Family-Friendly 7-Day Multigenerational Cape Cod Adventure Itinerary

Day 1: Outer Cape Exploration

Provincetown, Massachusetts on June 1, 2025

8:00am

Breakfast at The Mews Restaurant & Cafe

Enjoy a family-friendly breakfast offering locally sourced ingredients and kid favorites such as pancakes and scrambled eggs. The cozy atmosphere is perfect for all ages.
USD30 per person, 1h

9:30am

Provincetown Whale Watching Tour

Depart on a renowned whale watching tour from Provincetown Harbor. Children will be fascinated by the close-up views of whales and other marine life. Tours usually last around three hours.
USD50 per adult, USD30 per child, 3h

1:00pm

Lunch at The Purple Feather Cafe & Treatery

Stop at this charming spot for casual sandwiches, soups, and homemade ice cream — a delight for kids and adults alike.
USD15-25 per person, 1h

2:30pm

Pilgrim Monument & Provincetown Museum

Visit the tallest granite monument in the U.S., climb to the top for panoramic views, and explore the museum to learn about Pilgrim history and Cape Cod heritage. Suitable for all generations.
USD20 adults, children under 5 free, 1h30m

5:00pm

Relax at Herring Cove Beach

Unwind with the family on this gentle sandy beach known for calm waters, ideal for small children to splash and play.
Free, 1h30m

7:00pm

Dinner at The Lobster Pot

Dine family-style with iconic New England seafood alongside kid-friendly options in a casual waterfront setting.
USD30-50 per person, 1h30m
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Day 2: Truro & Wellfleet Wildlife

Truro and Wellfleet, Massachusetts on June 2, 2025

8:00am

Breakfast at Truro Vineyards Cafe

Start the day with wholesome breakfast fare, including fresh pastries and farm eggs, surrounded by beautiful vineyard views.
USD20 per person, 1h

9:30am

Visit the Cape Cod National Seashore - Head of the Meadow Beach

Enjoy a morning walk at a family-friendly beach known for its gentle waves and picturesque dunes.
Free, 1h30m

11:15am

Wellfleet Bay Wildlife Sanctuary

Explore this nature center with walking trails and a touch tank, perfect for kids to learn about coastal ecosystems.
USD5 per adult, children free, 2h

1:30pm

Lunch at Mac's Shack

Enjoy a casual meal of seafood and fresh salads with outdoor seating suitable for families.
USD20-35 per person, 1h

3:00pm

Explore Wellfleet Drive-In Theatre

Experience a unique Cape Cod drive-in movie theater. Catch an early family-friendly movie or explore the area attractions nearby.
USD12 per person, 2h

6:00pm

Dinner at Kream 'N Kone

Savor classic New England clam chowder and homemade ice cream at this local favorite, great for all ages.
USD15-25 per person, 1h
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Day 3: Mid-Cape Culture

Eastham and Orleans, Massachusetts on June 3, 2025

8:00am

Breakfast at Hole in One Donuts & Breakfast

Treat the family to freshly made doughnuts and breakfast sandwiches, a quick and delicious start for everyone.
USD10-15 per person, 45m

9:00am

Visit to Nauset Light Beach

Spend the morning at this iconic Cape Cod lighthouse site with safe swimming areas and gorgeous sandy beaches suitable for kids.
USD15 parking, 2h

11:30am

Cape Cod National Seashore Salt Pond Visitor Center

Explore interactive exhibits and walking trails showcasing local flora, fauna, and pirate history.
Free, 1h

12:30pm

Lunch at The Knack in Orleans

Enjoy fresh seafood, clam cakes, and kid-friendly meals in a casual and welcoming environment.
USD20-30 per person, 1h

2:00pm

Skydive Cape Cod Observation Area

Watch skydivers land and enjoy the stunning panoramic views - fun and exciting for the whole family.
Free, 1h

3:30pm

Explore Orleans Farmers Market (if open) or local shops

Shop for fresh local produce, crafts, and snacks, experiencing local culture in a fun setting.
Varies, 1h

6:30pm

Dinner at The Oyster Company

Enjoy a family-friendly fine dining experience with locally sourced seafood and non-seafood options for children.
USD30-60 per person, 1h30m
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Day 4: Chatham Charm

