Best Weekend Itinerary For Boston

Picture of Boston tea party ships


Boston is a city with much to offer in terms of culture, entertainment, and history. It’s also one of the oldest cities in America! One could spend weeks exploring all that Boston has to offer, so it can be hard to narrow down what you should do during your weekend visit. That’s why this blog post will help give you some ideas for things to do on your next trip.


1. Do a Trolley Tour



Boston Duck Tours is one of the most popular activities in Boston. The tours are an old-fashioned way to enjoy the city; however, you’ll get a modern twist with this special type of amphibious vehicle. You can take a classic sightseeing tour around Boston while riding on a boat or go for a thrill ride through the streets of Boston and see all the sights from ground level. While going through history, your guide will also offer interesting stories about famous people who lived in Boston.



2. Visit Fenway Park



Home of the Boston Red Sox, Fenway Park is a historic stadium that offers tours to visitors. You’ll learn about the ballpark’s history and see some of the famous spots where players have hit home runs or made catches. If there’s a game going on while you’re in town, be sure to buy tickets and enjoy America’s favorite pastime alive.



3. Have Lunch at Quincy Market



This famous marketplace is located in downtown Boston and offers a variety of food options worldwide. There are also plenty of souvenir shops if you’re looking for a trinket to take home with you. It can be busy during the tourist season, so try to go during the week if you can.



4. Visit the New England Aquarium



This popular attraction is a great place for people of all ages to see sea creatures from around the world. You can watch otters play or look at sand tiger sharks as they swim by in huge tanks. There are also touch pools where you can pet small jellyfish and rays! If you’re not interested in seeing marine life, there’s still plenty to do with interactive exhibits, an IMAX theater, and a 4-D ride simulator where you’ll learn about ocean conservation.



5. Take a Harbor Cruise



You’ll have beautiful views of Boston from any angle on this tour! Hop on board one of several boats, including a traditional yacht or a modern catamaran and enjoy a leisurely cruise around the harbor. You’ll see the city skyline, the USS Constitution Museum, and the Boston Tea Party Museum. If you’re lucky, you might even spot some dolphins or whales.



6. Climb the Bunker Hill Monument



This 221-foot granite monument commemorates an important battle in the American Revolution. It’s a challenging climb, but the view from the top is worth it! You’ll be able to see all of downtown Boston as well as parts of Cambridge and Somerville. Here, you can find out more about early American history and see some of the memorials from throughout the centuries.



7. Check Out a Red Sox Game at Fenway Park



Home of the Boston Red Sox, this stadium is one of America’s most beloved ballparks due to its history and unique features. There are tours available where you can get behind-the-scenes access and learn about what goes on in the clubhouse before a game. If you’re going to be visiting during baseball season, buy tickets for a game! See if you can catch a home run while you’re there.



8. Walk the Freedom Trail



This 2.5-mile trail winds through downtown Boston and takes you by 16 different historical sites. You’ll learn about the American Revolution, the Civil War, and more as you walk. The trail is easily accessible and free to use, so it’s perfect for a weekend visit. Be sure to wear comfortable shoes because you’ll be doing a lot of walking.



9. Take a Boston Bike Tour



If you want to see as much of the city as possible, why not try a bike tour? This is a great way to cover more ground than you would on foot and see some of the sights further from downtown. Several companies offer bike tours, so choose the one that fits your interests and schedule.



10. Get Dinner at Cheers



Did you know that the TV show “Cheers” took place in Boston? You can visit this famous bar (fictional or not) for a drink and some grub. It’s located on Beacon Hill near several other landmarks like the State House, Louisburg Square, and Charles Street. Be sure to order Sam Adams beer because it was created right next door.



11. Take an Architecture Tour of Back Bay



Learn about Boston‘s buildings on this walking tour through one of its most famous neighborhoods. You’ll see Victorian mansions as well as Art Deco skyscrapers from all eras of American history. There are plenty of historical sites along the way, so you’re constantly learning something new. This is a great way to spend an afternoon if you’re interested in architecture or Boston history.



12. Walk Along The Charles River



Bostonians love their river – it even inspired their beloved football team name! Pack your camera because there are plenty of photo opportunities here with scenic views of both towns. You’ll see boats sailing by, kayakers paddling along, and the Boston skyline in the distance. Check out some of the Charles River Reservation’s public art, or take a peaceful stroll by yourself.



13. Visit the Boston Public Garden



Another highlight of the Emerald Necklace, this historic garden is frequented by locals year-round. It features fountains, statues, ponds – even swan boats! During fall/winter, you can skate on Frog Pond then warm up inside The Bose Center for the Arts. There are plenty of photo opportunities here, so be sure to bring your camera.



14. Enjoy Some Live Music at Fort Hill Bar


Located in Roxbury, this bar has live music every weekend! The cover charge varies depending on what band is performing, but it’s usually pretty cheap. You can enjoy beer, wine, and specialty cocktails while you listen to bands of different genres. There are also food specials on weekends like steak night.


There are plenty of things to do in Boston for tourists and locals alike. Be sure to have a stay at Airbnb Turnaround Service for a home away from home. When on a quick trip, finding the time to clean your space can be a real challenge. Worry less as we are here to help! Cleanzen offers the best maid service for vacation rental properties in greater Boston area! Book your appointment as easy as 1-2-3!


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