Visit Boston for three nights before flying to Dominican Republic and spending a week on this stunning Caribbean Island.
Boston Holidays
Expect to find
Historical Attractions
Follow the Freedom Trail or visit Old North Church
Parks and Outdoor Spaces
Breathe in the fresh air in Boston Common
Museums
Visit one of the largest art museums in the USA
Overview
Experience Boston
Boston holidays are the perfect blend of big city and historic neighbourhood charm. Even if you’re not a ‘big city’ kind of person, you can’t help but fall in love with its neighbourhoods and glorious open spaces. Every neighbourhood has its own personality and with so much to experience, it’s a great city to visit at any time of year.
Bursting with pride, Boston celebrates its past, while looking to the future. With a thriving arts scene, world famous academic institutions and an unwavering passion for sport, there are always plenty of interesting things to discover in Boston.
Call us to Tailor Make your Boston Holidays
Experience the amazing sights and sounds of Boston. Check out our exciting range of Boston holidays, the possibilities are unlimited!
Call our Personal Travel Planners to book your next Boston break.
Multi-Centre Holidays to Boston
A visit to Boston combined with one or two other iconic American cities makes for an amazing holiday. East Coast highlights, city and beach, or Boston on a stay and cruise package, there is a combination to suit every taste. Our Personal Travel Planners can create a custom itinerary for you, just decide which destinations you want to combine.
Boston & Dominican Republic
Boston & Dominican Republic
10 Nights From €1895 per person
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Boston, New York & Washington, DC
Boston, New York & Washington, DC
9 Nights From €2269 per person
Visit three of America’s most famous cities Boston, New York & Washington DC in one incredible holiday.
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New York & Boston
New York & Boston
6 Nights From €1889 per person
Fly to New York and take a bite out of the Big Apple before a second city break in Boston.
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Boston City Breaks
A Boston city break is a great option. It’s one of the USA’s best shopping cities, with everything from international and US brands to local boutiques and design stores that will appeal to every type of shopper.
Boston
Boston
4 Nights From €999 per person
This itinerary is the perfect opportunity to explore Boston in one of America's most traditional holidays!
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Boston Easter
Boston Easter
4 Nights From €1599 per person
Boston is perfect for a delightful city break! An eclectic mix of historic monuments and bohemian neighbourhoods.
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Boston Thanksgiving
Boston Thanksgiving
5 Nights From €1274 per person
Boston is the perfect city to explore on foot, dotted with hip and trendy neighbourhoods, modern sky scrapers and historic monuments all within easy walking distance of one another.
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Boston Escorted Tour Offers
Visit Boston on an escorted tour with American Holidays. Enjoy the highlights of a holiday in Boston while discovering the East Coast or New England on one of our popular escorted tours.
Colours of New England Escorted Tour
Colours of New England Escorted Tour
9 Nights From €2994 per person
Discover Maine, Vermont, Massachusetts and New Hampshire on this picturesque tour, be sure to have your camera ready!
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Fall Colours of New England Escorted Tour
Fall Colours of New England Escorted Tour
9 Nights From €4199 per person
New England is famous for picturesque towns that showcase the spectacular colours of Fall.
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Eastern Discovery Escorted Tour
Eastern Discovery Escorted Tour
10 Nights From €2584 per person
Embark on this incredible escorted tour to see some of the beautiful sights of the East Coast of the US and Canada.
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Things to Do
See the sites
Boston is a city steeped in history, and no visit is complete without walking the Freedom Trail. This 2.5-mile-long path guides visitors through 16 significant historical sites, including the Massachusetts State House, Paul Revere’s House, and the Old North Church, where the famous “One if by land, two if by sea” signal was sent. Each stop offers a glimpse into pivotal moments of the American Revolution, making it a must for history buffs.
Additionally, the Boston Tea Party Ships and Museum provides an immersive experience where you can participate in a reenactment of the Boston Tea Party, throwing tea into the harbour just like the colonists did in 1773.
Discover World-Class Museums
Art and science enthusiasts will find Boston’s museums captivating. The Museum of Fine Arts houses an extensive collection of art from various cultures and periods, from ancient Egyptian artefacts to contemporary pieces.
For a unique blend of art and history, visit the Isabella Stewart Gardner Museum, which showcases a vast array of European, Asian, and American art in a building styled after a Venetian palace. The Museum of Science provides hands-on exhibits, a planetarium, and an IMAX theatre, making it a favourite for families and curious minds.
