5-Day Romantic Getaway: Fall in Love with Boston

Experience love in history's embrace in Boston, USA.

22 April 2023

Boston is a charming city with rich history and plenty of romantic attractions. Visit the picturesque Beacon Hill neighborhood and stroll hand-in-hand among the colorful historic houses. Enjoy a sunset sail on the iconic Charles River or indulge in a cozy dinner at one of the many intimate restaurants in the North End.

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Travel plan

Getting latest place information
Day 1

Arriving in Beantown

  • Check into the charming Beacon Hill Hotel and Bistro for a vintage New England experience
  • Grab a hearty brunch at Tatte Bakery & Cafe to fuel up for the day
  • Walk the Freedom Trail and learn about Boston's history, including the famous Paul Revere House
  • Hop over to Fenway Park to catch a Red Sox game and enjoy America's favorite pastime
  • Finish the night with a candlelit dinner at the cozy Italian eatery, Giacomo's Ristorante
Day 2

Exploring the City

  • Fuel up with a classic New England breakfast at The Paramount in Beacon Hill
  • Take a ferry to the infamous Boston Harbor Islands for stunning views of the city skyline
  • Grab lunch at Union Oyster House, the oldest continuously operated restaurant in the country
  • Visit the Isabella Stewart Gardner Museum for art and gardens, and perhaps a bit of mystery
  • Enjoy a cocktail and live music at the intimate jazz club, Wally's Cafe
Day 3

Cambridge Vibes

  • Start the day with a breakfast sandwich from the acclaimed Flour Bakery + Cafe
  • Cross the river to Harvard Yard and explore the Ivy League campus
  • Fuel up with a burger and shake at Craigie on Main, featuring locally sourced ingredients
  • Browse the bookshelves at the cozy Harvard Book Store
  • Catch a performance at the American Repertory Theater for some culture and entertainment
Day 4

All about Food

  • Brunch at Stephanie's on Newbury for classic American fare and bottomless mimosas
  • Take a food tour of the North End, sampling the best Italian cuisine in the city
  • Visit the Boston Public Market for fresh produce and artisanal goods
  • Try the famous clam chowder at Legal Sea Foods for a taste of the sea
  • End the night with a dessert crawl, hitting up Mike's Pastry, Modern Pastry, and Bova's Bakery
Day 5

Sights and Sounds

  • Breakfast at the appropriately named The Friendly Toast in Back Bay
  • Walk along the Charles River for breathtaking views and fresh air
  • Visit the Museum of Fine Arts for art spanning centuries and cultures
  • Catch a show at the historic Orpheum Theatre for some live entertainment
  • End the trip with a nightcap at the rooftop bar Lookout Rooftop in the Seaport District, overlooking the Boston skyline.

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

Discover Boston: A 3-Day Family Adventure on a Budget!

Experience the rich history and culture of Boston on a family-friendly trip. Explore the iconic Freedom Trail, discovering the birthplace of American independence. Immerse yourselves in the world-class museums, enjoy interactive exhibits at the New England Aquarium, and embark on a thrilling whale-watching adventure in the nearby waters.

5 Days in Boston: Budget-Friendly Adventure!

Boston is a vibrant city with a rich history and plenty of attractions. To experience it on a budget, consider staying in a hostel or budget hotel and taking advantage of free activities like museum visits and walking tours. You can also sample some of Boston's famous seafood without breaking the bank by seeking out casual eateries and food trucks.

Budget-Friendly Boston: A Two-Day Adventure

Boston is a great city that can be explored even on a limited budget. Visitors can enjoy the historic sites and museums like the Freedom Trail, the USS Constitution Museum and the Harvard Art Museums. One can also indulge in delicious fresh seafood at affordable prices and explore the city's parks and gardens for free.

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.