Experience Boston Beyond the City
Walk historic streets, taste coastal flavors, and explore Boston’s blend of charm, culture, and waterfront views — all in just a 2-day escape from NYC.
Day 1: History & Harbor
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Morning
- Arrive in Boston — start with coffee and pastries at Tatte Bakery or Flour Bakery + Café.
- Walk the Freedom Trail, stopping at Boston Common, Massachusetts State House, and Park Street Church.
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Afternoon
- Continue along the trail to Faneuil Hall and Quincy Market for lunch (clam chowder, lobster rolls, or pastries).
- Explore the North End — Boston’s Little Italy — visit Paul Revere House and grab a cannoli at Mike’s Pastry or Modern Pastry.
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Evening
- Head to the Seaport District for sunset views over the harbor.
- Dinner at Legal Harbor side or Lookout Rooftop overlooking the waterfront.
Day 2: Local Vibes & Green Escapes
Morning
- Breakfast in Beacon Hill, stroll the charming streets of Acorn Street and Charles Street.
- Walk through the Boston Public Garden, and if the weather’s nice — ride a Swan Boat across the lagoon.
Afternoon
- Cross the river to Cambridge — explore Harvard Yard, indie bookstores, and cafés like Tatte Cambridge.
- Grab lunch at Felipe’s Taqueria (with rooftop seating) or a cozy spot in Harvard Square.
Evening
- Return to Boston for one last walk along the Charles River Esplanade or Newbury Street shopping.
- Dinner in Back Bay or North End — try Giacomo’s, The Friendly Toast, or Mamma Maria for something special.
- Optional: Catch live jazz at Wally’s Café or drinks at Trillium Brewery.
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Boston is very walkable — wear comfy shoes, grab a CharlieCard for the “T” subway, and plan for weather (it changes fast!).
✨ Insider Tip