Boston's Best: A Romantic Weekend Getaway

Boston: Where history and romance meet.

03 May 2023

Enjoy a romantic trip for two to the historic city of Boston. Stroll hand in hand through the charming streets of Beacon Hill and take in the beauty of the autumn leaves in the Public Garden. Indulge in a romantic dinner at one of the city's award-winning restaurants and catch a show at the Boston Opera House for an unforgettable evening.

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Travel plan

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Day 1

Bite into Beantown's Best

  • Start with breakfast at the iconic Mike's Pastry in the North End for cannolis and coffee
  • Take a stroll along the Freedom Trail and visit historical sites like the Paul Revere House and Faneuil Hall
  • Grab lunch at Union Oyster House, the oldest continuously operating restaurant in the US, and try their famous clam chowder
  • Explore the picturesque Beacon Hill neighborhood and take in the charming cobblestone streets and colorful rowhouses
  • Have dinner at Top of the Hub, a romantic spot with stunning views of the city as you dine on contemporary American cuisine
  • Hotel Recommendation: The Lenox Hotel, an elegant boutique hotel in Back Bay with luxurious accommodations and exceptional service.
Day 2

Park it in Boston's Green Spaces

  • Start the day with a visit to the stunning Boston Public Library, a beautiful Beaux-Arts building with incredible architecture and artwork
  • Spend the afternoon in the sprawling Boston Common and Public Garden, the oldest public park in the US, and take a swan boat ride on the lake
  • Refuel with lunch at the famous Shake Shack, serving up delicious burgers and shakes in a fun atmosphere
  • Walk to the nearby Fenway-Kenmore neighborhood and tour historic Fenway Park, home of the Boston Red Sox
  • End the day with dinner at SRV, an Italian-inspired spot in the South End with incredible wine and pasta dishes.
  • Overall, Boston is a perfect destination for a romantic getaway with its rich history, charming neighborhoods, and delicious food scene.

Length of stay

1 day 2 days 3 days 4 days 5 days

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

A great way to get to Boston is by bus. Greyhound and Peter Pan Bus Lines both offer service to Boston from cities across the United States. The main bus station in Boston is the South Station Bus Terminal, which is located in the heart of the city.

Destination

Boston

Welcome to a city where beans are baked, tea is dumped and accents are wicked awesome. Boston, home to both the Red Sox and the Cheers bar, is waiting to charm you with its unique blend of history and humor.

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Number of days

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Type of trip

Standard trip Budget Family Friendly Romantic Stag do

More travel plans

Boston's Best: Romantic Weekend Getaway in 3 Days

. Experience a romantic getaway in Boston, starting with strolling down the cobbled streets of Beacon Hill, admiring the charming brownstone homes, and savoring delectable lobster rolls. Revel in the historic architecture of Fenway Park or catch a show at the Boston Opera House before ending the perfect day with a sunset dinner at Top of the Hub, overlooking the city skyline.

Boston in a Day: History, Food, and Fun

Explore the rich history of the United States by visiting Boston. Tour the Freedom Trail and visit historical landmarks like Paul Revere's House, the Old North Church, and the USS Constitution. Experience the vibrant food scene by trying the famous clam chowder and lobster rolls.

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Fun-Filled Family Adventure: 2 Days in Historic Boston

A family trip to Boston offers a perfect blend of educational and enjoyable experiences for all ages. Explore famous historical sites like the Freedom Trail and USS Constitution Museum to learn about the birth of the nation, while the New England Aquarium and Franklin Park Zoo provide opportunities for kids to marvel at marine life and wildlife. End the day with a stroll along the picturesque Boston Common or enjoy a delicious meal at the family-friendly restaurants in the city.