Sarasota County Fair

The 81st annual Sarasota County Fair will take place from March 17th to the 26th. There is always plenty of entertainment at the county fair including rides, crafts, a science fair, livestock and horticulture displays, shows and performances, contests, a live auction and more.


This family friendly event includes rides and activities for all ages. This year, there will be sea lions, a bear show, a hypnotist, racing pigs and much more.


There is a variety of favorite fair food options sure to satisfy everyone’s taste buds. If you love fair food, the Sarasota County Fair is the place that will have it all.

General Information

The Sarasota County Fair is located at 3000 Ringling Blvd, Sarasota. Parking is free at Robarts Arena. Proceeds for this event will be donated to the promotion of 4-H and Future Farmers of America groups around the county. You can access the official website here.

The Sarasota County fair is a great activity for the whole family to enjoy. If you’re here on vacation during the dates of this event, it’s definitely worth a visit.

Sarasota Spring Festivals

Spring is a time full of activity with plenty of events for all ages and interests. Here are some options for festivals during your spring vacation.

Sarasota Jazz Festival

The Sarasota Jazz Festival will take place on March 5th – 11th, 2017. The festival is the signature annual event of the Sarasota Jazz Club, one of the biggest and most active jazz clubs in the U.S. The event features free concerts in the park, evening concerts with national and international jazz artists, jazz trolley and pub crawl in downtown Sarasota.

Top musicians of the area will be performing.  

Sarasota Film Festival

2017’s film festival will be the 20th annual event. This year the event takes place on…The mission of this event is to celebrate filmmaking  and develop year-long programs to benefit our community economically, educationally and culturally. This ten day event features symposiums, special events around Sarasota, panels and conversations with leaders in the film industry as well as screenings.

More than 200 films are screened every year at the Sarasota Film Festival with over 250 filmmakers in attendance. Screenings include features, documentaries, shorts and kid-friendly films. You can purchase tickets online, by phone or at the box office at the lobby of the Regal Hollywood 20 Theater (1993 Main St. Sarasota).

Folk Music Festival?

This year the Folk Music Festival will take place on March…2017 in Oscar Scherer Park in Osprey. The gates open both days at 9:30 am. Three stages will run all day from 10 am to 10 pm Saturday and 10 am to 5 pm Sunday. A jam tent will be set up for performances by aspiring musicians and workshop tent where guests can get tips from the artists. The headliner artist will perform Saturday in the large tent. There will be a children’s area with workshops and other fun activities next to the playground and Family Stage. There will also be folk life exhibits and crafts, art and food for sale at the event.

Seasonal Activities Guide

Sarasota hosts many annual activities that residents and visitors anticipate. Whatever the season, there is always something to do in Sarasota. Here are just some of Sarasota’s favorite annual events:

Sarasota Exotic Car Fest

Every year, exotic cars are displayed in downtown Sarasota. Ferraris, Rolls-Royces, Lamborghinis, Bentleys, Alfa Romeos and more are on display. This event typically takes place on a weekend in late February. The weekend also includes an opportunity to drive around in a sports car during Road Rally and enjoy a meal at the Closing Brunch. As the date approaches, tickets for the Sarasota Exotic Car Fest will become available online.

Siesta Fiesta

Siesta Fiesta is an annual open street fair featuring Sarasota’s arts and crafts vendors, merchants, food stands and live musicians. The weather is usually wonderful for the street fair; warm and sunny with a nice breeze blowing from the ocean. This free outdoor event in late April showcases some of the best parts of Sarasota’s culture; just down the street from the Inn on Siesta Key.

Savor Sarasota

Entrepreneurs and chefs from all over the world come to Sarasota, sharing their culture and cuisine. Savor Sarasota is an annual event where, with the purchase of tickets, you can eat meals from these authentic chefs and their restaurants. Savor Sarasota takes place every year, typically in June. Through the purchase of a $15 lunch and/or $29 dinner ticket, you can experience three-course meals from Sarasota’s award-winning eateries.

Suncoast Offshore Grand Prix

The Suncoast Offshore Grand Prix Festival takes place from late June into early July, with a multitude of events and activities. The two official race days occur in July. The annual Suncoast Offshore Grand Prix brings boat racers and enthusiasts together for a spectacular summer experience.

Fourth of July

Every year the Siesta Key Community hosts an official fireworks display on the north end of Siesta Key Beach. This is a free event, however, there is a VIP party at 5 pm for anyone who wishes to purchase a ticket. Fireworks start around 9:15 pm and run for 25 minutes. Make sure to come early to get a good viewing spot.

