Chalk Festival

Anytime is a Good Time for Sarasota

No matter when you’re looking for a visit, Sarasota has something special waiting for you.

“When’s the best time to visit?” It’s a common question by guests coming to see me and Sarasota. And it’s a question that’s both easy and hard to answer because, the truth is, anytime is a great time. At any time of the year, there is something special happening in Sarasota. And, weather-wise, the skies are blue year-round and the sun is our best friend. While many destinations have a “season,” and, consequently, an off-season where things may or may not be happening or the weather may or may not be cooperative, Sarasota is easy and is great always. Oh, and how we love our festivals. So no matter when you’re looking for a visit, Sarasota has something special waiting for you.


With our consistently pleasant weather, Sarasota’s seasons are not always based on foliage or calendar, but by what’s where at a particular time. A few of our “seasons” include turtle, citrus, berries, fish, rain, and manatees.

Turtle nesting season spans from May 1 through October 31. Nesting areas are marked along the beaches and rescued hatchlings can be viewed at Mote Marine. Please keep it dark so they can find their way to shore.

Citrus season, including oranges, grapefruit, lemons, and kumquats, peaks from January through March. They become especially sweet after a cold front (by Florida standards) comes through.

Strawberry season runs from October to May. Hit up the local markets or pick your own of these tasty treats, best enjoyed outside.

Tarpon season peaks during the months of May through July.

Snook, while found in our waters year-round, can be kept starting in September and through the end of November and again March through the end of April.

Stone crab, a delicious delicacy that should be enjoyed as often as possible, becomes available on October 15th and lingers until May 15th.

Rain tends to appear most afternoons during the summer months. Typically short and warm, it gives beachgoers a daily reminder to pop out of the sun for a smidge to reapply that sunscreen and have a snack before coming back for the sunset.

Manatees, the friendly vegetarian giants of the sea, enjoy warmer water and can be seen frequently throughout the Bay, Gulf, Intercoastal, Phillippi Creek, and more through the late Spring, Summer, and early fall seasons.


While New Year’s Eve happens everywhere, Sarasota celebrates in its own distinctive way with the Pineapple Drop. Imagine it’s Times Square but less crowded, warm, and everyone downtown is watching an illuminated pineapple instead of an orb.

Begin the year with Myakka River State Park’s First Day Hike. Fresh air, nature, and a little exercise on the first day of January is quite the way to kick of a year.

The Sarasota Seafood and Music Festival brings together the essentials of any great party – music, food, drinks, and smiling faces under blue skies.

The Suncoast Blues Festival, where I first heard Trombone Shorty play and will forever remember it, takes jazz and blues lovers out of the dark jam session headquarters and outside to enjoy the soulful songs with thousands of fellow fans. Bring a chair to relax to the music or dance like no one’s watching.

Sarasota Polo’s Sunday season begins with weekly games open for public viewing. At 1:00pm each Sunday from January through April, bring snacks, grab a seat (tailgating welcome), and enjoy the “Game of Kings.”


Few events scream Old Florida as much as the Cortez Fishing Festival. Undoubtedly the freshest fish imaginable served along ten blocks filled with music, crafts, and fishing history.

February kicks off MLB’s Spring Training and the arrival of the Baltimore Orioles to Ed Smith Stadium. Perfect weather paired with America’s favorite pastime is hard to beat. Games run through March.


It’s Spring Break time! Visitors from around the world flock to our beaches to indulge in sun and fun, taking that reprieve from everyday stresses.

“The Largest World Whiskey Festival in the US” fully summarizes the Whiskey Obsession Festival. Over four days, sample 250 whiskeys (not a typo – two hundred and fifty whiskeys!) from around the world. Yes, we have Uber.

The bees of the world are in peril and we need to save them. The Honeybee Festival will not only leave you enlightened on the buzzing beauties, but also full of yummy goodies and handpicked strawberries and memories of crafts, music, and all things sweet.


With a claim to fame as awesome as Shark Tooth Capital of the World, Venice has a moral obligation to celebrate itself and it does so well with their annual Shark Tooth Festival. Now on its 25th year, the gathering features local food, music, crafts, and, of course, all things shark teeth related.

The Sarasota Film Festival spans for ten days and features independent cinema at its finest. No, really. It was voted as such by Movie Maker Magazine. Filmings, panels, and celebrities merge to satisfy everyone from the novice blockbuster movie lover to the diehard indie buff.

From yachts to inflatables, speedboats to catamarans, the Suncoast Boat Show has them all. Hop aboard and see what it’s like to have champagne wishes and caviar dreams or how you’ll fish the coast of Italy once you’ve won the lottery.

