Despite having only two days in Boston, you can still see a lot and get a good feel for the city. Here’s a detailed itinerary to make the most of your weekend in this historic Massachusetts capital.
Boston is a city rich in American history, and a weekend visit provides plenty of opportunities to explore its many landmarks. My first visit was a whirlwind of history, beautiful parks, waterfront views, and delicious local cuisine. Here’s my ideal weekend itinerary for Boston.
On day one, we’ll focus on Boston’s historical attractions. Start your day with a visit to Boston Common, America’s oldest city park, dating back to 1634. A stroll through the park is a wonderful way to kick off your weekend. You can also explore the Boston Public Garden and relax by the Frog Pond before embarking on the Freedom Trail.
The 2.5-mile Freedom Trail takes you past 16 historical sites, starting from Boston Common and passing landmarks like King’s Chapel and Bunker Hill. You can join a guided walking tour or create your own with a downloadable map and audio narration. Some sites are free to visit, while others, like the Old State House Museum and Paul Revere’s house, require tickets. Consider the Go Boston pass for savings on ticketed attractions.
Faneuil Hall, a historical marketplace, is an excellent stop along the Freedom Trail. Try local seafood at places like Wicked Lobsta and Boston Chowda, enjoy street performances, and shop for souvenirs. From Faneuil Hall, you can continue the Freedom Trail or head to Boston Harbor for a duck tour, an amphibious vehicle offering unique land-and-sea views of the city.
In the evening, consider exploring Bunker Hill/Charlestown. Visit historic taverns like Warren Tavern and Brewer’s Fork, both offering a taste of old Boston with great beer.
Start your second day with a leisurely brunch at spots like Peregrine in the Whitney Hotel or The Emory. Continue your historical exploration with a visit to the Boston Tea Party Ships & Museum or the JFK Presidential Library, depending on your interests.
The Boston area is home to prestigious universities like MIT and Harvard. You can tour Harvard’s campus, led by students, and visit the Museum of Natural History.
In the afternoon, head to Newbury Street in the Back Bay area. Enjoy boutique shops, cafes, and historic brownstones. Even if there isn’t a baseball game, a visit to Fenway Park, America’s oldest ballpark, is worthwhile. Guided tours are available, and if you’re lucky, secure tickets for a Red Sox game.
For those not interested in baseball, Castle Island offers a beach getaway with Fort Independence, historic tours, and relaxing at Pleasure Bay Beach. Another fantastic option is a VIP brewery tour, visiting different breweries and sampling craft beers.
On your last night, enjoy Boston’s live music scene or unwind with a craft cocktail at Drink, a bar known for its custom-made drinks. Alternatively, visit 21st Amendment, a bar celebrating the end of prohibition, and join the Sunday trivia night.
Food lovers can indulge in Boston’s culinary scene with various food tours:
1. North End Walking Food Tour – Sample authentic Italian dishes in Little Italy.
2. North End Little Italy Pizza Tour – Taste some of the best pizzas in the area.
3. Underground Donut Tour – Enjoy unique donuts while learning about Boston’s history.
4. Seafood and History Walking Tour – Feast on classic seafood while exploring the city.
5. Brewery Tour with Lunch – Visit breweries, cider houses, and distilleries, including a meal and transportation.
For a smooth trip, remember these tips:
– Avoid visiting in winter due to the cold weather.
– Book early for summer trips to ensure accommodation and activity availability.
– Check Boston’s event calendar to avoid crowded weekends.
– Engage with locals for unique recommendations.
– Try to experience a local sports event, especially a Red Sox game.
Getting around Boston is easy. Logan International Airport is close to downtown. Use the free Silver Line bus to South Station or rideshare apps. Amtrak and various buses also connect Boston with other East Coast cities.
Stay downtown for convenience, putting you near most attractions. Options include luxury hotels on the Waterfront or trendy areas like Back Bay.
Spending a weekend in Boston provides a great introduction to the city’s history, culture, and cuisine, making it a trip you’ll want to repeat. Enjoy your Boston adventure!
