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10-Day New England Coastal Itinerary from Boston with 3 Base Stays and Arcadia Park Visit

Viewed by 135 travelers

Day 1: Boston Stay & Explore

Boston, Massachusetts, USA on June 3, 2025

9:00AM

Breakfast at Flour Bakery + Cafe

Kick off your trip with a delicious dog-friendly breakfast at this popular bakery known for fresh pastries and breakfast sandwiches.
USD15, 1h

11:00AM

Walk Boston Harborwalk

Enjoy a scenic, dog-friendly stroll along the waterfront with views of the harbor and Boston’s skyline.
Free, 1h30m

1:00PM

Lunch at The Barking Crab

Eat fresh seafood with your service dog on the dog-friendly patio overlooking the harbor.
USD25, 1h

3:00PM

Visit Boston Public Garden

Explore this iconic garden where dogs are welcome on leash, famed for the swan boats and beautiful flowerbeds.
Free, 1h

6:00PM

Dinner at Legal Sea Foods - Harborside

Enjoy New England seafood and waterfront views with dog-friendly outdoor seating.
USD40, 1h30m
Find Hotels in Boston

Day 2: Day Trip to Rhode Island Coast

Boston, Massachusetts, USA on June 4, 2025

8:00AM

Drive Boston to Narragansett

Take a 1.5-hour day trip to charming Narragansett, Rhode Island with dog-friendly beaches and coastal sights.
Gas approx USD20, 1h30m

9:30AM

Breakfast at Coast Guard House

Breakfast with ocean views at a dog-friendly restaurant with outdoor seating.
USD20, 1h

11:00AM

Scarborough State Beach Visit

Relax with your service dog on this pet-accommodating beach area during designated hours.
USD10 parking, 2h

2:00PM

Point Judith Lighthouse Walk

Enjoy coastal views and a historic lighthouse walk pet-friendly accessible with your service dog.
Free, 1h

5:00PM

Dinner at Matunuck Oyster Bar

Savor fresh oysters and seafood with dog-friendly outdoor seating before heading back to Boston.
USD40, 1h30m

7:00PM

Drive back to Boston

Return from Narragansett to Boston for overnight stay.
Gas approx USD20, 1h30m
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Day 3: Day Trip South Massachusetts Coast

Boston, Massachusetts, USA on June 5, 2025

8:00AM

Drive Boston to Marshfield

Head 1.5 hours south for a day exploring the South Shore beaches and parks with your service dog.
Gas approx USD20, 1h30m

9:30AM

Breakfast at The Studio Coffee

Enjoy light breakfast and coffee in this cozy dog-friendly café.
USD15, 1h

11:00AM

Walk Rexhame Beach

Take a peaceful beach walk suitable for service dogs in this relaxed coastal setting.
Free, 1h30m

1:00PM

Lunch at Yarmouth House Restaurant

Savor classic seafood fare with dog-friendly outdoor seating available close by.
USD25, 1h

3:00PM

Visit Daniel Webster Estate and Trails

Explore scenic and pet-friendly walking trails near the historic estate for an afternoon adventure.
Free, 1h30m

5:30PM

Drive back to Boston

Return to your Boston hotel for the night, resting up for the next leg of the journey.
Gas approx USD20, 1h30m
Find Hotels in Boston

Day 4: Move to Portsmouth NH Base

Portsmouth, New Hampshire, USA on June 6, 2025

9:00AM

Drive Boston to Portsmouth

Travel about 1 hour north to Portsmouth, your next base with great pet-friendly hotels for three nights.
Gas approx USD15, 1h

10:30AM

Breakfast at The Friendly Toast

A fun, quirky dog-friendly cafe for a hearty breakfast upon arrival.
USD20, 1h

12:00PM

Walk Prescott Park

Enjoy relaxing waterfront gardens and dog-friendly walking paths.
Free, 1h30m

2:00PM

Explore Historic Portsmouth

Visit pet-friendly historic neighborhoods with colonial architecture for an easy cultural stroll.
Free, 2h

5:30PM

Dinner at Portsmouth Brewery

Casual dining with local brews and dog-friendly outdoor seating.
USD35, 1h30m
Find Hotels in Portsmouth

Day 5: Day Trip Southern Maine Coast

Portsmouth, New Hampshire, USA on June 7, 2025

8:00AM

Drive Portsmouth to Kennebunkport

About 40 minutes north to Kennebunkport, a lovely coastal town ideal for a day trip with your service dog.
Gas approx USD10, 40m

9:00AM

Breakfast at Mornings in Paris Café

European-style bakery with dog-friendly outdoor seating perfect for breakfast.
USD15, 1h

10:30AM

Walk Kennebunk Beach

Take your service dog for a beach stroll during dog-friendly hours on this popular shore.
Free, 2h

1:00PM

Lunch at Alisson's Restaurant

Dog-friendly dining on local seafood and casual fare.
USD30, 1h

3:00PM

Explore Dock Square

Shop and walk the historic town center with many pet-friendly areas.
Free, 1h30m

5:30PM

Return to Portsmouth

Head back to Portsmouth for overnight stay.
Gas approx USD10, 40m
Find Hotels in Portsmouth

