Morning: Breakfast in Beacon Hill and a stroll through the park
Start your vacation with a trip to Boston’s Beacon Hill neighborhood, one of the most historic and stately parts of the city. The district is home to several cozy breakfast joints, including The Paramount, The Tip Tap Room and Beacon Hill Bistro. The brownstones in this neighborhood date back to the early 1800s, so take in the majestic views (complete with gas lamps and cobblestones), especially in the quaint Louisburg Square.
Afterward, head down Charles Street towards the Boston Common and Public Garden – where you can take a short ride on the Swan Boats – and stroll through the parks before walking to the Back Bay.
Afternoon: The Back Bay for lunch and a duck boat tour
The Back Bay neighborhood is brimming with elegant architecture and picturesque tree-lined streets. Meander down Commonwealth Avenue or Marlborough or Beacon streets. At some point, cross over to Newbury Street, known for high-end shopping tucked into rows of brownstones. The street has numerous options for lunch, including Piattini, La Voile and Stephanie’s on Newbury.
Later on, check out Copley Square – home of the Boston Public Library and the Boston Marathon finish line (and memorial) – on your way up Boylston Street towards the Prudential Center. Here, buy tickets and line up for a Boston duck boat tour, a unique 80-minute sightseeing tour through the city and onto the Charles River. It’s a great way to get acquainted with Boston’s major attractions and ready yourself for the rest of the week.
Evening: Dinner and drinks on top of the city
The duck boat will return you to the Prudential Center, which is perfect for the next stop. Once off the boat, head into the Pru and take the elevator to the 50th floor to check out the Skywalk Observatory, which provides 360-degree views of the city and harbor islands.
For dinner, take a quick commute up the elevator to the Top of the Hub on the 52nd floor. Sip a glass of wine and watch the evening descend over the sparkling city below you.
Morning: Markets and fishy views
Begin your morning with a trip to Boston Public Market or Faneuil Hall Marketplace – both are within walking distance of each other. Between the two, there are over 70 eateries and shops. With some chains throughout, Faneuil is geared more towards tourists, while the Public Market, with its many local vendors, provides a more authentic taste of Boston.
From here, the New England Aquarium is a short walk down the Rose Kennedy Greenway – a beautiful pedestrian connector to the harbor, full of plants, striking garden designs and art. After exploring the aquarium, walk down the Boston Harborwalk, a near-continuous linear park that stretches along 43 miles (69 kilometers) of Boston’s shoreline.
Afternoon: Cannolis and freedom walks
Boston’s North End is an easy walk up the Harborwalk and is among the most-visited neighborhoods in the city. The area, which was the first residential neighborhood in Boston, is now home to a slew of Italian restaurants and bakeries. Choose from one of the fine-dining options or grab a slice of pizza at Regina Pizzeria or Galleria Umberto. Make sure to stop by Modern Pastry or Mike’s Pastry for a cannoli or another Italian dessert.
Once you’re satisfied, begin one of the quintessential guided walks in Boston to learn the city’s (and nation’s) formative history. Start with The Freedom Trail – which has three stops in the North End – or make your way to the Black Heritage Trail or Women’s Heritage Trail (both of which are within walking distance).
Evening: Boston cream pie and ghosts
Relax with dinner at Parker’s Restaurant at the Omni Parker House, located in Downtown. The restaurant, which serves classic New England food, is the birthplace of the Boston cream pie. It’s here where Malcolm X worked as a busser and John F Kennedy supposedly proposed to Jackie. Also, across the street is a historic graveyard where Paul Revere and Samuel Adams are buried. End your evening with a nightcap at 21st Amendment, jm Curley or Bostonia Public House.
Morning: Bookstore breakfast and the Charles River Esplanade
Start your morning with a good book and a full breakfast at Trident Booksellers and Cafe on Newbury Street. The bookstore has a breakfast menu that features a number of egg dishes.
