Sailing Charters

Top 6 Sailing Charters on Nantucket

top 6 sailing charters on nantucket

September 21, 2023

Nantucket, an island jewel off the coast of Massachusetts, is renowned for its picturesque landscapes, rich maritime history, and vibrant coastal culture. What better way to immerse yourself in the island’s coastal charm than by embarking on one of the sailing charters on Nantucket?

Welcome to “Sailing Charters on Nantucket,” your comprehensive guide to discovering the beauty, tranquility, and exhilaration of Nantucket’s waters. Prepare to set sail on a maritime journey that will capture your heart and leave you with lasting memories of this captivating coastal paradise.

“The sea speaks a language polite people never repeat. It is a colossal scavenger slang and has no respect.”
―Carl Sandburg

Why  Consider Sailing Charters on Nantucket?

There are numerous reasons why you should consider one of the sailing charters on Nantucket. A few of them are:

Scenic Beauty

Nantucket is renowned for its picturesque coastal landscapes. Sailing provides an unparalleled opportunity to take in the island’s stunning vistas, including pristine beaches, rolling dunes, and charming coastal villages. You’ll have the chance to see Nantucket from a unique perspective, away from the crowded streets.

Local Knowledge

Experienced captains and crews on Nantucket sailing charters are well-acquainted with the island’s waters. They can take you to hidden coves, secluded beaches, and prime spots for wildlife viewing or fishing, enriching your Nantucket experience.

Unhurried Relaxation

Sailing is all about slowing down and savoring the journey. If you embark on one of the sailing charters on Nantucket, you can relax on deck, soak up the sun, or even take a refreshing dip in the ocean. It’s an opportunity to disconnect from the fast pace of daily life and unwind.

Customized Experiences

Sailing charters in Nantucket can be tailored to your preferences. Whether you want to go fishing, enjoy a romantic sunset cruise, or embark on a family adventure, you can work with the charter company to create a personalized itinerary.

Our Top Picks for Sailing Charters on Nantucket

1. Endeavor Sailing Excursions

top 6 sailing charters on nantucket

Address: Slip #1015, Straight Wharf
City/State/Zip Code: Nantucket, MA 02554

Endeavor Sailing Excursions is a premier sailing charter provider offering captivating experiences around Nantucket, MA. Captain James Genthner, a seasoned sailor with over 40 years of expertise in Nantucket’s pristine waters, commands the Endeavor—a United States Coast Guard certified vessel. Operating from May to October, Endeavor offers private charters and per-person fare sailing trips, catering to both novice and experienced sailors of all ages.

Guests can actively participate in setting sail or simply relax while taking in the breathtaking views. Captain Jim can regale passengers with Nantucket’s rich maritime history and waterfront sights. The vessel offers the opportunity to bring refreshments on board, ensuring a comfortable and enjoyable journey.

“A sailing vessel is alive in a way that no ship with mechanical power ever be.” —Aubrey de Selincourt

2. ACK Sail

top 6 sailing charters on nantucket

Address: 34 Washington Street
City/State: Nantucket, Massachusetts

ACK Sail is a family-owned sailing charter provider located on the picturesque island of Nantucket, Massachusetts. With over two decades of history on this beautiful island, ACK Sail has established itself as a leading provider of sailing charters and harbor cruises that pay homage to the rich maritime heritage of the community.

As a testament to their commitment to creating unforgettable experiences, ACK Sail specializes in bringing friends and families together for various occasions, from engagements and weddings to family reunions and quality time spent with friends. They take pride in ensuring that every moment spent on their sailing vessels becomes a cherished memory that guests will reminisce about for years to come.

Guests can choose from a range of sailing experiences, including day and sunset harbor cruises on the historic sailing yacht Fetch, where they can soak in the stunning Nantucket coastline as the sun dips below the horizon. For those looking to celebrate extraordinary events, ACK Sail offers unique Nantucket Special Event Charters, providing couples with a dreamy sailing experience around the harbor on their big day.

“We can battle the sea, or we can embrace it. Sometimes she will be sweet and sometimes mean as a snake. We must embrace the experience and trust we will get through it.”—Michelle Segrest

3. Nantucket By Water

top 6 sailing charters on nantucket

Address: Straight Wharf, Slip #1011,
City/State: Nantucket, MA

Embark on a maritime adventure with Nantucket By Water, formerly known as Shearwater Excursions, a locally owned and family-run eco-tour company. Established in 1999, they specialize in offering unique tours and sailing charters to individuals and families of all ages on the captivating island of Nantucket, Massachusetts.

Nantucket By Water takes pride in catering to a wide range of preferences. Whether you’re seeking a short, leisurely tour around the scenic Nantucket Harbor or yearning for a more extended adventure that includes exploring the wildlife sanctuary of Coatue or visiting the distinctive 5th Bend Oyster Farm, they have the perfect cruise for you.

“You can. You should. And if you are brave enough to start, you will.”

4. Nantucket Mermaids Yacht Charters

top 6 sailing charters on nantucket

Address: Nantucket Harbor
City/State/Zip Code: Nantucket, Massachusetts 02554

Nantucket Mermaids Yacht Charters, operating around Nantucket, MA, boasts the largest fleet of yacht charter boats, promising unforgettable sailing experiences. Their pride and focus, the 50′ Catamaran, offer a perfect blend of sophisticated sailing and modern comfort, with ample lounge space. Starting at $6000, it’s an excellent choice for those seeking a luxurious getaway.

Nantucket Mermaids Yacht Fleet provides a perfect escape from the summer rush on the Islands. Their expert team customizes your water adventure, from sunset cruises to island hopping. With a variety of packages to suit your needs, they ensure an unforgettable journey on the water.

Whether you’re looking for a romantic evening or an exciting day out at sea, Nantucket Mermaids Yacht Charters has something for everyone. So, book your charter today and embark on a journey you’ll cherish forever, discovering the enchantment of Nantucket’s coastal beauty from the deck of their magnificent vessels.

5. Lisa Lynn Charters

top 6 sailing charters on nantucket

Address: 34 Washington St
City/State/Zip Code: Nantucket, MA 02554

Lisa Lynn Charters is a renowned sailing charter provider operating around Nantucket, MA, offering a range of exciting fishing and sailing experiences. Their custom charters stand out as a highlight, allowing guests to tailor their trips to their preferences and desires, ensuring a personalized and unforgettable adventure.

For those looking to dip their toes into angling, Lisa Lynn Charters offers a 2 ½-hour beginner-friendly fishing trip. This excursion is perfect for all ages, including kids, and stays relatively close to the shore for convenience. It provides ample time for reeling in the feisty and action-packed Bluefish, making it a fantastic choice for novice anglers.

For a more comprehensive fishing experience, their 5-hour trips are ideal. These excursions target larger species like Striped Bass, Black Sea Bass, and Fluke. Departing twice daily, these trips explore the famous Nantucket shoals and are perfect for those seeking both adventure and delicious table fare.

“If you nurse every wound you get on a sailboat, you will spend all your time nursing wounds. It’s best to just blurt a four-letter word and keep going.” —Michelle Segrest


The enchanting waters surrounding Nantucket, with their beautiful coastal waters and maritime heritage, is an excellent place for charter sailing. When booking one of the sailing charters on Nantucket, consider your group size, the type of experience you’re looking for, and your preferred departure location.

It’s a good idea to make reservations in advance, especially during the summer months when Nantucket is a popular destination for sailing enthusiasts. Additionally, be sure to check with the charter company regarding their availability, rates, and any specific requirements or preferences you may have for your sailing adventure.

Check out other ideas for a Day Trip to Nantucket.

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