Where to Enjoy Wine in Fort Myers

Fort Myers, Florida, offers more than sunlit beaches and historical estates—it also embraces a growing wine scene that surprises visitors and residents alike. From welcoming tasting rooms nestled in the city to nearby craft-focused vineyards and cideries, Southwest Florida's wine offerings invite discovery. Below is a look at some beloved local establishments where Fort Myers and Florida’s wine enthusiasts can indulge.

Blending handcrafted wine with modern casual dining, Cooper’s Hawk Winery & Restaurant in Fort Myers offers a dynamic all-in-one experience that celebrates the connection between food, wine, and friendship. The concept features four integrated elements under one roof: an upscale restaurant, full-service bar, Napa-style tasting room, and a retail gift shop—creating a seamless and elevated environment for wine lovers and foodies alike. Guests can enjoy monthly Wine Club Dinners, thoughtfully curated to pair award-winning wines with multi-course menus that spark conversation and build community. The rotating "Wine of the Month" highlights global varietals, such as the bold Portuguese Vinho Tinto, known for its earthy notes of plum, coffee, and dark chocolate. Whether sipping in the tasting room, dining with friends, or browsing artisanal gifts, Cooper’s Hawk delivers a sophisticated yet approachable atmosphere where memorable moments are made over every meal and every pour.

Located just minutes from Fort Myers in Estero, R.A.D. Winery & Cidery—short for “Really Awesome Drinks”—is a family-run gem founded by Rockie, Allison, and their son Dylan. With roots on a family farm and a passion that began in orchards and vineyards, the R.A.D. team has been crafting exhilarating wines and ciders since 2006. Their offerings range from crisp Pinot Gris to bold Bourbon Barrel-aged Merlot, as well as inventive canned cocktails—each viewed as a work of art meant to be savored uniquely. But R.A.D. is about more than just the wine—it’s also about creating joyful, welcoming spaces where people can relax and connect. Whether visiting their full-scale winery on Corkscrew Road or the stylish tasting room at Miromar Outlets, guests enjoy a vibrant mix of tastings, live music, food events, and even garden plots. With a calendar full of festivals and a genuine commitment to hospitality, R.A.D. delivers flavorful fun and heartfelt experiences in every glass.

Located on McGregor Boulevard, Jordan’s Wine Bar and Cellar delivers a cozy yet sophisticated urban escape without the drive to a larger city. Guests are welcomed by a rich, inviting atmosphere where evenings often feature live piano music—usually jazz or classic standards—enhancing the curated food‑and‑wine experience. The tapas menu is presented with care, often plated on vintage china or rustic barked wooden platters. Signatures include a fresh bread service with mini‑loaf drizzled in olive oil and herbs, paired with sun‑dried tomato tapenade and melting whipped butter; tomato carpaccio drizzled in passionfruit‑lemon sauce with Manchego cheese and paprika; and 24‑month‑cured Jamón Serrano with crostini, pistachios, and apricot jelly—all crafted to pair perfectly with one of the approximately 20 wines offered by the glass. This combination—elegant small plates, a refined selection of wines, live music, and a warm, local feel—makes Jordan’s a standout destination for intimate evenings, date nights, or any occasion seeking both flavor and ambiance in Fort Myers.

Locally and family-owned, Flock Wine Bistro is a stylish, European-inspired wine bar in Fort Myers offering a curated international wine list alongside Mediterranean small plates and vibrant, shareable boards. Founded by Matteo Affatati and Alyson Casey—who met in Rome and relocated to Fort Myers after marrying—Flock reflects their shared vision and love for food, culture, and hospitality. Matteo brings over a decade of culinary experience from operating Pier 1 Café in Rome, and together they’ve crafted an elegant space that celebrates the Italian tradition of “aperitivo.” This social pre-meal custom invites guests to unwind with wine and appetizers in good company. Flock is known for its daily wine and small plate specials, a festive happy hour from 4–6 p.m., and lively monthly wine tastings that draw a loyal local following. The bistro's upscale yet welcoming ambiance makes it a go-to for anyone seeking a refined evening in Fort Myers infused with European charm.

This intimate tasting space on Second Street offers more than great wine—it’s also a dessert lover’s dream. With a perfect 5/5 rating and an ambiance described as quiet and romantic, The Box blends the sophistication of a wine bar with the whimsical indulgence of a gourmet dessert shop. Located at 2502 Second Street, Suite #104, it’s a standout for those seeking a cozy yet elevated experience. The dessert menu is a highlight in itself, offering crowd favorites such as churros with a caramelized exterior, fried cheesecake topped with strawberries and white chocolate, and maple glazed bacon mini donuts for a savory-sweet kick. Patrons also enjoy deep-fried Oreos, rich brownie sundaes, and a variety of milkshakes including Cakes-R-Us Cookies and Cream. With warm reviews praising both the desserts and the drinks, The Box earns its reputation as a must-visit for wine and dessert aficionados alike. Whether for a casual date night or a celebratory outing, The Box exemplifies hospitality and creativity in every detail.

Just as Fort Myers has cultivated its local wine scene with care and character, McMurray and Members of Royal Shell Real Estate curate standout property experiences across Florida’s Gulf Coast. The team can guide clients with expertise, precision, and taste—matching them with homes that pair perfectly with their lifestyles.