HitTheRoad
Download on the App Store Get it on Google Play
AI-planned road trip

MA, USA → NH, USA

4 days · 193 km · 16 stops

4Days
193 kmDistance
16Stops
$1,280Est. cost

A 4-day coastal culture road trip from Boston toward Portsmouth

Estimated cost

$1,280estimated total
Stays $660
Fuel $45
Food $300
Other $275

Estimates generated at planning time — your actual costs may vary.

Day-by-day itinerary

Day 1
69 km1h 14mDepart 08:30
Start
MA, USA
Walk 1 km through Salem’s historic center for lunch, about 15 minutes.
1
Attraction4.6

Salem Maritime National Historical Park

Salem, United States
09:15–11:452h 30m here$10

Historic waterfront, tall ship, and colonial trade stories

Salem Maritime National Historical ParkSalem Maritime National Historical ParkSalem Maritime National Historical ParkSalem Maritime National Historical Park
Use public lots near Derby Street; easy sedan parking early.
Drive 32 km along the North Shore to Gloucester, about 45 minutes.
2
Food4.3

The Lobster Shanty

Salem, United States
12:00–13:001h here$55

Casual local seafood and New England classics

The Lobster ShantyThe Lobster ShantyThe Lobster ShantyThe Lobster Shanty
Try lobster roll or fried clams; expect casual service.
Drive 5 km to the waterfront hotel area, about 12 minutes.
3
Attraction4.8

Cape Ann Museum (CAM)

Gloucester, United States
13:45–16:152h 30m here$30

Regional art, maritime history, and Cape Ann culture

Cape Ann Museum (CAM)Cape Ann Museum (CAM)Cape Ann Museum (CAM)Cape Ann Museum (CAM)
Good rainy-day option; nearby metered parking.
Settle in by the harbor for the night.
4
Overnight4.6

Beauport Hotel Gloucester

Gloucester, United States
16:30–17:301h here$230

Waterfront hotel with harbor views

Beauport Hotel GloucesterBeauport Hotel GloucesterBeauport Hotel GloucesterBeauport Hotel Gloucester
Reserve parking with room; walkable dinner options nearby.
Day 2
52 km1h 3mDepart 08:30
Drive 23 km to Essex for a classic clam-shack lunch, about 30 minutes.
5
Activity4.7

Good Harbor Beach

Gloucester, United States
08:45–10:452h here$25

Scenic sandy beach walk and ocean views

Good Harbor BeachGood Harbor BeachGood Harbor BeachGood Harbor Beach
Arrive early for beach parking; bring layers for wind.
Drive 48 km north to Newburyport’s historic waterfront, about 55 minutes.
6
Food4.5

Woodman's of Essex

Essex, United States
11:15–12:151h here$60

Iconic fried clams and local seafood counter

Woodman's of EssexWoodman's of EssexWoodman's of EssexWoodman's of Essex
Share fried clams; casual counter-service seafood.
Drive 2 km to the downtown hotel, about 8 minutes.
7
Attraction4.6

Custom House Maritime Museum

Newburyport, United States
13:15–15:152h here$25

Compact museum on Newburyport’s seafaring past

Custom House Maritime MuseumCustom House Maritime MuseumCustom House Maritime MuseumCustom House Maritime Museum
Use nearby municipal lots; walk the waterfront after.
Rest downtown and enjoy Newburyport in the evening.
8
Overnight4.5

Blue - Inn on the Beach

Newbury, United States
15:30–16:301h here$190

Boutique downtown stay near shops and waterfront

Blue - Inn on the BeachBlue - Inn on the BeachBlue - Inn on the BeachBlue - Inn on the Beach
Confirm parking details before arrival.
Day 3
59 km1h 13mDepart 08:30
Drive 20 km to Hampton Beach for casual food, about 25 minutes.
9
Attraction4.7

Maudslay State Park

Newburyport, United States
08:45–11:152h 30m here$5

Gardens, river trails, and historic estate landscapes

Maudslay State ParkMaudslay State ParkMaudslay State ParkMaudslay State Park
Good walking shoes; state park parking is sedan-friendly.
Drive 8 km along the coast to Rye, about 15 minutes.
10
Food4.4

Blink's Fry Doe

Hampton, United States
11:45–12:451h here$35

Classic beach-boardwalk snack stop

Blink's Fry DoeBlink's Fry DoeBlink's Fry DoeBlink's Fry Doe
Try fried dough and beach snacks; save room for dinner.
Drive 9 km into Portsmouth’s hotel district, about 20 minutes.
11
Attraction4.6

Seacoast Science Center

Rye, United States
13:00–15:302h 30m here$30

Ocean ecology exhibits beside rocky shore trails

Seacoast Science CenterSeacoast Science CenterSeacoast Science CenterSeacoast Science Center
Great mix of museum time and coastal walking.
Park once and enjoy Portsmouth on foot tonight.
12
Overnight4.5

Hampton Inn & Suites Portsmouth Downtown

Portsmouth, United States
16:00–17:001h here$240

Comfortable downtown hotel near Market Square

Hampton Inn & Suites Portsmouth DowntownHampton Inn & Suites Portsmouth DowntownHampton Inn & Suites Portsmouth DowntownHampton Inn & Suites Portsmouth Downtown
Use hotel garage or nearby public parking; compact downtown streets.
Day 4
13 km32mDepart 08:45
Walk 1 km into Market Square for lunch, about 12 minutes.
13
Attraction4.7

Strawbery Banke Museum

Portsmouth, United States
09:00–12:003h here$40

Outdoor history museum with restored waterfront homes

Strawbery Banke MuseumStrawbery Banke MuseumStrawbery Banke MuseumStrawbery Banke Museum
Allow time for house exhibits and gardens.
Drive 5 km to the riverside mansion area, about 12 minutes.
14
Food4.5

The Friendly Toast

Portsmouth, United States
12:15–13:151h here$55

Colorful local brunch spot with hearty plates

The Friendly ToastThe Friendly ToastThe Friendly ToastThe Friendly Toast
Popular spot; join waitlist if available.
Drive 6 km to Newcastle for a final coastal viewpoint, about 15 minutes.
15
Attraction4.6

Moffatt-Ladd House & Garden

Portsmouth, United States
13:30–15:302h here$30

Historic Georgian mansion and garden

Moffatt-Ladd House & GardenMoffatt-Ladd House & GardenMoffatt-Ladd House & GardenMoffatt-Ladd House & Garden
Check tour availability locally before committing.
16
Activity4.7

Great Island Common

New Castle, United States
15:45–17:452h here$10

Harbor views, lighthouse glimpses, and easy paths

Great Island CommonGreat Island CommonGreat Island CommonGreat Island Common
Bring a light jacket; exposed coast can be breezy.
Finish
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.

Plan your own road trip in seconds

Tell the AI where you're headed — get a real day-by-day route with genuine stops, photos, costs and live guidance.

Download on the App Store Get it on Google Play