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Home / Journeys / Tea, Mansions & Maritime Trails: A New England Journey
10 nights · Boston, United States → New Haven, United States · Car

Tea, Mansions & Maritime Trails: A New England Journey

Walk the Cliff Walk past Newport’s Gilded Age mansions, then Yale University’s historic architecture in New Haven – ten nights through New England’s maritime and academic heritage.

From£1,911pp
Duration10 days
StyleSelf-guided
Best suited toDrivers who want the road to be the holiday
Find out more
An independent Stradora pick. Details from the operator's published information, last checked 28 Oct 2026. Stradora DiscoveryChosen independently by our editors because we think it's worth the drive. We're not partnered with this operator: dates, prices and booking are handled by them, and we last checked their published details on 28 Oct 2026.
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10 nights through United States

Ten nights from Boston to New Haven, self-guided, through southern New England, with the flights included.

Ten nights across five stops and only six days of car hire tells you the shape: this is a city and coast trip with short drives between them rather than a touring holiday, and the car is handed back before the end.

Boston opens it for three nights, with the Freedom Trail, Beacon Hill’s gas lamps and brick, and the Italian North End. Providence follows for two, a small city with a serious food reputation and a good deal of art. Newport comes next for two, where the Gilded Age families built summer houses the size of palaces along the cliffs and the Cliff Walk runs behind them with the Atlantic below. Mystic follows for a night, a seaport town with a whaling history, then New Haven for two, with Yale and its Gothic quadrangles, and the departure from Hartford.

Direct flights out to Boston and home from Hartford, a checked bag each way, six days of car hire with unlimited mileage and all ten nights at the named hotels, some with breakfast, are included; fuel, most meals, the mansion and attraction admissions, resort fees of 125 euros and a one-way drop-off fee of 46 euros, both payable locally, are not. The price shown is per person sharing. Late September and early October bring the autumn colour, which is the obvious window, though Newport is at its best in summer. Eleven days with only five bases and short legs between them is a gentle itinerary by the standards of American road trips, and the car being handed back at Hartford keeps the cost down.

Style
Self-guided
Duration
A week or so (7-10 nights)
Region
North America
Vehicle provision
Vehicle provided
Departures
September
Starts/ends
Boston, United States → New Haven, United States
Accommodation
Hotels
Suitable cars
Drivers who want the road to be the holiday
Vehicle
Car
Price basis
Per person (sharing)
Run by
Independent specialist operator

What's included

  • Direct flights to Boston
  • returning from Hartford (Aer Lingus)
  • 1 checked bag per person roundtrip
  • 6 days car hire with unlimited mileage
  • 10 nights' accommodation at named hotels
  • some with breakfast.

Not included

  • Fuel
  • a one-way car drop-off fee of EUR46 (paid locally)
  • total resort fees of EUR125 (paid locally)
  • most meals
  • mansion/attraction admission.

Ready to drive it?

10 days, from £1,911pp

Independent Stradora pick
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