Planning a trip to Boston? With its rich history, vibrant neighborhoods, and coastal charm, Boston is a city that seamlessly blends the past and present. Whether you’re strolling along the historic Freedom Trail, indulging in fresh seafood by the waterfront, or exploring world-class museums and charming cobblestone streets, the city offers something for every traveler. Four days is the perfect amount of time to dive into Boston’s highlights while leaving room to explore its hidden gems and nearby attractions. Follow along as we share the ultimate itinerary for an unforgettable four days in Boston!
Getting there
Boston Logan International Airport serves as the main gateway for domestic and international travelers, with numerous flights arriving daily. From nearby cities like New York or Providence, you can take Amtrak trains, including the high-speed Acela service, which provides a comfortable and efficient ride to Boston’s South Station. For budget-friendly travel, bus services like Greyhound and Peter Pan offer frequent routes to the city. Those driving can easily access Boston via I-90 (Massachusetts Turnpike) or I-93, though traffic can be heavy during peak hours. Once you arrive, Boston’s compact layout and public transit system make getting around simple.
Where to stay
When staying in Boston, choose a neighbourhood that fits your interests. For historic charm and proximity to landmarks like Faneuil Hall and the Freedom Trail, consider Downtown or Beacon Hill, where boutique hotels offer classic New England ambiance. Back Bay is perfect for those seeking luxury accommodations, with elegant brownstones, shopping on Newbury Street, and views of the Charles River. If you prefer a trendy vibe, Seaport and South Boston boast modern hotels with waterfront views and easy access to dining and nightlife. For a budget-friendly option, look to Cambridge, home to Harvard and MIT, where you can enjoy a lively, intellectual atmosphere just across the river.
4 Days in Boston
Day 1: Explore Boston’s Historic Heart
Morning: The Freedom Trail
Start your trip by immersing yourself in Boston’s history. Walk the Freedom Trail, a 2.5-mile red-brick path that winds through 16 historically significant sites. Highlights include:
- Boston Common: America’s oldest public park. Don’t miss the ‘Make Way for Ducklings’ statue and check out their seasonal outfits.
- Massachusetts State House: An architectural gem with its gold dome.
- Paul Revere’s House: A glimpse into colonial life.
Grab a coffee at Tatte Bakery near Faneuil Hall to refuel.
Afternoon: Quincy Market and Waterfront
Explore Quincy Market, a bustling hub filled with food stalls and local vendors. Although now incorporated into the new (1976) Faneuil Hall Marketplace, Quincy Market continues to be a source of food for Bostonians. Try a classic lobster roll or a bowl of New England clam chowder.
Although its character has changed, from providing grocery and other foodstuffs to in general food outlets, food-stall, fast-food, and restaurants, it remains it remains a popular and busy meeting place for locals. The market is two-stories tall, rectangular in shape with a grand dome at its centre. The space beneath the Dome now serves as the seating area for the food court as is suitably adorned with various sign boards relating to businesses and merchants from previous eras.
Whilst you’re in the area, also check out the Public Market. This indoor market specializes in ‘locally sourced groceries and specialty agricultural products’ (produce sold must be produced or originate in New England). I’d highly recommended the Taza Hot Chocolate and of course a helping of homemade donuts.
After lunch, head to the Boston Tea Party Ships and Museum. Voted the best family attraction in Boston, the museum provides a modern, multi-sensory experience for the visitor. Live actors recreate this piece of American history whist, high-tech, interactive exhibits and authentically restored tea ships, the Eleanor and the Beaver, help deliver the story of that that fateful night of December 16, 1773. For those of you who might not know The Boston Tea Party was the beginning a rebellion by the American colonists, forced on them by the injustices of the tax system that used the colonists’ tax revenues to repay British war debts. As a calculated response tea, a prized commodity, was thrown overboard from the three ships in Boston harbour. Two years later, war broke out, with the result that on 4th July 1776, America, specifically the Thirteen Colonies, formally declared its independence from Great Britain
Whilst we weren’t prepared to pay the $30 entrance fee to the museum, we did head up to Abigail’s Tea Room – a cosy and comfortable room overlooking the waterfront and harbour, where we were welcomed and served by tea ladies equipped with suitable period attire. Quite an experience!
Evening: North End Dining
Boston’s North End, also known as “Little Italy,” offers incredible dining options. North End is the city’s oldest residential community and people have lived in the neighbourhood since the 1630s. Less than a third of a square mile in area, it is incredibly walkable, and has a whole host of tourist attractions and popular establishments (particularly eateries) to offers its visitors. Enjoy handmade pasta at Giacomo’s or pizza at Regina Pizzeria. End your day with a cannoli from Mike’s Pastry or Modern Pastry.
Day 2: Harvard, Museums, and Fenway Park
Morning: Harvard Square and Cambridge
Cross the Charles River to Harvard Square in Cambridge. Tour Harvard University, soak up its academic atmosphere, and explore quirky bookstores like The Harvard Coop. Stop by LA Burdick, a popular hot chocolate café and chocolatier establishment for a mid-morning drink.
