Epic Road Trip from Boston to Bar Harbor, Maine with Scenic Coastal Stops

Day 1: Exploring Boston

Boston, MA on August 31, 2024

8:00AM

Breakfast at Tatte Bakery & Cafe

Start your journey with a delightful breakfast filled with fresh pastries and artisan coffee.
Walk from your hotel if downtown or drive with nearby parking options.
USD20, 1 hour

9:30AM

Freedom Trail Walk

Immerse in American history as you follow the Freedom Trail, visiting 16 significant historic sites.
Starting from Boston Common, easily accessible.
Free, 3 hours

12:30PM

Lunch at Quincy Market

Enjoy lunch at this bustling marketplace with a variety of local food options.
Just a short walk from the end of the Freedom Trail.
USD30, 1 hour

1:30PM

Boston Tea Party Ships & Museum

Participate in a historical reenactment and learn about the famous Boston Tea Party.
After lunch, a brief walk will take you to the museum.
USD30, 2 hours

3:30PM

Explore Boston Public Garden

Stroll through the stunning Boston Public Garden, featuring beautiful swan boats.
A short, pleasant walk from the museum.
Free, 1 hour

5:00PM

Dinner at Legal Sea Foods

Savor a meal at a renowned Boston restaurant offering fresh seafood.
Short drive or ride-hailing service can take you there.
USD50, 1.5 hours

6:30PM

Evening Walk Along the Boston Harbor

Relax with a sunset stroll along the scenic Boston Harbor.
Short drive or Uber back towards the harbor area.
Free, 1 hour
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Day 2: More of Boston

Boston, MA on September 1, 2024

8:00AM

Breakfast at Flour Bakery and Cafe

Enjoy a delicious breakfast at this beloved bakery, famous for its creative pastries.
Drive or take public transportation to the South End.
USD20, 1 hour

9:30AM

Visit the Museum of Fine Arts

Explore an impressive collection of art, from ancient artifacts to contemporary works.
Short drive or subway ride to the Fenway area.
USD25, 2 hours

11:30AM

Fenway Park Tour

Experience a guided tour of Fenway Park, one of America's most iconic baseball stadiums.
A short walk from the Museum of Fine Arts.
USD20, 1 hour

1:00PM

Lunch at Jerry Remy's Sports Bar & Grill

Enjoy a laid-back lunch at this casual eatery close to Fenway Park.
A simple walk from Fenway Park.
USD30, 1 hour

2:30PM

Explore Isabella Stewart Gardner Museum

Visit this unique museum housed in a beautiful Venetian-style palace.
Quick drive or taxi ride from Jerry Remy’s.
USD20, 2 hours

4:30PM

Harvard University Campus Tour

Take a leisurely stroll through the historic campus of Harvard University.
Drive or take public transportation to Cambridge.
Free, 1 hour

6:00PM

Dinner at The Capital Grille

Savor fine dining with dry-aged steaks and an extensive wine list.
Short drive back from Harvard to downtown Boston.
USD80, 1.5 hours

8:00PM

Evening Walk Along the Esplanade

Enjoy a peaceful evening stroll along the Esplanade by the Charles River.
Drive to the Esplanade or take public transport.
Free, 1 hour
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Day 3: Day Trip to Salem

Salem, MA on September 2, 2024

8:00AM

Breakfast at The Happy Belly

Kick off your day with a healthy breakfast at this charming quaint café.
Short drive or public transport to Salem.
USD15, 1 hour

9:00AM

Visit The Salem Witch Museum

Learn about the infamous witch trials of 1692 at this engaging museum.
Easily accessible via walking from breakfast.
USD15, 1.5 hours

10:30AM

Explore the House of the Seven Gables

Take a tour of this historic 1668 mansion, famously associated with Nathaniel Hawthorne.
Short walk from the museum.
USD15, 1 hour

12:00PM

Lunch at Olde Main Street Pub

Enjoy a laid-back lunch in a popular tavern known for its cozy atmosphere.
Close walk from The House of the Seven Gables.
USD25, 1 hour

1:30PM

Witch Trials Memorial and Common

Reflect at this solemn memorial dedicated to the victims of the trials.
Short drive or walk to the memorial.
Free, 1 hour

3:00PM

Snap Pictures at the Salem Maritime Historic Site

Enjoy the beautiful waterfront and historic buildings of Salem while capturing photos.
Short walk from the memorial.
Free, 1.5 hours

4:30PM

Depart for Kennebunkport, ME

Begin your drive to Kennebunkport, admiring scenic views along the way.
Drive via I-95 N, taking approximately 1 hour.
GasUSD20, 1 hour

5:30PM

Check into Hotel

Arrive and check into your accommodation in Kennebunkport.
Follow directions to your booked hotel.
Varies, 1 hour

6:30PM

Dinner at The Clam Shack

Savor a delicious lobster roll at this famous roadside eatery.
Nearby your hotel, easily reachable.
USD30, 1 hour
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Day 4: Kennebunkport Exploration

Kennebunkport, ME on September 3, 2024

8:00AM

Breakfast at The Village Coffee Shop

Start your day with a hearty breakfast at this cozy local café.
Short drive from your hotel.
USD15, 1 hour

9:30AM

Visit the Seashore Trolley Museum

Explore the history of public transportation in America at this unique museum.
Drive to the museum, about 20 minutes away.
USD12, 2 hours