See the beauty of Boston
Boston’s green spaces are perfect for relaxation and recreation. Boston Common, America’s oldest city park, offers expansive lawns, walking paths, and the historic Frog Pond, which becomes an ice-skating rink in the winter. Adjacent to the Common, the Public Garden features beautifully landscaped grounds, the iconic Swan Boats, and a picturesque lagoon.
For a scenic walk or bike ride, head to the Charles River Esplanade, which stretches along the river with stunning views and plenty of spots for picnics. If you’re up for an adventure, take a ferry to the Boston Harbor Islands, where you can hike, camp, and explore historic forts.
A Culinary Melting Pot
Boston’s shopping and dining scenes are vibrant and diverse. Quincy Market and Faneuil Hall Marketplace offer a bustling atmosphere with an array of food vendors, restaurants and shops, housed in historic buildings.
For upscale shopping, Newbury Street is lined with chic boutiques, galleries, and cafes set in charming brownstones. The North End, Boston’s Little Italy, is famous for its authentic Italian cuisine. Wander the narrow streets and savour traditional dishes in family-owned restaurants, and don’t miss trying the cannoli at a pastry shop.
Something for Everyone
Boston’s entertainment options cater to a wide range of interests. The Theatre District is the place to enjoy Broadway shows, musicals, and performances at venues like the Boston Opera House and the Wang Theatre.
Sports fans can catch a game at Fenway Park, the iconic home of the Boston Red Sox. For live music, head to the House of Blues, a premier venue hosting a variety of artists and bands. Classical music aficionados will appreciate the Boston Symphony Orchestra, renowned for its performances at Symphony Hall.
Location
Founded in 1630 and set along New England’s coast, Boston is one of America’s oldest cities, known for its history, culture and sports. Follow the Freedom Trail past historical landmarks like the Boston Tea Party site, the Old North Church, then catch a game at Fenway Park, baseball’s oldest stadium. With its cosy pubs, waterfront seafood spots and leafy parks like the Public Garden, Boston is the perfect destination for history buffs.
Best Times To Travel
March – May
Early spring in Boston is brisk, with temperatures ranging from 5°C to 10°C in March, rising to 15°C to 20°C by May. It’s the perfect time to experience Patriot’s Day in mid-April, when the city commemorates its revolutionary past with vivid reenactments.
June-August
Boston summers are warm, with temperatures between 20°C and 28°C. This is the city’s peak season, when the Freedom Trail buzzes with visitors and Fenway Park is filled with cheering baseball fans. Celebrate July 4th at Boston Harborfest, a week-long waterfront party with reenactments, concerts and fireworks.
September-November
In Autumn, days will be sunny, bright and crisp, while evenings will get a bit chilly. Temperatures begin to cool from around 20°C in September to 5°C by November. It’s the perfect time to visit one of Boston’s beautiful parks and take in the autumn leaves. Quieter than the summer season, it’s ideal for exploring museums and going on walks. Catch the Head of the Charles rowing event in mid-October, a three-day competition held annually on the Charles River.
December – February
Boston winters are cold but charming, with temperatures between 0°C and 5°C. The Christmas season lights up the city with festive displays. Visit Frog Pong Ice Rink or stroll along Beacon Hill’s carefully decorated houses.
Guides
Staff Tips
Boston is very easy to walk around, but when your feet get tired make a beeline for the Boston Library on Copley Square. Not only is it incredibly interesting, it's an oasis of calm in this busy city. The Courtyard Café in the central quadrangle is a great place to have lunch or a coffee.
Angel ChuaPersonal Travel Planner
American Holidays Brochures
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Boston FAQs
How many days should I plan for my first trip to Boston?
For your first visit, three to four days is ideal. This gives you time to walk the Freedom Trail, explore the local neighbourhoods, catch a game and visit the city’s museums.
What’s the best way to get from Logan Airport to downtown Boston?
You can catch the free bus from the airport to South Station, or alternatively, catch a taxi or Uber, which takes around 15 minutes.
Is Boston a walkable city, or should I use public transportation?
Boston is very walkable, especially downtown, where attractions and landmarks are situated close together. For longer distances, the subway (called the ‘T’) is affordable and efficient.
What’s the best way to get around Boston—subway (the “T”), taxis, Uber, or rental car?
