Weekend Getaway: Boston
Get ready for this destination with the next installment in our Weekend Getaway series: Boston, Massachusetts. Boston is home to Boston Logan International Airport, making it the perfect spot for a quick flight to enjoy a weekend away. We’ll explore the rich history, cultural diversity, and hidden gems that make Boston a unique and captivating destination. From historic landmarks to modern marvels, delectable culinary adventures to scenic outdoor escapes, join us as we unravel the tapestry of experiences waiting to be discovered in this dynamic city. Here’s our picks for the best way to spend three days in Boston:
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Day 1
Spend your first day orienting yourself with the city. Get ready to delve into the heart of Boston, where every cobblestone street tells a story, and each neighborhood offers distinctive charm. Begin your trip with a walk around the Boston Harbor, with a rich maritime history and a plethora of activities for visitors to enjoy.
Take a ferry to the Boston Harbor Islands for opportunities for hiking, picnicking, and exploring historic sites. Top choices in Spectacle Island and Georges Island. For roundtrip transfer to the islands and a guided tour, check out this Boston Harbor Sightseeing Cruise! Pro-tip: hike to the top of North Drumlin on Spectacle Island for stunning views of the harbor.
If you prefer to stay on the mainland, take a stroll along the Boston Harborwalk, a picturesque pathway along the waterfront where you can enjoy scenic views, public art installations, and access various neighborhoods in the area. While you’re exploring, be sure to stop for a lobster roll at one of the many harborside shops. Lobster rolls are a quintessential summertime treat and are commonly found in seafood shacks, coastal restaurants, and food trucks throughout the Northeast. Boston is no exception, and there is no better place to try a lobster roll than on your weekend getaway to Boston.
Immerse yourself in history at the Boston Tea Party Ships and Museum, complete with interactive exhibits, reenactments, and learn about the events that led to the American Revolution. The experience is guided by fully costumed interpreters who will lead you through 18th century restored replica sailing vessels and view the Robinson Tea Chest: the only known surviving tea chest from the Boston Tea Party. After your tour, visit Abigail’s Tea Room where you can enjoy freshly baked goods, lunch items, and a spot of tea and learn more about the types of tea thrown overboard in 1773. General admission for an adult is $34, but can be paired with other attractions, such as the Old Town Trolley Tour, to increase savings. Click here to book your ticket today!
Walking along the shoreline not enough adventure? Rent a kayak or paddleboard and explore the Harbor from a new perspective. Many rental facilities along the harbor provide equipment for water enthusiasts of any level. Stop by the Boston Harbor Marina for sit-on-top kayaks. Rental prices are $25 (single)/$40(tandem) for the first two hours, or $65/$85 to rent for the entire day.
Cap off your evening by enjoying a refreshing cocktail or mocktail at one of Boston’s many rooftop bars. One of my favorites was the Rooftop@Revere atop the Revere Hotel. Enjoy beautiful views of the Boston skyline while sipping on one of their creative and well-crafted drinks. Make sure to get back to your hotel and get a good night’s sleep to be ready for another full day of adventure in Boston.
Day 2
Get a good start to the day with a hearty breakfast at one of the many local cafes in the charming Beacon Hill neighborhood. Grab yourself a cup of coffee or tea to go and enjoy a leisurely walk down Acorn Street, one of the most photographed streets in the country. Marvel at the 19th century Federal-style rowhouses that make up the street’s historical charm. Any time of year is perfect to visit this quaint neighborhood, with vibrant flowers blooming in the spring and summer, colorful foliage in the fall, and a snowy and cozy atmosphere in the winter. Enjoy the morning quiet before you begin your journey into the most popular landmarks in the city with a walk along the Freedom Trail.
