AIRBNB EXPERIENCES

Sightseeing activities in Massachusetts

Book unique activities hosted by local experts on Airbnb.

Top-rated sightseeing activities

View our most highly rated experiences, loved by guests.

4.97 out of 5 average rating, 868 reviews

Boston's Grand Tour: The Full Revolutionary Story

A curated, chronological journey that delivers real understanding — not just random sightseeing. Explore the Freedom Trail and trace the full story of America from Boston’s founding to Independence.

4.98 out of 5 average rating, 1867 reviews

Walk your way through Boston's history

Walk through the historic neighborhoods of Boston, learning about their past and present.

4.98 out of 5 average rating, 1008 reviews

Explore the freedom trail and historic Boston

Walk through Boston’s rich history, learning about the American Revolution and landmarks Tour must have a 2 person minimum

4.86 out of 5 average rating, 849 reviews

Mobsters, mayhem and murder in Boston

Stroll around Boston, learning about Whitey Bulger, the Boston mob, murders and more!

4.88 out of 5 average rating, 88 reviews

Boston Historic Freedom Trail & Beacon Hill Walk

Walk Boston’s iconic sites from the Harbor to Beacon Hill. Discover history, architecture, and stories that shaped the city.

5 out of 5 average rating, 98 reviews

Remember the ladies on a historic Boston walk

Join me for a 2-hour walk through 400 years of local women’s stories.

4.9 out of 5 average rating, 187 reviews

Providence history: sugar, cotton, slavery

Explore College Hill’s rich and at times disturbing history with a journalist..

4.98 out of 5 average rating, 84 reviews

Explore the beach on fat tire bikes

Bike down Cape Cod's expansive tidal flats, learn about oyster farming, enjoy the beach.

5 out of 5 average rating, 11 reviews

Savor the flavors of Boston’s North End

Explore the city's oldest neighborhood, known for its Italian heritage and top pizzerias.

4.98 out of 5 average rating, 121 reviews

Meet Revolutionary heroes along the Freedom Trail

Walk Boston’s colonial streets, meet Revolutionaries, and visit historic sites.

Latest Activities

Explore new local experiences, activities for everyone.

5 out of 5 average rating, 11 reviews

Savor the flavors of Boston’s North End

Explore the city's oldest neighborhood, known for its Italian heritage and top pizzerias.

4.17 out of 5 average rating, 6 reviews

Soak up Boston's nightscapes

Bask in the glow of Boston at night with a small group.

5 out of 5 average rating, 4 reviews

Explore Boston's highlights in a small group

Enjoy a narrated drive through Boston, visiting key sites and attractions.

5 out of 5 average rating, 98 reviews

Remember the ladies on a historic Boston walk

Join me for a 2-hour walk through 400 years of local women’s stories.

4.98 out of 5 average rating, 1008 reviews

Explore the freedom trail and historic Boston

Walk through Boston’s rich history, learning about the American Revolution and landmarks Tour must have a 2 person minimum

4.88 out of 5 average rating, 88 reviews

Boston Historic Freedom Trail & Beacon Hill Walk

Walk Boston’s iconic sites from the Harbor to Beacon Hill. Discover history, architecture, and stories that shaped the city.

4.9 out of 5 average rating, 187 reviews

Providence history: sugar, cotton, slavery

Explore College Hill’s rich and at times disturbing history with a journalist..

5 out of 5 average rating, 33 reviews

Guided Night Photography Tour on Cape Cod

Photograph unique Cape Cod locations under moonlight and starlight.

4.98 out of 5 average rating, 84 reviews

Explore the beach on fat tire bikes

Bike down Cape Cod's expansive tidal flats, learn about oyster farming, enjoy the beach.

4.96 out of 5 average rating, 112 reviews

Wander historic South End

Trace the steps of Patriots and Redcoats.