11:30AM

Go to Goose Rocks Beach

Unwind at this serene beach, perfect for a morning swim or relaxing on the sand.
Short drive from the trolley museum.
Free, 2 hours

1:30PM

Lunch at The Nonantum Resort

Enjoy lunch with beautiful views of the Kennebunk River.
Drive back towards the resort.
USD30, 1 hour

2:30PM

Exploring Dock Square

Wander through this charming area filled with shops, galleries, and quaint boutiques.
Short drive to Dock Square.
Free, 1.5 hours

4:00PM

Visit Cape Porpoise

Explore the picturesque atmosphere of this coastal village with stunning views.
A quick drive from Dock Square.
Free, 1.5 hours

5:30PM

Dinner at David's KPT

Indulge in a gourmet meal featuring fresh local seafood.
Drive back towards Kennebunkport area.
USD60, 1.5 hours
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Day 5: Portland Adventure

Portland, ME on September 4, 2024

8:00AM

Breakfast at The Holy Donut

Enjoy a delightful breakfast of gourmet potato donuts and coffee.
Short drive from your hotel to Portland.
USD15, 1 hour

9:00AM

Explore the Portland Head Light

Visit this iconic lighthouse and the beautiful park surrounding it.
Drive to Fort Williams Park.
Free, 1.5 hours

10:30AM

Visit the Portland Museum of Art

Explore contemporary and classic works at this vibrant museum.
Drive to downtown Portland from the lighthouse.
USD20, 2 hours

12:30PM

Lunch at Eventide Oyster Co.

Indulge in a seaside lunch featuring fresh seafood and local flavors.
Easy drive from the museum to the restaurant.
USD40, 1.5 hours

2:00PM

Explore the Old Port District

Stroll through Portland’s historic waterfront, filled with shops and galleries.
Short drive or walk from Eventide.
Free, 2 hours

4:00PM

Take the Ferry to Peaks Island

Enjoy a scenic ferry ride to Peaks Island for stunning views of the harbor.
Catch the ferry from the Old Port.
USD18, 2 hours

6:30PM

Dinner at The Lobster Shack

Return to Portland for a delicious dinner of traditional New England lobster.
Drive back from the ferry terminal.
USD50, 1.5 hours
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Day 6: Boothbay Harbor and Journey to Bar Harbor

Boothbay Harbor, ME on September 5, 2024

8:00AM

Breakfast at Boothbay Harbor Ovens

Start your day with a hearty breakfast at this local favorite, known for its pies.
Short drive or walk from your hotel.
USD15, 1 hour

9:30AM

Visit Coastal Maine Botanical Gardens

Explore the beauty of Maine's flora in this stunning garden setting.
Short drive to the gardens.
USD20, 2 hours

11:30AM

Explore Boothbay Harbor

Spend some time enjoying the beautiful scenery and charming shops in Boothbay Harbor.
Drive back into Boothbay Harbor town center.
Free, 1.5 hours

1:00PM

Lunch at The Boathouse Bistro Tapas Bar

Indulge in a varied lunch menu featuring local seafood and tapas-style dishes.
Located conveniently near the harbor.
USD30, 1.5 hours

2:30PM

Depart for Bar Harbor

Hit the road for your final destination, Bar Harbor, enjoying the scenic coastal route.
Drive via ME-27 N, taking about 1.5 hours.
GasUSD30, 1.5 hours

4:00PM

Check into Hotel in Bar Harbor

Arrive in Bar Harbor and check in to your accommodation.
Follow the directions to your selected hotel.
Varies, 1 hour

5:30PM

Dinner at The Reading Room Restaurant

Wrap up your day with a fine dining experience featuring locally sourced ingredients.
Short drive or walk from your hotel.
USD60, 1.5 hours
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Day 7: Exploring Bar Harbor

Bar Harbor, ME on September 6, 2024

8:00AM

Breakfast at Jeannie's Breakfast

Enjoy a hearty breakfast at this popular local spot for fresh and tasty dishes.
Short drive or walk from your hotel.
USD15, 1 hour

9:30AM

Explore Acadia National Park

Dedicate the morning to hiking or biking the beautiful trails in Acadia, such as the Jordan Pond Path.
Head to the park entrance within minutes from downtown.
USD30, 3 hours

12:30PM

Lunch at The Thirsty Whale Tavern

Feast on casual seafood and a friendly atmosphere at this local eatery.
Short drive from the park.
USD25, 1 hour

2:00PM

Kayak in Frenchman Bay

Experience the beauty of Bar Harbor from the water with a guided kayaking adventure.
Meet at the harbor's kayak rental location.
USD50, 2.5 hours

4:30PM

Visit the Bar Harbor Whale Museum

Explore marine life and whale-watching history at this engaging museum.
Short walk from the kayak rental location.
USD10, 1 hour

5:30PM

Final Dinner at Galyn's

Enjoy a farewell dinner featuring delicious seafood and scenic harbor views.
Drive back to Galyn’s from the museum.
USD45, 1.5 hours
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Day 8: Departure Day

Bar Harbor, ME on September 7, 2024

All Day

Travel Day

Pack up and reflect on your incredible journey while traveling back home.
Navigate your way home using your preferred mode of transport.
Varies, All Day
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