Follow your meal with a walk up Massachusetts Avenue to the esplanade, a 3mi (4.8km) tree-lined walkway along the Charles River. It is a favorite hang-out spot for Bostonians, including fitness lovers, and hosts free concerts and outdoor movies and a beer garden. You’ll also find plenty of water activities at Community Boating Inc., including kayaking and paddleboarding.
Afternoon: Cambridge lunch and college campuses
Take the Red Line on the T (Boston’s subway system) across the river to Cambridge, where you’ll find the Massachusetts Institute of Technology, which offers self-guided walking tours of the riverfront campus. A little farther up Massachusetts Avenue is Central Square, which has many lunch spots, including Pagu, Little Donkey and Pammy’s.
If you’re still in the college mindset, head to Harvard Yard (within walking distance or easily accessible via one more stop on the Red Line), with its iconic white tower peaks, beautiful red-brick walls and climbing ivy. While here, also check out the bustling area and many stores of Harvard Square (such as The World’s Only Curious George Store and kitschy Black Ink), just a stone’s throw from the famed university.
Evening: Dinner and nightlife in Somerville
Adjacent to Cambridge is the city of Somerville, which is practically considered another Boston neighborhood. This vibrant area holds six main squares that each have a bounty of bars and restaurants. Davis Square (continuing another two stops up the Red Line) is home to several cocktail bars, comedy clubs and Somerville Theatre. End the evening with dinner at Redbones or Spoke Wine Bar before having a drink at Saloon or Aeronaut Brewing Company.
Morning: Breakfast in Brookline and museum walks
Begin with coffee and breakfast (try either Zaftigs Delicatessen or Brothers Restaurant) in the historic Coolidge Corner section of Brookline, a quaint town within Boston. The charming square features a host of interesting buildings and is home to movie theater the Coolidge Corner Theatre and indie bookstore Brookline Booksmith. After eating, mosey through the wealthy residences in the area (including JFK’s home-turned-museum).
A short walk away, over a few stone bridges in the Riverway park, is Fenway, a neighborhood flush with universities and museums. The Isabella Stewart Gardner Museum – the site of the largest art heist in history – houses significant art collections in a Venetian-style palace. Continue east to the Museum of Fine Arts, Boston (MFA), which has a vast collection of paintings and artefacts.
Afternoon: Lunch in Kenmore Square and Fenway Park
Amble through the Back Bay Fens, a large urban park that surrounds the museum and connects walkers to Boston’s Emerald Necklace – a string of parks that run through the city. In the Fens, check out the pristine Kelleher Rose Garden or patches of community gardens before stopping for lunch in Kenmore Square. Options include Island Creek Oyster Bar, Eastern Standard, and Fin’s Sushi and Grill. Kenmore is also the site of the Citgo sign, which Bostonians embrace as an essential part of the skyline. Finish the afternoon with an hour-long tour of Fenway Park, America’s oldest ballpark.
Evening: Taste the party scene in Allston-Brighton
Stay in the Fenway area for dinner – try Bleacher Bar or Tiger Mama – before beginning a night out. Start revving up the evening with a stop at either Nathálie (a wine bar that stocks only female-produced labels) or Fool’s Errand (it’s standing room only but worth it for James Beard Award-nominated bites).
Afterward, spend the night like a Boston college student in the nearby Allston-Brighton neighborhood. The district, which is home to a large student population, has a vibrant and youthful nightlife with numerous bars and live-music venues. Head to Common Ground, Wonder Bar or Model Cafe for dancing. Drink hip cocktails at Deep Ellum or try rowdy Tavern in the Square for a true college experience. Check out low-key dive bars at The Avenue, Harry’s Bar & Grill or Silhouette Lounge. Alternatively, go to Paradise Rock Club, Brighton Music Hall or Great Scott for live music.
