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Summertime in Boston: Create Your Ideal Bucket List

We may be a little bit biased, but for us, Boston is the ideal city to visit in the summertime. 

“We have a little bit of everything here,” says Jake Quigley, Executive Director of Waterstone at the Circle. “There are historic sites, beaches, sports, so much culture ... it’s no wonder that we have so many visitors coming to our city every summer.”

Even if you’re a lifelong Bostonian, says Jake, summer is a great time to experience the city and be a tourist for a while. 

“Sometimes we forget everything that’s just outside our doorstep,” he says. “Actively seeking out the very Boston things to do will give you a chance to fall in love all over again with this great city. For retirees who are getting the chance to truly take advantage of free time – like the residents of Waterstone at the Circle – this summer is a great time to see the city with new eyes and perhaps find your next favorite activity.”

Here are our top Boston activities that should definitely go on your “must-do” summertime list.

Take a tour of the city. 

Boston is one of the most historical yet modern cities in the United States, with famous sites next to top-notch current attractions. Taking a sightseeing tour around the city is a great way to get an overview of everything there is to offer. There are many, many tours to choose from, but here are a few that make the top of our list:

  • The Boston Hop On Hop Off Trolley Sightseeing Tour is a narrated tour that takes you to more than 125 interesting sites in the retro comfort of a trolley. The full tour lasts two hours, but you’re able to hop on and off (hence the name) to see an attraction or site that catches your eye. If you stay on the trolley, the tour lasts a comfortable two hours – just don’t forget to make note of places you’d like to visit later. 
  • History buffs will definitely want to check out the 4.5-hour American History Tour, which takes you to the neighboring towns of Cambridge, Lexington, and Concord. You’ll not only see Boston’s top attractions, but you’ll also get your fill of Revolutionary War and Civil War history and ride along the same route Paul Revere rode during his legendary midnight ride. 

Enjoy a concert under the stars.

Summertime means outdoor concerts, and Gillette StadiumFenway ParkRockland Trust Bank Pavilion and Xfinity Center have jam-packed schedules featuring today’s hot artists, up-and-coming favorites and classic megastars like the Rolling Stones. 

Go whale-watching. 

Launch from Boston Harbor and experience the best whale watching the East Coast has to offer. Stellwagen Bank National Marine Sanctuary is 25 miles by water from the Boston and is home to numerous species of marine wildlife. Grab your binoculars and, if you’re lucky, you’ll see schools of whales (including some endangered species), along with seals, water birds, dolphins and more. You’ll also get a chance to go past many of Boston’s little harbor islands and see some of our historic lighthouses.

Spend a day at the beach. 

What says “summertime” more than grabbing your sunscreen and heading to the beach? And in Boston, you can be on the sands without having to travel too far from the city. The best of Boston’s beaches can be reached by public transportation. Check out Carson Beach, Castle Island or Revere Beach (the oldest public beach in the United States). 

Cheer on the Sox at Fenway Park.

Fenway Park is home to the Red Sox, and even if you’re not a baseball buff, the stadium itself is worth the price of admission. Cheer on the home team (or the visiting team, if you’d like), enjoy some delicious stadium food and experience an all-American pastime in an all-American location. 

Dine al fresco at one of our many local restaurants. 

Enjoy a glass of wine and a balmy breeze at one of the many Boston cafés or restaurants that offer patio seating. The Seaport Neighborhood is a popular spot for locals and visitors alike, with a slew of options that overlook the harbor as well as activities, events and pop-up galleries. You can also enjoy the summertime-only beer garden, a pop-up beer garden with local food, drink and activities right across from City Hall. 

Walk the Freedom Trail. 

The Freedom Trail takes you on a casual stroll past 16 historic sites that tell the story of the American Revolution. You’ll pass Paul Revere’s house, the Old North Church, the site of the Boston Massacre and other critical points for the fight for independence. Along the way, actors dressed in period garb bring 18th-century Boston to life.

Ride a bike.

Boston is a very bike-friendly city, and you’ll find paved bike trails all throughout parks, roads and along the waterfront. Biking along the Charles River is a much-loved pastime by locals. Grab your own two wheels, or if you aren’t a proud bike owner, there are many places to rent one for the afternoon. 

Shop until you drop at Faneuil Hall.

Faneuil Hall Marketplace has been a meeting hall and marketplace since 1742, and it remains one of the most popular destinations for Bostonians. With more than 70 retailers, street performers and some of Boston’s best restaurants, it’s a historic-yet-modern site where you can easily spend a day people-watching and experiencing the best of everything Boston has to offer. 

If you’d like to learn more about Boston in the summer, or if you’re wondering how a luxury retirement community like Waterstone at the Circle can help you live a vibrant, active and fulfilled life, contact us today at 617.431.1880.

Luxury Senior Living in Boston

Waterstone at the Circle, located in Boston’s historic Cleveland Circle neighborhood, is more than just independent living in Boston … it’s a sophisticated urban setting for today’s active seniors. Enjoy best-in-class service and a vibrant lifestyle with arts and cultural, and historical attractions right outside your front door. From high-end amenities to gourmet dining and more, experience the best of city and suburban life at our upscale senior living community located on the crossroads of Brookline and Chestnut Hill. 

Elegant Independent Living Apartments

Each of our 92 independent living apartments is the height of luxury and modernity, with sophisticated design, upscale features and stunning views of the city. Create the urban senior living experience you want with one- or two-bedroom apartments, a variety of floor plans and monthly rentals.  

Senior Living Supportive Services

As an over-62 community, residents may require support from time to time. That’s why we’ve developed an on-site coordinated care program, in cooperation with our premier community partners, that allows our independent living residents to receive the assistance they need.

The best part? Residents don’t have to leave our senior living community – or even their apartment – to receive high-quality support. They can receive the services they need, when they need it, in the comfort of their own homes or in our on-site therapy gym.

Waterstone at the Circle is the opposite of retiring. . . it’s a place to enhance your active, on-the-go lifestyle. Call 617.431.1880 for more information or to schedule a visit of our vibrant Boston independent living community and discover The Circle lifestyle today!