Last Updated January 15, 2026
I’m sure we can all agree that Florida is a pretty special place to live or even to visit. Its glorious beaches, diverse wildlife, laidback lifestyle, and strong community vibe make it a place to experience. One of the best things about it is the vast variety of events hosted throughout the area. Whether small or large, weekly or annually, the impressive selection of events and festivals sponsored throughout Southwest Florida capture the region’s unique charm and bring people together for fun and connection. We’ve curated some of the upcoming Winter 2026 events in Venice, Florida, and surrounding areas (including Wellen Park) below, so read on to find your perfect day out and remember to mark them in your calendar!
Venice, Florida Events and Festivals
Regular and Recurring Events in Venice, Florida
Venice has an impressive list of things to do. In addition to the year-round options, the Venice, Florida, event calendar is vast and varied. The area has a massive selection of regular events scheduled daily, weekly, or monthly especially during the winter months (which is considered high-season here). No matter how you spend your ideal day, there is something for everyone to enjoy.
Held every Saturday morning in Venice City Hall, this market features fresh produce, handmade items, and live music. From 8 AM til 1 PM, you can soak up the lively community atmosphere of historic downtown Venice while filling up on seasonal and artisanal goods.
On January 16th and February 20th, Centennial Park hosts a movie night, offering free entertainment for all ages. Remember to bring your chairs!
Start your day right with an early morning yoga session on the pristine Gulf Coast sand. Every morning from 8 AM, and every evening from 5 PM, you can nourish your mind, body, and soul with some sun, sand, and stretching right here on Venice Beach!
Whether you want to tour Venice’s architecture, golf scene, wild women, or haunted history, you won’t be disappointed! Daily tours of historic downtown Venice are scheduled throughout the week/month.
Major Events in Venice, Florida Winter 2026
In addition to the regular daily and weekly schedule, Venice has some more significant events that happen annually or even as a one-off. Some of our favorite picks from this winter’s schedule include.
Wine & Chocolate Walk (February 12, 2026)
Indulge in a decadent evening exploring downtown Venice’s shops and restaurants, each offering unique wine and chocolate pairings. This beloved annual event is a favorite for couples and friends looking for a fun and flavorful night out.
Guests can expect an evening filled with delicious flavors, lively conversation, and a warm, inviting atmosphere. Downtown Venice provides the perfect backdrop, with its twinkling lights, boutique storefronts, and welcoming restaurants creating a truly magical experience. Many businesses also offer special promotions and discounts, making this an excellent opportunity to shop locally while you sip and snack.
The event’s walkable nature ensures an easy and enjoyable experience, and it is also accessible for guests with mobility needs.
Online tickets will go on sale closer to the date, costing $10 each, and a limited number of tickets will be available for in-person purchase at the Information Kiosk in Centennial Park. Be sure to grab yours before they’re gone.
Exotic Race Car Event (February 21, 2026)
Car enthusiasts and casual spectators alike won’t want to miss this once-in-a-lifetime automotive spectacle as the world-famous 1000 Miglia road race makes its way through Downtown Venice. This legendary 3-day, 1,000-mile journey takes drivers on an incredible route across Florida, from Miami to Naples, Cape Canaveral, West Palm Beach, and back to Miami, with Venice as one of its most exciting stops along the way.
Prepare to be amazed as over 70 vintage race cars and modern supercars cruise into Centennial Park, showcasing a dazzling lineup of rare, historic, and high-performance machines. The event is free and open to the public, making it an unmissable opportunity to witness some of the world’s most stunning and exclusive cars.
The festivities begin at 3 PM, when the Venice AACA Car Club kicks off the celebration with a display of classic and collector vehicles, offering a glimpse into automotive history. The 1000 Miglia race cars make their grand entrance between 4 and 5 PM. Be sure to arrive early, grab a great viewing spot, and be ready to capture an unforgettable moment in Venice’s automotive history!
Italian Feast and Carnival (February 19-22, 2026)
Get ready for a four-day celebration of all things Italian at the Annual Italian Festival hosted by the Italian American Club of Venice. This beloved tradition has brought the community together for an impressive 37 years, offering an authentic taste of Italy with delicious food, live entertainment, and family-friendly fun. At the Venice Airport Festival Grounds, the festival is a must-visit event for locals and visitors alike who want to experience Italian culture in a lively, welcoming atmosphere.
Of course, the highlight of the festival is the incredible Italian cuisine. Enjoy all your favorites, from freshly made pasta, meatball subs, and sausage and peppers to crispy cannoli, tagliatelle, and homemade Italian desserts. Pair your meal with a glass of fine Italian wine or a refreshing beer as you take in the sights and sounds of the festival.
