Epic Road Trip from Boston to Bar Harbor, Maine, August 2024

Day 1: Exploring Boston

Boston, MA on August 31, 2024

8:00AM

Breakfast at Tatte Bakery & Cafe

Start your journey with a delightful breakfast at Tatte Bakery, known for its pastries and artisan coffee.
Walk from your hotel if located 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, a 2.5-mile red-brick path leading through 16 historic sites.
Starting from Boston Common, which is central and easy to access.
Free, 3 hours

12:30PM

Lunch at Quincy Market

Enjoy lunch at Quincy Market with a variety of local foods from clam chowder to lobster rolls.
Short walk from the ending point of the Freedom Trail.
USD30, 1 hour

1:30PM

Visit the Boston Tea Party Ships & Museum

Explore the interactive museum that offers a historical reenactment of the Boston Tea Party.
A short walk from Quincy Market.
USD30, 2 hours

3:30PM

Parks and Public Gardens

Stroll through the beautiful Boston Public Garden, where you can see the famous swan boats.
A pleasant walk from the museum.
Free, 1 hour

5:00PM

Dinner at Legal Sea Foods

Enjoy a seafood dinner at a Boston institution, famous for fresh catch and New England clam chowder.
A short drive or an Uber from the gardens.
USD50, 1.5 hours

6:30PM

Evening at the Boston Harbor

Take a sunset walk along the Boston Harbor, soaking in the views of the skyline and the sea.
Short drive back towards the harbor or Uber.
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

Start your day with a scrumptious breakfast and pastries at this beloved local spot.
Drive or take public transport to the South End.
USD20, 1 hour

9:30AM

Visit the Museum of Fine Arts

Admire an impressive collection of artwork, featuring everything from Ancient Egyptian artifacts to contemporary pieces.
Short drive or subway ride to the Fenway area.
USD25, 2 hours

11:30AM

Fenway Park Tour

Experience the iconic Fenway Park with a guided tour of one of the oldest ballparks in the country.
Easy walk from the Museum of Fine Arts.
USD20, 1 hour

1:00PM

Lunch at Jerry Remy's Sports Bar & Grill

Refuel at this casual eatery close to Fenway Park, perfect for a post-tour lunch.
Walking distance from Fenway Park.
USD30, 1 hour

2:30PM

Explore the Isabella Stewart Gardner Museum

Visit this unique museum featuring an enchanting collection of art in a Venetian-style palazzo.
A quick drive or short taxi ride from Jerry Remy’s.
USD20, 2 hours

4:30PM

Harvard University Campus Tour

Take a stroll through the historic Harvard University, soaking in the collegiate atmosphere.
Drive or public transport to Cambridge.
Free, 1 hour

6:00PM

Dinner at The Capital Grille

Indulge in a fine dining experience with dry-aged steaks and fresh seafood.
Short drive from Harvard back to downtown Boston.
USD80, 1.5 hours

8:00PM

Evening Stroll Along the Esplanade

Enjoy a relaxing evening walk along the Charles River Esplanade.
Drive to the Esplanade or use public transport.
Free, 1 hour
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Day 3: Final Day in Boston

Boston, MA on September 2, 2024

8:00AM

Breakfast at South End Buttery

Enjoy a hearty breakfast at this cozy cafe in the South End.
Drive to the South End.
USD20, 1 hour

9:30AM

Visit the New England Aquarium

Discover the underwater world at the New England Aquarium, complete with an IMAX theater.
Drive or take the metro from the South End.
USD30, 2 hours

11:30AM

Walk through Faneuil Hall Marketplace

Take a leisurely walk through the vibrant Faneuil Hall, shopping and enjoying street performances.
Short walk from the Aquarium.
Free, 1 hour

12:30PM

Lunch at Bell in Hand Tavern

Stop for lunch at the oldest continuously operating tavern in the U.S. for a taste of local culture.
A short walk from Faneuil Hall.
USD25, 1 hour

2:00PM

Visit the Boston Science Museum

Explore hands-on exhibits at one of the most popular science museums in the U.S.
Take a quick drive or public transit to the museum.
USD28, 2.5 hours

4:30PM

Relax at the Boston Common

Unwind in the scenic Boston Common before your road trip to Bar Harbor.
Drive back to the Common from the Science Museum.
Free, 1 hour

5:30PM

Dinner at Mamma Maria

Relish authentic Italian cuisine in the North End, known for its charming atmosphere.
Drive or Uber to the North End.
USD50, 1.5 hours
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Day 4: Drive to Bar Harbor

Boston, MA to Bar Harbor, ME on September 3, 2024

8:00AM

Breakfast at The Paramount

Fuel up with breakfast at The Paramount, famous for its fresh and flavorful dishes.
Drive to the restaurant in Beacon Hill.
USD20, 1 hour

