AI-planned road trip
Boston, MA, USA→Portsmouth, NH, USA
“A 4-day coastal culture road trip from Boston toward Portsmouth”
4days
193 kmDistance
16stops
$1,280Est. cost
Shared by a traveler · city-level only, no dates, private notes stay private
- ~4h 2m driving
- Day 1
- Day 2
- Day 3
- Day 4
Day-by-day itinerary
Day 1
Boston → Gloucester
69 km1h 14mDepart 08:30
Day 1
Boston → GloucesterStart
Boston, MA, USA
Walk 1 km through Salem’s historic center for lunch, about 15 minutes.
1
AttractionSalem, United States
Salem Maritime National Historical Park
09:15–11:452h 30m here$10
Historic waterfront, tall ship, and colonial trade stories
Use public lots near Derby Street; easy sedan parking early.
Drive 32 km along the North Shore to Gloucester, about 45 minutes.
2
FoodSalem, United States
The Lobster Shanty
12:00–13:001h here$55
Casual local seafood and New England classics
Try lobster roll or fried clams; expect casual service.
Drive 5 km to the waterfront hotel area, about 12 minutes.
3
AttractionGloucester, United States
Cape Ann Museum (CAM)
13:45–16:152h 30m here$30
Regional art, maritime history, and Cape Ann culture
Good rainy-day option; nearby metered parking.
Settle in by the harbor for the night.
4
OvernightGloucester, United States
Beauport Hotel Gloucester
16:30–17:301h here$230
Waterfront hotel with harbor views
Reserve parking with room; walkable dinner options nearby.
Day 2
Gloucester → Newbury
52 km1h 3mDepart 08:30
Day 2
Gloucester → Newbury
Drive 23 km to Essex for a classic clam-shack lunch, about 30 minutes.
5
ActivityGloucester, United States
Good Harbor Beach
08:45–10:452h here$25
Scenic sandy beach walk and ocean views
Arrive early for beach parking; bring layers for wind.
Drive 48 km north to Newburyport’s historic waterfront, about 55 minutes.
6
FoodEssex, United States
Woodman's of Essex
11:15–12:151h here$60
Iconic fried clams and local seafood counter
Share fried clams; casual counter-service seafood.
Drive 2 km to the downtown hotel, about 8 minutes.
7
AttractionNewburyport, United States
Custom House Maritime Museum
13:15–15:152h here$25
Compact museum on Newburyport’s seafaring past
Use nearby municipal lots; walk the waterfront after.
Rest downtown and enjoy Newburyport in the evening.
8
OvernightNewbury, United States
Blue - Inn on the Beach
15:30–16:301h here$190
Boutique downtown stay near shops and waterfront
Confirm parking details before arrival.
Day 3
Newbury → Portsmouth
59 km1h 13mDepart 08:30
Day 3
Newbury → Portsmouth
Drive 20 km to Hampton Beach for casual food, about 25 minutes.
9
AttractionNewburyport, United States
Maudslay State Park
08:45–11:152h 30m here$5
Gardens, river trails, and historic estate landscapes
Good walking shoes; state park parking is sedan-friendly.
Drive 8 km along the coast to Rye, about 15 minutes.
10
FoodHampton, United States
Blink's Fry Doe
11:45–12:451h here$35
Classic beach-boardwalk snack stop
Try fried dough and beach snacks; save room for dinner.
Drive 9 km into Portsmouth’s hotel district, about 20 minutes.
11
AttractionRye, United States
Seacoast Science Center
13:00–15:302h 30m here$30
Ocean ecology exhibits beside rocky shore trails
Great mix of museum time and coastal walking.
Park once and enjoy Portsmouth on foot tonight.
12
OvernightPortsmouth, United States
Hampton Inn & Suites Portsmouth Downtown
16:00–17:001h here$240
Comfortable downtown hotel near Market Square
Use hotel garage or nearby public parking; compact downtown streets.
Day 4
Portsmouth
13 km32mDepart 08:45
Day 4
Portsmouth
Walk 1 km into Market Square for lunch, about 12 minutes.
13
AttractionPortsmouth, United States
Strawbery Banke Museum
09:00–12:003h here$40
Outdoor history museum with restored waterfront homes
Allow time for house exhibits and gardens.
Drive 5 km to the riverside mansion area, about 12 minutes.
14
FoodPortsmouth, United States
The Friendly Toast
12:15–13:151h here$55
Colorful local brunch spot with hearty plates
Popular spot; join waitlist if available.
Drive 6 km to Newcastle for a final coastal viewpoint, about 15 minutes.
15
AttractionPortsmouth, United States
Moffatt-Ladd House & Garden
13:30–15:302h here$30
Historic Georgian mansion and garden
Check tour availability locally before committing.
16
ActivityNew Castle, United States
Great Island Common
15:45–17:452h here$10
Harbor views, lighthouse glimpses, and easy paths
Bring a light jacket; exposed coast can be breezy.
Finish
Portsmouth, NH, USA
Before you go
Local tips
- 1Book hotels with parking in advance for coastal towns.
- 2Start beach days early to reduce parking stress.
- 3Use one fuel top-up near Newburyport or Portsmouth.
- 4Keep evenings flexible for seafood spots and harbor walks.
Good to know
- 1Coastal parking can fill quickly in warm September weather.
- 2Downtown Portsmouth streets are narrow; park once and walk.
- 3Some small museums may have seasonal hours; verify ahead.
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