Events & Activities

The Best New England Sailing Trips & Boat Tours

A maritime journey through the enchanting waters of New England with the best sailing trips and boat tours. 

From historic harbors steeped in seafaring lore to breathtaking coastal landscapes that beckon adventurers, New England offers a sailor’s paradise waiting to be explored. 

Whether you seek the thrill of open seas or the tranquility of secluded coves, these sailing trips promise unforgettable experiences that blend natural beauty, maritime history, and coastal charm. 

Join us as we set sail on a virtual voyage to discover the top destinations for sailing enthusiasts in the picturesque region of New England.

Best New England Sailing Trips & Boat Tours

Here’s a chart outlining some of the best New England sailing trips and boat tours along with their necessary descriptions:

Tour/ TripDescription
Boston Harbor Sailing CruiseEnjoy a scenic sailing tour of Boston Harbor, passing by iconic landmarks such as the Boston Tea Party Ships and Museum, USS Constitution, and the Boston skyline.
Newport Harbor SailExplore the historic Newport Harbor aboard a classic sailboat, taking in views of lavish waterfront mansions, historic forts, and picturesque scenery.
Schooner Excursion in MaineExperience the beauty of Maine’s coastline aboard a traditional schooner, sailing past rugged cliffs, quaint fishing villages, and lighthouses.
Martha’s Vineyard Catamaran CruiseSail around Martha’s Vineyard on a catamaran, soaking in the island’s natural beauty, pristine beaches, and charming coastal towns.
Block Island Day SailSet sail to Block Island from Point Judith, Rhode Island, for a day of sailing, swimming, and exploring the island’s beaches, hiking trails, and historic sites.
Cape Cod Sunset SailRelax and unwind on a sunset sail off the coast of Cape Cod, enjoying breathtaking views of the sun setting over the Atlantic Ocean.
Nantucket Island Yacht TourDiscover the charm of Nantucket Island aboard a luxury yacht, with opportunities for swimming, snorkeling, and beachcombing on remote island beaches.
Portland Harbor Lighthouse TourCruise through Portland Harbor, Maine, on a lighthouse tour, visiting iconic lighthouses such as Portland Head Light and Ram Island Ledge Light.
Mystic Seaport Schooner CruiseStep back in time aboard a historic schooner at Mystic Seaport, Connecticut, and learn about maritime history while sailing along the Mystic River.
Provincetown Whale Watching CruiseEmbark on a whale watching excursion from Provincetown, Cape Cod, and witness the majestic beauty of humpback whales, dolphins, and other marine life.

These sailing trips and boat tours offer a diverse range of experiences, allowing you to explore the beauty and history of New England’s coastal regions in various ways.

Best Sailing Trips In New England For Families With Children

For families seeking memorable sailing adventures in New England, there are several top-rated options that cater to children. 

Let’s delve into some of the best sailing trips in New England that are perfect for families with children.

Maine Windjammer Association

Maine Windjammer Association

The Maine Windjammer Association offers unique sailing experiences aboard historic windjammers along the stunning Maine coast, providing families with an opportunity to immerse themselves in maritime history while enjoying family-friendly activities on board.

Boston Duck Tour

Boston Duck Tour

Families can embark on the original Boston Duck Tour, a fun and interactive amphibious adventure that combines sightseeing on land with a splash into the water, offering children a unique and entertaining way to explore Boston’s landmarks.

Boston Harbor Sunset Cruise

Boston Harbor Sunset Cruise

Enjoy a relaxing Boston Harbor Sunset Cruise with your family, where kids can marvel at the city’s skyline as the sun sets, creating a picturesque backdrop for an evening of leisurely sailing and quality family time on the water.

Boston Whale Watching Catamaran Cruise

Boston Whale Watching Catamaran Cruise

Set sail on a thrilling Boston Whale Watching Catamaran Cruise, where families can witness majestic whales in their natural habitat, providing children with an educational and awe-inspiring experience while cruising along the New England coast.

Small Boat Adventure in New England

Families can embark on a small boat adventure in New England, exploring hidden coves, charming harbors, and scenic coastlines aboard a family-friendly vessel that offers a personalized and intimate sailing experience for all ages to enjoy.

FAQs

How can I book the best sailing tours in New England?

You can book the best sailing tours in New England through reputable platforms like Viator, GetYourGuide, and local tour operators. 

Look for options like Boston Duck Tours, whale watching excursions, and sunset cruises to make the most of your sailing experience.

What makes sailing in New England unique?

Sailing in New England offers a unique blend of historic charm, stunning coastal landscapes, and diverse sailing experiences. From exploring rugged coastlines to cruising past iconic lighthouses, each sailing trip in New England promises a memorable adventure on the water.

Are there family-friendly sailing tours in New England?

Yes, there are family-friendly sailing tours in New England that cater to all ages. Options like lighthouse cruises, wildlife tours, and America’s Cup Charters provide engaging experiences for families to enjoy the beauty of New England’s waters together.

What should I expect on a sailing trip in New England?

On a sailing trip in New England, you can expect breathtaking views, opportunities to spot wildlife like whales and seals, visits to historic landmarks, and a chance to relax and unwind on the water. Each tour offers a unique perspective on the region’s maritime heritage.

How are the best sailing tours in New England ranked?

The best sailing tours in New England are ranked based on factors like popularity, customer ratings, availability, and the diversity of experiences offered. 

Platforms like Viator and GetYourGuide curate top-rated sailing tours to ensure a memorable and enjoyable experience for travelers seeking the best of New England’s maritime adventures.

Conclusion 

As the wind fills your sails and the sun sets on your New England sailing adventure, you carry with you memories of pristine waters, rugged coastlines, and maritime magic that define the best sailing trips and boat tours in the region. 

From Martha’s Vineyard to Acadia National Park, each destination offers a unique blend of natural wonders and cultural richness that captivate sailors and travelers alike. 

Whether you’re a seasoned mariner or a first-time sailor, the allure of New England’s sailing trips and boat tours is undeniable, beckoning you to return and explore more of the region’s maritime treasures on the horizon.

Photo of author

Laura Chassaigne

After spending her early years in Boston, Laura moved abroad and has lived in Montreal, London, and Paris. She now shares a home with her husband and daughter at the top of Beacon Hill, and these days, she can often be found chasing her daughter in the Public Garden or downtown playgrounds. Laura has a background in art history and archaeology and is also a certified Kripalu yoga teacher. Connect with Laura on Twitter or Instagram.

Leave a Comment