Perhaps the most iconic tourist attraction in Boston is the historic Freedom Trail, a fantastic way to explore the city’s history and landmarks associated with the American Revolution. Begin with a stop at the Boston Common, the official starting point of the trail. It is the oldest public park in the United States and is located near the Massachusetts State House. Also in Boston Common, you will find the visitor information center where you can pick up a map or choose to join a guided tour for in-depth insights into each stop. Visit Park Street Church and Granary Burying Ground, where you will find the final resting place of several notable figures in American history, including Paul Revere and John Hancock. As you continue your walk through the trail, you will see the Old South Meeting House, where the Boston Tea Party was organized, as well as the site of the Boston Massacre. You will conclude your journey at the Bunker Hill Monument, where you can climb to the top for panoramic views of the city. The trail is 2.5 miles long, and you should plan for 2.5-3 hours to walk the trail at a moderate pace and allow time to explore some of the stops. For a truly unique experience and way to see the Freedom Trail, consider booking this food and walking trail along the Freedom Trail!
For the evening, take in a game at the oldest park in Major League Baseball, Fenway Park. Stepping into Fenway is not just a visit to a baseball stadium; it is an immersive journey into the heart of American sports history. The iconic Green Monster looms over the outfield, echoing the cheers of countless Red Sox wins. Game days are electric, when the cheers of passionate fans resonating throughout the century-old ballpark. There is nothing quite grabbing a ballpark hotdog and enjoying Fenway Park, the embodiment of the spirit of Boston sports culture. Bonus points if you get to witness an infamous rivalry game with the New York Yankees. Even if the Sox don’t have a home game scheduled during your trip, you can still tour the iconic Fenway Park for an up-close and insider look of America’s most beloved ballpark.
Day 3
Start your final day in Beantown with a visit to the Isabella Stewart Gardner Museum, located near the Back Bay neighborhood. Isabella Stewart Gardner was a wealthy art collector and philanthropist, who founded the museum in 1903. The museum itself is a work of art, designed to resemble a 15th-century Venetian palace, complete with an interior courtyard. The museum houses an eclectic collection of over 7,400 paintings, sculptures, decorative arts, and rare books, spanning over various periods and cultures. Get lost in the peaceful oasis of the inner courtyard within the museum’s architectural splendor and browse the many special temporary exhibitions. Learn about the unsolved case of the notorious 1990 art heist, which resulted in several priceless works being stolen, including pieces from Rembrandt, Vermeer, and Manet. The museum is open daily from 11am-5pm (open until 9pm on Thursdays!) and a basic admission costs $20.
Make a stop at the Boston Public Library, another cultural and architectural gem that offers a compelling and intellectually stimulating environment for visitors of all ages and interests. The library features beautiful reading rooms adorned with intricate woodwork and large chandeliers that provide a serene environment for reading and studying. Along with its extensive collection of books, manuscripts, and print, the library also houses several special collections, including rare manuscripts and early printed books and archives. Take a moment to search for notable collections such as the John Adams Library and the Boston Anti-Slavery Collection.
Whether you are interested in history, art, science, or simply soaking in the local atmosphere, Cambridge has something to offer for everyone. Most famously known as an academic hub, home to both Harvard University and Massachusetts Institute of Technology (MIT), the city attracts scholars, researchers, and students from across the globe. Spend some time walking around the prestigious campus of Harvard and the nearby Harvard Square for bookshops, cafes, and street performers.
Check out one of the many parks and green spaces along the Charles River Esplanade, which provides scenic views and recreational activities for all to enjoy. If you are visiting in late October, you cannot miss the Head of the Charles Regatta, the largest rowing regatta in the world. Watch as 11,000 athletes compete in over 60 different events over the three-day period.
Another can’t-miss opportunity in Cambridge in the fall is the Mount Auburn Cemetery. Built in 1831, Mount Auburn is home to historical monuments, intricate gravestones, and mausoleums During the fall, these structures are surrounded by a carpet of colorful leaves to create a unique blend of history and nature. Enjoy a tranquil walk around the ponds and water features that add to the fall scenery on one of the many well-maintained walking trails and paths that meander through the grounds. The cool and crisp autumn air adds to the overall ambiance as you take in the stunning display of red, orange, and yellow paints that is especially captivating during peak fall foliage.
