Ultimate 20028-Day Boston Adventure and Relaxation Itinerary

Day 1: Exploring Boston

Boston, Massachusetts

8:00AM

Breakfast at Flour Bakery

Start your day with a delicious breakfast at Flour Bakery, known for its fresh pastries and hearty breakfast options like the famous Breakfast Sandwich.
Walk for 15 minutes to the Boston Common.
USD 20, 1 hour

9:30AM

Stroll through Boston Common and Public Garden

Enjoy the picturesque landscapes of the Boston Common, the oldest public park in the US, and the enchantment of the adjoining Public Garden.
Explore on foot.
Free, 1.5 hours

11:00AM

Visit the Massachusetts State House

Take a guided tour of the Massachusetts State House, with its iconic golden dome that adds charm to the skyline.
Located at the edge of Boston Common.
Free, 1 hour

12:30PM

Lunch at The Capital Grille

Indulge in a fine dining experience with dry-aged steak and fresh seafood at The Capital Grille, an upscale venue located near the Boston Common.
Catch a quick ride or walk back towards the city center.
USD 75, 1.5 hours

2:00PM

Explore the Freedom Trail

Start your walking tour along the Freedom Trail, visiting historical sites like the Old State House and Faneuil Hall.
Follow the marked trail through downtown Boston.
Free, 3 hours

5:30PM

Relax at the Boston Harbor

Take a leisurely stroll along the Boston Harbor, enjoying the fresh sea air before dinner.
Walk towards the waterfront.
Free, 1 hour

7:00PM

Dinner at Legal Sea Foods

Savor the freshest seafood in town, known particularly for its clam chowder and lobster dishes at Legal Sea Foods.
A short walk from the harbor.
USD 80, 1.5 hours

9:00PM

Evening dessert at Mike's Pastry

End your day with a sweet treat from Mike’s Pastry in the North End, famous for its cannoli.
Hop on a ride or take a walk to the North End.
USD 10, 1 hour
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Day 2: Art and History

Boston, Massachusetts

8:00AM

Breakfast at Tatte Bakery & Cafe

Enjoy unique Mediterranean breakfast dishes or classic pastries at Tatte Bakery.
Short drive or T ride to Tatte.
USD 25, 1 hour

9:30AM

Visit the Museum of Fine Arts

Explore vast collections of art from around the world, from ancient times to contemporary pieces.
Take the Green Line T to Museum of Fine Arts station.
USD 25, 2 hours

12:00PM

Lunch at the New England Soup Factory

Warm up with locally made soups, sandwiches, and baked goods at this cozy eatery.
Take a short walk from the museum.
USD 20, 1 hour

1:30PM

Afternoon at the Isabella Stewart Gardner Museum

Enjoy the unique collection and stunning architecture of this enchanted museum, which resembles a Venetian palace.
Walk or take a quick Uber from the earlier lunch spot.
USD 15, 2 hours

4:00PM

Walk through the Back Bay area

Stroll through the beautiful Back Bay neighborhood, marveling at its Victorian brownstones and chic boutiques.
Walking through Back Bay district.
Free, 1.5 hours

5:30PM

Take a Charles River Esplanade Walk

Enjoy a peaceful walk along the esplanade with waterfront views, ideal for relaxation.
Head towards the river bank from Back Bay.
Free, 1 hour

7:00PM

Dinner at Oleana

Dine at this acclaimed restaurant offering Mediterranean dishes with a creative twist, surrounded by beautiful garden views.
Drive or take a rideshare from the Esplanade.
USD 90, 1.5 hours

9:00PM

Nightcap at The Hawthorne

End the night with specialty cocktails at this intimate and elegant bar known for its mixology.
Quick rideshare or a short walk from Oleana.
USD 30, 1 hour
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Day -20028: Farewell to Boston

Boston, Massachusetts

8:00AM

Final breakfast at The Friendly Toast

Enjoy a whimsical breakfast at The Friendly Toast with its funky decor and extensive breakfast menu.
Walking or T ride to Cambridge.
USD 20, 1 hour

9:30AM

Reflect at Boston's North End

Take a moment to reflect on the memories made in Boston while strolling through its enchanting North End one last time.
Walking tour.
Free, 1 hour

11:00AM

Visit the Boston Tea Party Ships & Museum

Engage with interactive exhibits that recount the famous Boston Tea Party, a defining moment in American history.
Walk towards the waterfront.
USD 30, 1.5 hours

12:30PM

Lunch at Union Oyster House

Savor traditional New England seafood at the historic Union Oyster House, America's oldest restaurant.
A short walk from the museum.
USD 50, 1.5 hours

2:00PM

Last-minute shopping at Faneuil Hall Marketplace

Pick up some souvenirs and gifts at the lively Faneuil Hall Marketplace before departing.
Simple walk from Union Oyster House.
Free (souvenirs additional), 1 hour

3:30PM

Check-out and Departure

Check out of your hotel and prepare for the departure journey while reminiscing about your wonderful stay in Boston.
Head back to the hotel for check-out.
Dependent on travel arrangements., 1 hour
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