Sarasota in 4 days: island-hopping, foodie finds and cultural gems
When it comes to beachy vacation spots, destinations all along Florida’s ample coastline fit the bill. But only one features an ideal blend of laid-back Florida charm, sophisticated cultural allure, picturesque islands, rave-worthy dining and nature-rich attractions. And that’s Sarasota County, on the Gulf Coast. Its nicknames—which range from Circus City to Florida’s Cultural Coast—give an inkling to the wide-ranging appeal of this southwest Florida destination, but to truly “get it,” you’ve just got to go.
Indeed, the region’s diversions are so varied, you could return again and again and never do, see or eat the same thing twice. To save you the tough task of narrowing the list into an itinerary you could manage in an extra-long weekend, we’ve put together a day-by-day guide—with options to fit different travel styles. Sample a little bit of everything that makes Sarasota County such a standout vacation spot with this flexible 4-day itinerary.
Day 1: Sarasota—The Ringling connection, outstanding art & garden walks
In the early 1900s, John and Mable Ringling, owners of many of the largest circuses in the United States, began spending winters on the sunny shores of Sarasota. In 1927, they brought their circus to town, along with an influx of tourists and performers, many of whom made Sarasota their permanent home. The Ringling family's love of art, culture and architecture continues to have a profound impact on the area, and one of the best ways to experience that is via a visit to The Ringling. The 66-acre estate, which John Ringling bequeathed to the people of Florida upon his death in 1936, houses six major cultural and educational attractions.
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There's scarcely a better way to get to know Sarasota's artistic roots than through an exploration of Ca' d'Zan, Ringling's 56-room mansion, and the 21-gallery Museum of Art, which the Ringlings built to house their world-class art collection. The property also includes a circus museum, a historic theater, sprawling bayfront gardens, the Glass Pavilion art gallery and the Center for Asian Art.
Tip: If your visit happens to fall on a Monday, admission to the art museum, the grounds and gardens (but not the property's other features) is free. This once-weekly free admission day was a condition of John Ringling's bequeathing the museum to the state. Budget at least four hours at the attraction (which features a restaurant and cafe, plus allows picnicking on the grounds) since there's so much to see.
Afterwards, you can soak in more of Sarasota's botanical beauty and animal life at a variety of natural attractions. The exceptional gardens and architecture at Marie Selby Botanical Gardens in downtown Sarasota, along with its Historic Spanish Point Campus in Osprey, Florida, have won numerous accolades from the likes of Travel + Leisure, Vogue, USA Today and Time magazine.
Families with young children may prefer Sarasota Jungle Gardens, where free-roaming flamingos, giant tortoises, parrots and an alligator feeding pool will delight guests of all ages. If the day calls for a climate-controlled environment, check out the Mote Science Education Aquarium instead—an exciting new science-focused attraction with aquariums, wildlife and interactive exhibits on three floors. Sea otters, manatees, penguins, sharks and a variety of jellyfish are among the marine life you'll encounter there.
There's one other option for those looking to get as much of the city into a single day as possible: a Sarasota City Sightseeing Tour. These 90-minute trolley tours visit several historic neighborhoods and include narration from an expert guide. Hear stories about the Ringling family, the architects behind some of Sarasota's most celebrated buildings, the local Amish community and much more. The tour company also features specialty tours, like their hop-on, hop-off art crawl tour, and a tasting tour at a local vineyard.
Where to eat: Lucky 8 for New Orleans-inspired comfort food served in cozy and casual setting; Der Dutchman Restaurant for home-cooked Amish cuisine served buffet-style for breakfast, lunch or dinner; Michael’s on East for romantic fine dining that consistently earns rave reviews; MYMAMMA for rustic Italian dishes and a homey atmosphere; or Selva Grill for exquisitely presented and innovative Spanish- and Peruvian-influenced cuisine.
Where to stay: If you'd like to make Sarasota the base for your trip, consider Art Ovation Hotel, Autograph Collection for boutique stays near shopping and the airport; The Ritz-Carlton, Sarasota for luxurious beachfront accommodations; or Ameniti Bay, BW Signature Collection, a budget- and family-friendly find with a central location, large rooms and a beloved included breakfast buffet.
If you have more time: Take in the natural beauty of Sarasota's waterways and wildlife (bottlenose dolphins and manatees, for example) with a Sarasota Bay Explorers Sea Life Encounter Cruise. Paddle, hike or bike your way through Myakka River State Park's unspoiled wetlands, prairies, pinelands and hammocks. Or spend a relaxing afternoon at Ed Smith Stadium, where the Baltimore Orioles spring training games take place from late February through early May.
Day 2: Longboat Key, Lido Key & St. Armands Circle: Exquisite sands, addictive shops, upscale eats & cool cocktails
On your second day in Sarasota County, cross over the sparkling waters of Sarasota Bay via the Ringling Bridge. On the other side is Lido Key, a beach and leisure destination that's equal parts relaxing and engaging. Tip: A complimentary trolley called the Bay Runner rides between downtown Sarasota and Lido Key, with multiple stops along the way.
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Morning is usually one of the quietest times to hit the soft white sand of Lido Beach, a chill and family-friendly spot. Waters here are typically calm and great for splashing with kids or enjoying a saltwater float session. While you could easily lounge here indefinitely, it's worth checking out South Lido Nature Park as well, where you can follow boardwalks through mangroves, wade in shallow waters and scout out beautiful shells and exotic birdlife. There's also a kayak launch where you can embark on a paddling tour through mangrove tunnels, checking out vibrant local marine life along the way.
As alluring as the broad sands and turquoise waters may be, it's absolutely crucial to take some time to explore another famous fixture of Lido Key: St. Armands Circle, just a short walk from the sand. Developed by none other than John and Mable Ringling in the 1920s, the upscale shopping district is home to over 140 stores, art galleries and restaurants.
In between shopping stops, stroll the tree-lined walkways of Circle Park at the center of the complex to view statues from the Ringlings' own collection and to see the Circus Ring of Fame, a series of bronze plaques that pays tribute to more than 150 of the circus's most influential performers and executives.
As the sun starts dipping lower, head north to the beaches of Longboat Key in time to catch the sunset. Post up at a waterfront restaurant, or simply spread a blanket on the sand to take in the cotton candy skies and, if you're lucky, the fabled "green flash."
Where to eat: On Longboat Key: Dry Dock Waterfront Grill is a top spot for fresh seafood and stellar Bay views; Harry's Continental Kitchens offers tasty sandwiches, salads and seafood in a laid-back setting. In St. Armands Circle: Crab & Fin Restaurant is an elevated spot to grab beautiful and tasty appetizers, cocktails and satisfying mains; Cafe on St. Armands has a Mediterranean flair, which you'll notice even on its breakfast menu (Baklava pancakes? Yes please.); Daiquiri Deck St. Armands Circle is a two-story venue great for brunching and people-watching. On Lido Key: Contemporary American restaurant Drift Kitchen & Bar at the Lido Beach Resort sits on the 8th floor, providing 180-degree views of the beach and the Gulf of Mexico.
Where to stay: On Longboat Key: The St. Regis Longboat Key is an 18-acre coastal resort that offers butler service and an oceanfront spa; The Resort at Longboat Key Club is a longtime favorite for luxe stays, offering modern suites with full kitchens, plus activities like tennis and golf; condo rentals like Veranda Beach Club and The Diplomat Beach Resort put guests steps from the beach, with amenities like beach chairs, umbrellas and towel use all included. On Lido Key and St. Armands Circle: Lido Key Vacations offers top-tier vacation rentals, ideal for longer stays and larger groups; Cirque St. Armands Beachside features circus-inspired decor and a location across the street from the beach and a short walk from St. Armands Circle.
If you have more time: Visit Lido Key's Save Our Seabirds wild bird rescue and rehabilitation sanctuary, which admits around 1,400 distressed birds annually with the objective of rehabilitating and releasing them. View the center's rescued birds, aviaries, ponds and native foliage with a self-guided tour of its Bird Walk. Admission is free, though donations to support the non-profit organization are welcome.
Day 3: Siesta Key & Venice: White sands, water sports, shark teeth and Old Florida history
On your third day in Sarasota County, head to Siesta Key Beach, where the bright-white sands are made of quartz crystal and the waters look like liquid sea glass. The beach here was ranked the #1 in the US in TripAdvisor's 2025 Traveler's Choice Awards, and there's little wonder why. A large parking area, food and drink stands and public restrooms make it easy to spend the whole day playing, sunning and swimming at the beach. Or opt to get out on the water with CB's Saltwater Outfitters, which offers half-day boat rentals, jet skis or even parasailing experiences for a bird's-eye view of the idyllic coastline.
In the afternoon, drive south to Venice for fantastic snorkeling or to comb the sand for natural treasures—indeed, Venice is known as the "Shark Tooth Capital of the World" for the beach's high concentration of the fossilized fangs. The teeth are remnants of ancient history—we're talking millions of years ago—when Florida existed only under shark-teeming waters. Scan the shore, or scoop up a bucket of sand and sift through to find your own prehistoric treasures.
For more on the history of the area, visit the Venice Museum & Archives, whose collection includes over 30,000 photographs, objects and publications. On view through January 20, 2027 is the Grover Koons Collection: Constructing Venice, a photography exhibit presented in conjunction with Venice's Centennial celebration, documenting the construction of the city exactly 100 years ago.
As the day winds down, take some time to explore downtown Venice, where picturesque 1920s architecture, dozens of restaurant options, boutique shopping opps (from fashion to home decor to toy stores) and a beautiful community space—Centennial Park—await. The park is the site of festive events throughout the year, and also has a fun splash pad for children.
