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7-Day Road Trip Itinerary The New England Good Life

Take to the Open Road

Itinerary Highlights

Tour New England and discover unique history, view stunning design Savor al fresco drinking and dining at its most charming, take a private America’s Cup yacht charter, or a design tour of Newport’s ‘cottages’. Delight in simple pleasures and create unforgettable memories. Inquire at 844-836-5506.

Includes daily breakfast, and a customized program of private experiences
Exclusive antiquing experience with the owners of Plain Goods
Tour Jamestown in private aboard an America’s Cup yacht
Private helicopter trip to the lighthouses of Block Island
A lively fishing experience alongside local lobster fishermen
Private seaplane tour of Acadia National Park

Fire pits

Day 1-2


From your Connecticut base, the Mayflower Inn & Spa, the epitome of New England panache, meet leading artisans and enjoy curated dining experiences.
Building Entrance

Day 3-4

Rhode Island

Journey onwards to historic Newport and a stay at The Vanderbilt, a Gilded Age mansion, built by Alfred Gwynne Vanderbilt in 1909.

Day 5-7


Feel the wind in your hair as you tour this coastal town by land, sea or sky before continuing to Kennebunk Beach in Maine for an unforgettable stay at the elegant White Barn Inn & Spa.

Other Sample Itineraries

Maine, the Way Life Should Be | 2 Days