7 Days in South New England

Inspiring Itinerary

7 Days in South New England

7 Days6 NightsNew Bedford to Newport
183 nautical miles
SeasonIdeal for Summer Season

Itinerary summary


Day 1New Bedford

Day 2Martha's Vineyard

Day 3Nantucket

Day 4Block Island

Day 5Sag Harbor

Day 6Mystic

Day 7Newport

About

Set sail on a 7-day yachting journey through the charming coastal towns and island gems of Southern New England. Begin in New Bedford, rich in maritime history, before heading to the iconic shores of Martha’s Vineyard for a taste of relaxed island life. Continue to the cobblestone streets and classic charm of Nantucket, then cruise to Block Island, where rugged cliffs and scenic beaches offer the perfect nature escape. From there, make your way to Sag Harbor, a stylish haven in the Hamptons known for its vibrant waterfront. Next, explore Mystic, Connecticut — home to a legendary seaport and quaint New England character. Conclude your voyage in the yachting capital of the region, Newport, Rhode Island, where historic mansions and bustling harbor views bring your coastal adventure to a perfect close.

Destination image
Destination image
Destination image
Day 1 - New Bedford
Day 1

New Bedford

A historic harbor rooted in whaling tradition

LocationStarting point

New Bedford, which was the world center for whaling in the middle of the nineteenth century, served as the setting for Herman Melville's 1841 classic American book, Moby Dick. It retains its historic whaling-era nickname, "The Whaling City," thanks to the city's preserved seaport village, sizable fishing fleet, and active waterfront.

Day 2 - Martha's Vineyard
Day 2

Martha's Vineyard

A classic New England retreat by the sea

Distance25nm

Martha's Vineyard is a far cry from the mainland; you won't find restaurant chains or generic hotels here, instead you'll find boutique inns, chef-owned eateries, and sprawling coastline. The island is a patchwork of farms, old lighthouses and stunning beaches, like South Beach and Aquinnah Beach, that bustle with artistic energy and have visitors coming in search of the world-class music performances. The picture-perfect ambiance sets the scene for a vibrant art culture, which is instantly recognisable in the unique architecture and the endless galleries. The island's towns, including Edgartown and Oak Bluffs, are home to many unique shops, where you can get some handcrafted souvenirs. And if you're after some of the island's raw beauty, head to Chappaquiddick Island, which has a remote beach with excellent surf and natural scenery, or the Aquinnah Cliffs, a magnificent natural landmark with breathtaking views of the ocean and countryside.

Day 3 - Nantucket
Day 3

Nantucket

Home to the oldest operating windmill in America

Distance26nm

An iconic island off Cape Cod, Nantucket has long been a popular stop for yachting in New England. Head to Jetties Beach for a refreshing dip and satisfy your tastebuds with lunch at Sandbar at Jetties Beach, where you can grab a seat on the open-air deck and enjoy a slushie and a waterfront seafood lunch. For some pretty great views head to Sankaty Head Lighthouse, Brant Point Lighthouse or Great Point Lighthouse. Step back in time at the Whaling Museum and learn some of the island's rich history.

Day 4 - Block Island
Day 4

Block Island

40% preserved land, 100% New England charm

Distance67nm

Block Island is considered "One of the Last 12 Great Places in the Western Hemisphere" by The Nature Conservancy. Some have likened the island's network of walking and hiking trails to the coastline of Ireland owing to its verdant hills and steep bluffs. Fresh lemonade, salt water taffy, renovated Victorian hotels, artist studios, and a bustling historic port provide the fuel for long walks along miles of gorgeous beaches and 365 ponds. Mohegan Bluffs are impressive clay cliffs with a stony beach below, and the red-brick Southeast Lighthouse, constructed in the 1800s, sits atop them.

Day 5 - Sag Harbor
Day 5

Sag Harbor

The heartbeat of the Hamptons

Distance34nm

This idyllic destination boasts stunning waterfront views, unique boutiques, galleries, and world-class restaurants. Visitors can enjoy a leisurely stroll through the town's picturesque streets, explore the quaint harbor, or relax on one of the nearby beaches. Be sure to visit the Sag Harbor Whaling Museum, which offers a glimpse into the town's whaling past. You should also explore the charming streets of Sag Harbor, which are lined with local shops, restaurants, and art galleries. Other must-visit destinations include the Mashomack Preserve, a 2,039-acre nature reserve with stunning landscapes and abundant wildlife, and the Shelter Island, which is home to beautiful beaches, hiking trails, and historic sites. With its rich maritime history and stunning natural beauty, Sag Harbor is a must-visit destination for any yacht charter vacation in the Hamptons.

Day 6 - Mystic
Day 6

Mystic

A seaside village anchored in maritime history

Distance26nm

An enchanting village that has a rich maritime history as a significant seaport. Today, it's a quintessential New England destination with nautical landmarks like Mystic Seaport and USS Nautilus. Visitors can enjoy cruises, encounter beluga whales, and explore historic downtown. The village offers great seafood, including unique dining experiences like a treehouse restaurant. Mystic's charm extends to Olde Mistick Village and the Denison Pequotsepos Nature Center. Don't forget to snap a picture with the wooden anchor in Liberty Pole Square before leaving.

Day 7 - Newport
Day 7

Newport

Home of America's Cup and gilded age mansions by the sea

Distance30nm

Salty summer days, pastel sunsets, and overt mega-mansions all add to the allure of a town made famous by Edith Wharton's The Age of Innocence. One of the country's oldest resort towns, Newport is a premier yachting location rich in maritime history and oozing with coastal charm. Sail along the picturesque coastline dotted with opulent Gilded Age mansions, iconic lighthouses, and immaculate beaches. Learn about the hidden gems of Narragansett Bay like Rose Island or Jamestown where you can anchor up and enjoy a range of water sports and fishing, or simply relax in the calm waters. Go ashore to experience the lively atmosphere of Thames Street, which is teeming with quaint shops, art galleries, and a variety of top-notch restaurants that perfectly capture the flavours of New England's culinary scene. Check out The Breakers - an 1800s Vanderbilt mansion - and take a stroll along the Cliff Walk at sunset for some panoramic ocean views. Build up an appetite for a seafood feast at Newport Lobster Shack, or set sail for an unforgettable sunset cruise as the day comes to an end.