Afternoon: Museum Time
Return to Boston and visit the Museum of Fine Arts or the Isabella Stewart Gardner Museum. Both offer world-class art collections in stunning settings. If you’re more of a sport fans enjoy a walk through The Sports Museum at TD Garden.
Alternatively spend some time indulging in some retail therapy. Check out Downtown Crossing for high street stores, the Prudential Centre off Bolyston, or Newbury Street a lovely avenue of upmarket shops and restaurants.
Evening: Fenway Park
Catch a Red Sox game at Fenway Park, the oldest Major League Baseball stadium. If it’s not baseball season, consider a behind-the-scenes tour to learn about its storied past.
Day 3: A Day Trip to Salem
Morning: Travel to Salem
Take the MBTA commuter rail or a ferry to Salem, about 30 minutes from Boston. Known for its infamous witch trials, Salem blends history and charm. Highlights include:
- Salem Witch Museum: A must-visit to understand the trials that defined its history.
- The House of the Seven Gables: Explore the inspiration behind Nathaniel Hawthorne’s novel.
- Peabody Essex Museum: A treasure trove of maritime art and global artifacts.
Afternoon: Stroll the Historic District
Wander through Chestnut Street, lined with grand Federal-style mansions. Don’t miss the witch-themed shops and boutiques in downtown Salem for unique souvenirs.
Evening: Return to Boston
Enjoy dinner back in Boston at Union Oyster House, one of the oldest restaurants in America.
Day 4: Back Bay Beauty and Seaside Serenity
Morning: Back Bay and Beacon Hill
Start your day with a leisurely walk along Newbury Street, known for its boutique shops and cafés. Stop at Thinking Cup for a morning coffee or check out brunch at Stephanie’s.
Then, head to Beacon Hill to admire its gaslit streets and the charming Acorn Street. Beacon Hill is one of America’s most historic neighbourhoods, characterised by its Federal, Greek Revival, and Victorian architecture, elegant buildings, including The Massachusetts State House, with its magnificent gilded dome. The area is also graced by charming brick and cobblestoned streets adorned with period lampposts, whose glimmering light just adds to the atmosphere. Check out the swanky Louisburg Square (America’s most expensive address) and the amazing array of door knockers! The door with the shiny (Boston-) lobster shaped knocker was once home to the author William Dean Howells and on that the house on the opposite side of the Square, where the US flag was flying, was the home of John Kerry, the former United States Secretary of State.
Afternoon: Boston Public Library and Copley Square
Visit the Boston Public Library, a masterpiece of architecture and culture. The Library was founded in 1848 and, as well as serving the people of Boston, it also acts as the Library for the Commonwealth (of Massachusetts). It is truly a magnificent building, especially once you get inside and you are met with the grand marble stair case and ornate decor. It’s mindboggling to think that within the building are approximately 23 million items encompassing all formats including books, maps, prints and CDs etc. Spend some time (quietly) wandering around the Library taking in all of the surroundings and peek into the gorgeous reading room. Named after its first great benefactor Joshua Bates, Bates Hall is as you might imagine a vast space with a coffered ceiling, large research desks decorated and illuminated by a profusion of green lampshades.
Stroll through Copley Square, home to the stunning Trinity Church.
Evening: Charles River Esplanade
End your trip with a sunset walk along the Charles River Esplanade. For dinner, consider Legal Sea Foods for a classic seafood feast or Eataly Boston for Italian delights.
Suggestions for an extended stay in Boston:
If you’re extending your stay in Boston, there are plenty of activities to make your trip unforgettable.
Whale watching is a must—hop on a tour from Boston Harbor to see humpbacks, finbacks, and dolphins in the Stellwagen Bank Marine Sanctuary. Tip: Calm, clear days are best for whale-watching tours, so keep an eye on the forecast when planning.
Dive into Boston’s rich history with visits to the Paul Revere House and the USS Constitution Museum, or explore the neighbourhoods of Charlestown and South End for local charm.
Take a day trip to Plymouth, where you can visit Plimoth Patuxet Museums and see the famous Plymouth Rock, or head to Concord and Lexington for Revolutionary War history.
For a breath of fresh air, stroll through the Arnold Arboretum, kayak on the Charles River, or take a ferry to the Boston Harbor Islands for hiking and picnicking.
Tips for Your Trip:
Seasonal Highlights: Visit in the fall for breathtaking foliage or spring for blooming gardens.
Getting Around: Boston’s compact layout makes it a walkable city. Use the T (subway) for longer distances. Consider purchasing a CharlieCard for unlimited rides on buses and subways.
Dress in Layers: Boston weather can change quickly, so pack versatile clothing to stay comfortable throughout the day.
Book Ahead: Popular attractions, like whale watching tours or Fenway Park tours, often sell out, so reserve your tickets in advance.
1 comment
Looks like a comprehensive trip… but you didn’t miss Mike’s Pastries, did you?!? I’d fly to Boston for one of their cannolis!