Jessica Simmons and Kim Cressell have big plans for The Reserve—coffee, wine, books, music, four-course dinners and vacation rentals are just the beginning. Partners in business and in life, the duo have revitalized a set of buildings you’ve probably passed by and wondered about a thousand times; set on the North Trail, steps away from both Ringling College and Main Street, two funky rust-red cottages stand out from the pack of new high-rises and on-their-last-legs motels. 

Photography by Wyatt Kostygan.


First thing’s first: the buildings themselves. The three, two-story bungalows remain true to their original facades, with russet-red painted wood and evergreen window and stair trims, gorgeous lacquered maple floors that hid beneath carpeting and the teeny upstairs apartments now rented out to vacationers. “The buildings just speak to you,” says Simmons. “It’s a community.” The building facing the Trail is home to shelves full of cookbooks, biographies, non-fiction bestsellers, essays and poetry, a full bar complete with a “wine wall” housing red and white nectars from Italy, Chile, Spain and France and a space large enough to hold wine-pairing dinners and supper club evenings. 

Cross the red brick courtyard with tables full of students on laptops, local politicians holding informal meetings and young mothers and their bouncing babes, to the second structure, where the aroma of freshly brewed Buddy Brew beans greets you. This side plays host to a busy barista surrounded by bagels from Shapp’s, dairy from Dakin and pastries from local purveyors such as C’est La Vie. Another wall of books houses fiction authors ranging from Roxane Gay and Jonathan Safran Foer to Haruki Murakami, Ann Patchett and Chuck Palahniuk. “We really curate our collection—it’s centered around things we are passionate about,” says Cressell. “We also have a bookseller who has worked with big-time bookstores in Paris and Madrid, so she is helping us expand. We’re trying to be ahead of the curve.”

A refrigerated case of craft beers (Grolsch, Lagunitas’ Aunt Sally and several offerings from Florida-based breweries) stands to the side of hand-made reclaimed wooden tables (tall, café-style and regular short square) and a milk-and-sugar cabinet emblazoned with “The Reserve,” made by local woodworker Shawn O’Malley of Heart’s Arts. And finally, the last building on the backside gets rented solely as residences for out-of-towners. “The goal was to open these buildings back up to Sarasota and let people enjoy it,” says Cressell. “We don’t sell anything here that we don’t love ourselves.” Now, let’s talk shop. Simmons and Cressel will soon be opening a gourmet market that will feature not only local goods, but also items from their 25-acre farm in Virginia’s Blue Ridge Mountains—think honey from family-tended honeycombs, jams, jelly, apples and tomatoes. They also hope to expand into farm-to-table dinners partnering with local chefs and farms, and have already begun hosting craft beer tastings (a recent one featured brews from Lagunitas and Cigar City). Live music will continue to be a mainstay for the outdoor space, along with indoor meeting rooms available for rent in the street-facing cottage, while plans are in the works to expand into book clubs, open mics, birthday parties—even weddings. “The first thing I would tell people as a business consultant was to just focus on one thing,” says Simmons. “And of course, we are doing at least five.”