Come Sail with us for an Authentic Cape Experience

Morning & Afternoon Charters & Sunset Cruises from Wellfleet Harbor

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 3 hour morning and afternoon trips. Each day is topped off with a beautiful 2 hour sunset cruise.

3 Hour Morning & 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!

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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!