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Private Literary Tour!

I really enjoyed how being physically present in the moment gave me glimpses into the lives of different writers who once shared the same spaces. It felt like a thread connecting all of us. Walking the streets and seeing each corner through their eyes made the experience feel alive.

– Lena

Walk the streets of Boston and experience its literary past on a private literary tour. We’ll explore historic neighborhoods, uncover hidden literary history, and read works by Boston authors along the way. Perfect for school groups, book clubs, corporate teams, and groups of friends looking for a meaningful way to experience the city.

Private Literary Tours

  • $450 flat rate for groups up to 10 (additional attendees $40 per person)

  • $350 school rate (up to ~15 students)

  • Multi-tour bookings welcome

  • Bookings require a minimum of five people

Booking details

  • 50% deposit required to hold dates

  • Remaining balance due one week prior

  • Full refund available with one week’s notice

Interested in a private tour? Fill out the form below to get started.

Your Tour Guide

Hi! I’m Jessica, and I’m the founder and director of Literary Boston, which I started in 2012 as a place as a website where people could find everything there was to know about the Boston literary community. But you could say that Literary Boston may have truly started on a trip to Walden Pond in 1999. I fell in love with the literary history of Boston then and I’m still fascinated with it today, so much so that I’ve made it a pillar of my work on Literary Boston.

For the past 25 years, I’ve been studying Boston literary history, from structured study in academic programs to reading historical markers all over the city. Now, I want you to know about our rich literary past, too.

A little bit more about me:

I’m a freelance marketing writer by day and creative writer by night. I’m the founder of Literary Boston, a website that covers the local literary community, and other past literary roles include library assistant, bookseller, and book festival director. I hold a BFA in Creative Writing from Emerson and a Master’s in Literature from Harvard, where my thesis on Moby-Dick and Calvinism won the Director’s Prize. My short fiction has appeared the North American Review, the Emerson Review, and others, and has received the Leah Lovenheim Award for Short Fiction. I recently graduated from GrubStreet's Novel Incubator program, where I’m working on a novel about paramedics in 1970s Boston.

If you would like to book me for a private walking tour, contact me through the form on the “About” page.

F.A.Q.

  • The Ink & Cobblestones Tour runs approximately 90 minutes. We’ll cover about one mile of walking with plenty of stops to talk, learn, and take photos.

  • You’ll receive a confirmation email with the exact meeting point after booking. The route begins at the Old State House and ends on Beacon Hill — close to the T and plenty of cafes, shops, and even a bookstore for post-tour coffee or browsing.

  • We’ll walk at a comfortable pace, with frequent stops. The route includes hills and uneven brick sidewalks typical of historic Boston, so comfortable shoes are a must!

  • All tours are led by Jessica A. Kent, founder and director of Literary Boston. Jessica has spent over a decade researching, writing about, and connecting Boston’s literary past and present — and she’s excited to share those stories with you! Read a bio below.

  • Groups are capped at 10 to encourage conversation and connection.

    Please note: Tours require a minimum of five registered participants to run. In the rare case that fewer than five people sign up, you’ll be notified 24 hours in advance and offered a full refund or reschedule option.

  • Tours run rain or shine! Please dress appropriately for the weather—umbrellas and layers are encouraged. In severe weather (thunderstorms, heavy snow, etc.), you’ll be notified of cancellation and offered a full refund or reschedule.

  • Cancellations made at least 48 hours before the tour will receive a full refund. Within 48 hours, tickets are non-refundable but may be transferred to another date (if available).

  • Boston’s historic sidewalks can be uneven and narrow in places, especially in Beacon Hill, which is where half of the tour takes place. Reach out and we can talk through options. Look for accessible tours in the Spring!

  • Absolutely! Please tag @literary_boston on social media if you post, as sharing helps others discover Boston’s literary history too. I just ask that you refrain from filming large chunks or the whole thing.

  • Yes! I’m happy to arrange private tours for schools, book clubs, corporate outings, or visiting groups. Use the contact form to inquire about rates and custom scheduling.