Boston's Best: Romantic Weekend Getaway in 3 Days

Fall in love with Boston's charm on a romantic getaway.

22 April 2023

. 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.

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Travel plan

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Day 1

Exploring the Historic Heart of Boston

  • Stay: The Lenox Hotel a luxurious romantic oasis in the heart of the city
  • Start the day with a visit to the famous Freedom Trail and make your way to the Old State House and King's Chapel
  • Take a stroll through the beautiful Boston Common and Public Garden, enjoying the scenery and people-watching
  • Stop for lunch at Quincy Market, a bustling food hall with a variety of diverse options
  • Head to the top of the Prudential Tower for breathtaking views of the city and a romantic dinner at their restaurant, Top of the Hub
  • Finish the evening with a show at the historic Boston Opera House, showcasing world-class performances
Day 2

Indulging in Boston's Culinary Scene

  • Stay: The Four Seasons Hotel a luxurious retreat with stunning city views
  • Start the day with brunch at The Beehive, a unique restaurant with live jazz music and delicious food
  • Take a hands-on cooking class at the famous Boston Public Market, learning about local cuisine and ingredients
  • Explore the North End, Boston's Little Italy, with a walking food tour and taste authentic Italian food and pastries
  • Enjoy an upscale dinner at No. 9 Park, a Michelin-star restaurant with French and Italian influences
  • End the night with drinks at the rooftop bar of The Envoy Hotel, with stunning views of Boston's Seaport District
Day 3

Unwinding and Relaxing in Boston's Beautiful Parks

  • Stay: XV Beacon a luxurious boutique hotel with beautiful modern design
  • Start the day with a peaceful morning yoga session at the Arnold Arboretum, surrounded by nature and tranquility
  • Pack a picnic and head to Jamaica Pond, with beautiful walking trails and serene water views
  • Visit the Isabella Stewart Gardner Museum, a stunning museum with a courtyard garden and impressive art collection
  • Take a sunset sail on a harbor cruise, enjoying the skyline views and refreshing sea breeze
  • For the perfect end to the trip, enjoy a romantic dinner at the Cambridge restaurant, Harvest, with fresh seasonal ingredients and a cozy atmosphere.

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

1 2 3 4 5

Type of trip

Standard trip Budget Family Friendly Romantic Stag do

More travel plans

Romantic Escape: A Day in Boston

Experience the charm of Boston, United States on a romantic getaway with your loved one. Stroll hand in hand along the historic Freedom Trail, explore the cobblestone streets of Beacon Hill, and indulge in delicious seafood at one of the city's upscale restaurants. With its picturesque scenery and rich history, Boston is the perfect destination for a romantic escape.

Boston: Budget-Friendly 3 Days of Fun & Culture

A trip to Boston on a limited budget can be a great way to experience this historic city. Visitors can explore the Freedom Trail, visit the Public Library, and enjoy a picnic in Boston Common. Low-cost accommodations can be found in areas like Back Bay and Cambridge, and a variety of budget-friendly dining options are available throughout the city.

5-Day Boston Adventure: History, Food, and Fun

Boston, United States is a one-of-a-kind destination that's perfect for tourists seeking a unique and vibrant experience. This historic city boasts a plethora of famous landmarks, such as the Freedom Trail, the USS Constitution Museum, and Fenway Park. Additionally, visitors can enjoy delicious food, exciting shopping, and a lively nightlife scene during their trip to Boston.

Boston Bonanza: An Exciting Family Day Trip!

A family-friendly trip to Boston, United States offers an exciting blend of history, culture, and entertainment. Explore iconic sites like the Freedom Trail, where kids can learn about the American Revolution, or visit the New England Aquarium to marvel at marine life. Don't miss the interactive exhibits at the Boston Children's Museum or take a leisurely stroll along the picturesque Boston Common.