For my annual birthday trip this year, we chose Boston as our destination and booked a stay at the Omni Seaport (review here). Since we had so much fun exploring New York City on bikes last year (blog post here), we were looking for another bike-friendly city for this trip, and Boston was the perfect fit.
I can’t express enough how much I fell in love with Boston! Not only is it incredibly clean, but it also exudes a storybook-like charm. Boston offers a ton of activities, sights, and delicious food options.
Our trip spanned a long weekend, with our arrival on Friday night and departure on Tuesday morning, we had three full days to enjoy the city. I have to say, those three days were fantastic, but I’m definitely interested in returning for more time in the city. Boston captured our hearts, and our group of 8 adults unanimously declared it the best U.S. city we’ve ever visited. Keep reading below for our 3-day Boston Itinerary.
Getting Around
Boston is similar to New York— it has a big city vibe but is not hard to navigate. We primarily got around using the blue city bikes, which were both a blast and budget-friendly. As I mentioned above, Boston is super bike-friendly, with dedicated bike lanes on nearly all streets. You can always find bikes sprinkled throughout the city. The Blue Bikes app shows the nearest bike station and bike rentals available and offers variously priced ride options. While most of the spots we wanted to check out were a 10-20-minute Uber ride, thanks to traffic, biking turned out to be just as fast- and way more fun. We did some walking too, but with the heat, biking was the cool choice for getting around.
Things to see
Boston Public Garden
Boston Commons
Newbury Street (shopping)
Fenway Park
Boston Tea Party Ships
Faneuil Hall Marketplace/Quincy Market
North End
The Paul Revere House
Old North Church
Freedom Trail
Boston Public Library (heard they have an awesome tea service)
Beacon Hill
Charles Street Shops (Beacon Hill)
Cambridge/Harvard University
Martha’s Vineyard (day trip)
Cape Cod (day trip)
Restaurants/Food
Mike’s Pastry
Union House
Uni
Neptune Oyster
Mamma Maria
Regina Pizzeria
Quincy Market
Amorino Gelato
Our Itinerary
Here is a glance at what we did during our 3-day Boston Itinerary.
Day 1:
We started our first day with a walking food tour through the North End, which I had booked through Viator. The nice thing is that this tour caps out at 8 people, so our group essentially had a private tour. It turned out to be a perfect introduction to the North End! We indulged in coffee and cannolis, savored some pizza, and relished fresh-made bread. As we strolled through the charming cobblestone streets, our guide shared tales of the area’s history and made stops at iconic spots like the Paul Revere House and the Old North Church. The North End is a must-visit for anyone exploring Boston. We actually returned multiple times during our 3-day trip to enjoy desserts and explore the local shops.
After our food tour, we hopped on city bikes and made our way to Beacon Hill. Let me tell you, Beacon Hill lives up to its name- those hills were quite the workout, especially in the sweltering 90-degree weather. Biking through Beacon Hill was an absolute blast. We made a quick stop to see Acorn Street, which is one of the most photographed streets in the US. It is nestled away and a little hard to find on Google Maps. We passed it at least 3 times!
From Beacon Hill, a quick 5-minute bike ride took us to the Boston Public Garden/Boston Commons area, a truly enchanting spot perfect for a leisurely picnic or a tranquil stroll. We found ourselves returning here a few days later just to be able to enjoy the serene beauty once more.
We finished the day exploring Newbury Street, which is across the street from the park area. Newbury Street is home to some of the world’s most luxurious stores, including Rolex, Cartier, Tiffany’s, Van Cleef & Arpels, Chanel, Louis Vuitton, and many more! We happened to visit on a weekend, and the streets and shops were bustling with activity. One of my highlights was buying an $8 overpriced mango from one of the fruit carts on the street— it turned out to be the best mango I’ve ever had, and I highly recommend trying one!
After a bit of shopping, we returned to our hotel to unwind and wrapped up the night with dinner at Uni, an awesome sushi joint. It was a jam-packed first day, but we had an absolute blast biking and exploring the streets of Boston.
Day 2:
Our second day was a bit more relaxing. Our group of 8 decided to take a day trip to Martha’s Vineyard, as none of us had ever been. I arranged this tour through Viator and also opted for the optional Island Tour— a choice I highly recommend for first-time visitors.
This was an ALL day trip to Martha’s Vineyard, we got picked up at 6 a.m. and dropped off at 7 p.m. The tour started with an hour-and-a-half drive to Falmouth, MA, where we caught the 30-minute ride on the Island Queen Ferry to Martha’s Vineyard. All that to say we were officially on Martha’s Vineyard by about 10 a.m.
Once we arrived at Martha’s Vineyard, we hopped on a school bus (yes school bus) for the full driving Island tour. This was such a great way to see all the towns: Oak Bluffs, Vineyard Haven, Edgartown, West Tisbury, Chilmark, and Aquinnah. We loved Edgartown for shopping! Aquinnah had the most beautiful views of the Gay Head Lighthouse. Nancy’s, back at the port, had amazing lobster rolls and was one of our favorite stops for food! All in all, this tour was such a great way to see Martha’s Vineyard.
Day 3:
We spent our 3rd day in Boston by visiting Cambridge and hanging out around Harvard University. While Boston is very clean, to my surprise, the Cambridge area wasn’t as nice. The campus is worth a visit, but note that the surrounding area was filled with garbage throughout the streets. Nonetheless, we still had a great time riding our bikes around campus and exploring. From there we Ubered back to the city for a late lunch at the Union House, the oldest restaurant in the US. The food was decent but completely overpriced. After lunch, we had some free time exploring Boston. We spent some time at the Holocaust Memorial, and TD Garden, and ventured back to Newbury Street and the Boston Public Garden. 
We had a busy 3 days in Boston and can’t wait to come back! The city offers an experience for every type of traveler, from history buffs to foodies and sports fans.
