Buckle up—this isn't your typical road trip. Hike, shop, dine, and sail your way through New England with a custom itinerary from our partner, All Roads North. Immerse yourself in Maine's seafaring history while hauling traps on a lobster boat, drive up Mount Washington on the famed 7.6-mile Auto Road, detour in Vermont to meet and work alongside local cheese and maple syrup producers, and more. Travel south on Route 100 following the Mad River Valley through the Southern Green Mountains to the far western edge of Massachusetts. You’ll get your culture fix in the Berkshires, home to acclaimed institutions including Tanglewood, the Clark Institute and Mass MOCA. Stay in hotels and inns delivering five-star New England hospitality along the way.

Bicycle through the East Coast gems of Massachusetts’s Colonial Islands, Martha’s Vineyard, and Nantucket during this five-day excursion. Pedal along rolling hills past scenic beaches, historic homes, and woodlands while exploring the rich colonial roots and maritime history of these famed destinations. Off the saddle, wander cobblestone streets lined with galleries, upscale boutiques, steepled churches, and mouthwatering restaurants serving up some of the freshest seafood—and of course, lobster rolls. Learn the rich history and local tales through private guided walking tours, while museum stops enrich your immersive Colonial Island experience.

Laid out like a string of pearls in turquoise water, the Exumas is an idyllic collection of islands on the eastern edge of the Bahamas. Get to know these beautiful islands at your own pace during a week on the private yacht, All In. Cruise in incomparable luxury and style on this one-of-a kind, 145-foot tri-deck private yacht — with a crew dedicated to your every need. Dig your toes into remote beaches, snorkel with a rainbow of fish on stunning reefs, and return to your floating sanctuary for chef-prepared meals under the stars between island-hopping.