A Very "Holdovers" Trip to BostonThis trip is inspired by an impromptu trip to Boston from the Oscar-nominated film, "The Holdovers." In the film set in the early 1970s and is about a cranky history teacher at a New England prep school who stays on campus during the holidays with a handful of students who have no place to go.AuthorsSteller
DestinationsBostonItinerary

Prep School Vibes

Boston Public Library
Get that last-minute study sesh in.
See More
Public Garden
Stroll with your sweetheart.
See More
Museum of Fine Arts, Boston
Soak up some culture.
See More
Book Tour
Schoolmaster Hill
Once the home of Ralph Waldo Emerson!
See More
Harvard University
A must-visit when in the Boston area.
See More
Book Tours

Staying In

The Liberty, a Luxury Collection Hotel, Boston
Somewhat fitting for this film, The Liberty was a former prison, but is now a quirky luxury hotel. If you just love to stay in at your hotel most of the time during a trip, this is the one for you.
See More
Book
citizenM Boston North Station
This is a cool mod-style place to stay with incredible views.
See More
Book
Hotel AKA Boston Common
It has that retro chic vibe.
See More
Book
Longwood Inn
Set in a Victorian mansion from the early 1900s and featuring dark solid wood railings, and floral wall papering...if you want to feel like you've stepped back in time in New England and that you're staying in an actual house, check out the Longwood.
See More
Book

From the Film

St. Mark's School of Southborough
Where most of "The Holdovers" was actually filmed.
See More
Boston Common
The Boston Common scene was not actually shot at Boston Common, but in Worcester, MA.
See More
Book Tours

Comfort Food

MIDA
Italian comfort food is the name of the game during a cold New England winter.
See More
Happy Lamb Hot Pot, Allston
When you need to be warmed up from the inside out during a Boston winter.
See More
Tatte Bakery & Cafe | Back Bay
All the pastries and coffee you can eat!
See More

Tis the Season

Boston Common Frog Pond
See More
Faneuil Hall Marketplace
See More