Live music and entertainment will keep the energy high throughout the event, featuring a mix of traditional Italian performances and popular favorites. Dance along, sing with the crowd, or soak up the festive atmosphere. Kids and thrill-seekers will love the carnival rides and games, making this a perfect event for the whole family.
At just $5 per person, the festival is affordable and fun for all. Even better, kids under 10, active military, veterans, police officers, and firefighters get in free as a token of appreciation for their service.
Whether you’re craving authentic Italian flavors, looking for great entertainment, or want to enjoy a fun-filled weekend with friends and family, the Venice Italian Festival is the place to be. Come hungry, bring your dancing shoes, and celebrate Italian heritage in true Venetian style!
Venice Art Classic Festival (February 28 – March , 2026)
Enjoy a weekend of art, creativity, and community spirit at the Venice Art Classic Festival, where downtown Venice transforms into an open-air art gallery! Taking place Saturday, February 28, and Sunday, March 1, 2026, from 10 AM to 5 PM, this juried art festival brings together talented artists from across the country to showcase their finest work along West Venice Avenue.
Art lovers can browse and purchase a diverse selection of artwork, including captivating sculptures, striking paintings, intricate jewelry, hand-crafted ceramics, and more. Whether you’re a seasoned collector or just looking for the perfect statement piece for your home, this festival offers something for everyone.
Beyond the stunning artwork, this event is one of the most inspiring art festivals in southwest Florida. It’s also an excellent way to support the local community. Proceeds from the event benefit Venice MainStreet, a nonprofit dedicated to preserving and enhancing historic downtown Venice. By attending, you’re celebrating the arts and helping keep Venice’s cultural heart thriving.
As a free outdoor event, the festival is perfect for a leisurely day of strolling, shopping, and soaking in the artistic atmosphere. Parking is available in public lots and nearby street parking, but arriving early is recommended to secure a good spot.
Venice Sharks Tooth Festival (April 11-12, 2026)
Celebrate Venice’s reputation as the “Shark’s Tooth Capital of the World” at Centennial Park with fossil and beach-inspired merchandise vendors, live music, and delicious food. Although technically, it doesn’t take place until Spring, as it’s scheduled for April, it’s such a great event that we want to ensure you have plenty of notice to bookmark it in your calendar!
Venice’s beaches are renowned for their abundance of fossilized shark teeth, which attract enthusiasts worldwide. The area’s unique geological history has resulted in a rich deposit of these fossils along its shores. You can check out some great fossil finds on our YouTube video here.
This weekend-long family-friendly festival is free and packed with fun activities for all ages. Kids can enjoy the interactive shark-themed play area, which includes face painting, shark tooth hunting, and more.
While leashed dogs are permitted at the festival, it is recommended that pets be left at home due to the expected crowds. Attendees are encouraged to bring their own chairs to enjoy the musical performances comfortably; however, coolers are not allowed.
Wellen Park® Events and Festivals
You’re missing out if you haven’t attended an event at Wellen Park yet! It’s not just a place to live—it’s a whole lifestyle. The downtown area is the heart of it all, with live music, markets, and fun events happening all the time. The downtown area is regularly alive with the Friday Night Concert Series, the ever-popular Wellen Night Market, and rotating live performances that turn an ordinary evening into a reason to hang out a little longer. On top of that, there are ongoing community offerings like toddler groups, theatre workshops, line dancing classes and other casual gatherings that make it feel easy to plug in whether you live nearby or are just visiting from a bit farther afield.
Luminescence Festival (January 9, 2026)
This is one of those events that feels genuinely magical without trying too hard. Think glowing installations, artful lighting, and an evening atmosphere that’s perfect for wandering with friends or family. Set in Wellen Park’s town center, it’s a brand new event for the cooler winter months and is designed to be immersive rather than rushed. It runs from 5pm onwards and is free to attend. The luminary bags are on a first come first served basis though so get there early to make sure you don’t miss out. Participants can personalize their luminary bags with New Year wishes or messages of rememberance, which adds a special intimate vibe to the event. Take part in the parade and release and then enjoy the live music, art, and fireworks.
Wellen Night Market (2nd Thursday of every month)
If you love browsing handmade goods with a drink in hand, the Wellen Night Market is an easy favorite. Local makers, small businesses, and food vendors line the streets, often with live music adding to the vibe. It’s casual, social, and very much a “let’s just stroll and see what we find” kind of evening. These markets are usually free to attend, making them a low-key way to experience the community while supporting local creatives.