Chalk Festival

The Chalk Festival is one of Sarasota’s most anticipated annual events; the first and only internationally acclaimed festival in Sarasota County. Every November, artists decorate the pavement with their creations using chalk as their medium. From traditional and 3D chalk paintings to performing artists such as mimes, dancers, magicians and theatrical artists, there is much to see at the Chalk Festival.

Holiday Night of Lights

Taking place in early December, the Annual Holiday Night of Lights on St. Armand’s Circle is a great family friendly event to kick off the holiday season. The night begins with a Christmas carol sing-a-long, followed by a lighted parade highlighted by Santa on his sleigh. Lastly, the evening ends with a tree-lighting ceremony. This spirited event is fun for all age groups.

Whenever you vacation in Sarasota, there is always something to do here. If the time of your stay happen to coincide with the dates of one of these events, we encourage you to give them a try. The residents of Sarasota are eager to share their most beloved traditions with you during your stay.

Performing Arts in Sarasota

Sarasota is home to many talented people. Orchestra, circus, dance and opera are a few of the many arts that have shaped Sarasota into the city it is today. If you enjoy the performing arts, you may want to visit these locations during your vacation.

The Players Centre for Performing Arts

The Players Centre for Performing Arts features both new and professional local actors. The community theater is dedicated to presenting productions of mainstage classics.

Van Wezel

Widely recognized by its unique purple color, the Van Wezel Performing Arts Hall hosts scores of plays and performances throughout the year. These performances include: Broadway musicals, performers, comedians, orchestras, classic, modern and ethnic dance, as well as local performance groups: the Sarasota Orchestra, Sarasota Ballet, Sarasota Concert Association and the Ringling Library Town Hall Lecture Series.

Photo Credit: iTravelopedia

Asolo Repertory Theatre

The Asolo Repertory Theatre is a professional theater in Sarasota that stages up to fifteen productions per season. Home to more than 100 talented artists, this theater is the largest professional not-for-profit theater in the U.S. south of Atlanta.

Sarasota Opera House

This opera house originally opened in April, 1926 as a theatre. The beautiful and historic performance space was restored in 2008. The Sarasota Opera House places importance on education through performance. There are a variety of performances offered, for both the novice and seasoned opera-goer.

Sarasota Opera's production of Jerusalem
Photo Credit: Classical Voice North America

The Circus Arts Conservatory Sarasota

John Ringling brought his circus to Sarasota in the late 1920s. This circus then became an important part of Sarasota’s identity as a community. The Sarasota Circus stages professional performances throughout the year. 80% of ticket revenue for the circus goes to outreach programs in Sarasota.

Photo Credit: Ticket Sarasota

Holiday Events in Sarasota

Do you enjoy viewing lighted displays, drinking hot chocolate and singing carols? Then you won’t want to miss Sarasota during the holiday season. Here a just a few of the festive events that take place during December:

The 13th Annual Lights in Bloom at Selby Gardens

Selby Gardens will host their annual “Lights in Bloom” event, December 16th to December 30th, 2016 from 6 pm to 9 pm. Half a million lights will illuminate the gardens with displays at some of the garden’s most iconic locations. There will be traditional holiday music, photo opportunities and food and drink available from Michael’s On East.  Please note:  the event does not occur on December 24th and 25th.

Photo Credit:

A Taste of Chanukah at Sarasota Fairgrounds

Celebrate Chanukah in Sarasota on December 26th from 4 pm to 6 pm at the Sarasota Fairgrounds. Bands, kosher food, inflatables, a petting zoo, carnival games, ice menorah and a giant dreidel are just some of the things to look forward to at the 6th annual Taste of Chanukah.

Moscow Ballet’s Great Russian Nutcracker

The classic Nutcracker Ballet, performed by the The Moscow Ballet, will run on December 29th, 2016 at the Van Wezel. With a 60-foot growing Christmas tree; hand-made costumes and stunning, hand-painted sets designed by an Academy Award nominee, Sarasota audiences are sure to be delighted. Tickets are available online.

Holiday Boat Parade?

The Sarasota Holiday Boat Parade is a dazzling light show on water. Boats of every size are decked out in creative displays of holiday fun. If you are planning to attend the parade, please keep in mind that the best locations for viewing are Marina Jack, City Island and Centennial Park.

Photo Credit: Ticket Sarasota

Sailor Circus Holiday Spectacular

The Sailor Circus Holiday Spectacular runs from December 26 to December 29th, with eight shows in all. The thrilling performances feature students ages 8-18. Don’t miss the country’s oldest running youth circus as they delight audiences of all ages.

