Pack Curiosity, Not Coats: Cool Weather Adventures in Sarasota

Hunting for fossilized shark teeth is a treasured Sarasota County pastime. A bountiful cache wash up along the beaches of Venice Island and Manasota Key every year for barefooted beachcombers to find and keep. Simply stroll along the shoreline and collect exciting finds, or put on a light wetsuit and snorkel our refreshingly cool waters to unearth a some larger toothy treasures. 

A trek around Sarasota County's beautiful bay waters, inner canals and mangrove tunnels gives kayakers and stand up paddleboarders a unique adventure through a hidden ecosystem. Fish will swim just inches away in crystal-clear water, crabs scurry along the exposed mangrove roots at eye-level as the sun peeks through a private tunnel of natural Florida beauty. Sea birds dive right next to you for their next meal. And the best part is, once you're done paddling through this special piece of nature, you can head right to the beach to enjoy an afternoon siesta under the palms at places like South Lido Key or Manasota Key. 

During the fall and winter in Sarasota, you can catch a variety of fish and crabs, with some of the most prevalent being stone crabs, snook, redfish and sheepshead. Stone crab season runs from mid-fall to late spring, so it's a great time if you want to see how crab traps are done here. Other fish to target include flounder and snapper, which can be found in both shallower and deeper waters as temperatures drop. For your best bet, book a local charter captain that will show you prime biting spots for the time of year. 

Trade the treadmill for the trails. No overheating, no layers—just perfect weather to actually enjoy the great outdoors. With cool, comfortable temps, fall and winter are prime time for cycling miles upon miles on the Legacy Trail or hiking through one of our many nature preserves with just a hat and windbreaker. You can even go horseback riding or mountain biking through state forests without even breaking a sweat.

In Sarasota, the words “outdoor seating closed for the season” simply don’t exist. Enjoy oysters and live music at a tiki bar, sip craft beer under string lights at one of our local breweries or linger over dinner with Gulf views that go on forever. From fine-dining terraces and lakeside firepits to sidewalk cafés and rooftop lounges where you can catch an extra hour of sunlight down south, every table is an alfresco experience.

When Florida’s humidity finally gives way to crisp coastal breezes, it’s prime time to pitch a tent. With fewer bugs, comfortable temps and starry night skies that practically demand a campfire, cool-weather camping here feels like nature’s invitation to linger a little longer. Think Myakka River State Park’s sprawling oak hammocks or the peaceful waterfront campsites at Turtle Beach Campground. There are even chances to glamp in a safari-style tent at Oscar Scherer State Park for those who are "thin blooded" and prefer to keep toasty under canvas. 

While other cities wind down for winter, Sarasota’s cultural calendar hits full stride. Catch a show at Florida Studio Theatre or Asolo Repertory Theatre, stroll the galleries and murals of Downtown Sarasota or enjoy a pop-up symphony at one of our lakeside communities or public parks. Don't miss one of Circus Arts Conservatory's spectacular circus performances under the Big Top, or the Winter Opera Festival at Historic Sarasota Opera House – there really is something going on every weekend of the arts and cultural season.

Parasailing is one of the coolest ways to spend your fall or winter break while everyone back at home is raking leaves or shoveling snow. Take in the spectacular views of the best beach in the U.S. and hope for dolphin or manatee sighting. The trip to the top can be an exhilarating one, where many find a surprising tranquility high above the turquoise waters of the Gulf Coast.

Our “snow” is made of sand, our Christmas trees sparkle with seashells and yes—Santa might show up in swim trunks. From holiday boat parades and illuminated botanical gardens to festive farmers markets and warm winter nights shopping and strolling University Town Center's spectacular light show, Sarasota’s coastal celebrations add a tropical twist to traditional cheer.

Forget the frostbite and frozen windshields to get to yoga class or pilates. There are plenty of places to throw on your leggings, grab a blanket or mat and drop in to a public yoga class in a beautiful outdoor setting. From the beaches of Manasota Key and Siesta Key to Waterside Place's lakeside park, Selby Gardens' bayfront oasis and The Ringling museum courtyard, there are so many seasonal opportunities to mindfully move and warm the body and soul. 

Trade bulky coats for breezy strolls through Sarasota’s many open-air shopping districts. Browse the 100+ boutiques of St. Armands Circle, where Mediterranean-inspired architecture meets palm-lined charm, or wander through the shops and farmers markets of Downtown Venice and Waterside Place. Pick up holiday gifts and souvenirs venturing through Siesta Key Village or Olde Englewood Village. Shopping in Sarasota isn’t just retail therapy—it’s a sun-drenched experience.

While much of the country is layering up, Sarasota golfers are teeing off under cloudless blue skies. Fall and winter bring ideal playing conditions—cool mornings, low humidity and perfectly manicured fairways that stay lush year-round. Whether you’re sinking putts along the Gulf breeze at University Park Country Club, taking in scenic nature views at The Legacy Golf Club or practicing at the driving range, Sarasota’s golf scene proves that the game doesn’t have an off-season here—just endless sunshine and smooth swings.