14-Day Adventure and Foodie Road Trip in Boston and Surroundings

Day 1: Explore Historic Boston

Boston, USA

8:00AM

Breakfast at Tatte Bakery

Start your day with a delicious pastry and coffee at Tatte, popular for its fresh ingredients.
Walk from hotel or take the T.
USD15, 1 hour

9:30AM

Freedom Trail

Walk the 2.5-mile Freedom Trail, a path through Boston that connects 16 historic sites.
Begin at Boston Common.
Free, 3 hours

1:00PM

Lunch at Quincy Market

Enjoy a variety of local food stalls at the historic Quincy Market.
Short walk from the end of Freedom Trail.
USD20, 1 hour

3:00PM

Visit the New England Aquarium

Explore marine life exhibits and the delightful sea lions at the aquarium.
Walk or ride the T to the aquarium.
USD32, 2 hours

6:00PM

Dinner at Legal Sea Foods

Savor fresh seafood at this renowned Boston institution.
Short walk from the aquarium.
USD35, 1.5 hours
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Day 2: Cambridge Culture

Cambridge, USA

8:00AM

Breakfast at Flour Bakery

Grab a scrumptious breakfast sandwich and coffee at this popular spot.
Take the T to Kendall/MIT.
USD15, 1 hour

9:30AM

Harvard University Tour

Take a guided tour of one of the most prestigious universities in the world.
Walk to Harvard Yard.
USD15, 2 hours

12:00PM

Lunch at Mr. Bartley's Burger Cottage

Enjoy an infamous burger in historic Harvard Square.
Short walk from Harvard.
USD20, 1 hour

1:30PM

MIT Museum

Discover the intersection of art and science at the MIT Museum.
Walk or use the T to go to MIT.
USD10, 1.5 hours

4:00PM

Boston Public Library

Enjoy the architectural beauty and free exhibitions of this historic gem.
Take the T back to Boston.
Free, 1.5 hours

6:00PM

Dinner at The Capital Grille

Savor a premium steak at this upscale steakhouse, if budget allows; otherwise, choose from nearby eateries.
Walk nearby for a choice of budget-friendly options.
USD50, 2 hours
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Day 3: Witchy Salem

Salem, USA

8:00AM

Breakfast at A&J King Bakery

Indulge in fresh-baked bread and pastries to fuel your Salem adventure.
Drive to Salem, about 30 minutes from Boston.
USD10, 1 hour

9:30AM

Salem Witch Museum

Learn about the infamous witch trials in this engaging museum.
Short walk from the bakery.
USD12, 1 hour

11:00AM

House of the Seven Gables

Visit the historic house and beautiful gardens of the famous Nathaniel Hawthorne.
Short walk to the location.
USD15, 1.5 hours

1:00PM

Lunch at Turners Seafood

Delight in fresh seafood in a historic setting, an elegant experience.
Walk back to the downtown.
USD30, 1.5 hours

3:00PM

Peabody Essex Museum

Discover rich cutures through the vast art exhibits at PEM.
Walk to the museum from lunch.
USD18, 2 hours

6:00PM

Dinner at Finz Seafood & Grill

Choose from a variety of local catches in a relaxed atmosphere.
Walk from PEM.
USD25, 1.5 hours
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Day 4: Historic Plymouth

Plymouth, USA

8:00AM

Breakfast at The Blueberry Muffin

Start your day with a hearty breakfast featuring local and fresh ingredients.
Drive to Plymouth, about 30 minutes from Salem.
USD10, 1 hour

9:30AM

Plymouth Rock

Visit the rock where the Pilgrims landed in 1620, a must-see landmark.
Drive short distance to waterfront.
Free, 1 hour

11:00AM

Plimoth Patuxet Museums

Experience early colonial life in this outdoor living history museum.
Walk from Plymouth Rock.
USD35, 2.5 hours

2:00PM

Lunch at East Bay Grille

Enjoy waterfront dining while savoring New England seafood specialties.
Short drive from Plimoth Patuxet.
USD25, 1.5 hours

4:00PM

Visit Mayflower II

Board a full-scale replica of the Mayflower, an iconic piece of history.
Walk from lunch.
USD20, 1 hour

6:00PM

Dinner at Mamma Mia’s

End your day with familiar Italian comfort food in charming Plymouth.
Drive back to downtown.
USD20, 1.5 hours
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Day 5: Relax in Cape Cod

Cape Cod, USA

8:00AM

Breakfast at A Little Sandwich Shop

Indulge in hearty breakfast sandwiches made with fresh ingredients.
Drive to Cape Cod, about an hour from Plymouth.
USD12, 1 hour

9:30AM

Cape Cod National Seashore

Explore sandy beaches and scenic trails in this stunning natural preserve.
Drive to the national park entrance.
Free, 4 hours

1:30PM

Picnic Lunch at Coast Guard Beach

Pack your own lunch from the sandwiches in the morning and enjoy it on the beach.
Set up at a picnic spot on the beach.
USD10, 1 hour