Chatham, Massachusetts on June 4, 2025

8:00am

Breakfast at The Chatham Squire

Casual breakfast with pancakes, eggs, and kid-friendly options in a classic Cape Cod setting.
USD20 per person, 1h

9:30am

Visit Chatham Lighthouse Beach

Spend the morning exploring a serene beach famous for its lighthouse views and calm waters safe for children.
USD15 parking, 2h

12:00pm

Lunch at Impudent Oyster

A casual seafood spot with excellent chowder and sandwiches, perfect for a relaxed family lunch.
USD20-35 per person, 1h

1:30pm

Monomoy National Wildlife Refuge

Explore family-friendly walking trails and enjoy bird watching in one of Cape Cod’s premier wildlife sanctuaries.
Free, 2h

4:00pm

Shopping in Downtown Chatham

Browse charming boutiques, toy stores, and ice cream shops in the heart of town, perfect for multigenerational shopping fun.
Free to browse, 1h

6:30pm

Dinner at Del Mar Bar & Bistro

Enjoy upscale dining with ocean views and dishes that cater to both adventurous adults and picky kids.
USD40-70 per person, 1h30m
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Day 5: Harbor & History

Hyannis, Massachusetts on June 5, 2025

8:00am

Breakfast at The Java Room

Start the day with great coffee and freshly baked goods in this cozy Hyannis spot popular with families.
USD15-20 per person, 45m

9:00am

John F. Kennedy Hyannis Museum

Learn about JFK’s connection to Cape Cod with engaging exhibits suitable for visitors of all ages.
USD10 adults, children under 12 free, 1h

10:30am

Hyannis Harbor Cruise

Enjoy a relaxing cruise around the harbor with views of the waterfront, ideal for families looking for light outdoor activity.
USD25 per adult, USD15 per child, 1h

12:00pm

Lunch at Lobster Pound

Famous for lobster rolls and fresh seafood, this spot offers quick and casual dining with a kids’ menu.
USD20-30 per person, 1h

1:30pm

Cape Cod Children's Museum

Interactive museum offering hands-on exhibits and activities designed specifically for young children and families.
USD10 adults, children USD10, 2h

4:00pm

Walk Main Street Shops

Explore boutique shops and ice cream parlors. It’s a great way for the family to unwind after a busy day.
Free to browse, 1h

6:30pm

Dinner at Black Cat Tavern

Enjoy waterfront dining with a menu offering seafood and child-friendly options in a lively setting.
USD30-50 per person, 1h30m
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Day 6: Falmouth Family Fun

Falmouth, Massachusetts on June 6, 2025

8:00am

Breakfast at Coffee Obsession

Enjoy gourmet coffee, breakfast sandwiches, and pastries in a relaxed, welcoming atmosphere.
USD15-20 per person, 45m

9:00am

Woods Hole Science Aquarium

Explore marine life exhibits and touch tanks; this free aquarium is engaging for kids and adults alike.
Free, 1h30m

10:45am

Shining Sea Bikeway Ride

Rent bicycles or bring your own and enjoy a scenic, mostly flat bike trail perfect for families and multi-generation groups.
USD20 bike rental per hour, 2h

1:00pm

Lunch at Quahog Republic Seafood

Feast on fresh seafood and classic New England dishes in a casual, family-friendly environment near the water.
USD20-35 per person, 1h

2:30pm

Nobska Lighthouse Visit

Take a short trip to explore the lighthouse and enjoy sweeping ocean views; fun photo spot for all ages.
Free, 1h

4:00pm

Meserve Memorial Park Beach Time

Relax on a kid-friendly beach with calm waters and playground facilities to finish the day.
USD15 parking, 1h30m

6:30pm

Dinner at The Dam Bar & Grill

Enjoy a laid-back seafood and grill menu with options suitable for the whole family, including children.
USD20-40 per person, 1h30m
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Day 7: Relax and Departure

Falmouth, Massachusetts on June 7, 2025

8:30am

Breakfast at Scranton Avenue Coffee House

Casual breakfast spot with great coffee and pastries, perfect to fuel up before the trip home.
USD15 per person, 45m

9:30am

Visit to Coonamessett Farm

Enjoy a morning walk around this family-run farm with pick-your-own fruits and farm animals for kids to interact with.
Free to visit, picking fees vary, 1h30m

11:30am

Packing and checkout

Prepare for departure with ample time to get ready and head home.
Free, 1h
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