Visit Boston with my Quick 3-Day Itinerary

Here’s a weekend itinerary for a 3-day trip to Boston that offers a mix of history, food, and romance perfect for a young couple:

Day 1: Arrival & Exploring Downtown

  • Morning:

    • Breakfast at Tatte Bakery & Café – Start the day with a delicious pastry and coffee at this popular local café.

    • Freedom Trail – Begin your exploration of Boston by following the Freedom Trail, a 2.5-mile red line that guides you to 16 historical sites like Boston Common, Massachusetts State House, Granary Burying Ground, and the Old State House.

  • Lunch:

    • Faneuil Hall & Quincy Market – Explore this vibrant marketplace with plenty of food stalls. Try a lobster roll or some clam chowder!

  • Afternoon:

    • New England Aquarium – Spend some time wandering through the aquarium, especially the giant ocean tank.

    • HarborWalk & Rose Kennedy Greenway – After the aquarium, enjoy a leisurely stroll along the waterfront, with views of the harbor and parks along the Rose Kennedy Greenway.

  • Evening:

    • Dinner at North End – Boston’s historic Italian neighborhood. Try a romantic dinner at Mamma Maria or Carmelina’s.

    • Dessert at Mike’s Pastry or Modern Pastry – Both are famous for their cannoli, so it’s a must-try when you’re in the North End.

Day 2: Arts & Nature

  • Morning:

    • Brunch at The Friendly Toast – Known for its quirky décor and hearty breakfast dishes.

    • Isabella Stewart Gardner Museum – A beautiful and romantic museum housed in a Venetian-style palace with lush indoor gardens and a world-class art collection.

  • Lunch:

    • Lunch at Eataly – Located in the Prudential Center, this Italian food marketplace has multiple restaurants and cafes to choose from.

  • Afternoon:

    • Boston Public Garden & Swan Boats – Take a romantic walk around the Public Garden, and if it’s the right season, go for a swan boat ride.

    • Shopping on Newbury Street – Boston’s iconic shopping street, where you can browse both high-end and unique boutique stores.

  • Evening:

    • Dinner in Back Bay – Enjoy dinner at The Capital Grille or Atlantic Fish Company for an upscale dining experience.

    • Sunset at the Skywalk Observatory – Head to the Skywalk at the Prudential Center for stunning panoramic views of the city at sunset.

Day 3: Day Trip & Departure

  • Morning:

    • Breakfast at Flour Bakery – Another local favorite with amazing pastries and breakfast options.

    • Day Trip to Cambridge – Just across the Charles River, visit Harvard University and take a stroll around Harvard Square. You can also visit the Harvard Art Museums or take a free walking tour of the campus.

  • Lunch:

    • Lunch at Russell House Tavern – A cozy spot near Harvard Square known for its creative American cuisine.

  • Afternoon:

    • Charles River Esplanade – Before heading back to Boston proper, walk along the scenic Charles River Esplanade. If you’re feeling adventurous, rent kayaks or take a boat cruise.

  • Evening:

    • Early Dinner at Legal Sea Foods (Seaport) – Enjoy seafood with a view of the harbor before heading out.

    • Catch a Movie or Show – Depending on your departure time, consider catching a movie at the Coolidge Corner Theatre in Brookline or a live show at the Boston Opera House.

This itinerary covers Boston’s rich history, iconic sights, and romantic spots, with plenty of time to relax and enjoy the city’s ambiance.

Kevin Woo