Stick to the subway or ‘T’ for most trips; the extensive routes and frequency of services make it a great way to get around. CharlieCards, a free reusable pre-loaded pass, can be used for bus and subway fares. You can also use contactless pay, a tappable ticket. Taxis and Ubers are handy for neighbourhoods not well served by the subway. You can also choose to rent a car if you’re planning to visit nearby Salem, or you can reach it by train. Cape Cod is reachable by ferry. For convenience, transfer from Logan Airport by bus, shuttle or private transfer to Downtown or the Back Bay.
What is the Freedom Trail, and how long does it take to walk it?
The Freedom Trail is a 2.5-mile path that links 16 historical sites across the city. Walking the full trail takes around 2-3 hours, but allow half a day if you want to visit the museums and churches along the way, and it is a great way to get your bearings in the city.
Should I take a guided tour of Boston, or can I explore on my own?
From foodie, history and even ghostly, locally guided tours are a fun way to explore the city and get insider information. Alternatively, you can pick up a map or download a self-guided tour app if you’d prefer to go at your own pace.
What are the best museums to visit in Boston?
Top picks include the Boston Tea Party Museum, the Isabella Gardner Museum for its beautiful courtyard and the Boston Children’s Science Museum, perfect for families. As both Harvard University and MIT are so close to the city, a visit and a decent tour of their campuses should not be missed.
What are the best day trips from Boston?
Salem is perfect for those looking for something spookier and can be reached by train in about 40 minutes, while Cape Cod is perfect for lounging on the beach and sampling seafood, and is best visited by ferry. Harvard’s campus in Cambridge is also just a short subway ride away.
What are the best neighborhoods to explore in Boston?
The North End is a must for Italian food and historic sites, while Back Bay has elegant brownstones and boutique shops. Beacon Hill takes you back to old-world Boston with its cobbled streets with locally owned stores, and coffee shops.
What is the best way to experience Harvard and MIT in Cambridge?
Walk around Harvard Yard and take a peek into the Harvard Museum of Natural History. Explore the back streets to experience student life, from hidden tiki bars to local restaurants and collegiate merchandise stores. MIT’s futuristic campus is in Cambridge, just over the Charles Riverand it’s museum is not to be missed, showcasing quirky robotic exhibits and stories of ground breaking scientific work. End your day at Kendall Square, MIT’s tech hub, packed with cafés and bookshops.
What are the best waterfront activities in Boston?
Take a stroll down the Harborwalk or relax at Christopher Columbus Park. A Boston Harbor dinner cruise is a great way to explore the waterfront while enjoying live music and fresh local seafood. In the summer, take a ferry to Boston Harbor Islands for hiking and picnics or tour the USS Constitution, the world’s oldest commissioned warship that’s still afloat today.
Where can I catch a live sports game (Red Sox, Celtics, Bruins, Patriots)?
Both located downtown, head to Fenway Park for Red Sox games and TD Garden for the Celtics and Bruins. For Patriots games, Gillette Stadium is about a 45-minute drive from the centre.
What are some unique or off-the-beaten-path things to do in Boston?
For a fun twist on sightseeing, hop on the Boston Duck Tour, a World War II-style amphibious vehicle. Historic trolley tours let you explore at your own pace with the ability to hop on and off, or wander the hidden courtyards of Bay Village, Boston’s tiniest neighbourhood.
What are the must-try foods in Boston?
When visiting Boston, be sure to try a New England clam chowder, a creamy soup made with fresh clams and potatoes. Lobster rolls are also a must, with fresh lobster meat served in a brioche bun. Finish it off with a classic Boston cream pie, a layered cake filled with custard and topped with a chocolate glaze. For adult beverages, Boston is home to Samuel Adams IPAs.
Where can I find the best seafood in Boston, especially lobster rolls and clam chowder?
For the best seafood in Boston, head to Legal Sea Foods, known for its clam chowder, or visit Faneuil Hall in Quincy Market or High Street Place for more casual options, dishing up fresh seafood and lobster rolls doused in butter.
What are the best spots for scenic views of the Boston skyline?
The Skywalk Observatory in the Prudential Center provides stunning panoramic views with bars, restaurants and cafes for you to enjoy the city, view and beyond. For an alternative, head to a rooftop bar like The Envoy or the Long Bar & Terrace in Raffles for afternoon tea or cocktails..
What’s the best way to budget for a trip to Boston, and is it an expensive city to visit?
Boston can get pricey, but there are plenty of ways to save on costs. Boston is a very walkable city, so getting around is easy. For longer distances, use public transport where possible and eat at local neighbourhood food spots or food trucks.
