10-Day Family Friendly Road Trip Itinerary from Boston, MA - June 2025

Day 1: Explore Boston

Boston, MA

8:00AM

Breakfast at Flour Bakery

Start your day with delicious pastries and coffee at Flour Bakery, a local favorite.
Head northeast on Washington St toward Kneeland St.
USD20, 1 Hour

9:30AM

Visit Boston Freedom Trail

Explore the historic Freedom Trail, which leads you to key sites in American history.
Follow the trail starting at Boston Common.
USD0, 3 Hours

12:30PM

Lunch at Legal Sea Foods

Enjoy a seafood feast at this iconic restaurant known for its fresh catch.
Head to the nearest Legal Sea Foods location in the downtown.
USD60, 1.5 Hours

2:00PM

Boston Children's Museum

Let the kids discover interactive exhibits and play areas at the Boston Children's Museum.
Walk or take a short drive southeast.
USD50, 2 Hours

5:00PM

Dinner at The Capital Grille

Savor an upscale dinner in a family-friendly environment.
Drive back towards the downtown restaurant.
USD100, 2 Hours
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Day 2: Plymouth Adventures

Plymouth, MA

8:00AM

Breakfast at your hotel

Enjoy a hearty breakfast at your Boston hotel before heading out to Plymouth.
Drive south to Plymouth, about 45 minutes.
USD0, 1 Hour

9:30AM

Visit Plimoth Patuxet Museums

Engage with history at living museums that recreate the lives of the Pilgrims and Native Americans.
Follow signs to the museum upon arrival.
USD75, 3 Hours

1:00PM

Lunch at The Lobster Hut

Grab a casual lunch featuring local lobster dishes and other seafood.
Short drive from the museum.
USD60, 1 Hour

2:30PM

Explore Plymouth Rock

Visit the famous Plymouth Rock and learn about its historical significance.
Walk to the waterfront area.
USD0, 1 Hour

4:00PM

Visiting Mayflower II

Take a tour of the replica of the Mayflower, offering insights into the Pilgrims' journey.
Adjacent to Plymouth Rock.
USD20, 1.5 Hours

6:00PM

Dinner at Tavern on the Wharf

Enjoy dinner with a view of the harbor and a family-friendly menu.
Head a few blocks towards the waterfront.
USD80, 1.5 Hours
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Day 3: Cape Cod Beach Day

Cape Cod, MA

8:00AM

Breakfast at Nick's Breakfast & Lunch

Fuel up with hearty breakfast options including pancakes and omelets.
Drive to Cape Cod, about an hour.
USD40, 1 Hour

9:30AM

Visit Cape Cod National Seashore

Spend the morning exploring the beautiful beaches and hiking trails at this stunning national seashore.
Drive to the coastal area.
USD15, 3 Hours

12:30PM

Lunch at The Town Bar & Grill

Enjoy a laid-back lunch with burgers and sandwiches perfect for families.
Short drive to the restaurant.
USD50, 1 Hour

2:00PM

Swim at Race Point Beach

Have fun swimming and building sandcastles at one of Cape Cod’s most family-friendly beaches.
Continue driving to Race Point Beach.
USD0, 3 Hours

5:00PM

Dinner at Mac's On the Pier

Enjoy fresh seafood selections while the family watches the sunset.
Drive to the nearby pier.
USD80, 2 Hours
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Day 4: Martha's Vineyard Exploration

Martha's Vineyard, MA

7:30AM

Breakfast at your hotel

Eat a quick breakfast at your Cape Cod hotel before heading for the ferry.
Drive to Woods Hole ferry terminal.
USD0, 1 Hour

9:00AM

Ferry to Martha's Vineyard

Take the ferry over to Martha's Vineyard (make sure to book tickets in advance).
Catch the ferry at Woods Hole.
USD150, 1 Hour

10:30AM

Explore Oak Bluffs

Visit the charming town of Oak Bluffs, including the famous gingerbread cottages.
Walk around the town center.
USD0, 2 Hours

12:30PM

Lunch at The Seafood Shanty

Dine on seafood dishes with a picturesque view of the harbor.
Short walk to the restaurant.
USD70, 1.5 Hours

2:00PM

Visit Edgartown

Take a scenic drive to Edgartown and explore its historic shops and lighthouse.
Drive a short distance from Oak Bluffs.
USD0, 2.5 Hours

5:00PM

Dinner at The Wharf

Enjoy dinner at The Wharf with family-friendly options and views of the harbor.
Head to the waterfront area in Edgartown.
USD90, 2 Hours
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Day 5: Newport, RI Getaway

Newport, RI

8:00AM

Breakfast at your hotel

Savor a leisurely breakfast at your hotel before departing Martha's Vineyard.
Catch the ferry back to Woods Hole.
USD150, 1 Hour

9:30AM

Drive to Newport

Travel to Newport, which offers scenic coastal views along the way.
Drive along Route 28 and Route 24.
USD0, 1.5 Hours

11:00AM

Visit Breakers Mansion

Explore the grand summer home of the Vanderbilt family and its beautiful gardens.
Directions available at the entrance.
USD30, 1.5 Hours

1:00PM

Lunch at The Red Parrot

Enjoy a tropical-themed restaurant with options ranging from burgers to seafood.
Short drive to the restaurant.
USD70, 1.5 Hours

2:30PM

Explore the Cliff Walk

Take a beautiful walk along the oceanfront, perfect for families and taking photos.
Walk to Cliff Walk entrance.
USD0, 2 Hours