3:00PM

Biking around Cape Cod

Rent a bike and explore the scenic Cape Cod Rail Trail.
Nearby bike rental shops are available.
USD25, 3 hours

6:00PM

Dinner at The Lobster Pot

Enjoy a spectacular view and delicious seafood at this iconic restaurant.
Drive to Provincetown.
USD35, 2 hours
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Day 6: Island Getaway - Martha's Vineyard

Martha's Vineyard, USA

8:00AM

Breakfast at The Black Dog Tavern

Begin your day with a homemade breakfast in a quintessential island tavern.
Take the ferry from Woods Hole to Martha's Vineyard.
USD20 (ferry included), 1 hour

9:30AM

Rent a bike

Rent a bike to explore the beautiful coastline and charming towns.
Multiple bicycle rental shops available by the ferry terminal.
USD25, 10 minutes

10:00AM

Tour Edgartown

Visit historic Edgartown with its picturesque streets and boutiques.
Bike to Edgartown.
Free, 2 hours

12:30PM

Lunch at The Wharf Pub

Have a lovely lunch with views of the harbor while enjoying classic American fare.
Bike back to Edgartown.
USD25, 1.5 hours

2:00PM

Visit Aquinnah Cliffs

Marvel at the stunning multi-colored cliffs and coastal views.
Bike to Aquinnah.
Free, 3 hours

5:30PM

Dinner at The Seafood Shanty

Enjoy a casual dining experience with fresh seafood and a lively atmosphere.
Bike back to Edgartown.
USD30, 1.5 hours
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Day 7: Discover Nantucket

Nantucket, USA

7:30AM

Breakfast at The Morning Glory Farm

Savor freshly made pastries and coffee at this lovely farm stand.
Take the ferry from Martha's Vineyard to Nantucket.
USD25 (ferry included), 1 hour

9:00AM

Whaling Museum

Learn about Nantucket’s whaling history in this engaging museum.
Walk from the ferry terminal.
USD15, 1 hour

11:00AM

Explore Nantucket Town

Stroll through charming streets filled with boutiques and local art.
Walk around town.
Free, 1.5 hours

1:00PM

Lunch at Black-Eyed Susan's

Delight in seasonal dishes at this cozy eatery cherished by locals.
Short walk from the town center.
USD25, 1.5 hours

2:30PM

Hit the Beaches

Enjoy some relaxation time at Surfside Beach, perfect for sunbathing.
Local shuttle or bike rental available.
Free, 3 hours

6:00PM

Dinner at The Club Car

Wrap up your Nantucket experience with a delicious meal in a historic train station.
Take the shuttle or bike back to town.
USD40, 1.5 hours
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Day 8: Return to Boston

Boston, USA

8:00AM

Breakfast at The Downy Flake

Enjoy the famous donuts and hearty breakfasts at this local favorite.
Take the ferry back from Nantucket to the mainland.
USD15 (ferry included), 1 hour

9:30AM

Explore Fenway Park

Take a tour of the historic ballpark, home to the Boston Red Sox.
Drive to Fenway.
USD20, 1.5 hours

12:00PM

Lunch at The Cask 'n Flagon

Enjoy pub fare in the heart of the Fenway area, a popular spot for fans.
Short walk from Fenway Park.
USD25, 1.5 hours

1:30PM

Isabella Stewart Gardner Museum

Discover unique art and stunning gardens in this remarkable museum.
Drive or T to the museum.
USD15, 2 hours

4:00PM

Explore the North End

Wander through Boston's Little Italy and sample Italian pastries.
Drive or T to the North End.
Free, 1.5 hours

6:00PM

Dinner at Giacomo’s

Enjoy one of the best Italian meals in town with robust flavors.
Short walk through the North End.
USD40, 2 hours
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Day 9: Lexington Adventure

Lexington, USA

8:00AM

Breakfast at The Depot

Enjoy a quaint breakfast in a historic setting before heading to Lexington.
Drive to Lexington, about 30 minutes from Boston.
USD12, 1 hour

9:30AM

Lexington Battle Green

Learn about the historic Battles of Lexington and Concord at the iconic green.
Short drive to the site.
Free, 1 hour

11:00AM

Minute Man National Historical Park

Visit this park that commemorates the beginning of the Revolutionary War.
Short drive to the park.
Free, 2 hours

1:00PM

Lunch at Lexington Center

Enjoy a casual meal with local flavors at one of the area’s eateries.
Short drive to the town center.
USD20, 1.5 hours

3:00PM

Explore Louisa May Alcott’s Orchard House

Visit the home where the author wrote Little Women and learn about her life.
Drive to Orchard House.
USD12, 1.5 hours

5:00PM

Dinner at The Colonial Inn

Dine in a quaint atmosphere, enjoying New England cuisine.
Short drive back to town center.
USD30, 1.5 hours
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Day 10: Inspiring Concord

Concord, USA

8:00AM

Breakfast at Concord's Colonial Inn

Enjoy breakfast in this historic inn known for its charm.
Short drive to Concord from Lexington.
USD15, 1 hour

9:30AM

Concord Museum

Explore exhibits related to Concord’s rich literary history and artifacts.
Drive to the museum.
USD10, 1 hour