Morning/afternoon: Day trip to the Boston Harbor Islands
After a night out, take a leisurely morning brunch at The Friendly Toast (a ’50s-themed diner) or Citrus & Salt (a beachy Mexican spot) in the Back Bay. Then, head over to the Long Wharf along Boston Harbor for a relaxing day out on the ocean.
Many of Boston’s 34 harbor islands are accessible to the public in the warmer months. A ferry is available for daily trips to and from the open islands where you can camp, hike, visit one of the historical sites or view local wildlife. There’s also “Junior Ranger” courses hosted for children, and Boston Harbor Cruises offers lighthouse tours and whale watching.
Evening: Dinner and jazz in the South End
Once back on the mainland, head to the South End for dinner. Options include Gaslight (a French bistro), Myers + Chang (an upscale, Asian-inspired restaurant) and The Gallows (a gastropub with eccentric decorations). Finish the evening with drinks and live jazz at either The Beehive or Wally’s Cafe Jazz Club.
Morning: Jamaica Pond and Jamaica Plain
A quick ride away on the Orange Line, Jamaica Plain (known locally as JP) is Boston’s hippest neighborhood. Choose from one of several breakfast spots here, including Ula Café or Little Dipper. After fueling up, head over for a stroll along Jamaica Pond and the Emerald Necklace – created more than 100 years ago by architect Frederick Law Olmsted.
Next, roam down Centre Street, a thoroughfare lined with multiple shops and cafés. Visit Papercuts JP for books, Boomerangs for vintage items, Tres Gatos for records or Fire Opal for handmade jewelry and art.
Afternoon: Eats, sweets and the Sam Adams Boston Brewery
Centre Street also has a range of restaurants, including Brassica Kitchen + Cafe, Ten Tables and much more. After eating, indulge your sweet tooth with home-made ice cream at JP Licks or vegan ice cream and baked goods at FoMu. The Samuel Adams Boston Brewery, home to arguably the city’s most famous craft beer, is also located in this neighborhood. Brewery tours and tastings are available daily.
Evening: Red Sox game
Back in Fenway, catch an evening Red Sox game at the historic Fenway Park (built in 1912). Sport is huge in Boston and the only way to experience this passion is by going to a game. Even if you don’t follow baseball, the experience is cheerful and fun with drinks, fried dough, Fenway Franks or lobster rolls, singing and crowd camaraderie.
Morning: Seaport cafés and abstract art
Start your final day in Beantown with coffee and breakfast at one of the Seaport’s most popular bakeries. Both Flour and Tatte are local chains that are famous for their French pastries and breakfast items.
Next, head over to the Institute of Contemporary Art (ICA) for waterfront exhibitions, film and music. First opened in 1936, the ICA’s presence helped pioneer the regeneration of the surrounding neighborhood.
Afternoon: Lunch and stroll near South Station (but don’t depart just yet)
Once an industrial wasteland in Boston, the Seaport District is now highly developed with condos, hotels, trendy bars and restaurants, and lively public spaces. Try one of the local breweries (Trillium or Harpoon) for lunch and drinks or one of the numerous seafood restaurants, including the boisterous Barking Crab and sleek Row 34.
Afterward, take a walk up the Rose Kennedy Greenway past South Station and Dewey Square (with art, food trucks, benches and music). Wander towards the Chinatown Gate, which marks the start of the bustling Chinatown-Leather District.
Evening: Harborside dinner and an evening performance
For your last evening in Boston, take a scenic boat ride (via one of Boston’s water taxis or Spirit of Boston cruises) across the harbor. Have dinner at Bar Mercato in the boutique Hyatt Centric Faneuil Hall or ferry across the bay to dine at ReelHouse in East Boston.
Finish the trip with an evening show. The Boston Opera House hosts numerous performances each year, including the Boston Ballet and several musicals. Meanwhile, the Boston Pops play regularly at Boston Symphony Hall or outdoor concerts throughout the summer. Take one in along the Charles River Esplanade for a uniquely Boston final night.
Danielle Hallock contributed additional reporting to this article.