Luxury Itinerary
LUXURY: 14-Day Itinerary
No luxury experience is more “iconic New England” than an evening at Tanglewood, where the Boston Symphony Orchestra serenades an audience enjoying gourmet picnics under the stars. Let this world-famous music festival be your inspiration for a five-star escape that’s all about the best in life.
DAYS 1 & 2: WESTERN CONNECTICUT
Learn more about visiting Connecticut
Lodging ideas: Delamar Greenwich Harbor (Greenwich), Madison Beach Hotel (Madison), Mayflower Inn & Spa (Washington), Winvian Farm (Morris)
Close to New York City, the Gold Coast is peak Connecticut glitz. Shoppers make a beeline to Greenwich, where stores like Tiffany & Co., Hermès, and Baccarat line up along Greenwich Avenue. Charter a private yacht experience with Delamar Greenwich Harbor, which can customize the trip with a gourmet picnic meal and champagne, or book a private tour of Philip Johnson’s The Glass House in New Canaan for an intimate experience of an architectural gem.
Up next is another posh region: the Litchfield Hills. You don’t need to be a guest to enjoy five-diamond spa treatments at Winvian Farm or to take a “Field & Farm” cocktail-making class at the Mayflower Inn & Spa. For dinner, try Arethusa al Tavolo, a farm-to-table restaurant whose adjoining Arethusa Farm Dairy offers truly indulgent ice cream.
DAY 3: MASSACHUSETTS BERKSHIRES
Learn more about visiting Massachusetts
Lodging ideas: Miraval Berkshires (Lenox), Canyon Ranch (Lenox), Hotel on North (Pittsfield), Blantyre (Lenox; reopening late 2024)
Warm up for an evening at Tanglewood with a day of art and culture. North Adams is home to Mass MoCA, one of the world’s biggest contemporary art museums; not far away, the Clark Art Museum has masterworks dating back to the Renaissance. Americana reigns at the Norman Rockwell Museum in Stockbridge, which also boasts Naumkeag, a Gilded Age estate with sprawling manicured gardens.
Berkshire Picnics ensures you’ll dine like royalty at Tanglewood with prepared baskets of goodies—or even a deluxe picnic that’s already set up for you on the lawn. All that’s left for you to do is sit back and let the music play.
DAYS 4 & 5: VERMONT GREEN MOUNTAINS
Learn more about visiting Vermont
Lodging ideas: Twin Farms (Barnard), The Woodstock Inn & Resort (Woodstock), The Equinox Golf Resort & Spa (Manchester), The Reluctant Panther (Manchester)
Begin the day with an early-morning hot-air balloon adventure from Quechee Balloon Rides, followed by lunch at Simon Pearce, a Quechee-based artisan company known for hand-blown glassware but also for its lovely river-view Simon Pearce Restaurant. Then it’s off to the Woodstock Inn & Resort, where you can get a massage at the spa, arrange a private fly-fishing lesson, and even try your hand at a “sport of kings” with help from New England Falconry. For dinner, the inn’s Red Barn Dinner Series offers a four-course farm-to-table feast.
Drive over to Manchester to explore the amenities at The Equinox, from its championship 18-hole golf course to its pampering spa. Car buffs, meanwhile, will love the on-site Land Rover Experience Driving Center. For dinner, opt for classically prepared French cuisine at Mistral’s at Toll Gate or upscale American fare at The Copper Grouse inn, overseen by Michelin-starred executive chef Nicolas Houlbert.
DAYS 6 & 7: NEW HAMPSHIRE LAKES & MOUNTAINS
Learn more about visiting New Hampshire
Lodging ideas: Adair Country Inn (Bethlehem), Church Landing at Mill Falls (Meredith), The Inn at Thorn Hill (Jackson), Omni Mount Washington Resort (Bretton Woods)
Get a soaring introduction to Lake Winnipesaukee during a one-hour flight with Epic Seaplane Adventures, then hit the water on a private charter or a sunset boat cruise at Mill Falls at the Lake. End the day on a culinary high note at Wolfeboro’s Pavilion, owned by Top Chef alum Chris Viaud.