Day 6: Day Trip Cape Ann

Portsmouth, New Hampshire, USA on June 8, 2025

7:30AM

Drive Portsmouth to Gloucester

Drive 1.5 hours south to Gloucester for a day of ocean views and art, exploring with a service dog.
Gas approx USD20, 1h30m

9:30AM

Breakfast at Short & Main

Fresh bakery items with dog-friendly outdoor seating to start your day.
USD15, 1h

11:00AM

Whale Watching Tour

Join a whale watch with dog-friendly deck space available, seasonal tours from April to October.
USD55, 3h

3:30PM

Stroll Rocky Neck Art Colony

Explore galleries and outdoor art spaces walking easily with your service dog.
Free, 1h

5:00PM

Drive back to Portsmouth

Return to Portsmouth for your last night in this base.
Gas approx USD20, 1h30m
Find Hotels in Portsmouth

Day 7: Move to Bar Harbor Base

Bar Harbor, Maine, USA on June 9, 2025

7:00AM

Drive Portsmouth to Bar Harbor

Longer drive of approximately 2.5 hours to Bar Harbor, your final base with pet-friendly lodging for 4 nights to explore Acadia National Park fully.
Gas approx USD30, 2h30m

10:00AM

Breakfast at Café This Way

Relaxed dog-friendly café with creative breakfast dishes upon arrival in Bar Harbor.
USD20, 1h

11:30AM

Explore Downtown Bar Harbor

Stroll the harborfront and shops with your service dog to get acquainted with the town.
Free, 1h30m

1:00PM

Lunch at Stewman’s Lobster Pound

Classic Maine lobster dinner with dog-friendly outdoor seating on the waterfront.
USD50, 1h30m

3:00PM

Relax at Agamont Park

Enjoy a peaceful park area near the harbor perfect for a gentle walk with your dog.
Free, 1h
Find Hotels in Bar Harbor

Day 8: Acadia National Park & Arcadia Park

Bar Harbor, Maine, USA on June 10, 2025

8:00AM

Breakfast at Mainely Judies

Hearty, dog-friendly breakfast option to start your park day.
USD20, 1h

9:30AM

Visit Acadia National Park - Carriage Roads

Hike scenic, dog-friendly carriage roads and enjoy the outdoors with your service dog for several hours.
USD30 per vehicle, 4h

1:30PM

Picnic Lunch at Jordan Pond House

Famous popovers and tea on the spacious pet-friendly outdoor seating overlooking Jordan Pond.
USD25, 1h

3:00PM

Drive Cadillac Mountain

Take the scenic drive to Cadillac Mountain lookout points, with dog-friendly trails and panoramic views.
Included in park fee, 2h

6:00PM

Dinner at Cafe at Garden Gate

Casual dining with local food and dog-friendly outdoor seating.
USD35, 1h30m
Find Hotels in Bar Harbor

Day 9: Bar Harbor Leisure Day

Bar Harbor, Maine, USA on June 11, 2025

8:00AM

Breakfast at Jordan’s Restaurant

Classic breakfast fare in a dog-friendly setting close to downtown Bar Harbor.
USD20, 1h

9:30AM

Explore Shore Path

Walk this easy, dog-friendly coastal path enjoying ocean views and harbor sights throughout.
Free, 2h

12:00PM

Lunch at Geddy’s

Popular seafood spot with dog-friendly outdoor seating perfect for a relaxing midday meal.
USD30, 1h

2:00PM

Visit Bar Harbor Historical Society (Dog Accommodations Confirmed)

Experience history and culture with pet-friendly arrangements by appointment.
USD10, 1h

4:00PM

Relax and Explore Local Shops

Enjoy some last-minute shopping and walking with your dog through pet-welcoming local shops.
Free, 2h

6:30PM

Dinner at Havana

Upscale Cuban and Latin cuisine with dog-friendly outdoor dining for your farewell Bar Harbor meal.
USD45, 1h30m
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Day 10: Return to Boston

Boston, Massachusetts, USA on June 12, 2025

7:30AM

Drive Bar Harbor to Boston

Start early for the 4-hour drive south to Boston to conclude your trip comfortably at your original base.
Gas approx USD40, 4h

12:00PM

Lunch at Tatte Bakery & Cafe

Enjoy a last light meal at this dog-friendly Boston favorite with excellent baked goods and sandwiches.
USD25, 1h

2:00PM

Relax at Christopher Columbus Park

Take one last stroll at this waterfront dog-friendly park before departure or onward travels.
Free, 1h

4:00PM

Optional sightseeing or shopping

Spend your afternoon as you choose with dog-friendly options in Boston’s city center.
Varies, 2h

6:30PM

Farewell Dinner at The Daily Catch

Enjoy fresh seafood with dog-friendly outdoor dining and reflect on your New England coastal adventure.
USD40, 1h30m
Find Hotels in Boston
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