Wellen Park Fine Arts Festival (February 15th, 2026)
The Wellen Park Fine Arts Festival draws artists from across the region and turns the downtown area into an open-air gallery. You’ll find everything from paintings and photography to sculpture and functional art, all set against Wellen Park’s waterfront backdrop. Admission is typically free, making it a lovely daytime event to wander through, chat with artists, and maybe come home with something truly one-of-a-kind.
Half Marathon & 5K (March 21st, 2026)
Whether you’re running or cheering from the sidelines, the Wellen Park Half Marathon & 5K is a standout winter event. The course weaves through the community, showing off the scenery while keeping things festive. Registration fees vary by race and timing, but it’s well-organized and welcoming to runners of all levels. Even if racing isn’t your thing, it’s a fun morning to be out and about in Wellen Park, soaking up the energy.
Nearby Events & Festivals in Southwest Florida
Southwest Florida is the perfect place to experience vibrant events and festivals celebrating art, culture, and community. With its coastal charm and lively downtown hubs, the region sets the stage for everything from intimate local gatherings to major festivals that draw crowds from near and far. Whether you’re strolling through an art show, enjoying live music by the water, or indulging in a seasonal food festival, there’s no shortage of ways to get out, have fun, and soak up the sunshine. If you’re ready to explore beyond Venice, buckle up because you’re never far from an unforgettable event! Look at our top picks of what’s on offer this season from nearby areas in Southwest Florida.
Fort Myers Beach – Shrimp Festival (March 7 – 8, 2026)
A much-loved Florida tradition celebrating the local shrimping industry, the Fort Myers Beach Lions Club Shrimp Festival is the premier annual Fort Myers event. The pre-festival activities kick off on March 1 with a kids’ shrimp run, and the full festival schedule commences March 7-8, 2026, at Lynn Hall Memorial Park. The festival features a parade, arts and crafts fair, Queens Pageant, and a shrimp-eating contest.
Parking is available at North Beach Park Plaza, offering over 600 spaces at $3 per hour. Additionally, the LeeTran trolley service is a regular public transport option.
The best thing about this event is that while it’s free to attend, the festival is a huge fundraising event for local charitable initiatives. Proceeds from the event support everything from local eye surgeries and vision care to scholarships for students and programs like Southeastern Guide Dogs. It also helps fund youth sports, large-print books for the library, and essential resources for local schools.
So, while you’re enjoying a plate of fresh “Pink Gold” shrimp and checking out the parade or craft fair, you’re also helping support amazing causes that directly benefit the area. It’s a win-win—good food, good times, and giving back!
Sarasota Winefest (March 21, 2026)
Mark your calendar for the Sarasota Wine Festival on Saturday, March 21, 2026, at Selby Five Points Park in Downtown Sarasota! Enjoy an unforgettable evening filled with world-class wines, craft cocktails, gourmet food trucks, live music, and unique lifestyle vendors.
General Admission (6–9 PM) includes unlimited wine tastings, a souvenir wine glass and tote bag, a food truck voucher, craft cocktail samples, and access to a pop-up wine shop.
VIP Admission (5–9 PM) includes everything in General Admission plus early entry, a private lounge with seating, exclusive wine selections, sommelier access, private bathrooms, heavy hors d’oeuvres, and a VIP swag bag. Limited VIP tickets are available!
Admission to the festival is free, so you can enjoy live music and browse vendors. Still, tasting tickets are required to indulge in wine and spirits, and will go on sale from February 1st. This year’s festival supports the Women’s Resource Center, a nonprofit helping women in Sarasota and Manatee Counties through education, career guidance, wellness programs, and more. Plus, the event will spotlight local women entrepreneurs and businesses. So gather your friends, sip, shop, and savor an incredible night—all for a great cause!
Sarasota Jazz Festival (March 9-14, 2026)
Tickets are on sale now for the 46th annual Jazz Festival, which will take place March 9-14 at various venues throughout Sarasota. Music lovers can enjoy a week of this fantastic festival, which offers world-class cabaret performances and lively jazz trolley pub crawls. Tickets are sold individually for each event so that you can curate your perfect jazz experience. Food and drinks will be available at all venues.
Jazz enthusiasts can upgrade to a VIP Experience, which includes priority seating at all main stage performances, entry to the Monday Night Jazz Cabaret, access to the Jazz Trolley Pub Crawl, and an exclusive VIP Reception on March 17 featuring a special performance by Danny Spinoff at the John C. Court Cabaret, Florida Studio Theatre.
