Planning your next Florida Gulf Coast escape? Look no further than Siesta Key and Sarasota! Where powder-soft sand meets vibrant culture, world-class dining, and unforgettable local experiences. Whether you’re booking a romantic beach retreat or a family vacation, this area offers something for everyone.
From Siesta Key’s award-winning beaches to the rich arts and foodie scene in downtown Sarasota, here’s your go-to local guide packed with the best restaurants, activities, nightlife, and travel tips to help you plan the ultimate Gulf Coast getaway.
Best Places to Eat in Siesta Key
Whether you’re grabbing a casual lunch after the beach or planning a special dinner, Siesta Key restaurants serve up plenty of fresh coastal flavor:
The Cottage – Siesta Key Village
Island-inspired dishes with an Asian-Latin fusion twist, craft cocktails, and relaxed outdoor seating just steps from the sand.
An upscale dining experience in the heart of Siesta Key Village. Locals love the lobster tail, prime cuts, and stylish interior.
A cheerful garden cafe perfect for breakfast or brunch. Try the eggs benedict, omelets, or fresh-squeezed juices.
A no-frills favorite offering fish tacos, grouper sandwiches, and local seafood in a laid-back setting.
Great for burgers, flatbreads, and craft beer. Ideal for a relaxed night out in flip-flops.
Where to Eat in Sarasota: Local Favorites
Sarasota’s food scene is full of culinary gems, from coastal fine dining to hip brunch spots:
Indigenous – Downtown Sarasota
A must-visit for food lovers. Known for sustainable, locally sourced menus and ever-changing seasonal dishes.
Owen’s Fish Camp – Burns Court
Southern seafood served in a historic cottage under banyan trees. Don’t miss the hush puppies and front-porch live music.
Veronica Fish & Oyster – Southside Village
Stylish seafood spot with a great raw bar, happy hour specials, and buzz-worthy cocktails.
Columbia Restaurant – St. Armands Circle
A historic restaurant serving authentic Spanish-Cuban cuisine, tableside sangria, and the iconic 1905 Salad.
The Shore – Longboat Key
Waterfront dining just minutes from Siesta Key. Known for fresh seafood, modern coastal vibes, and gorgeous bay views.
Nightlife in Siesta Key & Sarasota
Looking for live music, tropical cocktails, or rooftop lounges? Here’s where locals go after dark:
Siesta Key Village
- Siesta Key Oyster Bar (SKOB): Lively beach bar with live music and cold drinks.
- Gilligan’s Island Bar & Grill: Tiki-style fun, dancing, and frozen cocktails.
- The Hub Baja Grill: Great margaritas, tacos, and regular live entertainment.
Downtown Sarasota
- Sage Rooftop Bar: Chic rooftop views and upscale cocktails.
- Pangea Alchemy Lab: A hidden speakeasy with handcrafted drinks.
- The Gator Club: Historic lounge with live DJs and a fun late-night scene.
St. Armands Circle
- The Lounge at Café L’Europe: Sophisticated wine and cocktails.
- Crab & Fin: Sip a martini on the patio while enjoying live music on select evenings.
Fun Things to Do in Siesta Key & Sarasota
Whether you’re visiting with kids or planning a couples getaway, there are tons of things to do in Sarasota and Siesta Key beyond the beach:
Siesta Key Beach
Voted one of the best beaches in the U.S. for its powdery quartz sand and turquoise waters. Come early for a peaceful sunrise or stay for a glowing sunset.
- Siesta Key Drum Circle (Sundays) Join the rhythm with locals and visitors at this unique sunset tradition filled with dancing, music, and beach vibes.
- Bayfront Park – Downtown Sarasota A beautiful waterfront park with walking trails, playgrounds, and perfect sunset views of the marina.
- The Bay Sarasota An urban park with kayaking, events, nature trails, and family-friendly green space near Sarasota’s arts district.
- Sarasota Farmers Market – Saturdays One of the best weekend activities in downtown Sarasota. Enjoy live music, local produce, gourmet coffee, and artisan goods.
- South Lido Nature Park Perfect for kayaking through mangroves, paddleboarding, birdwatching, and picnicking just minutes from the key.
Travel Tips from the Locals
- Book early — for Siesta Key vacation rentals during high season, especially for spring break and holidays.
- Ride the Siesta Key Breeze Trolley — for a free and fun way to explore the Village without parking stress.
- Plan ahead for live music nights — check restaurant and bar schedules for performances.
- Bring water shoes — if you plan to kayak or paddleboard through the mangroves or tidal areas.
- Explore Sarasota midweek — for fewer crowds and easier parking downtown and around St. Armands.
Stay with Us and Vacation Like a Local
When you stay in one of our Siesta Key or Sarasota vacation rentals, you’re not just booking a beach house, you’re stepping into the heart of Florida’s Gulf Coast lifestyle. From early-morning beach walks to cocktail hours on rooftop bars, every day brings a new memory. Whether you’re planning a family vacation, a romantic getaway, or a girls’ weekend, our rentals place you near the best beaches, dining, and attractions Sarasota has to offer. Browse our vacation homes and start planning your Siesta Key escape today!
