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Boston

8 day itinerary for Boston

Personalized with:

No art museums

Couple activities

Adventure

Beach

City sightseeing

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Itinerary

Here's an ideal itinerary for 8 days in Boston that meets all your constraints:

Day 1: Arrival and City Sightseeing

  • Start your day with a walk along the Freedom Trail, which is a 2.5-mile-long path that takes you through 16 historical sites in Boston.
  • Visit the USS Constitution Museum, which is dedicated to the history of the US Navy and the War of 1812.
  • Take a stroll through the Boston Public Garden, which is a beautiful park located in the heart of the city.
  • End your day with dinner at one of the many restaurants in the North End, which is Boston's Little Italy.

Day 2: Beach Day

  • Head to Revere Beach, which is just a short train ride from downtown Boston.
  • Spend the day lounging on the beach, swimming in the ocean, and playing beach volleyball.
  • Grab lunch at Kelly's Roast Beef, which is a local institution known for its delicious sandwiches and seafood.

Day 3: Adventure Day

  • Go kayaking on the Charles River, which offers stunning views of the Boston skyline.
  • Take a bike tour of the city, which will take you to some of the lesser-known neighborhoods and landmarks.
  • End your day with a sunset sail on Boston Harbor, which is a great way to see the city from a different perspective.

Day 4: Couple Activities

  • Start your day with brunch at The Friendly Toast, which is a quirky restaurant known for its creative menu and funky decor.
  • Take a cooking class together at the Boston Center for Adult Education, where you can learn how to make everything from pasta to sushi.
  • End your day with a romantic dinner at Top of the Hub, which is a restaurant located on the 52nd floor of the Prudential Tower and offers breathtaking views of the city.

Day 5: City Sightseeing

  • Visit the Boston Tea Party Ships and Museum, which is an interactive museum that tells the story of the Boston Tea Party.
  • Take a tour of Fenway Park, which is the oldest ballpark in Major League Baseball and home to the Boston Red Sox.
  • End your day with dinner at Legal Sea Foods, which is a local chain known for its fresh seafood and chowder.

Day 6: Beach Day

  • Head to Castle Island, which is a beautiful park located on a peninsula in South Boston.
  • Spend the day swimming in the ocean, walking along the beach, and exploring the historic Fort Independence.
  • Grab lunch at Sullivan's, which is a local institution known for its hot dogs and fried seafood.

Day 7: Adventure Day

  • Go rock climbing at Brooklyn Boulders, which is an indoor climbing gym located in Somerville.
  • Take a hike in the Blue Hills Reservation, which is a beautiful state park located just outside of Boston.
  • End your day with dinner at Oleana, which is a Mediterranean restaurant located in Cambridge and known for its delicious small plates.

Day 8: Departure

  • Start your day with breakfast at Flour Bakery, which is a local chain known for its pastries and sandwiches.
  • Take a stroll through the Boston Common, which is a beautiful park located in the heart of the city.
  • End your trip with a visit to the New England Aquarium, which is home to thousands of marine animals and offers a great way to learn about the ocean.

Places of interest

Freedom Trail Boston

Freedom Trail

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USS Constitution Museum Boston

USS Constitution Museum

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Boston Public Garden Boston

Boston Public Garden

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North End Boston

North End

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Revere Beach Boston

Revere Beach

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Kelly's Roast Beef Boston

Kelly's Roast Beef

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Charles River Boston

Charles River

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Bike tour of the city Boston

Bike tour of the city

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Sunset sail on Boston Harbor Boston

Sunset sail on Boston Harbor

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The Friendly Toast Boston

The Friendly Toast

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Boston Center for Adult Education Boston

Boston Center for Adult Education

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Top of the Hub Boston

Top of the Hub

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Boston Tea Party Ships and Museum Boston

Boston Tea Party Ships and Museum

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Fenway Park Boston

Fenway Park

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Legal Sea Foods Boston

Legal Sea Foods

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Castle Island Boston

Castle Island

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Fort Independence Boston

Fort Independence

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Sullivan's Boston

Sullivan's

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Brooklyn Boulders Boston

Brooklyn Boulders

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Blue Hills Reservation Boston

Blue Hills Reservation

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Oleana Boston

Oleana

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Flour Bakery Boston

Flour Bakery

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Boston Common Boston

Boston Common

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New England Aquarium Boston

New England Aquarium

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