New England: A Coastal Adventure for all the Family


May To October


From $14,030pp excl. flights
(based on 2 ppl sharing)

How long

13 nights ideal length

From the gateway city of Boston to the mountains of Maine, the sugar-white sand beaches of Nantucket Island and the deep American history of Newport; New England has no shortage of charm. Six states, each with their own slice of something special, it’s hard to think of anywhere better for a family road trip. Packed full of seaside stops and fun-fuelled hijinks, it’s enough to keep those ‘are we there yet’ moans at bay. Set off on a road trip that you’ll all never forget, as while the kids will remember the 50ft 66,000lb humpback whale breaching out of the water right before their eyes, you’ll always remember the look on their face when it happened.

Catch of the Day

Checking into Four Seasons Boston, you’ll head out on a private city tour, visiting the famous Harvard University and exploring the interactive exhibits at Boston’s Museum of Science. Spend the next day at sea, sailing past the historic coastal towns of the North Shore and hauling lobsters off the back of a boat with seasoned lobstermen, ready to cook them for dinner later. Retire to the Four Seasons for an afternoon with the pastry chef first, as he guides you and the kids through a cookie-making class before you sit down to your own treat at the Bristol Bar. The next morning, pick up the keys and head off to Newport, stopping along the way at Plimoth Plantation where you’ll get a glimpse of how the Colonists lived.

Make this itinerary yours

Each and every Black Tomato trip is tailored exactly to who you are and what you want to do So tell us about yourself and we’ll create something that’s entirely you.

Start Planning


The Vanderbilt on Rhode Island in Newport will be your new home from home for the next three nights. Setting off on a walking tour of Newport, its mansions and its cliffs, you’ll stroll along the seaside town admiring the 19th-century mansions on one side and the Atlantic Ocean on the other. Take a walk along Ocean Drive, ten miles of historic seaside landmarks, and find the perfect spot for a family picnic with just the crashing of the waves before you. Retreat back to the hotel for a relaxing child-free evening of signature cocktails at the mansion’s rooftop bar before setting sail on a 12-meter classic America’s Cup Racing Yacht in Narragansett Bay the following day; something the kids are sure to tell all their friends about.


Drive to Cape Cod tomorrow and catch the ferry over to Nantucket Island, checking in at the White Elephant for four nights. Overlooking Child’s Beach and Nantucket Harbor, the hotel is the perfect base for exploring the island. Take a private tour of the island and learn all about Nantucket’s original native American inhabitants, the Wampanoag people, before sinking your toes into the sands of the beach and feeling the sun on your skin. With a day to spare, why not escape to the spa while the kids have their own fun out on paddleboards and kayaks with the hotel’s friendly beach team? Really, it’d be rude not to.


The last stop will be Chatham Bars Inn in Cape Cod where you’ll spend three nights sipping champagne fireside and lying on the beach taking in the uninterrupted views of Chatham Harbor. Whale watching off the coast of Chatham is an absolute must; set out on the Shooting Star in search of humpback whales, and don’t be surprised if you also spot pilot and minke whales, whale sharks and giant mola mola along the way. As your New England road trip nears the end, grab a picnic and a bottle of bubbly and head out on a bike ride or take some time to simply relax on the beach and soak up the sun. However you choose to spend the last few days, we’re certain that the memories you made on your New England road trip will last a lifetime.

Where to rest your head

White Elephant

White Elephant has been considered a Nantucket landmark since the 1920s - and rightly so. Perched alongside a glamourous harbour, what began as an eclectic…
View hotel

The Vanderbilt, Auberge Resorts Collection, Newport

Tucked away on Rhode Island is one of Newport's best-kept secrets: The Vanderbilt, Auberge Resorts Collection. The former Newport mansion, dating back to 1909, is…
View hotel

Chatham Bars Inn, Cape Cod

A hotel with more than a century of character and charm, the Chatham Bars Inn beachside retreat in the small town of Chatham, New England,…
View hotel

“Many companies brag about offering once-in-a-lifetime experiences. But with Black Tomato it’s not hyperbole”

“Black Tomato is a super innovative company where the sky is the limit for their clients”

“Black Tomato prides itself on meeting customers every minor need or desires”

“Black Tomato is the choice provider of mind-expanding vacations”

“Black Tomato has made it a mission to keep the world of travel fresh, responsible, and exciting”

“Tailor-made travel experiences that truly get under the skin of a country and its people”

“Black Tomato is a leading luxury travel company that provides innovative and inspiring experiences”