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Sunset On The Charles River | © Jeff Turner/Flickr
Sunset On The Charles River | © Jeff Turner/Flickr
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How to Spend 24 Hours in Boston

Picture of Natasha Chang
Updated: 29 August 2017
Boston may be small but it’s packed with a big personality that will surprise you at every turn. Discover the highlights of Massachusetts’ bustling capital—where modernity meets history—in 24 hours with this guide. Here’s how to conquer the challenge the Boston way.

Day 1

8:00 p.m.: Catch the sunset over the Charles River

Start by catching the sunset from the picturesque banks of the Charles, or rent a kayak and soak up the rest of the sunlight from the waters of the river. Half the fun is paddling out to the center of the river for a scenic view of the sun setting behind the city.

Sunset on the Charles River
Sunset on the Charles River | © Jeff Turner/Flickr

9 p.m.: Fill your stomach with Boston classics

After you’ve experienced the sunset, head on over Faneuil Hall and Quincy Market to fill your stomachs. Quincy Market, located near the waterfront and the Government Center T stop, is home to 36 international food vendors. However, no trip to Boston is truly complete without a bowl of clam chowder, so make sure to indulge yourself in a bread bowl filled with the creamy Boston classic and worry about calorie count another day.

Just a 10-minute walk from Faneuil Hall is where you’ll enter the cobblestone streets of the North End—Boston’s “Little Italy.” This one-square-mile waterfront community is Boston’s oldest neighborhood, famous for its authentic Italian food and feasts. Top off your meal with a Cannoli from Mike’s Pastry and find out why it keeps loyal Bostonians and tourists from around the world coming back for more.

Courtesy of Mike’s Pastry Inc.
Courtesy of Mike’s Pastry Inc.

10:30 p.m.: Sip on a cocktail to end the evening

Boston is an early-to-bed kind of city, with the majority of bars and clubs closing their doors at 2 a.m., and public transportation making its last rounds starting at 12:30 a.m. However, if you’re in need of a post-dinner cocktail to finish off the day, head on over to Envoy Rooftop bar for a drink and a breathtaking view of the harbor.

Envoy Rooftop Bar, 70 Sleeper St, Boston, U.S.A, +1 617 338 3030

Courtesy of The Envoy Hotel, Autograph Collection
Courtesy of The Envoy Hotel, Autograph Collection

Day 2

9 a.m.: Tours, tours, tours

Wakey-wakey! Strap on your walking shoes, it’s time to take a tour or two of the city. Famous for its historical significance, it’s only fitting that one of the best and most popular things to do in Beantown is to take a walking tour of the Freedom Trail (with or without a guide). The Freedom Trail is a 2.5-mile, brick-lined route that takes you to various historical sites in downtown Boston.

Want to check out the best sites but too tired to walk? Hop on a double deck old town city tour bus or a duck tour. Enjoy waddling through Boston in a renovated World War II amphibious vehicle for an informative and comprehensive tour by land and water.

Courtesy of Boston Freedom Trail Tours
Courtesy of Boston Freedom Trail Tours

11 a.m.: Wander the Isabella Stewart Gardner Museum

Visit one of Boston’s most treasured cultural landmarks. While many people will feel intimidated by today’s art, the featured painting, sculptures, tapestries, furniture, manuscripts, rare books, and decorative arts at the Isabella Stewart Gardner Museum will leave you in awe. You’ll leave the three-story, 15th-century Venetian-style palace really appreciating the finer things in life.

Isabella Stewart Gardner Museum, 25 Evans Way, Boston, U.S.A, +1 617 566 1401

Courtesy of Isabella Stewart Gardner Museum
Courtesy of Isabella Stewart Gardner Museum

12 p.m.: Stop to refuel

After a very cultural morning, it’s time to reward yourself with a hearty meal. Head on over to Chinatown to find the very best in Asian cuisine— and check out our guide on how to make the most out of your time there.

1 p.m.: Enjoy the green spaces in the heart of the city

Grab a coffee and stroll through, or sit on a bench in the Boston Commons and Public Garden; it’s a green sanctuary from the hustle and bustle of the city. Be sure to also go and find the famous ducks which depict the characters from Robert McCloskey’s 1941 children’s book, Make Way for the Ducklings. If you want to really enjoy the serenity of this green space, hop into a Swan Boat for an idyllic ride on the pond.

Swan Boats in the Public Garden – Kyle Klein Photography
Swan Boats in the Public Garden – Kyle Klein Photography | © Massachusetts Office of Travel & Tourism/Flickr

2 p.m.: Head on over to Copley

Copley Square is located in the heart of Boston and provides an incredible combination of culture, architecture, and greenery.

Here you’ll find the Boston public library and the infamous Boston Marathon Finish line. Make sure to head inside the library to see some incredible architecture. You can walk around the square and up and down Boylston Street for some shops, cafés, and eateries.

Boston Public Library
Boston Public Library | © Isaac Wedin/Flickr

3 p.m.: Say hello to Boston’s most enchanting street

Saunter your way down Newbury Street where you’ll find a number of boutique shops and restaurants. Stop at Georgetown Cupcakes for something sweet, or Trident Café for a cup of coffee and a good book. In need of a quirky gift? Try Newbury Comics. Whatever you need, chances are you’ll find it on Newbury.

5 p.m.: Sweet Caroline (Ba ba ba!)

Boston may be famous for its historical significance, but it’s also famous for its die-hard sports enthusiasm, which means a tour of Fenway Park is a must. Home of the Boston Red Sox since 1953, you’ll feel the intensity of Boston loyalty right as you enter the park.

Fenway Park
Fenway Park | Eric Kilby/Flickr

8 p.m.: Time to say goodbye

Before jetting off to your next destination, have dinner at Sweet Cheeks Q, Boston’s best BBQ place, and enjoy a taste of southern heaven right by Fenway. You’ll leave with a happy belly and sore feet, but that’s just the Boston way.