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

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
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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
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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
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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
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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
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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
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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
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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
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