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Ultimate Boys Weekend in Boston Itinerary

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day 1

Historic Trails and Culinary Delights

Boston Itinerary - February 22

Morning. Start your boys weekend with a hearty breakfast at the iconic Mike's Pastry in the North End, known for its mouthwatering cannolis. After fueling up, embark on the Boston Freedom Trail Walking Tour, visiting historic sites like the Boston Common, Faneuil Hall, and the Old State House.
Afternoon. For lunch, savor the fresh seafood at Neptune Oyster, also located in the North End. Afterward, take a guided stroll through the vibrant marketplace on the Boston North End to Freedom Trail Food and History Tour. Taste local favorites and learn about the area's rich culinary and cultural history.
Evening. As the sun sets, enjoy a sophisticated dinner at Top of the Hub with panoramic views of the city. Cap off the night with a memorable Boston Harbor Sunset Yacht Cruise, cruising past the skyline while enjoying drinks and good company.
day 2

Interactive History and Modern Eats

Boston Itinerary - February 23

Morning. Kick off the day with a visit to the Boston Tea Party Ships and Museum Interactive Tour. Immerse yourselves in the events that led to American independence. Afterward, enjoy a classic New England breakfast at Legal Sea Foods.
Afternoon. Explore the prestigious Harvard University with a Cambridge Harvard University Student-Guided Walking Tour. For lunch, head to Cambridge and indulge in the innovative Japanese cuisine at O Ya.
Evening. Return to Boston and take a leisurely walk through the charming Boston Public Garden. For dinner, experience the vibrant atmosphere and delicious bites at Row 34, known for its exceptional oyster selection and craft beers.
day 3

Spectacular Sights and Tasty Bites

Boston Itinerary - February 24

Morning. Start your morning with a guided tour of the Boston Fenway Park Guided Ballpark Tour with Options. Explore the historic stadium and learn about its storied past. After the tour, grab a coffee at Eastern Standard Kitchen & Drinks before heading out.
Afternoon. Enjoy a casual lunch at Santarpio's Pizza, a local favorite, before visiting the Boston View Boston Observatory Entry Ticket. Take in panoramic views of the city and its landmarks.
Evening. For dinner, indulge in the culinary delights of Giacomo's Ristorante, known for its Italian classics. Cap off the night with a Salem Night Tour Haunt and History Guided Night Tour, venturing to the nearby city for an evening of spooky tales and hidden history.
day 4

Maritime History and Gastro Pub Crawl

Boston Itinerary - February 25

Morning. Begin with a visit to the New England Aquarium, exploring the fascinating marine life. For a quick bite, enjoy breakfast at Union Oyster House, the oldest restaurant in the U.S.
Afternoon. Delight in a Boston Historical Sightseeing Cruise, learning about the city's seafaring past. Afterward, take a walk along the Charles River and stop for a refreshing drink at Craigie on Main.
Evening. Experience the lively atmosphere of a Boston Hop-on Hop-off Old Town Trolley Tour and use it to explore the city's best pubs and bars. Enjoy a progressive dinner, hopping off at spots like Myers + Chang for Asian-inspired dishes and Neptune Oyster for a late-night seafood snack.
day 5

Science, Spirits, and Secret Spots

Boston Itinerary - February 26

Morning. Start with an educational visit to the Massachusetts Institute of Technology Public Tour in Cambridge. Afterward, enjoy a well-crafted coffee at Barrington Coffee Roasting Company.
Afternoon. Have lunch at Menton, a fine dining experience that celebrates local and seasonal ingredients. Spend the rest of the afternoon exploring the innovative exhibits at the MIT Museum.
Evening. For your final night, dine at Craigie on Main, known for its farm-to-table American cuisine. Conclude your trip with a memorable Salem Boos and Brews Haunted Pub Crawl, sampling the spirits and stories of the witch city.
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