With a history spanning over 100 years, The Reserve Retreat (1322 N Tamiami Trail) has served as the home of the prominent Ringling family, a dress shop, a family photo studio, an art gallery, and residential tenements. Ten years ago, current owner Jessica Simmons transformed it into a boutique hotel after the property sat vacant and for sale for a decade, revitalizing and expanding the three historic buildings on-site.
Under Simmons’ guidance, the property evolved from her initial venture as a bookstore and coffee shop to a fully realized boutique experience. Today, The Reserve Retreat features six boutique rooms, a breakfast and lunch café, a market, and The Reserve Restaurant, serving premier Italian cuisine courtesy of Chef Antonio. While the property has transformed, Simmons retained the original essence, coining the tagline: “Northern Feel with Southern Vibes.”
The tagline echoes guests’ sentiments. General Manager Sarah Simmons notes, “Anybody who visits says the same thing: ‘This hotel feels like a place I know up North, in Vermont, or maybe Maine.’” The property’s charm evokes a sense of familiarity, making guests feel at home. As Sarah Simmons adds, “I fell in love with the space, and that was history. I just stayed.”
Rooms, fare, and amenities
As a piece of Sarasota’s storied past, The Reserve Retreat appeals to tourists and locals alike, offering a staycation experience or a step back in time. The rooms embrace an “old Florida” vibe, featuring restored original wood flooring and carefully preserved historical details. Three rooms offer full kitchens or kitchenettes, five rooms have king-sized beds with private baths, and one room includes two king-sized beds. Prices range from $125-$250 per night, depending on the season.
The on-site café, open Friday through Sunday, is managed by Sarah Simmons, who oversees the food and drink program. Guests can indulge in a French toast breakfast sandwich, made with brioche, scrambled eggs, cheese, and a side salad. Alternatively, freshly made mixed berry jam is used to stuff their signature French toast. For a savory option, the café also offers a hummus platter with warm pita, cucumbers, and grape leaves.
For a more substantial meal, The Reserve Restaurant showcases Chef Antonio’s expertise in authentic Italian cuisine, alongside modern American and Southern European dishes. Despite its modest location, The Reserve has become a hidden gem in Sarasota, winning Open Table’s Diners’ Choice Award in 2024. Explore The Reserve’s full menu here.