5:00PM

Dinner at 22 Bowen's Wine Bar & Grille

#### Indulge in steak and seafood dishes right by the harbor with family-friendly atmosphere.
Short drive to the restaurant.
USD90, 2 Hours
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Day 6: Cultural Providence

Providence, RI

8:00AM

Breakfast at your hotel

Enjoy breakfast before departing Newport.
Drive north to Providence, about 45 minutes.
USD0, 1 Hour

9:30AM

Visit Roger Williams Park Zoo

Get up close with exotic animals at one of the oldest zoos in the U.S.
Follow signs to the park.
USD60, 2 Hours

12:00PM

Lunch at The Grange

A family favorite serving brunch options with local ingredients.
Head west toward the restaurant.
USD70, 1.5 Hours

1:30PM

Explore WaterFire

Witness the famous WaterFire art installation during certain summer evenings and events.
Walk to the downtown area.
USD0, 2 Hours

3:30PM

Visit Rhode Island School of Design Museum

Take in art and history at one of the most impressive art museums in the region.
Short drive to the museum.
USD15, 2 Hours

6:00PM

Dinner at Federal Hill

Experience delightful Italian cuisine in the charming Federal Hill district.
Drive to Federal Hill.
USD80, 2 Hours
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Day 7: Hartford's Treasures

Hartford, CT

8:00AM

Breakfast at your hotel

Enjoy breakfast before the drive to Hartford.
Travel southwest, about 1 hour.
USD0, 1 Hour

9:30AM

Visit Mark Twain House

Explore the former home of the renowned author and enjoy guided tours.
Drive to the historic site.
USD18, 1.5 Hours

11:30AM

Explore Wadsworth Atheneum Museum of Art

Delight in diverse artwork, including classic and contemporary pieces.
Short drive to the museum.
USD15, 1.5 Hours

1:00PM

Lunch at Salty’s on the River

Dine along the Connecticut River with options for all ages.
Head to the restaurant on the riverbank.
USD70, 1.5 Hours

2:30PM

Visit Connecticut Science Center

Engage with interactive science exhibits—perfect for kids and adults alike.
Drive a short distance to the center.
USD60, 2.5 Hours

5:00PM

Dinner at The Russell

Enjoy a farm-to-table dinner featuring exquisite local dishes.
Drive to the restaurant.
USD90, 2 Hours
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Day 8: Mystic Seaport

Mystic, CT

8:00AM

Breakfast at your hotel

Have breakfast at the hotel before departing Hartford.
Drive to Mystic, about 1 hour.
USD0, 1 Hour

9:30AM

Visit Mystic Seaport Museum

Experience maritime history with hands-on exhibits and historic ships.
Follow signs to the museum.
USD40, 2.5 Hours

12:00PM

Lunch at Mystic Pizza

Grab a slice at the famous pizza shop featured in the movie Mystic Pizza.
Short drive to the restaurant.
USD50, 1.5 Hours

1:30PM

Explore Olde Mistick Village

Stroll through this quaint shopping destination with unique stores.
Walk a short distance from the restaurant.
USD0, 2 Hours

4:00PM

Visit Mystic Aquarium

Interact with marine animals, making this a perfect stop for the family.
Drive a short distance to the aquarium.
USD100, 2 Hours

6:30PM

Dinner at Captain Daniel Packer Inne

End your day with a dinner at a historic inn with excellent local fare.
Drive to the inn.
USD80, 1.5 Hours
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Day 9: New Haven Culture

New Haven, CT

8:00AM

Breakfast at your hotel

Enjoy breakfast before the drive to New Haven.
Drive to New Haven, about 1 hour.
USD0, 1 Hour

9:30AM

Visit Yale University

Take a guided tour of this prestigious university to see its historic architecture.
Walk to the campus from the parking area.
USD0, 1.5 Hours

11:30AM

Explore the Yale Peabody Museum of Natural History

Dive into exhibits featuring dinosaur fossils and natural wonders.
Short walk to the museum.
USD15, 2 Hours

1:30PM

Lunch at Louis' Lunch

Taste the original hamburger at the place that claims to have invented it!
Walk to the famous eatery.
USD50, 1.5 Hours

3:00PM

Visit New Haven Green

Relax at New Haven Green with playgrounds and picnic areas for the kids.
Drive to the Green Park.
USD0, 1.5 Hours

5:00PM

Dinner at The Union League Cafe

End your day with a fine dining experience featuring French cuisine.
Walk or take a short drive to the restaurant.
USD120, 2 Hours
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Day 10: Return to Boston

Boston, MA

8:00AM

Breakfast at your hotel

Have breakfast at your New Haven hotel before heading back to Boston.
Drive back to Boston, about 2 hours.
USD0, 2 Hours

10:30AM

Visit Boston Aquarium

Spend your last morning discovering marine life at the New England Aquarium.
Drive or walk to the aquarium.
USD38, 2 Hours

12:30PM

Lunch at Cheers Boston

Enjoy a meal at the iconic Cheers pub made famous by the TV show.
Head to the nearby Cheers pub.
USD70, 1.5 Hours

2:00PM

Explore Boston's North End

Stroll through the historic North End neighborhood known for its Italian heritage.
Walk towards the North End.
USD0, 2 Hours

4:00PM

Ice Cream at Mike's Pastry

Indulge in famous cannoli and gelato from this renowned bakery.
Walk a short distance to Mike's Pastry.
USD20, 1 Hour

5:30PM

Dinner at The Barking Crab

Wrap up your delightful trip with a relaxed dinner overlooking the harbor.
Drive towards the Barking Crab restaurant.
USD100, 2 Hours
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