Bayfront Park, located on the water in downtown Sarasota, features the annual Embracing our Differences exhibit each Spring. Meander the park and enjoy the free exhibit as the salty air wafts by.

Siesta Key hosts the Fiesta on Siesta volleyball tournament where spectators can set up their seats on the white sand and effortlessly swap from watching the elite athletes and frolicking in the surf.

The first Saturday and Sunday of the month are License-free Freshwater Fishing Days.


If you happen to miss the Venice Seafood and Music Festival early in the month, catch the fishy fun at the St. Armand’s Seafood and Music Festival in late May. Both feature local fish, drinks, music, crafts, and outside fun. If it’s an extended stay, give each a try and see whose local fare rules supreme.


Savor Sarasota Restaurant Week spans two weeks and features many of Sarasota’s Zagat-rated restaurants with prix-fixe menus to satisfy any palate and wallet.

My very favorite thing, the Siesta Beach Fun Runs, begin in June and continue for eight weeks. Spring, jog, trot, or walk the one-mile course along the water’s edge with fellow frolickers as the waves crash, kids giggle, and the sun sets.

The first Saturday and Sunday of the month are License-free Saltwater Fishing Days.

The second Saturday and Sunday of the month are also License-free Freshwater Fishing Days.


The 4th of July fireworks, though enjoyed across this great country, hold a special bit of magic when reflected in the calm waters below. Watch from Bayfront Park as they explode above Sarasota Bay, the iconic Ringling Bridge behind. Or head to the beach and watch as they illuminate the skies above the Gulf.

Other areas have their car races, dirt bike races, snowmobile races. Here we have Grand Prix Powerboat Races. Watching these sleek vessels zip through the water, be it from land or sea (I suggest the Old Salty Dog), is a rush, Florida-style.

Lionfish, though stunningly beautiful, are invasive and damaging our seas, leading to increased consumption and events such as the annual Lionfish Derby. Watch the event and enjoy savoring these tasty little beauties.


Sarasota and Manatee county schools resume mid-month. Helpful information if you are hoping to see or not see little ones during your visit.


For 70 years, hundreds of sailors have gathered from across the continent to participate in the Sarasota Sailing Squadron’s Labor Day Regatta.

The first Saturday of the month is a License-free Saltwater Fishing Days.


Halloween may be celebrated in most cities, but Sarasota’s celebration features underwater pumpkin carving in shark-infested waters. Mote Marine’s ( annual Night of Fish, Fun, and Fright merges candy and fish into one spooky undersea evening.

October kicks off the season for the Phillippi Farmhouse Market, the Wednesday fresh air farmer’s market bursting with produce, music, crafts, and baked goods galore. The market remains open through April.


I’ve watched them do it and I’ve heard the explanations, but I cannot fathom how the artists create their massive, detailed, increate creations at Siesta Keys’ annual Crystal Classic International Sand Sculpting Festival. Spectators are welcome to watch as these incredible sculptors create their art as well as to participate in the judging on the last day. Music, food, drinks, and crafts make the festival complete.

Like the Crystal Classic, the annual Chalk Festival allows guests to witness the creating of the art before experiencing it in its completion. It’s fascinating watching as it develops over hours, days, and meters. All attendees are welcome to participate in the Young and Young at Heart area and give chalk art a try.

The Saturday after Thanksgiving is a License-free Saltwater Fishing Day.


Lights in Bloom, Marie Selby Botanical Gardens’ annual December event, features myriad illuminated flowers, butterflies, birds, and more. Select nights feature Christmas elements or live music. Stroll through the sparkling paths with the sea breeze and floral aromas wafting by and forget about the snow back home.

Sand, music, and seafood. It’s the trifecta and it can all be fully enjoyed a the Siesta Beach Seafood and Music Festival. The free event bursts with joyous attendees happy to be at the beach with seafood and blue skies during the “winter.”

St. Armand’s Circle features an enormous Christmas tree each year, the lighting of which gathers crowds prepared to ooh and aah.

Sarasota’s Main Street features a holiday parade, which mainly differs from those I enjoyed up north in my youth due to its temperature (no winter coat needed!) and presence of the lions from Big Cat Habitat. But outshining even the king of beasts is the Holiday Boat Parade, in which decorated boat after decorated boat, each attempting to beat the next, meanders by on this Florida experience.

Year Round

Almost every attraction in Sarasota remains open throughout the year, including Mote Marine, Ringling Art Museum, Marie Selby Botanical Gardens, restaurants, parks, shops, and, of course, beaches. And there is never a bad time for the beach.