Come Sail With Us

An Authentic Cape Experience

Private Morning & Afternoon Charters & Sunset Cruises from Wellfleet Harbor

Up To 6 Passengers

★ Rated 5.0 out of 5 from 59 Google reviews · Private day & sunset charters from $689 for your group of up to 6.

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.

In accordance with Coast Guard regulations, we cannot accommodate more than six passengers.

Quick facts

Boat: Discovery, a 30-ft sailing catamaran
Departs from: Wellfleet Town Pier, 255 Commercial St, Wellfleet, MA
Trips: Private 3-hour day charters & 2-hour sunset cruises
Group size: Private — up to 6 guests
Pricing: From $689 for your whole group of up to 6
Captain: Keith — USCG 100-Ton Master, 30+ years on Cape Cod Bay
Good to know: Bring your own food & drinks · restroom on board

Private Boat Tours & Sailing Charters on Cape Cod Bay

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. Looking for a boat rental? Every trip aboard Discovery is a fully captained boat tour — our USCG-licensed captain handles the sailing while you relax, no experience needed. Guests join our tours from across the Outer Cape, including Provincetown, Truro, Eastham, Orleans, and Chatham.

Morning & Afternoon Charters

Private 3 Hour Trip, Up To 6 Passengers

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!

See full details of our day charter boat tour to Billingsgate Island & Jeremy Point →

Sunset Cruises

Private 2 Hour Trip, Up To 6 Passengers

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!

See full details of our Cape Cod sunset cruise →

What People Are Saying

Great time on the bay! We loved our time on the Cape Of Catamaran. The crew was kind, fun, and knowledgeable. I would absolutely go back.
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667jillm
7/19/2026
An amazing sunset sail for my husbands birthday surprise. Captain Keith and Paul were so knowledgable of the area, told stories, and gave us information that was so interesting. You can tell these guys love the job of creating wonderful experiences for those who take this trip. The boat was pristine and so comfortable. The calm ride and breeze were amazing. The sunset , the seals, the history of Wellfleet, and the area were so interesting. We had a great evening and an unforgettable experience. Their website give all the information y9ou need, easy to book and the communication before the trip was excellent. I will definitely do this catamaran sail again.
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Maureen Mack
8/31/2025
Got the most out of this fantastic catamaran tour. It was a wonderful trip at the sea. Everything was well planned.
Nice catamaran, clean, good seats.
The captain, Keith, was also a good guide.
We can highly recommend this tour and when we come back we will definitely book again.
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Monica M
7/08/2025
Thanks Keith and Paul for the great afternoon sail. Even though the weather was chilly and dreary we had a great time. Great accommodations and knowledge of the area! Highly recommended!!
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Daryn Sauder
6/26/2025
Great from start to finish As is normal these days, I booked this online after reading reviews. They did not lie! This was a birthday trip for my sister, her three adult daughters, my wife and myself. My sister sailed the waters of Cape Cod Bay as a teenager and hadn’t been there since. Keith & Paul welcomed us all like family. We had a 2 hour sunset cruise in perfect conditions minus the sun. Because the boat has a maximum of six passengers, this was the perfect size for us. We brought our own food & beverages which was great! Calm, relaxing, informative and a really enjoyable time! You will not be disappointed in the least by booking with Cape Cod Catamaran!
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S4384NLstevenr
6/19/2025
Great time, great crew, great boat Great time with Capt Keith and Paul the first mate. Boat is excellent for a cruise, comfortable and smooth. Highly recommend!
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gino m
9/13/2024
Great way to see Wellfleet and the sunset. Not a perfect sunset with overcast skies, but the ride out to Billingsgate Island and Captain Keith and Paul's knowledge and love of the Cape and Wellfleet in particular is evident. Our 2 hour ish ride with two adult children was a smooth and enjoyable one.
Friendly and relaxed other than the stories of 1903 - ask Paul - made a wonderful experience.
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Paradise546630
8/19/2024
Fantastic morning on the water! Had an amazing morning cruise with Captain Keith and first Mate Paul to Billingsgate and Jeremy’s Point. Very relaxing trip the boat was clean and very well maintained. Great commentary about the local sights and history. We all would give Cape Cod Catamaran the highest rating and recommend them for a memorable trip in Wellfleet!
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John O
7/28/2024
Great day on the water! Our family of four (2 twenties and 2 fifties) had a great afternoon out on the water with Captain Keith and First Mate Paul. Very relaxing and scenic - saw a bunch of seals and took a break to swim off a small sandbar that was formerly an island.
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Trail43578307432
7/18/2024
Fun & Memorable = Vacation! Thank you Captain Keith for a memorable afternoon on the water. The charter offered a great opportunity to learn about and appreciate the beautiful island of Cape Cod from a different vantage point. Your hospitality was also top notch. An adventure to be enjoyed whether you're a local or vacationer!
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P J
7/11/2024
Sunset sail The views were breathtaking sunset at thr Cape!
Keith and Paul were both excellent hosts and my family and I enjoyed every second with them! Highly recommend the experience!
The Bennetts from Alabama.
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Grant B
6/04/2024
A 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 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.
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Judy W
8/29/2023
Beautiful 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 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!!
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LeunerEclipse
8/24/2023
Wonderful 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 out of his way to make the day special.
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610bethk
7/21/2023
Wonderful Wellfleet harbor and the area around it is gorgeous, the boat was clearly well cared for and very comfortable, and Captain Keith was gracious and accommodating. Highly recommend.
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ptarlow
6/07/2023
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 of time, the accommodations were comfortable, and the sunset was unbelievable. I would book again in a heartbeat!
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Rebecca Kaplan
8/17/2022
Great 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 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.
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gsable1
8/15/2022
I 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.
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Madeline Steuber
8/04/2022
“Beautiful morning sail with congenial hosts” 3-hour morning sail. Keith and Paul were great company and guides. No matter what you're... read more
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RebDebGordon
8/02/2022
Fabulous day! I would highly recommend Cape Cod Cataraman.
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Stacey Panepinto
7/29/2022
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 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.
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Galina Pate
7/15/2022
We 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!!!
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Julie Leonard
7/01/2022
A lot of fun. Enjoyed the whole trip and even got in some swimming. Keith knows the area well and is very experienced.
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Dana Ritter
6/30/2022
Keith was a great captain. This is a beautiful boat and even more beautiful trip. Such calm waters, long sandy beaches, and a surprise visit from seals.
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Jamie Flaws
6/27/2022

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!