Ultimate 7-Day Boston to Bar Harbor Road Trip Itinerary with Kennebunkport and Boothbay Harbor

Day 1: Exploring Boston

Boston, MA

8:00AM

Breakfast at The Paramount

Start your day with a delicious breakfast at this iconic eatery known for its scrumptious pancakes and omelets.
Located in the Beacon Hill neighborhood, a short drive from most hotels.
USD20, 1 hour

9:30AM

Freedom Trail Walk

Embark on the historic Freedom Trail, visiting significant sites including Boston Common and Paul Revere's House.
Walk the 2.5 miles of the trail starting from Boston Common.
USD0, 3 hours

1:00PM

Lunch at Quincy Market

Indulge in local flavors at Quincy Market, known for its diverse food stalls and historic ambiance.
Located just a short walk from the Freedom Trail.
USD25, 1 hour

2:30PM

New England Aquarium

Visit one of the most renowned aquariums in America, showcasing marine life from the New England region.
A 10-minute walk from Quincy Market.
USD31, 2 hours

5:00PM

Dinner at Legal Sea Foods

Enjoy a seafood dinner at Legal Sea Foods, a Boston staple known for its fresh catch of fish.
Located on the waterfront, a short drive away.
USD40, 1.5 hours

7:00PM

Evening Stroll along the Harborwalk

Wrap up your day with a leisurely stroll along the Harborwalk, savoring the views of the Boston skyline.
Accessible directly from Legal Sea Foods.
USD0, 1 hour
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Day 2: Art and History in Boston

Boston, MA

8:00AM

Breakfast at Flour Bakery

Start your day with freshly baked pastries and artisanal sandwiches that define this Harvard Square favorite.
Located a quick drive from downtown Boston.
USD15, 1 hour

9:30AM

Museum of Fine Arts

Explore an exceptional collection of art, from ancient to contemporary, in this acclaimed museum.
A 15-minute drive from the bakery.
USD25, 2.5 hours

12:00PM

Lunch at Eataly

Enjoy a vibrant Italian lunch at Eataly, featuring fresh pasta and unique culinary specialties.
Located near the Museum of Fine Arts.
USD30, 1 hour

1:30PM

Isabella Stewart Gardner Museum

Marvel at this stunning museum modeled after a Venetian palace, showcasing art in a beautiful garden setting.
Walking distance from Eataly.
USD20, 1.5 hours

3:00PM

Boston Public Garden

Take a relaxing walk or a swan boat ride in the picturesque Boston Public Garden.
A short drive away or about 20 minutes walking.
USD15 (Swan Boat Ride), 1 hour

5:00PM

Dinner at North End (Carmine's)

Savor the Italian flavors in Boston’s North End at Carmine's, famous for its family-style meals.
A 10-minute drive from the Public Garden.
USD50, 2 hours

7:30PM

Visit the Skywalk Observatory

Catch breathtaking views of the city skyline from the 50th floor of the Prudential Tower.
A short drive away from North End.
USD20, 1 hour
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Day 3: Boston to Kennebunkport

Kennebunkport, ME

8:00AM

Breakfast at Tatte Bakery

Enjoy a delightful breakfast featuring Mediterranean-inspired pastries and dishes before hitting the road.
Located a short drive from downtown Boston.
USD20, 1 hour

9:00AM

Depart Boston for Kennebunkport

Begin your journey northeast along the I-95, soaking in the beautiful New England landscapes.
Approx. 90 miles, about a 1.5-hour drive.
USD0, 1.5 hours

10:30AM

Arrive in Kennebunkport

Discover the charming coastal town known for its scenic beauty and historic landmarks.
Park in the downtown area for easy exploration.
USD0, 0.5 hours

11:00AM

Stroll along Dock Square

Wander through Dock Square where local boutiques and cafés beckon visitors with charm and character.
Accessible by foot from the parking area.
USD0, 1 hour

12:00PM

Lunch at The Clam Shack

Indulge in classic Maine lobster rolls and fried clams at this casual seafood shack.
Located just off Dock Square.
USD25, 1 hour

