View of the Charles River in Boston

Hotels in this story

Price Dates

The Liberty, a Luxury Collection Hotel, Boston

The Ritz-Carlton, Boston

Omni Parker House

Hotel Commonwealth

In Boston you really get the best of both worlds: It’s a bustling city with fabulous shopping and nightlife, but it also provides outdoorsy types with plenty of al fresco activities to indulge in, especially during the summer. Check out our favorite activities below and the hotels to stay in that are convenient to each.

Sailboats on the Charles River

Do: Sail on the Charles River

Sailboats dot the Charles River all year long — sailing is a popular pastime for locals and tourists alike. If you’re looking to rent a boat for a few hours on your own, or would like to get a lesson from an instructor before you hit the open seas, head to Community Boating (the oldest public sailing facility in the country) right on the Charles. They offer rentals, lessons, and sailing programs from April through November — you can even rent kayaks or Windsurfers if you’d rather attempt to manage something a little smaller.

Stay: Liberty Hotel

Occupying a former jail, the 298-room Liberty Hotel is truly unique, with a playful design that incorporates the incarceration theme in fun ways. The stunning lobby, comfortable rooms, and quality on-site restaurants make this hotel a good choice. The hotel, located about two blocks from the Charles River, offers guests discounted rates on kayak rentals.

The pond in Boston Common

Do: Picnic in Boston Common

Boston Common is the country’s oldest public park, and has served as everything from a military camp to a cow pasture to a meeting spot for protest marches. Since 1640, when the town was just ten years old and the Boston Common property officially became public, numerous statues and monuments have been erected on the site. Stroll through the gardens before stopping by the Frog Pond for a picnic (and you can throw your leftovers to the ducks!).

Stay: The Ritz-Carlton Boston Common

Less than a block from Boston Common, the Boston Ritz-Carlton is refreshingly intimate with spacious, luxurious standard rooms and access (for a fee) to one of the city’s best gyms, with its own spa, salon, and pool.

The Sam Adams statue in Faneuil Hall

Do: Walk the Freedom Trail

Beginning in Boston Common and ending at the Bunker Hill Monument, the Freedom Trail is a “must-walk.” A two-and-a-half-mile trail, it links sixteen historic Boston sites, including Faneuil Hall and Paul Revere’s house. The great thing about the line of red paint (or brick in some areas) is that you can walk it on your own or opt for a tour, led by a guide outfitted in Revolution-era garb.

Stay: Omni Parker House

Steeped in history, stuffed with ghost lore, and teeming with old-world grandeur, the surprisingly affordable Omni Parker House is the place to stay for a taste of Boston’s literary and political past — and it has a great location only five minutes from Boston Common and the start of the Freedom Trail. But manage your expectations when it comes to service and rooms.

Fenway Park

Do: Visit Fenway Park

If your idea of an outdoor activity involves heckling and hotdogs, head to Fenway Park to catch a Red Sox game. Yet another “oldest” (it’s the oldest park in the major leagues), Fenway is packed with Red Sox fans from April to October, and before games, vendors set up shop on Yawkey Way. If you prefer to avoid the crowds, take a tour of the park instead.

Stay: Hotel Commonwealth

The 148-room Hotel Commonwealth is one of the most well-rounded boutique hotels in Boston. With its classical furnishings, large rooms, and impressive array of services, it captures the spirit of the city like few others. Fenway Park is only two blocks away and its high green field lights are visible from the hotel’s parking lot.