Whether you're planning a girls' trip, heading to Boston for a specific event, or you want a romantic getaway, this city is a great destination.
Boston is a hub of American history, but it's so much more than that. It's a beautiful, stylish city with charm, sophistication, and diversity. It's packed with culture as well.
First and foremost, if you just have a weekend in Boston, there's a ton to do, so you want to maximize your time there. If you have a later hotel check-in and an early flight in, store your luggage so that you can hit the ground running as soon as you arrive.
May through September tend to be optimal times to visit with the mild, warm weather. The winter is fine too, but be prepared for cold and potentially snowy weather.
Where to Stay
Boston is a good walking city because it's incredibly compact, and there are a lot of high-end hotels.
Some of the best hotels in Boston if you're aiming for style and luxury are:
- The Verb: This hotel is a resorted motor inn, and it is now redone to be modern and comfortable while still maintaining a trendy, retro feel. If your goal is to stay somewhere unique consider The Verb.
- Hotel Commonwealth: For something more Colonial but at the same time modern, there's Hotel Commonwealth, which is located near Boston University and the Museum of Fine Arts. It's also pet-friendly and has fantastic onsite dining and bar options.
- The Whitney: This is located in the Beacon Hill neighborhood, and the rooms have massive windows and the entire hotel is incredibly stylish but it maintains a boutique atmosphere.
- The Charles: Located in Harvard Square, The Charles is a long-time favorite of everyone from politicians to celebrities. You'll instantly feel like a Kennedy at The Charles.
- The Envoy: The Envoy is one of Boston's newer hotels, and it is in the Seaport District. The hotel's focus is on local art and wellness and despite being surrounded by history, it's a breath of fresh air.
What to Do
When you're in Boston for the first time, some of the must-sees and dos include:
- The Freedom Trail: This is the primary must-do in Boston above all others. The Freedom Trail runs for 2 ½ miles, and it goes past 16 of the nation's most historically significant sites, such as Boston Common and the Massachusetts State House. You can do a walking tour, or you can follow a red line that marks the route and do it on your own. If you're going to do it on your own, you can download a map and use it on your phone along the way. Other sites along The Freedom Trail are the Old State House, the Old North Church and the Paul Revere House. Stop at the Quincy Market for lunch and grab a bowl of New England clam chowder.
- Back Bay: The Back Bay neighborhood is one of the gems of Boston, particularly if you love shopping and great restaurants and cafes. Back Bay is somewhat like the West Village in New York City and the 19th-century homes are Victorian style and beautiful to look at. High-end shopping is a big draw in Back Bay too.
- Museums and Galleries: There are plenty of museums and galleries to choose from in Boston so you'll have to narrow your selections down based on what most interests you. The Institute of Contemporary Art is great, as is the Commonwealth Museum. There's also the Harvard Museum of Natural History and the Harvard University Art Museums. For something funny and quirky, there's the Museum of Bad Art.
- Harvard: You can take a free tour of Harvard, the oldest university in the country.
- The Red Sox: Boston residents love sports and especially their Red Sox. If you're there when there's a baseball game at Fenway, check it out or at least go to the bars around Fenway.
- Boston Public Garden: During the warmer months, go to Boston Public Garden, which is the first botanical garden in America. You can ride the swan boats, but only during the summer.
- Brattle Book Shop: It's a different kind of shopping then you might be used to but don't skip Brattle Book Shop. Brattle is a book shop that goes back to 1825 and they have more than 250,000 books as well as postcards and antique books.
- Prudential Tower: You can go up the Prudential Tower and get a view of the city. The Prudential Tower is the second-tallest building in the city behind only the John Hancock Tower.
- Riverfront: The Charles River Riverfront will be dotted with sailboats in the summer months, and there are often free shows this time of year at the Boston Hatch Shell.
- North End: The North End is the home of the vibrant Italian community in Boston. Check out the small shops and have some gelato and espresso.
What to Pack
A lot of what you pack for a trip to Boston is going to depend on what time of year it is. First of all, Boston is a walking city through and through. Sneakers are best during the day, and you have to think about the things that make Boston unique, such as the cobblestoned streets. This may make heels a bad option.
Even if you go to Boston in the summer, you might want to bring a lightweight jacket in case it gets chilly at night, or you get an unexpected bit of rain.
Layers are important too-for example, maybe brig a lightweight sweater or cardigan for a chilly morning that you can take off later.
Since you will be walking so much, bring a chic bag and an umbrella. Boston is a stylish, fascinating city and it should be on your radar for your next chic getaway for history, culture, food, and architecture all rolled into one place.