1:30PM

Visit the Rachel Carson National Wildlife Refuge

Explore serene trails and diverse wildlife in this beautiful refuge just a short drive from town.
A 10-minute drive from Kennebunkport.
USD0, 1.5 hours

3:30PM

Check-in at Kennebunkport Hotel

Relax and refresh at your hotel before heading out for dinner.
Choose from several hotels in downtown Kennebunkport.
Varies, 1 hour

5:30PM

Dinner at The White Barn Inn

Experience fine dining with a farm-to-table menu at this exquisite inn.
Walking distance from most hotels.
USD80, 2 hours

8:00PM

Evening at the Beach

Spend a relaxing evening at the beach, perhaps catching the sunset views over the ocean.
Nearby beaches are just a short drive away.
USD0, 1.5 hours
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Day 4: Kennebunkport to Boothbay Harbor

Boothbay Harbor, ME

8:00AM

Breakfast at Mabel's Lobster Claw

Fuel up with a hearty breakfast served in a cozy, nautical-themed restaurant famous for its friendly service.
Located in Kennebunkport.
USD20, 1 hour

9:00AM

Depart Kennebunkport for Boothbay Harbor

Take a scenic drive along Route 1 north, enjoying coastal views towards Boothbay Harbor.
Approx. 30 miles, about a 45-minute drive.
USD0, 1 hour

10:00AM

Arrive in Boothbay Harbor

Discover the beauty of this seaside town known for its fishing heritage and charming harbors.
Park near the waterfront to enjoy the area.
USD0, 0.5 hours

10:30AM

Visit the Coastal Maine Botanical Gardens

Stroll through stunning gardens showcasing indigenous plants and beautiful landscapes.
A short 15-minute drive from Boothbay Harbor.
USD20, 2 hours

12:30PM

Lunch at Boothbay Lobster Wharf

Enjoy delicious lobster dishes in a casual setting right on the water.
Return to Boothbay Harbor for lunch.
USD25, 1.5 hours

2:00PM

Boat Tour of Boothbay Harbor

Take a scenic boat tour to see lighthouses and marine wildlife up close.
Easily accessible from the harbor.
USD40, 2 hours

4:30PM

Check-in at Boothbay Harbor Hotel

Relax at your hotel and prepare for dinner.
Choose a waterfront hotel for stunning views.
Varies, 1 hour

6:00PM

Dinner at The Boathouse Bistro

Dine at this popular spot offering seafood and a beautiful view of the harbor.
Located within walking distance from your hotel.
USD35, 2 hours

8:00PM

Evening at the Harbor

Enjoy a peaceful evening stroll along the waterfront, taking in the beauty of the harbor.
Accessible from the restaurant.
USD0, 1 hour
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Day 5: Boothbay Harbor to Portland

Portland, ME

8:00AM

Breakfast at The Harbor Grill

Start your day with hearty breakfast options like omelets and pancakes with a scenic harbor view.
Located in Boothbay Harbor.
USD20, 1 hour

9:00AM

Depart Boothbay Harbor for Portland

Drive along the coastline to Portland, taking in the picturesque scenery.
Approx. 60 miles, about a 1.5-hour drive.
USD0, 1.5 hours

10:30AM

Arrive in Portland

Get settled and prepare for a day of exploring this vibrant food and arts destination.
Park in the Old Port section for easy access.
USD0, 0.5 hours

11:00AM

Visit the Portland Head Light

Experience the iconic lighthouse at Fort Williams Park, perfect for stunning ocean views.
A short drive from Old Port.
USD0, 1 hour

12:30PM

Lunch at Eventide Oyster Co.