Don’t miss this jazz celebration in the heart of Sarasota—secure your tickets here!
St Petersburg Firestone Grand Prix (Feb 27 – March 1 2026)
The Firestone Grand Prix of St. Petersburg, presented by RP Funding, will ignite the streets of downtown St. Petersburg from February 27 to March 1, 2026. This thrilling event features a 1.8-mile, 14-turn temporary circuit that winds through iconic landmarks such as Pioneer Park, the Duke Energy Center for the Arts, and The Dalí Museum. It even incorporates sections of the Albert Whitted Airport runway, all against the stunning backdrop of Tampa Bay.
Beyond the high-speed racing action, attendees can look forward to a festival-like atmosphere featuring speed zones, an IndyCar Series Fan Village, beer gardens, driver autograph sessions, and interactive games and exhibits.
Parking is available at several downtown garages, including the SouthCore Garage, Sundial Garage, and the University of South Florida (USF) Garage. Additional parking can be found at Tropicana Field, with a free shuttle service running to and from the race venue. Accessible parking is available on a first-come, first-served basis, and fans are encouraged to use public transportation or ride-sharing services for easier access.
Tickets start at $25 for a single day and go up to three-day general admission, priced at $75 for adults and $65 for children 12 and under. There’s also an option for three-day grandstand seats, which offer reserved seating with excellent views for just $135. You can purchase tickets here.
Florida Strawberry Festival (February 26 – March 8, 2026)
The Florida Strawberry Festival has been a cherished tradition since 1930, celebrating its 91st annual event in 2026. It’s one of the most popular events in the state, attracting over 600,000 visitors each year. This annual celebration honors the region’s rich strawberry harvest with entertainment, agriculture, and family-friendly activities. It runs from February 26 to March 8, 2026, in Plant City, Florida.
Attendees can explore displays showcasing local agriculture, including youth livestock shows and the Neighborhood Village, which features homemade crafts and goods. For thrill-seekers, the festival offers a variety of rides and games suitable for all ages. Not least, foodies can indulge in many strawberry-themed treats, from the classic strawberry shortcake to innovative culinary creations.
The festival also boasts an impressive lineup of headline performers. Tickets for these concerts are sold separately and can be purchased here.
On-site parking is available for attendees. It’s advisable to arrive early, especially on weekends, to secure a convenient spot.
Advance tickets are $10 for adults and $4 for children aged 6 to 12. Tickets at the gate are $15 for adults and $5 for children. Children 5 and under enjoy free entry.
Island Fest (March 28-29, 2026)
Get ready for a weekend of island vibes, art, music, and coastal fun at one of the best beach festivals in Florida! The 34th Annual Island Fest in Islamorada will be held March 28-29, 2026, at Founders Park (MM 87 Bayside). The festival is a free, family-friendly event that brings together the best of the Keys—live music, delicious food, stunning art, classic cars, and exciting competitions.
One of the highlights of Island Fest is the Plantation Yacht Harbor Arts & Crafts Show, featuring over 100 talented artists showcasing everything from paintings and sculptures to handmade jewelry and driftwood carvings. Music lovers can enjoy live performances all weekend, adding to the fun, laid-back island atmosphere. There’s also a Classic Car Show, where beautifully restored vintage automobiles will be displayed.
For families, there’s plenty to keep kids entertained, from hula hoop contests and kite flying to an epic sandcastle-building challenge. One of the most unique events of the festival is the “What Floats Your Boat?” homemade boat race, where teams construct their vessels and compete for fun and quirky awards, including the Lucky Ducky Admiral Award. The excitement continues with the Sand Sculpture Competition, where teams create stunning masterpieces inspired by this year’s theme, “Ocean Wonders.”
No festival is complete without fantastic food, and Island Fest delivers! Savor fresh seafood, tropical island flavors, and classic festival bites while enjoying the ocean breeze. Various vendors will offer everything from conch fritters to refreshing tropical drinks on-site.
Best of all, admission to Island Fest is entirely FREE! On-site parking is available for a $10 donation, and festival hours are 10 AM—5 PM both days. Bring your lawn chairs and blankets to stay comfortable and enjoy the festivities. In an effort to keep the scene green, attendees are encouraged to bring reusable drink containers to help reduce waste.
Don’t Miss Out on these Popular WinterVenice, Florida Events (and Nearby Areas)!
With so many exciting events in Venice, Florida, and some of the best festivals in Florida, there’s no shortage of fun this season! Mark your calendars, grab your tickets, and experience the vibrant culture, stunning coastal scenery, and community spirit that make Southwest Florida an incredible place to live and visit!
