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

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 16 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, soaking in the scenic views of the Boston skyline.
Accessible directly from Legal Sea Foods.
USD0, 1 hour
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Day 2: Art and History

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

3:30PM

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 Salem

Salem, MA

8:00AM

Breakfast at Tatte Bakery

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

9:30AM

Depart Boston for Salem

Travel to Salem, famous for its witch trials and rich history.
Approx. 15 miles, about 30-minute drive via I-93N and MA-107N.
USD0, 0.5 hours

10:00AM

Arrive in Salem

Explore the historic town, adorned with charming architecture and witch-related landmarks.
Park in the downtown area for easy exploration.
USD0, 0.5 hours

10:30AM

Salem Witch Museum

Dive into the history of the witch trials at this intriguing museum featuring exhibits and dioramas.
Located within walking distance of downtown Salem.
USD10, 1.5 hours

12:00PM

Lunch at Flying Saucer Pizza

Enjoy quirky and delicious pizza in this fun, UFO-themed establishment.
Located near the museum.
USD15, 1 hour

1:00PM

Salem Maritime National Historic Site

Discover the area’s maritime history and explore several historic buildings.
A short walk from the restaurant.
USD0, 1.5 hours

3:00PM

Explore The House of the Seven Gables

Visit this historic mansion made famous by Nathaniel Hawthorne’s novel, complete with stunning gardens.
Just a short walk away.
USD12, 1 hour

4:30PM

Depart for Kennebunkport

Head to Kennebunkport for a relaxing evening by the coast.
Approx. 35 miles, a 45-minute drive via MA-107N and I-95N.
USD0, 0.75 hours

5:15PM

Dinner at The Clam Shack

Arrive in Kennebunkport and enjoy lobster rolls and fried clams at this local favorite.
Easily accessible once you arrive in Kennebunkport.
USD30, 1.5 hours

7:00PM

Evening Stroll along Dock Square

Conclude your day with a pleasant evening stroll through Dock Square, famous for shops and views of the harbor.
A short walk from The Clam Shack.
USD0, 1 hour
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Day 4: Kennebunkport to Portland

Portland, ME

8:00AM

Breakfast at The Wayfarer Restaurant

Start your day with a delicious breakfast featuring locally sourced ingredients.
Located in Kennebunkport.
USD20, 1 hour

9:00AM

Depart Kennebunkport for Portland

Drive to Portland, enjoying the picturesque coastal views along the way.
Follow Route 1 north, approx. 30 miles.
USD0, 0.5 hours

9:30AM

Arrive in Portland

Explore the Old Port district, known for its cobblestone streets and charming boutiques.
Park near the waterfront area for easy access to shops and restaurants.
USD0, 0.5 hours

10:00AM

Visit the Portland Head Light

Check out this iconic lighthouse at Fort Williams Park, perfect for breathtaking photo opportunities.
A 15-minute drive from downtown Portland.
USD0, 1 hour

11:30AM

Lunch at Eventide Oyster Co.

Dig into some of the best seafood, featuring fresh oysters and delicious lobster rolls.
Located in the Old Port district.
USD35, 1.5 hours

1:00PM

Visit the Portland Museum of Art

Discover an impressive collection of American, European, and contemporary art at this well-rounded museum.
A short drive from the restaurant.
USD15, 1.5 hours

3:00PM

Hotel Check-in at Portland

Relax and refresh at your hotel before the evening activities.
Choose from several hotels in the downtown area.
Varies, 1 hour

6:00PM

Dinner at Duckfat

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

8:00PM

Evening at the Old Port

Enjoy a leisurely evening exploring the Old Port, filled with great shops, bars, and waterfront views.
Walking distance from Duckfat.
USD0, 2 hours
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Day 5: To Bar Harbor

Bar Harbor, ME

8:00AM

Breakfast at Bayside Bowl

Savor your morning meal in this colorful spot known for delicious breakfast bowls and coffee.
Located in Portland.
USD15, 1 hour

9:00AM

Depart Portland for Bar Harbor

Drive to Bar Harbor, enjoying the scenic views along Route 1.
Approx. 90 miles, around 2 hours drive.
USD0, 2 hours

11:00AM

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

11:30AM

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

1:30PM

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

3:00PM

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

6:00PM

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

7:30PM

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

9:00PM

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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Day 6: More of Bar Harbor

Bar Harbor, ME

8:00AM

Breakfast at Cafe This Way

Start the day with a hearty breakfast in this local favorite known for its innovative dishes.
A short walk from most hotels.
USD20, 1 hour

9:00AM

Bike the Carriage Roads

Enjoy breathtaking views as you bike along the scenic carriage roads in Acadia National Park.
Bike rentals are available in Bar Harbor.
USD20 (Bike Rental), 3 hours

12:30PM

Lunch at Cafe This Way

Return to Cafe This Way for delicious options, featuring locally sourced ingredients.
Walking distance from the bike rental.
USD25, 1 hour

1:30PM

Visit Acadia National Park's Cadillac Mountain

Drive to the summit of Cadillac Mountain to catch sweeping vistas of the surroundings.
About a 15-minute drive from Bar Harbor.
USD30 (National Park Pass if needed), 2 hours

4:00PM

Afternoon Kayaking

Experience the beauty of Bar Harbor from the water with an afternoon of kayaking along the coastline.
Kayak rentals and tours are available at the harbor.
USD50, 2 hours

6:30PM

Dinner at Stewman's Lobster Pound

Treat yourself to a classic Maine lobster dinner at this waterside establishment.
Short drive or walk from downtown.
USD45, 2 hours

8:30PM

Evening stroll around Bar Harbor

Enjoy your last evening in Bar Harbor with a leisurely stroll through the quaint streets.
Accessible from your dining location.
USD0, 1 hour
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Day 7: Departure from Bar Harbor

Bar Harbor, ME

8:00AM

Breakfast at Jeannie's Breakfast

Start with a classic breakfast diner experience, perfect for fueling up before your departure.
Located in Bar Harbor.
USD15, 1 hour

9:00AM

Last-minute exploration in Bar Harbor

Use this time to visit any shops or attractions you might have missed during your stay.
Easy to navigate through Bar Harbor’s downtown.
USD0, 1 hour

10:00AM

Depart Bar Harbor for Home

Begin your journey back home or to your next destination, reminiscing about your adventures.
Head south on Route 3.
USD0, Varies
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