Boston Layover Guide: Making the Most of Your Stopover

Attraction stop (2h)

We'll walk around Harvard Square and highlight various donut shops, historical landmarks, sights and recommendations for our guests.

Attraction stop (30 mins)

Right in the heart of downtown, Beantown Pub blends casual charm with classic Boston character — and boasts a view of history you can toast to. A beloved spot for locals and visitors alike, Beantown Pub is also the only remaining place in the city where you can find 2 Boston Classics on the menu. This once popular slow-cooked supper dish is also on our menu, and the first tasting on our tour.

Attraction stop (30 mins)

Explore Boston’s history one bite at a time! During this experience, travelers will enjoy a deliciously immersive journey through Boston’s culinary past and present. As we follow the historic Freedom Trail, we’ll share fascinating, lesser known food history at multiple sites, as well as stop to savor iconic local dishes at four beloved eateries, each with its own story to tell.

Attraction stop (10 mins)

*PHOTO OPP!* In the heart of Government Center, Boston announces itself in bold letters — a bright reminder of where history and modern energy meet. This is the perfect spot for a fund commemorative photo that literally spells out exactly where you are!

Attraction stop (30 mins)

A lively hub along the Freedom Trail, Faneuil Hall Marketplace blends history and modern-day charm with its cobblestone walkways, street performers, and a wide variety of local food vendors and shops. Once a meeting place for America’s early revolutionaries, Faneuil Hall Marketplace is now a bustling gathering spot filled with local flavor!

Attraction stop (15 mins)

Designed by Frederick Law Olmsted, the Fens is a treasured greenspace in Boston and features Americas oldest WW II, Victory Gardens. On the Modern Lovers EP, Jonathan Richman sings, “I walk through the 'Fenway with my heart in my hand". We will stroll through the gardens before heading into Kenmore Square.

Attraction stop (20 mins)

For decades, Kenmore Square was at the center of Boston's music scene thanks to the numerous record stores, and venues like Storyville and the legendary rock club, The Rathskeller. Here, we will learn about the numerous garage, punk, and new wave bands that crawled out of "the Rat" in the 70s and 80s. The Police played here 4 times on their first US tour in 1979. This is also the venue where Pixies first shared the same bill as the Throwing Muses. Also, we will stop by "Nuggets" one of the last records stores left in the neighborhood before winding our around Fenway Park

Attraction stop (20 mins)

Walk down Landsdowne Street in the shadow of Fenway Park and hear tales of venues past and present including the Boston Tea Party, Venus De Milo, Avalon/Axis, Spit, and more! At present, local and national bands load in on Landsdowne street to play at the House of Blues or the new MGM Music Hall.