End your time in Cambridge with a meal at one of the city’s many diverse restaurants. You can explore a variety of cuisines, reflecting the dynamic international community. For dessert, your trip to Cambridge is not complete without a stop at Toscanini’s Ice Cream. Called the “World’s Best Ice Cream” by the New York Times, Toscanini’s has been a staple in the Cambridge area for nearly 30 years. Try one of their unique flavors, including burnt caramel, matcha, or my personal favorite, B3 (brown butter, brown sugar, and brownies!). After you’ve had your fill of this charming city, make your way back to Boston to catch your flight home or get on the road.
Three days are not nearly enough to indulge in everything Boston has to offer, but I hope this quick weekend getaway leaves you wanting to come back again and again!
Where to Stay
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HI Boston is situated in downtown Boston, making it an ideal base for exploring the city’s attractions and a budget-friendly accommodation in the heart of the city. The hostel is within walking distance of several popular sites, like Boston Common, the Freedom Trail, and the Theater District. HI Boston offers a range of accommodation options, including dormitory-style rooms with shared facilities, as well as private rooms. If you are a budget-conscious traveler, this hostel is designed to be functional and comfortable for all of your needs. The hostel also features common areas to relax and socialize, a well-equipped kitchen if you wish to prepare your own meals, and WiFi access for guests. HI Boston staff organizes various cultural and social activities to encourage interaction among guests, so if you are a solo traveler looking for company, this is the place for you. Because it is centrally located, the hostel has good access to public transportation to allow you to easily explore different parts of the city.
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For a mid-level accommodation option in the heart of the city, check out The Verb Hotel, a boutique, music-themed hotel just steps away from Fenway Park. Room options include stadium-view, balcony-access, standard rooms, and The Verb’s authentic Backstage Trailers experience. Escape to one of their deluxe retro-chic Westcraft-inspired trailers that will make you feel like you’re on the road with your favorite band. The Verb also offers unique themed packages, designed for romantic getaways, wedding parties, and even a “Basic B” package that includes chilled hard seltzers and snacks. The Verb is the perfect place for travelers looking for a unique stay without breaking the bank.
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If you are looking for the luxury experience, look no further than The Langham. House in the former Federal Reserve Bank of Boston, The Lanham retains its historic charm while seamlessly blending modern luxury and reflects the grandeur of the building’s storied past. The hotel is located in a prime location in the Financial District, allowing for easy access to many of the popular attractions. The Langham offers elegantly appointed rooms and suites with a sophisticated blend of traditional and contemporary design. Guests can expect luxurious furnishings, plush bedding, and modern amenities. The hotel features the Chuan Body + Soul Spam offering a range of wellness and relaxation services. Treat yourself to a number of indulgent spa treatment options, including massages and facials, for a rejuvenating experience. You can also expect exceptional dining options at Cafe Fleuri and The Bond, the two on-site restaurants. Continuing with historic tradition, the Langham offers its signature afternoon tea service, which is worth checking out even if you are not staying at the hotel.
Where to Eat
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Located in the heart of the Financial District, Bostonia PUblic House offers a diverse menu of American cuisine, featuring a range of dishes inspired by regional flavors. Bostonia Public House strikes a balance between an upscale dining experience and a more casual, welcoming ambiance. Try the short rib breakfast poutine for a truly unique menu item. The venue incorporates elements of Boston’s storied history into its design, providing a unique and charming atmosphere in a building that dates back to the 19th century.
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Peach Farm is a well-known Chinese restaurant located in Boston’s Chinatown. It is recognized for its authentic Chinese cuisine, with a focus on seafood and Cantonese dishes. The menu typically features a variety of fresh fish, dim sum, and other traditional Chinese specialties. Reservations are recommended given the restaurant’s popularity with both tourists and locals.
