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Family Friendly Massachusetts Adventure

Viewed by 71 travelers

Day 1: City Exploration

Boston, Massachusetts

8:00AM

Breakfast at Flour Bakery + Cafe

Start your day with delicious pastries and coffee at Flour Bakery + Cafe to energize for a day of exploring Boston.
Head to Flour Bakery + Cafe located at 12 Farnsworth St.
$15, 1 hour

10:00AM

Freedom Trail Walking Tour

Embark on a guided walk along the historic Freedom Trail to learn about the Revolutionary War and see sites like Boston Common and Faneuil Hall.
Meet the tour guide at Boston Common Visitor Information Center.
$25 per person, 2 hours

1:00PM

Lunch at Union Oyster House

Enjoy a classic New England seafood meal at the historic Union Oyster House, the oldest continuously operating restaurant in the U.S.
Head to 41 Union St, Boston, for a taste of fresh seafood.
$30, 1 hour

3:00PM

Boston Children's Museum

Take the family to the Boston Children's Museum for interactive exhibits and hands-on activities that engage both kids and adults.
Drive to the museum located at 308 Congress St.
$20 per person, 2 hours

6:00PM

Dinner at Giacomo's Ristorante

Indulge in hearty Italian fare at Giacomo's Ristorante, known for its delicious pasta dishes and cozy ambiance.
Visit 355 Hanover St, Boston, for a memorable dining experience.
$40, 1.5 hours
Find Hotels in Boston

Day 2: Historic Salem

Salem, Massachusetts

9:00AM

Breakfast at The Ugly Mug Diner

Fuel up with a hearty breakfast at The Ugly Mug Diner before heading to Salem.
Grab breakfast at 122 Washington St, Salem.
$20, 1 hour

11:00AM

Salem Witch Museum

Learn about the infamous Salem witch trials at the Salem Witch Museum through exhibits and presentations.
Visit 19 1/2 N Washington Square, Salem.
$15 per person, 1.5 hours

1:00PM

Lunch at Sea Level Oyster Bar

Savor fresh seafood and scenic views of the harbor at Sea Level Oyster Bar for a relaxing lunch.
Head to 94 Wharf St, Salem, for a delicious meal.
$35, 1 hour

3:00PM

Explore Salem Maritime National Historic Site

Stroll through the Salem Maritime National Historic Site to see historic ships and learn about Salem's maritime history.
Walk to 160 Derby St, Salem.
Free, 1.5 hours

6:00PM

Dinner at Ledger Restaurant

Enjoy a farm-to-table dining experience at Ledger Restaurant, known for its innovative and locally sourced menu.
Dine at 125 Washington St, Salem, for a delicious dinner.
$50, 1.5 hours
Find Hotels in Salem

Day 3: Scenic Cape Cod

Cape Cod, Massachusetts

9:00AM

Breakfast at The Red Cottage

Start your morning with a cozy breakfast at The Red Cottage, known for its delicious homemade fare and cozy atmosphere.
Have breakfast at 36 Main St, South Dennis.
$25, 1 hour

11:00AM

Cape Cod National Seashore

Explore the pristine beaches and scenic trails of Cape Cod National Seashore for a relaxing outdoor experience.
Head to 99 Marconi Site Rd, Wellfleet, and soak in the natural beauty.
$20 per vehicle, 2 hours

1:00PM

Lunch at The Lobster Pot

Treat yourselves to a seafood feast at The Lobster Pot, a Cape Cod institution known for its fresh seafood and waterfront views.
Enjoy lunch at 321 Commercial St, Provincetown.
$40, 1 hour

3:00PM

Hyannis Main Street

Shop and stroll along Hyannis Main Street, known for its quaint shops, historic sites, and vibrant atmosphere.
Explore the street in downtown Hyannis.
Varies based on shopping, 2 hours

6:00PM

Dinner at The Naked Oyster

Savor upscale seafood dishes at The Naked Oyster, a cozy restaurant with a focus on fresh ingredients and creative cuisine.
Dine at 410 Main St, Hyannis, for a memorable dinner.
$60, 1.5 hours
Find Hotels in Cape Cod
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More About Massachusetts

Trip Packing List: Massachusetts (February 1)
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Salem, Massachusetts — October 6–10, 2025
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