Join Our Team
But First, Dessert!
If this motto sounds like fun, we may have a job for you!
We are seeking fun, friendly individuals who love food and talking to people from all across the U.S. and the world. Most importantly, you must enjoy bringing the best food and hospitality Boston has to offer to your guests, providing a quality experience that guests will be excited to share with their family and friends.
If you do it right, not only will you be rewarded financially, but you will have numerous connections across the globe.
If you want to join our amazing team, please send your resume to info@cocktailsandcannoli.com.
(Part-time only - looking for guides to give 1-2 tours weekly)
Patrick Alessi - Founder
I have deep roots here in Boston. My great-grandparents arrived here from Italy in the 1910s and my grandparents were a fixture of the West End community. My parents met here while in school. While my father’s work unfortunately took us away from Boston - I loved every moment visiting the city. I relished every occasion to explore the rich history and unique cultural experiences.
So of course I leapt at the opportunity to move here in 2007. Taking up a challenge from a friend, I made it a mission to visit every restaurant and bar in Boston – resulting in a passion for food and classic cocktails. My experiences led me to guide a pizza tour of the North End for 5 years, specializing in everything from pizza to pints to pizzelles (one of my grandmother’s favorite treats).
And now I have turned my attention to dessert. With a history background and culinary curiosity, I can’t wait to share some of my favorite drinks and desserts of the North End with you!
Gabrielle Guarracino - Tour Guide
I’m a lifetime Bostonian, second-generation Italian, and bonafide dessert aficionado. With all of this, along with a penchant for corny jokes and a voice strengthened by years of yelling over my boisterous Neapolitan family, I couldn't wait to sweeten the ranks of Cocktails & Cannoli as a tour guide and resident punster.
Before Cocktails & Cannoli, I spent four years as a guide, field manager, and communications director for Trademark Tours, the flagship student-led tour of the Harvard campus; a brief stint as a dessert tour guide of Boston's Back Bay; and an even briefer stint as a downtown ghost tour guide (until I realized was I was spooking myself).
When not leading tours, I work full-time at Harvard, dance and lead group fitness classes, volunteer at a farmer’s market, and play chef in my own kitchen.
Pat “Deuce” Kohout - Tour Guide
My personal motto is '“When life hands you lemons, make limoncello!”
I have lived and worked as a bartender in the North End neighborhood since college. I’m Italian on my Mom’s side, and Irish on my Dad’s - a combination as quintessentially Bostonian as, well, cocktails and cannoli.
Not only do I have a love of meeting new people and enjoying a drink or two (or three or four), but a habit of talking way too much.
While finishing up my BA at UMass Boston, I got the local history bug deep under my skin. Some of my favorites include works of Stephen Puleo, the North End’s own historian, and “The Mayflower” and “Bunker Hill” by Nathaniel Philbrick.
And then I heard that my buddy Pat could use a hand with Cocktails & Cannoli. It just seemed like the natural transition with my personal background, my hospitality experience, and all the years spent studying the history of the neighborhood.