Biking in Boston: A Summer Day Itinerary

Hannah Truman
Sep 5
3 min read

Looking for a Fun and Active Boston Itinerary to Explore the City in a Single Day?

Here’s a ready-to-go Boston itinerary that combines biking, beautiful sights, and a little bit of culture. From iconic parks to riverside paths, historic museums, and even Fenway Park, this route makes the most of a summer day in the city.

Itinerary in Brief:

Start: Boston Common
Fuel Up: Breakfast
Rent: City Blue Bikes
Ride: Charles River Esplanade
Stop: Christian Science Museum Plaza
Visit: Rose Garden
Explore: Isabella Stewart Gardner Museum
Game Time: Fenway Park

Kick Off Your Day at Boston Commons

Start your day at Boston Commons, the city’s iconic park and a perfect central hub. If you’re driving, you can park for the day at the Boston Commons Garage, making it easy to explore the city on foot or by bike. Take a few minutes to enjoy the greenery, swan boats, and historic monuments before heading off.

Enjoy Coffee & Treats at Tatte

No adventure starts on an empty stomach! Grab a coffee and pastry at Tatte Café, located right at the corner of Boston Commons. If you have time to linger, their breakfast plates are worth the wait. It’s the perfect spot to fuel up for a full day of biking and sightseeing.

Grab Your City Bike

Next, head to a nearby Blue Bikes station—Boston’s convenient city bike rental program. A day pass costs just $10 and gives you unlimited 30-minute rides, making it easy to hop between your planned stops. Whether you’re cycling along the Charles River Esplanade or weaving through the city streets, biking is one of the best ways to see Boston in a summer day.

Tip: Download the Blue Bikes app in advance so you can quickly scan and ride!

Ride Along the Charles River Esplanade

Hop on your bike and head to the Charles River Esplanade, one of Boston’s most scenic spots. This riverside path is perfect for a leisurely ride, offering gorgeous water views, sailboats, and plenty of spots to pause for photos.

Stop at the Christian Science Museum Plaza

From the Esplanade, ride over to the Christian Science Museum Plaza. The plaza itself is peaceful and beautiful, with fountains, sculptures, and well-kept gardens. This quiet escape in the heart of the city is perfect for a photo op and a quick break before continuing your ride.

Stroll Through the Rose Garden

Next, make your way to the James P. Kelleher Rose Garden. In the summer, the roses are in full bloom, creating a fragrant and colorful oasis. Stroll through the paths, take in the vibrant flowers, and snap a few photos—this is one of the city’s hidden gems for a relaxing pause.

Tip: Visit in late June through early July for peak bloom when the roses are most vibrant.

Visit Isabella Stewart Gardner Museum

The Isabella Stewart Gardner Museum is nearby and worth a stop. This historic museum is famous not only for its incredible collection of European, Asian, and American art but also for the infamous 1990 art heist, the largest unsolved art theft in history. Take your time exploring the galleries and the stunning courtyard.

Note: The museum is closed on Tuesdays. It is open from 11 AM to 5 PM Wednesday through Monday, with extended hours on Thursdays from 11 AM to 9 PM.

Catch a Game at Fenway Park

End your day with a visit to Fenway Park, even if you don’t catch a game. This historic ballpark is an iconic Boston landmark, and the surrounding neighborhood is full of energy, shops, and classic Boston vibes. If you’re lucky, you might even time your ride to coincide with a Red Sox game!

Tip: Buy your Boston Red Sox gear at the team stores before the game. Your purchase comes with a Fenway Park tag, making it a unique souvenir.

Tips for the Day

Start early: Summer days are long, but starting early helps you avoid crowds and enjoy cooler temperatures.
Stay hydrated: Bring water, especially while biking around.
Pack light: A small backpack is ideal for carrying essentials without getting in the way while cycling. Remember you must have a small bag under 12x12x6 to bring into Fenway Park!
Plan your breaks: Use the parks and plazas along the route to rest, snap photos, and enjoy the scenery.

Looking for more Boston adventures?

I've put together a comprehensive guide filled with must-see spots, hidden gems, and local favorites to help you make the most of your time in the city. From historical landmarks to delicious eateries, there's something for everyone.

Check out the full guide here: Boston Adventures: Exploring the Best Things to Do in the City