North-to-South Sarasota County Arts & Culture Trail

Start your cultural expedition at The Ringling, the former estate of John and Mable Ringling. Wander 66 acres of bayfront beauty, from Baroque masterpieces to the Circus Museum and the Ca’d’Zan mansion—an opulent Mediterranean Revival masterpiece.

Afterwards, walk over to Asolo Repertory Theatre, Florida’s premier professional theater company, to experience a world-class performance. From Broadway-caliber productions to bold new works, each show unfolds inside the historic Ringling complex.

Dine nearby: Sip cocktails and enjoy modern American cuisine at The Ringling Grillroom, the on-site restaurant offering brunch, lunch and dinner in a chic, sun-washed space overlooking the museum's grounds. 

Stay nearby: Just minutes from the stage and museum, voco Sarasota offers boutique comfort with contemporary flair—perfect for unwinding after a day strolling gardens and galleries. Enjoy stylish rooms, a tranquil pool, sweeping views of the bay and a tapas-inspired restaurant.

Journey down Tamiami Trail to a hidden gem located in Sarasota's Rosemary District. Westcoast Black Theatre Troupe is a powerhouse in performance dedicated to African-American stories and is the only professional Black theater company on Florida’s west coast. Grab tickets to a production in season, or take a fun improv acting class instructed by one of their professional actors.

While in the neighborhood, take a self-guided walking tour of the colorful street art decorating the walls of many buildings, or opt for a Rosemary Art & Design District (RADD) mural tour via trolley with a local guide to spotlight the history and vivid tales painted on building facades. 

Dine nearby: Enjoy happy hour at Arts & Central's expansive patio under the lights or by the firepit, or head inside the sophisticated dining room for dinner. This art-themed culinary destination serves shareable American fare in a neighborhood-friendly atmosphere. Each month, a local artist's work is chosen to be featured on the back of the menus while jazz singers perform in the lounge nightly.

Stay nearby: When it's time to head in for the night, walk down Boulevard of the Arts to check in to The Sarasota Modern. This is your boutique base in the Rosemary District where bold mid-century modern design meets snazzy amenities—just steps from gallery-lined streets, cafes, shops and the mural walk.

Just a minute's drive farther south, and you'll be in the heart of Sarasota's downtown district and performing arts corridor. Find bold, contemporary works, including laugh-out-loud improv shows, on the intimate stages of Florida Studio Theatre. 

A short walk away is the beautiful and historic Sarasota Opera House, a restored 1926 gem. There, the Sarasota Opera delivers grand performances in a setting that feels like Old Hollywood glamour. In between shows, stroll down Pineapple Avenue and Palm Avenue's scenic streets lined with numerous fine art galleries and studios. 

Dine nearby: Around the corner from the opera house, grab a seat on the sidewalk or inside Selva Grill's moody dining room and lounge. There, try Peruvian fusion dishes and outstanding craft cocktails. If you prefer seafood for the night, Duval's Fresh Local Seafood is also nearby for a Gulf-caught meal.

Stay nearby: The stylish Art Ovation Hotel, located right across the street from FST, features rotating art installations within its luxe lobby, piano-playing in the lounge, rooftop views from the pool bar, and distinctive artwork throughout the hotel and guest suites.

On the bayside of Tamiami Trail on the outskirts of downtown Sarasota, discover a hidden natural gem. Marie Selby Botanical Gardens is a living museum of tropical flora and world-class exhibitions, blending horticulture and visual art. The bayfront campus hosts celebrated events year-round, weekly yoga in the gardens and regularly features art inspired by nature’s design. Be sure to shop the Garden Shop on your way out for home décor, books on planting, ceramic pots and even custom orchid arrangements. 

Dine nearby: Grab a healthy bite at The Green Orchid, nestled within Selby’s lush grounds. Not only a beautiful place to relax and refuel, this is also the world’s first net-positive-energy restaurant—with garden-to-table fare and herbs sourced from the restaurant's rooftop garden.

Stay nearby: Just down the trail, past the sculptural art and sparkling marina of Bayfront Park, book a luxurious stay at The Westin Sarasota. Its location offers bay views from most of the guest rooms as well as its sophisticated rooftop pool—perfect for a post-garden sunset drink. The on-site spa and restaurant make your stay even more comfortable and convenient.

Slightly up the road, find a hub for contemporary creativity. The Sarasota Art Museum showcases rotating exhibitions of national and international artists within a beautifully reimagined historic high school. Stroll its outdoor courtyards to admire sculptures, then head inside to shop for coffee-table art books, jewelry, embroidered tote bags, stationery and more. 

Nearby, the Circus Arts Conservatory brings aerial feats rooted in Sarasota’s storied circus heritage. Witness one of its youth-driven Sailor Circus shows under the Big Top, or join the circus yourself by trying a new and exciting activity at one of its all-skill levels recreational classes.

Dine nearby: Conveniently located inside the museum campus, Bistro at SAM serves gourmet lunch fare inspired by Florida’s fruit stands and farmers markets in a bright, art-filled setting. For an elegant dinner close to all the action, head to the old-world wine cellar of Michael's on East, just across the street from the big white circus tent.

Stay nearby: Less than a mile away, Aloft Sarasota is a great choice for a modern, design-forward hotel. Located in the historic Burns District, you'll have walking access to galleries, shops, theaters and nightlife. Back at the hotel, unwind from a full day of exploration and entertainment with a drink at the vibrant lobby bar and lounge.

Jump in the car and drive south to the charming island city of Venice. There, the coast's historic cultural scene comes into full view. Catching a production at Venice Theatre—one of the largest and most respected community theaters in the nation—offers an intimate, high-quality performance experience where local talent shines. 

Time your evening for an orchestral performance from The Venice Symphony, presenting dynamic concerts at the Venice Performing Arts Center. To get hands-on with your creativity on this art expedition, the Venice Art Center welcomes both beginners and seasoned artists to join adult-friendly workshops and classes ranging from painting and pottery to mixed-media projects.

Dine nearby: For dining in the heart of downtown, walk to Cafe Venice Restaurant & Bar. This local landmark sets the stage by serving global fare amid stone walls, pillars and sidewalk seating—reminiscent of a European bistro. Enjoy boutique wines and a warm atmosphere that’s ideal before or after a show.

Stay nearby: Just minutes from Venice's cultural stops, relax for the night at Ramada by Wyndham Hotel Venezia. The hotel offers resort-style amenities, a large pool area, comfortable rooms and an on-site restaurant and bar—an ideal base for exploring the many artistic gems on the south end of Sarasota County.

Your journey down Tamiami Trail concludes in the relaxed, arts-rich community of Englewood, where creativity thrives along the waterfront. Catching a comedy or play at Lemon Bay Playhouse offers an intimate theater experience filled with heartfelt, candid stories that resonate long after the curtain falls.

After the applause, step out onto Old Englewood Village’s Dearborn Street to wander down the main drag, past a vibrant collection of art galleries, creative studios and eclectic shops showcasing the work of local artists and makers who shape the area’s distinctive charm.

Dine nearby: After an inspiring afternoon at the theater and shopping, enjoy a flavorful meal at Mango Bistro. This colorful, globally inspired café is known for its fresh crepes, vibrant bowls, craft drinks and desserts that infuse Englewood's energy.

Stay nearby: To fully embrace the area's coastal culture, stay waterfront with a vacation rental through Paradise Cove on Lemon Bay, where private decks, gentle breezes and serene bay views provide a peaceful retreat—and the perfect ending to Sarasota County’s north-to-south arts & culture trail.