Heading north, golf fans can play 18 holes surrounded by the majestic White Mountains at places like the Wentworth Golf Club and the Omni Mount Washington Resort. The Omni is also great for fly-fishing, mountain biking, and horseback riding—though you may prefer to luxuriate in its 25,000-square-foot spa. Back in Jackson, snag a dinner reservation for Thompson House Eatery, where James Beard Award nominee Jeffrey Fournier turns out seasonally, locally inspired food in a cozy farmhouse.
DAYS 8 & 9: MAINE COAST
Learn more about visiting Maine
Lodging ideas: Camden Harbor Inn (Camden), Cliff House (Ogunquit), White Barn Inn (Kennebunk). Inland options: The Blair Hill Inn (Greenville); The Tarratine (Bangor)
In Portland, you can take to the high seas—or at least Casco Bay—on a private charter with Portland Schooner Co., whose fleet ranges from an 88-foot schooner to a “picnic-style” motorboat. Later, treat yourself to dinner at a top Portland restaurant such as Twelve or Fore Street, both of which showcase locally sourced seafood and produce. Or head south to Kennebunkport for a memorable meal in one of Earth at Hidden Pond’s sumptuous private “sheds.”
Learn all about that luxury treat, oysters, at Brunswick’s Mere Point Oyster Co., on a 3.5-hour sea kayaking excursion led by Alice’s Awesome Adventures (available for private groups of up to 10). Finally take a leisurely drive up to the Acadia Region to discover one of the hottest restaurants in Maine, Aragosta at Goose Cove.
DAYS 10–12: MARTHA’S VINEYARD, MASSACHUSETTS
Learn more about visiting Massachusetts
Lodging ideas: Chatham Inn (Chatham), The Charlotte Inn (Martha’s Vineyard), The Christopher (Martha’s Vineyard), Faraway (Nantucket & Martha’s Vineyard), Hob Knob (Martha’s Vineyard), Ocean Edge Resort (Brewster), White Elephant (Nantucket)
The go-to for island shopping is Edgartown, where you’ll find fine jewelry, island crafts, and more. For a break from the retail scene, head to South Beach—a barrier beach with surf on one side and calm waters on the other—or visit iconic attractions such as the Aquinnah Cliffs, the Oak Bluffs gingerbread cottages, and the Flying Horses Carousel.
Splurge on an ocean adventure with a private boat charter; local options include a two-hour sunset cruise with Catboat Charters and fishing expeditions with Menemsha Blues Charters. Keep the salty vibe going with a prix-fixe “sea-to-table” dinner at Outermost Inn.
Or simply leave all the planning up to the pros at My Vineyard Concierge, who can coordinate everything from yacht rentals to golf outings to curated tours.
DAYS 13 & 14: NEWPORT, RHODE ISLAND
Learn more about visiting Rhode Island
Lodging ideas: The Beatrice (Providence), The Brenton (Newport), The Chanler at Cliff Walk (Newport), Ocean House (Westerly), Watch Hill Inn (Watch Hill), Weekapaug Inn (Westerly)
Experience Newport’s Gilded Age mansions like one of the industrial barons who built them. Both the Preservation Society of Newport County and the Newport Restoration Foundation offer luxury tour options such as personal guides, after-hours visits, and entry into homes and spaces usually closed to the public. Similarly, on Thursdays you can purchase a private tour of the Blue Garden and have the Frederick Law Olmsted Jr.–designed landscape all to yourself.
Taking luxury on the road is Newport Jaguar Tours, which provides full- or half-day private guided tours of the world’s sailing capital in a classic Jaguar “saloon” or convertible. Prefer an ocean setting? Book a charter with Newport Classic Yacht Company and tool around the harbor in an antique motor yacht.
Then head home like a jetsetter with Tradewind Aviation, which operates private charters to major cities in the Northeast and beyond.
Itinerary created in partnership with Yankee Publishing. DATTCO Coach & Tour is Discover New England’s transportation partner.