11:00AM

Explore Walden Pond

Visit the serene Walden Pond, where Henry David Thoreau found inspiration.
Short drive to Walden Pond.
USD10 (parking fee), 2 hours

1:00PM

Lunch at the Colonial Inn

Return for a delicious lunch surrounded by history.
Drive back to the inn.
USD20, 1.5 hours

2:30PM

Thoreau's Sleepy Hollow Cemetery

Visit the gravesite of Henry David Thoreau and other notable figures.
Short drive to cemetery.
Free, 1 hour

4:00PM

Dinner at the 99 Restaurant

Wrap up the day with casual dining at a family-friendly chain.
Short drive to the restaurant.
USD25, 1.5 hours
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Day 11: Nature at Walden Pond

Concord, USA

8:00AM

Breakfast at Helen's Restaurant

Enjoy classic American breakfast with a homey vibe in Concord.
Drive to nearby restaurant.
USD12, 1 hour

9:30AM

Biking around Walden Pond

Rent a bike to explore the scenic trails around Walden Pond.
Rental shops near the park.
USD25, 2 hours

12:00PM

Picnic Lunch

Pack a picnic to enjoy by the serene waters of Walden.
Bring your packed lunch or buy nearby.
USD10, 1 hour

1:00PM

Nature Walk at Walden

Enjoy a leisurely nature walk, reflecting on Thoreau’s philosophy.
Explore trails on foot.
Free, 2 hours

3:30PM

Visit Orchard House

Learn more about Louisa May Alcott in her home environment.
Drive to Orchard House.
USD12, 1.5 hours

6:00PM

Dinner at The Olde Magoun's Saloon

Relax at a cozy pub acclaimed for delicious comfort food.
Drive to the nearby restaurant.
USD20, 2 hours
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Day 12: Coastal Getaway to Gloucester

Gloucester, USA

8:00AM

Breakfast at The Coffee Shop

Start your day with delicious coffee and breakfast in scenic Gloucester.
Drive to Gloucester, about an hour from Concord.
USD10, 1 hour

9:30AM

Visit the Cape Ann Museum

Discover art and history from the Cape Ann region, celebrating local culture.
Short drive to the museum.
USD10, 1.5 hours

11:00AM

Take a Whale Watching Tour

Get ready for an exciting sea adventure as you encounter whales in their habitat.
Book a tour and depart from Harbor.
USD45, 3 hours

2:00PM

Lunch at The Lobster Bar

Enjoy fresh lobster rolls that Gloucester is known for.
Walk to the restaurant after whale watching.
USD25, 1.5 hours

3:30PM

Relax at Good Harbor Beach

Spend the rest of the afternoon relaxing on the beach.
Short drive from the restaurant.
Free, 2 hours

6:00PM

Dinner at The Cape Sea Grille

Conclude your day with a fine dining experience featuring fresh, local ingredients.
Short drive from the beach.
USD40, 2 hours
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Day 13: Discover Rockport

Rockport, USA

8:00AM

Breakfast at The Tea Room

Start your day with a delightful breakfast in a cozy café.
Short drive to Rockport, about 30 minutes from Gloucester.
USD12, 1 hour

9:30AM

Explore Bearskin Neck

Wander along this historic motif area filled with unique shops and galleries.
Walk around the promenade.
Free, 1.5 hours

11:00AM

Visit the Rockport Art Association

Immerse yourself in local art showcased in this charming setting.
Short walk from Bearskin Neck.
USD10, 1 hour

1:00PM

Lunch at The Lobster Pool

Enjoy a meal with astonishing views of the waterfront.
Short drive to the restaurant.
USD25, 1.5 hours

2:30PM

Relax at Front Beach

Spend some leisure time soaking in the sun at the beach.
Short drive from lunch location.
Free, 2 hours

5:00PM

Dinner at Dock Square Restaurant

Enjoy delicious seafood in a picturesque waterfront location.
Drive back to Rockport.
USD35, 2 hours
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Day 14: Wrap Up in Boston

Boston, USA

8:00AM

Breakfast at The Paramount

Indulge in a classic breakfast that’s beloved by locals in the South End.
Drive back to Boston.
USD15, 1 hour

9:30AM

Visit Boston’s Museum of Fine Arts

Admire an extensive collection of fine arts from around the world.
Drive or T to the museum.
USD25, 2 hours

12:00PM

Lunch at The Butcher Shop

Enjoy freshly made sandwiches and charcuterie at this trendy spot.
Short walk from the museum.
USD20, 1.5 hours

1:30PM

Last-minute Shopping on Newbury Street

Explore boutiques and shops on this famous shopping street.
Walk or take the T.
Varies, 2 hours

4:00PM

Relax at the Boston Public Garden

Conclude your trip with a stroll through this lush public garden.
Short walk from shopping.
Free, 1.5 hours

6:00PM

Dinner at The Capital Grille

For a final celebratory dinner, enjoy a fine multicultural dining experience.
Drive or T to the restaurant.
USD50, 2 hours
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