New Chat

Download App

Ask me about your trip!

There are no messages for this conversation.

Roam Around

Boston and Cape Cod Adventure - 5 Days Itinerary

Last updated: 2024 Jun 14

Historic Boston Beginnings

Morning

Start your day with a visit to the iconic Freedom Trail. This 2.5-mile-long path through downtown Boston passes by 16 locations significant to the history of the United States. It's a great way to get an overview of the city's rich history. For breakfast, head over to Tatte Bakery & Cafe, known for its delicious pastries and coffee.

Afternoon

In the afternoon, explore Boston Common, America's oldest public park. Stroll through its beautiful landscapes and enjoy a relaxing time by the Frog Pond. For lunch, visit Union Oyster House, one of the oldest restaurants in America, famous for its seafood dishes.

Evening

End your day with a visit to Faneuil Hall Marketplace, a vibrant marketplace with shops, eateries, and street performers. Enjoy dinner at Durgin-Park Restaurant, known for its traditional New England fare.

Bedtime

Find amazing hotels in Boston, MA.

4.54
Freedom Trail
Book Now

4.49
Boston Common
Book Now

Revolutionary Boston

Morning

Start your day with a visit to the historic site of the Boston Massacre Site. Learn about this pivotal event in American history. For breakfast, enjoy some delicious offerings at The Friendly Toast near Faneuil Hall.

Afternoon

In the afternoon, take part in an engaging activity: Boston Self - Guided Walking Tour of the Freedom Trail. This will allow you to explore various historical sites at your own pace. Have lunch at Neptune Oyster, famous for its oysters and seafood dishes.

Evening

Conclude your day with a visit to the picturesque neighborhood of Beacon Hill and explore its charming streets lined with historic homes. Dine at The Paramount, known for its classic American cuisine.

Bedtime

Find amazing hotels in Boston, MA.

4.64
Boston Massacre Site
Book Now

5.00
Boston Self - Guided Walking Tour of the Freedom Trail
Book Now

Cultural and Educational Exploration

Morning

Begin your day in Cambridge with a tour of Harvard University. Explore Harvard Yard and visit the famous John Harvard Statue. For breakfast, stop by Flour Bakery & Cafe for some delightful morning treats.

Afternoon

After exploring Harvard University, head over to the nearby MIT Museum to delve into fascinating exhibits on science and technology. Have lunch at Alive & Kicking Lobsters, renowned for its lobster sandwiches.

Evening

Spend your evening at Kendall Square, known as one of the most innovative squares in the world. Enjoy dinner at Legal Sea Foods, offering fresh seafood dishes in a modern setting.

Bedtime

Find amazing hotels in Cambridge, MA.

4.25
Harvard University
Book Now

3.69
John Harvard Statue
Book Now

Cape Cod Coastal Charm

Morning

Begin your day with a scenic drive to Cape Cod. Upon arrival, start with a visit to the picturesque town of Chatham. Stroll along Main Street and enjoy the charming shops and cafes. For breakfast, stop by Chatham Village Cafe & Bakery, known for its freshly baked goods and coffee.

Afternoon

In the afternoon, head to the Cape Cod National Seashore. Spend time exploring the beautiful beaches and take a leisurely walk along one of the many trails. For lunch, enjoy some fresh seafood at The Beachcomber, offering stunning ocean views.

Evening

End your day with a visit to Provincetown at the tip of Cape Cod. Explore its vibrant arts scene and unique shops. Enjoy dinner at The Lobster Pot, famous for its seafood dishes and waterfront views.

Bedtime

Find amazing hotels in Cape Cod, MA.

Cape Cod Adventures

Morning

Start your day with a visit to the Wellfleet Bay Wildlife Sanctuary. Explore the trails and observe various bird species in their natural habitat. For breakfast, visit The Flying Fish Cafe, known for its delicious breakfast options.

Afternoon

In the afternoon, take part in an exciting activity: From Boston Day Tour of Plymouth and Cape Cod. This guided tour will provide you with insights into the history and culture of both Plymouth and Cape Cod. Have lunch at Moby Dick's Restaurant, offering classic New England fare.

Evening

Conclude your trip with a relaxing evening in Hyannis. Stroll along Main Street, visit local shops, and enjoy dinner at Black Cat Tavern, known for its waterfront dining experience.

Bedtime

Find amazing hotels in Cape Cod, MA.