Destination 01
Boston
Freedom Trail
A walkable line through the city’s essential history
culture
North End
Old streets, bakeries, and a long dinner
food
Isabella Stewart Gardner Museum
Art-filled galleries surrounding a Venetian courtyard
culture
Curated Cities route
Boston to Portland
Historic streets, harbor towns & seafood
Route preview
5 days through Boston, Portsmouth, Portland, Maine.
Boston to Portland is a 5-day curated route with 3 destinations and 8 suggested stops. Preview the itinerary, best season, and open it in TripsCircle.
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13 stops
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22 stops
Destination 02
Portsmouth
Market Square
Independent shops and brick lanes near the water
culture
Prescott Park
Harbor gardens and waterfront paths
nature
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33 stops
Destination 03
Portland, Maine
Old Port
Cobblestone blocks packed with seafood and small bars
food
Portland Head Light
Classic lighthouse and cliff walk just outside town
sight
Eastern Promenade
A waterfront path with Casco Bay and island views
sight
Route highlights
The moments that shape this trip.
- 01Freedom Trail
- 02Portsmouth
- 03Old Port
- 04Portland Head Light
