4-Day Adventure: Romance & Culture in Boston

Fall in love all over again with a romantic getaway to historic Boston.

22 April 2023

A romantic trip to Boston promises a perfect blend of history, culture, and culinary delights. From visiting the Freedom Trail and strolling through the Boston Public Garden to indulging in some delicious seafood at the North End, Boston has it all. Don't forget to catch a sunset at the iconic Fenway Park and take a romantic stroll along the picturesque Charles River.

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Travel plan

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Day 1

Historic Hotspots

Check in at the enchanting Omni Parker House, Boston's oldest hotel
Stroll through the picturesque Boston Common, the country's oldest public park
Walk the Freedom Trail, visiting historic landmarks like Faneuil Hall and Paul Revere's House
Snap a pic with the statue of Samuel Adams before grabbing a pint at the famed Sam Adams Brewery
End the day with a romantic dinner at the elegant and delicious Top of the Hub

Day 2

Beantown Bites

Grab a classic Boston breakfast at The Friendly Toast, known for their funky decor and killer pancakes
Head to Quincy Market for a cornucopia of food options, like clam chowder at Boston Chowda Co. and cannolis at Mike's Pastry
Catch a game at Fenway Park, home to the beloved Boston Red Sox
Refuel with dinner at Neptune Oyster, renowned for its fresh seafood and lobster rolls
Indulge in a cocktail at the speakeasy-style Backbar, hidden behind a nondescript door in Somerville

Day 3

Culture Crawl

Start the day at the Institute of Contemporary Art, with stunning harbor views and cutting-edge exhibitions
Tour the gorgeous Isabella Stewart Gardner Museum, featuring an eclectic collection of art and artifacts
Grab lunch at Legal Sea Foods, a Boston institution with a focus on sustainable seafood
Explore the trendy South End neighborhood, with its charming brownstones and charming boutiques
Catch a show at the historic Boston Opera House, home to world-class productions

Day 4

Harbor Highlights

Take a harbor cruise and see the city from a new perspective
Visit the iconic USS Constitution Museum, with interactive exhibits and a glimpse into naval history
Stop by the Boston Tea Party Ships & Museum, where visitors can relive the famous event through reenactments and live actors
Score some fresh oysters at Row 34, a sleek spot with a hopping raw bar
End the trip on a high note with drinks and dancing at the glam Royale nightclub.

Length of stay

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Type of trip

Standard trip Budget Family Friendly Romantic Stag do

How to get there

Plane

The best way to get to Boston by plane is to fly into Boston Logan International Airport, which is located just 3 miles from downtown Boston. Major airlines such as American Airlines, Delta, United, JetBlue, and Southwest all service this airport from cities across the United States and around the world.

Car

Driving to Boston is an option if you live within a few hours of the city. However, be aware that parking in Boston can be expensive and difficult to find. If you do decide to drive, the easiest way to get into the city is via I-93 or I-90.

Train

While there are train stations in Boston, it may not be the most efficient way to get there. However, if you are coming in from other parts of Massachusetts or the Northeast Corridor, Amtrak offers service to Boston's South Station and Back Bay Station.

Boat

While Boston is located on the coast, taking a boat may not be the easiest or most efficient way to get there. However, there are ferry services from nearby islands, such as Martha's Vineyard and Nantucket, that dock in Boston's Long Wharf area.

Bus