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5-Day Boston Exploration Including Red Sox Game and Historic Sights

Viewed by 65 travelers

Day Day 1: Arrival & Evening

Boston, MA on July 31, 2025

Late evening

Arrival in Boston

Arrive at Boston Logan International Airport late evening; check into your hotel and settle in after your journey.
$, 1h
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Day Day 2: Fenway & Downtown

Boston, MA on August 1, 2025

8:30 am

Breakfast at Tatte Bakery & Cafe

Enjoy a hearty breakfast with baked goods, coffee, and local specialties to start your day.
$, 1h

10:00 am

Fenway Park Tour

Visit the historic Fenway Park, taking a guided tour of the oldest Major League Baseball stadium still in use, including the Green Monster.
$25, 2h

12:30 pm

Lunch at The Times Steak House

Enjoy classic Boston steakhouse fare just a short walk from Fenway, perfect for relaxing after the tour.
$40, 1h 30m

2:00 pm

Freedom Trail Visitor Center & Quincy Market

Begin exploring Boston’s famous Freedom Trail, visiting historic sites and enjoying the lively atmosphere at Quincy Market.
$0, 3h

6:00 pm

Red Sox Game at Fenway Park

Attend the evening game at Fenway Park, experiencing Boston’s beloved baseball culture; arrive early for pre-game festivities.
Ticket prices vary, 3h
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Day Day 3: Historic North End & Waterfront

Boston, MA on August 2, 2025

8:30 am

Breakfast at Mike's Pastry & Cafe

Savor Italian pastries and strong coffee at famous Mike’s Pastry in the North End.
$, 1h

10:00 am

Walk the Freedom Trail & Paul Revere House

Explore the historic trail with stops at Paul Revere’s House and Old North Church, immersing in Boston’s revolutionary history.
$15, 2h

12:30 pm

Lunch at Giacomo’s Ristorante

Enjoy fresh Italian seafood and pasta in a cozy North End setting.
$30, 1h 30m

2:30 pm

Boston Tea Party Ships & Museum

Learn about the American Revolution with interactive exhibits and reenactments at this engaging museum.
$30, 2h

5:00 pm

Harborwalk & Sunset

Stroll along Boston Harbor, enjoy scenic views, and perhaps grab a snack at one of the waterfront cafes.
$0, 2h
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Day Day 4: Museum & Fenway Visit

Boston, MA on August 3, 2025

8:30 am

Breakfast at Thinking Cup on Boylston

Relax with excellent coffee and pastries in a stylish setting.
$, 1h

10:00 am

Museum of Fine Arts Boston

Spend the late morning exploring one of the country’s most comprehensive art collections, including ancient to contemporary works.
$25, 3h

2:00 pm

Lunch at Aura Restaurant

Enjoy elegant American cuisine in the nearby Back Bay neighborhood.
$40, 1h 30m

3:30 pm

Relax or Explore Nearby Shops

Take some leisure time shopping or strolling in the Back Bay area, including Newbury Street.
$0, 2h
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Day Day 5: Final Sights & Departure

Boston, MA on August 4, 2025

8:30 am

Breakfast at Flour Bakery & Cafe

Start your day with renowned baked goods and coffee in a cozy local spot.
$, 1h

10:00 am

Visit Boston Common & Public Garden

Enjoy a relaxing morning walking through Boston's historic parks and scenic swan boats in the Public Garden.
$0, 1.5h

12:00 pm

Lunch at Samuel Adams Brewery (Tour & Tasting)

Tour the historic brewery with sampling opportunities; note the brewery closes early in the afternoon, confirm exact hours.
$20, 2h

2:30 pm

Final sightseeing & packing

Wrap up your trip with any last-minute sightseeing or shopping and pack for departure.
$0, 1.5h
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