There are few itineraries with as much history, culture, and beauty, with as many amenities, as that of America’s New England coast. Fabulous options in every port make this trip one of the most versatile for a private luxury yacht charter, offering as much social interaction, or as much quiet solitude as you wish.
While many of the smaller harbors cannot accommodate superyachts, choosing one remains an option with tendering, as the departure from Newport and conclusion in Boston are both well equipped to handle larger craft. With shorter distances here, however, smaller yachts enable more freedom to explore ports of interest along the way.
Both casual and sophisticated, you’ll want to dress well, but not shout, whether in fashion or form. It’s just not done. In the refined status and reserved atmosphere of these informal seafaring towns, sailing attire is welcomed almost everywhere. Extending the trip by a week or two allows stops north to Maine and Quebec, or south to Maryland and North Carolina, all worthy of your summertime attention.
Day 1: After settling into the sumptuous quarters on board your yacht in Newport’s Goat Island Marina, knock around town for a glimpse of the charming colonial era architecture, shop some lovely New England boutiques, and wander through a collection of the world’s most elaborate mansions along Cliff Walk’s Bellevue and Ocean Drives, where the Astors, Rockefellers, and Vanderbilts summered in gracious luxury along this glorious coast. Stop into the nation’s first of many, The White Horse Tavern, serving up farm-to-table cuisine and a happy pint since 1673. If you’re here during the Bucket Regatta at the end of August, capture a cocktail, and plant yourself on the expansive lawn of the Castle Hill Inn for a splendid view. Additional events include the famous Newport Jazz Festival the first week of August, Gallery Nights on the second Thursday each month, and live jazz every Saturday at exquisite mansions throughout Newport.
Day 2: Northward around the point, prepare to view all of Newport’s grand mansions from the water as you pass the Breakers, Roseclif, and Beechwood, among others, along the coast. Then, head north along Vineyard Sound to Martha’s Vineyard Marina. Onshore interest is piqued by festivals, markets, fairs, and celebrations every weekend. Stop into Alley’s General Store, established in 1858, for hardware, a snack, a souvenir, or just to chat with the owners for some local lore. Edgartown’s Wharf Pub and Oak Bluffs’ Lookout Tavern, Sand Bar, Lobsterville, and Nancy’s offer evening entertainment, club style, with DJs, dancing, and a little something to eat and drink.
Day 3: Cruise east across Nantucket Sound, slipping into the Nantucket Boat Basin for a gorgeous and protected coastal view of the island. An onshore excursion here rewards you with fine dining at TOPPER’S in the Relais & Châteaux Wauwinet, and quaint quarters of historic note. If you’re here for the 4th of July, you’ll find pie eating, dunk tank, and parade fun, along with fireworks at Jetties Beach. August brings Nantucket Race Week and a myriad of beautiful sailing yachts, as well as a concert from the Boston Pops.
Day 4: Chart a course to the north, pointing toward Hyannis, for some whale watching, beautiful beaches, internationally acclaimed musicians in concert at the Cape Cod Melody Tent, and a satisfying repast at the Naked Oyster Bistro and Raw Bar. The annual Figawi Weekend at the end of May is a popular charity event with a 200+ boat regatta with a Saturday night black tie competitor party and Sunday awards. Join in the festive atmosphere of Tunafest in late June, or the Bluefin Tourney in October, while enjoying a traditional New England atmosphere at the Hyannis Yacht Club.
Day 5: Provincetown, the most northern point of Cape Cod, exhibits the beauty of the New England coast all along the sand dunes, forests, and beaches of this National Seashore park. Lighthouses stand watch along stretches of sand and rock, simple in their beauty, while art galleries, boutiques, eclectic pubs and restaurants line the harbor, a hub of active visitors mixed with some well-known locals. No big box stores here, this is authentic Americana.
Day 6: Portsmouth, New Hampshire, the third oldest city in America settled in 1623, offers one of the most picturesque examples of the perfect New England town. Art galleries, historic buildings nestled next to sidewalk cafes, jazz clubs, antique gundalow sailing barges, and boutique shops, all connected with cobbled streets and a festive, friendly atmosphere contribute to the charm of this historic destination.
Day 7: Wrap up your New England week with a cruise of iconic Boston Harbor, watching tall ships, looking for whales, exploring the busy coastline, finally putting the exclamation point on your itinerary as you dock at Boston Yacht Haven Marina in the historic North End. As you disembark, tuck away into the Yacht Haven penthouse, or head out to explore City Landing, Legal Sea Foods, or Joe’s American Bar and Grille. Boston, of course, is THE place to be on the Fourth of July, with incredible fireworks, inspiring music, and a patriotic crowd reveling in the glow provided by Boston Harborfest. As you bask in the glow of the week, ensure you’ve got next year’s schedule nailed down by talking with Steve@TheBestofYachting.com.
Goat Island Marina, Newport, RI:
Newport Cliff Walk:
The White Horse Tavern:
Newport Bucket Regatta:
Castle Hill Inn:
Wharf Pub, Edgartown:
Nantucket Boat Basin:
TOPPER’S at the Wauwinet:
Nantucket Race Week:
The Naked Oyster Bistro:
Figawi Race Weekend in Hyannis:
Hyannis Yacht Club:
Boston Yacht Haven:
Joe’s American Bar & Grill: