Things to do and where to stay in Sarasota, Florida

It's the perfect time to hop on a quick flight for a two-day trip to the southwest coast of Florida. Locals love October and November before the snowbirds arrive and there is plenty of open seating in restaurants. The weather cools from the summertime flames to more comfortable 80-degree days. 

Located on the Gulf of Mexico, Sarasota has been named one of the best places to live and retire, but it is also a great place to spend a few days in the sun with some of the top-rated beaches and a hub for art and culture.

Getting there

There are no direct flights to Sarasota from Long Island MacArthur Airport in Islip, but there are direct and connecting flights from LaGuardia Airport and John F. Kennedy International Airport. Breeze Airways plans to have a flight route from Islip to Sarasota beginning in November.

If you plan to rent a car, it is better to fly into Tampa, which has cheaper and more direct flights, is about an hour's drive from Sarasota, and will send you over the delightful Skyline Bridge.

Day 1

Hotel check-in

The hardest part will be whether to stay in the vibrant seaside downtown or one of the tourist beach communities. Siesta Key and Lido Key offer small, beachy resorts, while downtown features mostly high-rise hotels.

Art Ovation (1255 N. Palm Ave., 941-316-0808, marriott.com) is a downtown Marriot hotel, complete with a rooftop bar and views of the marina, walking distance to a wide variety of restaurants along Main Street and its side streets. The walkable downtown features galleries, boutiques and coffee shops. Sarasota prides itself on its art culture and visitors can spot modern sculptures at the traffic roundabouts. Rates are about $217 a night.

If you want to stay on the beach, book a stay at Sandcastle Resort at Lido Beach (1540 Ben Franklin Dr., Sarasota, 855-410-3616, sandcastlelidobeach.com) which is a half-mile to St. Armand’s Circle, a shopping and restaurant mecca with a charming street scene. Shuttles are available, which is a big help because parking can be tough. Rates are around $219 a night.

On Siesta Key, there are several options, from bungalows to condos for rent, but no high-rise hotels. Free trolleys run up and down the village, including the whimsical Frog Hop for those looking to explore the nearby sites. You can hear the "croak" as it drives by.

Head to the beach and grab a bite

After you've checked in and dropped off the bags, head to the beach. Take your pick, but Siesta Key is a fan favorite known for its white quartz sand and its clear blue calm water. After, take one of the trolleys or walk the half-mile to the quaint village for dinner and drinks. With its live music wafting out of the restaurants and bars, it’s a walkable main street. It will remind Long Islanders of Montauk with the little village tucked between the beach and the bay.

Along Ocean Boulevard, you’ll find plenty of places to dine and shop. Try Siesta Key Oyster Bar, known locally as SKOB, (5238 Ocean Blvd., 941-34, -5443, skob.com) where you can eat outdoors or inside. It’s become a custom for visitors to write a message on a dollar bill and staple it to the wall of the beachy establishment and every few years staff members will donate the money to a charity. The menu consists of oysters, crab cakes and more. Or, grab a drink and people-watch at Gilligan’s (5253 Ocean Blvd., 941-346- 8122, gilligansislandbar.com) and Daiquiri Deck (5250 Ocean Blvd., 941-349-8697, daiquirideck.com)

Set sail

Take a boat ride on the bay with Sea Life Encounter Cruise (1609 Ken Thompson Pkwy., 941-388-4200, Sarasotabayexplorers.com; prices start at $36). A local sea biologist is onboard to point out all of the area’s teeming marine and plant life. Plan to see a dolphin or manatee on your trip.

Or if boozing and cruising is more your style, take a ride on a sunset LeBarge Tropical Cruise with Jimmy Buffett-style musicians and tropical cocktails on the menu (2 Marine Plaza, Bayfront Park, 941-366-6116, lebargetropicalcruises.com; prices start at $40).

Day 2

Have breakfast 

In the morning, grab an iced coffee and a muffin at Mojo Risin’ (5251 Ocean Blvd. mojorisincoffee.com) where the late author Jack Kerouac is king and surfboards hang from the ceiling. If you’re a New Yorker yearning for a bacon, egg and cheese sandwich, head to Sun Garden Café (210 Avenida Madera, 941-346-7170, sungardencafe.com) where you can grab one with meat and cheese for $13.95 and sip a Bellini for $10.95.

Embark on a journey through history 

There are plenty of historic things to see and nature centers for rest, relaxation and wildlife spotting, so visitors can pick their own adventure depending on their interest. 

Culture vultures can spend hours at the Ringling Museum (5401 Bay Shore Rd., Sarasota, 941-359-5700, ringling.org; $30, $5 for ages 6-17). Stroll the mansion estate of John and Mable Ringling of circus fame and explore the grounds along Sarasota Bay. Ringling’s art museum, housed in the home itself, has an impressive collection of ancient artifacts like the original train car used to transport animals to contemporary installations. It has one of the largest collections of Flemish painter Peter Paul Rubens’ art, including five works of his Triumph of the Eucharist series. The main attraction is the 3,800-square-foot miniature museum, a lifelong vision of one man, Sarasota resident Howard Tibbals, who died in 2022, with 45,000 handmade miniature figures depicting circus life under a large dome.

Take a 10-minute car ride to Marie Selby Botanical Gardens (1534 Mound St., 941-366-5731, selby.org; $28, $12 ages 5-17) for a peaceful afternoon in nature. The downtown location on Sarasota Bay is a small but visual treat, with epiphytic orchids, a Japanese garden and canopy of tree trails. There is also an educational children’s play area.

Before heading for the airport, go to Bayfront Park for a drink and a bite at O'Leary's Tiki Bar (5 Bayfront Dr., 941-953-7505, olearystikibar.com), where you can put your feet in the sand and watch the boats go by as the sun sets over the water. Serenity.