayed an hour. I’m so glad we didn’t cancel. The fog lifted and the weather gave us a little bit... read moreIt was foggy the morning of our sail so we delayed an hour. I’m so glad we didn’t cancel. The fog lifted and the weather gave us a little bit of rain, sun, and beautiful clouds. We had a great sail. The boat is beautiful and the captain and mate are so knowledgeable about the area and people. I will definitely take another cruise and recommend them to everyone. Thank you Keith and Paul. read lessJudy W8/29/2023Beautiful sunset on a lovely sail boat Thank you to Captain Keith and Paul for a magnificent sunset sail. We are Wellfleet residents who've never set sail in Wellfleet Harbor and what an experience! We had a... read moreThank you to Captain Keith and Paul for a magnificent sunset sail. We are Wellfleet residents who've never set sail in Wellfleet Harbor and what an experience! We had a date set originally and were going to treat my in-laws. Unfortunately it was half rain/half mist, so Captain Keith gave us an option for a refund or reschedule. I am so glad we chose to reschedule. Ended up bringing our friends from Chatham, and WOW. The sunset is incredible. The boat was spotless and child friendly. Wonderful company and beautiful sights! Thank you!! read lessLeunerEclipse8/24/2023Wonderful afternoon sail We went on a 4-hour afternoon sail and loved the smooth waters, seeing seals, and everything about the day. Keith was wonderful! He was so accommodating and friendly and went... read moreWe went on a 4-hour afternoon sail and loved the smooth waters, seeing seals, and everything about the day. Keith was wonderful! He was so accommodating and friendly and went out of his way to make the day special. read less610bethk7/21/2023 - Captain Keith was amazing! I booked this sailing charter for a bachelorette weekend and the entire group had a fabulous time. The two hour sunset cruise was the perfect amount... read moreCaptain Keith was amazing! I booked this sailing charter for a bachelorette weekend and the entire group had a fabulous time. The two hour sunset cruise was the perfect amount of time, the accommodations were comfortable, and the sunset was unbelievable. I would book again in a heartbeat! read lessRebecca Kaplan8/17/2022Great Boat Charter Every summer when our kids visit us in Eastham we charter a boat for a 3 -4 hour cruise. We have done this for the past 5 years with... read moreEvery summer when our kids visit us in Eastham we charter a boat for a 3 -4 hour cruise. We have done this for the past 5 years with varying success. This year we decided to try Cape Cod Catamaran. None of the previous charters compared to the experience we had today with Cape Cod Catamaran. We stopped at Jeremy Point and searched for shells. The boat is large and comfortable. Captain Paul was fun, entertaining and competent. Don’t miss this experience. read lessgsable18/15/2022I am a travel advisor and booked this for my family just to relax one weekend! Captain Keith was awesome! We enjoyed a beautiful sunset sail, he was patient with... read moreI am a travel advisor and booked this for my family just to relax one weekend! Captain Keith was awesome! We enjoyed a beautiful sunset sail, he was patient with my father and had so many fun stories to share. A beautiful boat and a fantastic way to experience the cape! Bring a bottle of wine and some snacks, relax, and enjoy the view! The back of the boat has a little table area and seating on both sides. read lessMadeline Steuber8/04/2022
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!