For a dose of local talent, stop in at the Clyde Butcher Artworks gallery to view the photographer's nature-focused work. Or book an evening show at one of two local performing arts venues: Venice Theatre for musicals, comedic plays or tribute bands; or Venice Chorale for community-based concert choir events.
Where to eat: On Siesta Key: Café Gabbiano serves authentic, handmade pasta and boasts an exceptional wine list to boot; Blasé Cafe & Martini Bar is beloved for its extensive drinks menu and nightly live music, while 3.14 Pi Pizza next door supplies delicious pies, wings and more when the late-night munchies set in; Miguel’s Restaurant is the spot for fine dining with a French flare. In Venice: BODRUM Restaurant blends fresh Mediterranean flavors from Turkey, Greece and beyond on its well-received menu; Café Venice Restaurant & Bar offers an eclectic menu—ahi tuna with seaweed salad, New England clam chowder and a delectable bouillabaisse are all featured—in an upscale setting; Crow’s Nest Restaurant, Tavern & Marina overlooks the bay and features a raw bar, plus a wide selection of hot seafood dishes.
Where to stay: On Siesta Key: Siesta Key Beach Resort & Suites is a quaint Mediterranean-style hotel set close to the beach, plus the shops and restaurants of Ocean Boulevard; vacation rental companies like The Cottages on the Key and Vunique Vacations feature homes with private pools, plus multi-bedroom units and pet-friendly rentals to accommodate any group; Spark by Hilton Sarasota Siesta Key Gateway is a budget-friendly hotel with complimentary breakfast, set just across the causeway from the beach.
If you have more time: Siesta Key: Check out the shops at Siesta Key Village or reset with some self-care at Mandala Med Spa, where you can book a massage or yoga class. Venice: Rent a bike at Bicycles International and set off on the Legacy Trail system, a 30-mile paved bike trail network that includes long waterfront stretches, running north all the way to downtown Sarasota; catch an equestrian show at Fox Lea Farm; or take a Friday-night, docent-led sunset walk at Venice Audubon Rookery Park to learn about the history of local bird species like great blue heron, double-crested cormorants and anhinga.
Day 4: North Port & Englewood: Spring training, water fun, nature parks & an artist retreat
If you're the kind of traveler who likes to dodge crowds and uncover hidden gems, it's worth heading to the southern part of Sarasota County on your final day in town. Coastal Englewood is a nature-rich and unfussy place to unwind; Manasota Key just across the water is the ultimate chill beach destination. Their inland neighbor, North Port, surprises with eclectic attractions.
CoolToday Park ranks high among North Port's unexpected draws. The spring training home of the Atlanta Braves hosts exciting, budget-friendly matchups from February through March, pitting "The Bravos" against teams like the Tampa Bay Rays (March 1 and 11), the Baltimore Orioles (March 7) and the New York Yankees (March 13). The stadium's Tiki Bar & Grill features ballpark classics like chili cheese dogs alongside more novel finds, like shrimp po'boys and cheesecake chimichangas.
Games typically start in the afternoon, so you've got a few options for morning activities. For wellness enthusiasts, that will be an easy choice: Warm Mineral Springs Park. North Port's natural warm spring is heated by geothermal activity, with waters rising from 200 feet underground. It's the only spring of its kind in Florida, and its waters reportedly have one of the highest mineral concentrations of all natural springs in the U.S. The park's permanent facilities (showers, restrooms, changing rooms and gift shop) are currently being restored, but a temporary admissions building and restroom trailer have been brought onto the property in the meantime.
If your traveling crew includes young ones who would rather careen down a water slide than soak in a mineral spring, however, North Port Aquatic Center may be your best choice. Its slides and lazy river re-open for the season March 13, while its heated outdoor pool is open year-round.
After a day spent splashing and cheering on your favorite team under the Florida sunshine, head to Downtown Wellen Park for dinner. You'll find everything from taco spots to healthy bowl eateries to upscale bistros at the open-air mall and community space. You might even catch a live band putting on a pop-up performance on the venue's stage. If you're looking for more evening entertainment, check the calendar at the community-based North Port Symphony.
Where to eat: Englewood: For breakfast, hit The Dearborn Coffeehouse and Bakery, where the pastries are freshly baked and available coffee preparations are nearly infinite; Farlow’s on the Water specializes in seafood and steaks for lunch and dinner, with live music most Thursdays-Sundays.
Where to stay: On Manasota Key: Set just west of Englewood across the waters of Lemon Bay, Manasota Beach Club is a quiet, historic beach retreat set on 11 acres, with shoreline on both the bay and Gulf sides of the island. In North Port: Hampton Inn & Suites North Port is an affordable find set just a few miles east of the Warm Mineral Springs.
If you have more time: Take a day to explore the natural Florida wilds at Myakkahatchee Creek Environmental Park. Trails for hiking, biking and birding encircle the 160-acre preserve. The dog-friendly park also features picnic tables, fishing spots and primitive camp sites, available by reservation.