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4-Day New England Scenic and Cultural Tour from Boston
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4-Day New England Scenic and Cultural Tour from Boston
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Day 1: Historic Boston
Boston, USA on June 21, 2025
9:00am
Breakfast at Flour Bakery + Cafe
Enjoy a delightful breakfast featuring fresh pastries and excellent coffee at this popular spot in Cambridge, open from 7:00am onwards.
USD15, 1h
10:00am
Freedom Trail Walk
Explore 16 historic sites in Boston by following the 2.5-mile Freedom Trail, including Paul Revere's House and Faneuil Hall. It's a must-do to grasp early American history.
USD0, 3h
1:00pm
Lunch at Union Oyster House
Savor classic New England seafood at America’s oldest restaurant, located near the Freedom Trail and open until late afternoon.
USD30, 1h
2:30pm
Museum of Fine Arts, Boston
Visit one of the largest art museums in the U.S., featuring American and international works, open 10:00am to 5:00pm.
USD27, 2h
5:00pm
Stroll the Boston Public Garden
Relax in America’s first public botanical garden and enjoy swan boat rides if time permits. The garden closes around sunset.
USD4, 1h
7:00pm
Dinner at Toro
Indulge in upscale Spanish tapas in Boston’s South End. The restaurant is open for dinner from 5:00pm to 10:00pm.
USD40, 1.5h
Find Hotels in Boston
Day 2: Witch City Salem
Salem, USA on June 22, 2025
8:00am
Breakfast at Red's Sandwich Shop
Enjoy a traditional American breakfast at this long-standing Salem eatery open from 6:00am, perfect to fuel your day.
USD15, 1h
9:30am
Salem Witch Museum
Learn about the notorious 1692 Salem Witch Trials through engaging exhibits and presentations. The museum opens at 9:00am.
USD14, 1h
11:00am
Explore Historic Downtown Salem
Stroll charming streets full of unique shops, cafes, and historic homes, capturing Salem's rich maritime and witch trial heritage.
USD0, 1.5h
12:45pm
Lunch at Turner's Seafood
Try fresh local seafood in a cozy setting, open 11:30am to 3:00pm.
USD25, 1h
2:00pm
House of the Seven Gables
Visit the colonial mansion made famous by Nathaniel Hawthorne’s novel and explore the beautiful seaside gardens. Open 10:00am to 5:00pm.
USD16, 1.5h
4:00pm
Drive to Rockport
A scenic 25-minute drive north along the coast to the quaint harbor town known for its art galleries and coastal views.
USD0, 0.5h
6:00pm
Dinner at Roy Moore Lobster Co.
Enjoy lobster and other seafood fresh from the Atlantic at this waterfront Rockport eatery open until 8:00pm.
USD40, 1.5h
Find Hotels in Salem
Day 3: Coastal Arts & Nature
Rockport & Gloucester, USA on June 23, 2025
8:00am
Breakfast at My Place by the Sea
A harborfront café in Rockport offering fresh, hearty breakfast fare with scenic views; open from 7:00am.
USD15, 1h
9:30am
Bearskin Neck Stroll
Explore the charming shops and art galleries along this famous Rockport street, absorbing local culture.
USD0, 1h
11:00am
Drive to Gloucester
A short 20-minute coastal drive to Massachusetts’ oldest seaport town.
USD0, 0.5h
11:30am
Cape Ann Museum
Discover Gloucester’s maritime heritage and unique art collections from the Cape Ann region. Open 10:00am-4:00pm.
USD15, 1.5h
1:00pm
Lunch at The Gloucester House
Popular spot for fresh seafood and waterfront views; open 11:30am-3:00pm.
USD30, 1h
2:30pm
Annisquam Lighthouse Visit
Drive up to this historic lighthouse for picturesque coastal views and photo opportunities. Open grounds, free access.
USD0, 1h
4:00pm
Return to Boston
Approximately 45-minute drive south to Boston to rest and prepare for next day.
USD0, 0.75h
7:00pm
Dinner at Legal Sea Foods
End the day with classic Boston seafood specialties, open until 10:00pm.
USD40, 1.5h
Find Hotels in Rockport & Gloucester
Day 4: Historic Portsmouth
Portsmouth, USA on June 24, 2025
7:30am
Breakfast at The Friendly Toast
Enjoy a quirky and hearty breakfast in Portsmouth, New Hampshire. Open from 7:00am.
USD15, 1h
9:00am
Strawbery Banke Museum
Explore New Hampshire’s outdoor history museum showcasing preserved houses and gardens from the 17th century onward. Open 10:00am-5:00pm.
USD20, 2h
11:30am
Walk Market Square and Downtown Portsmouth
Enjoy the vibrant shops, galleries, and architecture in the lively heart of Portsmouth.
USD0, 1h
12:30pm
Lunch at Jumpin' Jay’s Fish Cafe
Casual dining with creative seafood dishes in downtown Portsmouth, open till 3:00pm.
USD30, 1h
2:00pm
Drive back to Boston
A scenic 1-hour drive south to Boston International Airport or center.
USD0, 1h
3:30pm
Optional visit to Boston Public Library
If time permits, explore this historic library built in 1895, featuring beautiful architecture and art. Open till 5:00pm.
USD0, 1h
5:00pm
End of tour
Tour concludes with options for dinner or rest in Boston.
USD0, N/A
Find Hotels in Portsmouth
0
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Itinerary created by
Plantrip Team
June 21, 2025
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