Savor some of Portland's best seafood including fresh oysters and mouth-watering lobster rolls.
Return to Old Port for lunch.
USD35, 1.5 hours

2:00PM

Explore the Portland Museum of Art

Discover an impressive collection of art, from American to contemporary works, at this acclaimed museum.
A short walk from Old Port.
USD15, 2 hours

4:30PM

Check-in at Portland Hotel

Relax before your evening activities, settling into your hotel.
Choose from several downtown options.
Varies, 1 hour

5:30PM

Dinner at Duckfat

Indulge in gourmet fries and sandwiches at the famous Duckfat, known for its homestyle dishes.
Located near your hotel.
USD25, 1.5 hours

7:00PM

Evening at the Old Port

Enjoy a leisurely evening exploring Old Port, filled with shops, bars, and waterfront views.
Walking distance from Duckfat.
USD0, 2 hours
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Day 6: Portland to Camden

Camden, ME

8:00AM

Breakfast at Bayside Bowl

Savor your morning meal in this colorful spot known for delicious breakfast bowls and coffee.
Located a short drive from your hotel.
USD15, 1 hour

9:00AM

Depart Portland for Camden

Travel along the scenic coastline, enjoying the views as you head to Camden.
Follow Route 1 north, approx. 80 miles.
USD0, 1.5 hours

10:30AM

Arrive in Camden

Explore this picturesque town nestled between mountains and the sea.
Park near the harbor for easy access.
USD0, 0.5 hours

11:00AM

Camden Hills State Park

Hike up to the top of Mount Battie for breathtaking views of Camden and the Penobscot Bay.
A short drive from downtown Camden (10 min).
USD6, 2 hours

1:00PM

Lunch at The Waterfront

Enjoy waterfront dining with delicious seafood options and gorgeous harbor views.
Located back in Camden’s downtown area.
USD30, 1.5 hours

2:30PM

Stroll around Camden Village

Roam through Camden's vibrant shops and boutiques, perfect for souvenirs.
You can walk to most shops from the restaurant.
USD0, 1 hour

4:00PM

Check-in at Camden Hotel

Settle into your accommodation and rest before dinner.
Choose a hotel with a harbor view if available.
Varies, 1 hour

5:30PM

Dinner at Theθέατρο

Dine at Theθέατρο, acclaimed for its locally sourced foods and cozy atmosphere.
Walking distance from most hotels.
USD40, 1.5 hours

7:00PM

Sunset at Camden Harbor

End your day with a picturesque sunset by the harbor, a perfect way to unwind.
Directly accessible from your dinner spot.
USD0, 1 hour
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Day 7: Camden to Bar Harbor

Bar Harbor, ME

8:00AM

Breakfast at The Drouthy Bear

Enjoy a hearty breakfast in this cozy establishment known for its warm atmosphere and delicious fare.
Located in Camden.
USD15, 1 hour

9:00AM

Depart Camden for Bar Harbor

Drive toward Bar Harbor, enjoying the views along Route 1.
Approx. 50 miles, around an hour drive.
USD0, 1 hour

10:00AM

Arrive in Bar Harbor

Explore the charming town of Bar Harbor, nestled at the edge of Acadia National Park.
Park in the downtown area.
USD0, 0.5 hours

10:30AM

Acadia National Park - Jordan Pond

Hike around the scenic Jordan Pond, famous for its stunning views of the Bubbles mountains.
Drive to the park entrance, about a 15-minute drive.
USD30 (Park Pass), 2 hours

1:00PM

Lunch at Jordan Pond House

Savor classic popovers and local specialties while overlooking the picturesque Jordan Pond.
Located within Acadia National Park.
USD30, 1.5 hours

2:30PM

Explore Acadia National Park

Continue your adventure in the park by exploring more trails or riding the scenic loop road.
Various trails accessible from Jordan Pond.
USD0, 3 hours

5:30PM

Check-in at Bar Harbor Hotel

Relax and refresh at your hotel after an exciting day of exploring.
Choose a hotel in Bar Harbor for a convenient stay.
Varies, 1 hour

7:00PM

Dinner at The Lobster Shack

A must-visit for lobster lovers, offering fresh lobster rolls and classic New England clams.
Located near the waterfront.
USD35, 1.5 hours

8:30PM

Stroll along the Shore Path

Conclude your day with a peaceful walk along the scenic Shore Path in Bar Harbor.
Accessible from downtown.
USD0, 1 hour
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