9:00AM

Hit the Road to Bar Harbor

Start your scenic drive to Bar Harbor, taking in views along the way.
Drive via I-95 N for approximately 4.5 hours.
GasUSD40, 4.5 hours

1:30PM

Lunch at The Lobster Shack

Stop for a quintessential Maine lobster roll on the way to Bar Harbor.
Located conveniently off Route 1.
USD25, 1 hour

2:30PM

Arrive in Bar Harbor

Check into your accommodation and get settled before your adventures.
Drive to your selected hotel in Bar Harbor.
Varies, 1 hour

4:00PM

Explore Acadia National Park

Take the afternoon to start exploring the stunning landscapes of Acadia, enjoying hiking trails or scenic drives.
Drive to the park entrance from your hotel.
USD30, 2.5 hours

6:30PM

Dinner at Side Street Cafe

Relish a local dinner at this cozy cafe known for its fresh seafood and friendly atmosphere.
Drive back to Bar Harbor after your park adventure.
USD40, 1.5 hours
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Day 5: Adventure in Bar Harbor

Bar Harbor, ME on September 4, 2024

8:00AM

Breakfast at Jeannie's Breakfast

Start the day at Jeannie's, where you can find hearty breakfast options and homemade specials.
Short drive or walk depending on your accommodation.
USD15, 1 hour

9:30AM

Kayaking in Frenchman Bay

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

12:30PM

Lunch at The Thirsty Whale Tavern

Enjoy a casual lunch with fresh seafood, burgers, and salads at this local favorite.
Nearby the kayaking starting point.
USD25, 1 hour

2:00PM

Visit the Bar Harbor Whale Museum

Learn about the marine life in the area and the history of whale watching.
Short walk from The Thirsty Whale.
USD10, 1 hour

3:00PM

Relax at Sand Beach

Spend a relaxing afternoon unwinding at the picturesque Sand Beach.
Drive to Sand Beach, within Acadia National Park.
Free, 2 hours

5:00PM

Dinner at Galyn's

End the day with a meal at Galyn's, offering delicious dining and a great view of Acadia.
Drive back to Bar Harbor.
USD45, 1.5 hours
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Day 6: Final Day in Bar Harbor

Bar Harbor, ME on September 5, 2024

8:00AM

Breakfast at Café This Way

Savor a delightful breakfast at this popular café, known for its creative dishes and warm atmosphere.
Drive or walk from your accommodation.
USD20, 1 hour

9:30AM

Hike at Acadia National Park

Embark on a morning hike on one of Acadia's scenic trails, like the Jordan Pond Path.
Head back to Acadia National Park.
Free, 2.5 hours

12:00PM

Lunch at Beal's Lobster Pier

After your hike, enjoy fresh lobster at this iconic Maine lobster pound.
Drive to the pier located on the other side of the island.
USD40, 1 hour

1:30PM

Visit Cadillac Mountain

Take a drive and explore Cadillac Mountain, the highest point along the North Atlantic coast.
Drive from Beal's to Cadillac Mountain.
Free, 2 hours

3:30PM

Relax Before Departure

Spend some time resting and reflecting on your adventures before heading back to Boston.
Return to your hotel to gather your belongings.
Free, 1 hour

4:30PM

Departure Dinner at The Reading Room Restaurant

Have a farewell dinner at this upscale restaurant offering great seafood and a sophisticated atmosphere.
Drive to your chosen restaurant before departing Bar Harbor.
USD60, 1.5 hours
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Day 7: Return to Boston

Bar Harbor, ME to Boston, MA on September 6, 2024

7:00AM

Breakfast at The Breakfast Klatch

Start your day with a hearty breakfast before hitting the road back to Boston.
Drive to the Breakfast Klatch.
USD15, 1 hour

8:00AM

Depart for Boston

Drive back to Boston, reminiscing over the incredible experiences of your trip.
Follow directions back on Route 3 and I-95 S.
GasUSD40, 4.5 hours

12:30PM

Lunch at James Hook & Co.

Immediately upon returning, treat yourself to Boston’s famous lobster roll at this renowned seafood market.
Short drive from your accommodations.
USD30, 1 hour

2:00PM

Last-minute Shopping on Newbury Street

Spend your afternoon shopping at chic boutiques and stores before your flight.
Easily accessible by car or public transport.
Varies, 2 hours

4:00PM

Return Rental Car

Make sure to return your rental car before your flight.
Drive to the rental return location at the airport.
Free, 1 hour

5:30PM

Fly Out of Boston

Conclude your trip with a flight home, filled with unforgettable memories and experiences.
Head to the airport from the rental return.
Varies, As per flight schedule
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Day 8: Departure Day

Boston, MA on September 7, 2024

All Day

Travel Day

Enjoy recollecting your trip during your travel back home.
Navigate your way home using your preferred mode of transport.
Varies, All Day
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