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Known for its focus on serving a curated selection of wines in a chic contemporary setting, haley.henry is a unique wine bar concept located in downtown Boston. The establishment aims to create an inviting atmosphere for wine enthusiasts and those looking to explore diverse wine offerings. In addition to its wine, haley.henry services a variety of small plates and snacks, including charcuterie, cheeses, and other appetizers designed to enhance the overall tasting experience.
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Step back in time with one of Boston’s oldest and most iconic pizzerias. Serving delicious pizza to Boston’s North End since 1926, Regina Pizzeria is a longstanding favorite among locals and visitors alike. The North End is a historic Italian neighborhood known for its rich cultural heritage and diverse dining options, making it the perfect place to grab a slice. Regina is celebrated for its traditional brick-oven pizza, offering a crispy and flavorful crust. Customers can choose from an array of creative toppings to create a combination that suits their preference, or go for a classic Margherita.
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Blossom Bar is a stylish cocktail bar located in the Brookline neighborhood. They are known for their creative and expertly crafted cocktails, with a menu that showcases their diverse selection of unique and innovative drinks. The bar’s concept is influenced by Asian flavors and cuisines, so expect to find cocktails that incorporate ingredients and techniques inspired by this part of the world. Blossom Bar also serves a variety of small plates and appetizers to snack on while you sip your drink of choice.
Have a few extra days in the city and looking for more ways to spend your time? Check out our favorite day trips and excursions from Boston:
Day Trip to Salem
Start your day early to make the most of your time in Salem. If you have access to a car, the drive will take about 45 minutes to one hour. You can also take a commuter rail or ferry, both of which provide scenic views along the way. A roundtrip fare on the ferry will run about $30, with the commuter rail being the cheaper option at $3-5 each way.
Once you arrive, visit the Salem Witch Museum. Begin your exploration of the city and gain insights into the infamous Salem Witch Trials through informative visits and presentations. Explore the Witch House, the home of Judge Jonathan Corwin, one of the judges who presided over the witch trials. You can tour this well preserved 17th-century home to learn more about the time period and events that occurred.
Take a stroll through Salem Common, a historic park surrounded by charming homes. After you’ve worked up an appetite, stop at one of the many cafes surrounding the common. Shop, browse the galleries, and relax in the green spaces along the Pickering Wharf, enjoying the tranquil maritime atmosphere. Check out the House of the Seven Gables, a historic mansion renowned for its connection to American literature and its fascinating history. Opt for a guided tour of the mansion to learn about the history, architecture, and stories of the families who lived there. Visit various rooms of the mansion, including the secret staircase and the Judge’s Study. You can check out pricing and availability here.
The most popular time of year to visit Salem is October for the Haunted Happenings festival, when the streets come alive with various spooky events and attractions. Consider participating in this ghost tour, or a haunted house experience to delve into the ambiance of the season.
No matter what time of year you visit, you can return to Boston using the same transportation options listed above, but watch out for rush hour traffic in the evening!
Whale Watching Catamaran Cruise
Price: $65 per person
Hours: cruises leave at 12pm and 2pm
Whale watching catamaran tours in Boston offer an exhilarating and educational experience for nature enthusiasts. Depart from Boston Harbor and take in the stunning views of the city skyline before heading out to sea. Enjoy the spacious catamaran and listen to knowledgeable naturalists and marine biologists describe some of the marine life found in the area.As the catamaran approaches the whale feeding grounds, these guides will help you identify different species of whales. Common sightings include humpback whales, minke whales, and fin whales, among others.
The best time for whale watching in the Boston area is from spring to fall, when whales migrate along the coast. Many tour companies will schedule their tours during this peak season to allow for the best viewing possibilities. Check out this one with the New England Aquarium. The tour lasts from 3-4 hours and will bring you back to the Boston Harbor after its completion. Sightings of these majestic creatures in their natural habitat are guaranteed and will leave lasting memories for all participants.
Looking for more fun? Check out these top-rated experiences in Boston!