Holiday Nights at the Ca’ d’Zan

Situated on the same property as the Ringling Museum, Holiday Nights at the Ca’ d’Zan is free with museum admission. Festive fireplace mantels, decorative doors and a brilliantly lit 10 ft tree give the mansion a holiday make-over that will fill visitors with the holiday spirit.

holidaynightsPhoto Credit: The Ringling

21st Annual Sarasota Holiday Parade

The parade is one of Sarasota’s most anticipated events and will be held on Saturday, December 3rd. Illuminated floats, marching bands, musical performances and the arrival of Santa Claus are just a few of of the highlights as the parade moves down Main Street in front of a cheering crowd. One of the largest and best known holiday parades along the Sun Coast.

Holiday Night of Lights on St. Armand’s Circle

Now in its 38th year, the Holiday Night of Lights on St. Armand’s Circle is a holiday tradition. The festivities includes caroling, photo opportunities with Santa, musical performances and a tree-lighting ceremony. The event takes place on December 2nd from 5:30 pm to 9 pm.

Pineapple Drop

The Pineapple Drop is a Sarasota New Year’s Eve tradition, signifying the tail-end of the holiday season and the prospects of a new year. If you’ll be staying at the Inn On Siesta Key on December 31st, ring in 2017 with us in downtown Sarasota. It’s a great way to celebrate New Year’s Eve.

Photo Credit:

This holiday season is jam packed with festive events. Sarasota has plenty to do and see this holiday season. We hope that you will celebrate the holidays with us this year. Happy holidays from your friends at the Inn on Siesta Key!



November Activities

November is a time of tradition. If you’re staying with us this November, you have the opportunity to experience some of Sarasota’s favorite traditions. The annual Sarasota Medieval Fair and Siesta Key Sand Sculpting Festival are two well-attended events that occur in November each year.

Sarasota Medieval Fair

The Sarasota Medieval Fair takes place this year on November 5th-6th, 12th-13th, and 19th-20th, 2016 and is open from 10am-5:30pm. There will be activities for all ages at the fair. Every weekend has a different set of events. Live music, acting and comedic performances, aerial shows, the artisan marketplace and jousting are just a few things to look forward to this November. Tickets are available online. 

Photo Credit: Sarasota Medieval Fair

Photo Credit: Sarasota Medieval Fair

Siesta Key Sand Sculpting Festival

The Siesta Key Crystal Classic International Sand Sculpting Festival will be held this year from November 11th-15th, 2016. Professional sculptors, residents and visitors come to Sarasota each year in order to participate in this event. The sculptors turn Siesta Beach into an art gallery. Visitors are welcome to watch the sculpture building process on Friday and Saturday. The competition section of this event ends Sunday at noon, but the sculptures will remain open for viewing through Tuesday, the 15th. 

1st place Sculpture 2015
Photo Credit: Siesta Key Crystal Classic International Sand Sculpting Festival
Photo Credit: Siesta Key Crystal Classic International Sand Sculpting Festival

Events like the Sarasota Medieval Fair and the Siesta Key Sand Sculpting Festival are great opportunities to experience some of the energy and culture of Sarasota, Florida. We hope that you’ll take advantage of these events during your stay with us this November.

October Activities

There are plenty of activities to keep you busy here in Sarasota this October. Whether you’re looking for a family fun afternoon, want to explore German culture or just want to be spooked, our city has an abundance of activities for your stay. October in Sarasota is anything but uneventful. Check out some of these fun events this fall:

Pumpkin Festivals

The Sarasota Pumpkin Festival and Fruitville Grove Pumpkin Festival are two popular annual pumpkin festivals in Sarasota. 

The 8th annual Sarasota Pumpkin Festival takes place this year October 28th, 29th and 30th, 2016. The festival is open from 12pm – 10pm on Friday and Saturday and 12pm – 8pm on Sunday at the Premier Sports Campus in Lakewood Ranch. There will be performances, a pumpkin patch, maze, pie eating contests, an amusement area with rides, games, petting zoo, pony rides, food and drink stands, live bands and more. Information on ticket pricing is available online.

The Fruitville Grove Pumpkin Festival will be having their 28th annual family-friendly event this year. The festival will take place every weekend in October. There will be hayrides, festival food, BBQ, kettle corn, pie, live music, moon bounce, face painting, pumpkin painting, rock wall and a bungee jump.


Celebrate German culture and taste some German craft beer with Sarasota’s Oktoberfests. Here are a few options for events to attend:

WOBtoberfest- This is World of Beer’s biggest annual event of the year. The event will include craft beer, German food and live music. There will be an AC/DC tribute band at “WOBtoberfest Day 1 w/ Highway to Hell” and there will be a Pearl Jam tribute band at “WOBtoberfest Day 2 w/ Pearl Jamz”. This two-day event will take place on October 21st at 4pm and October 22nd, 2016 in Bradenton at 3pm.

Sip the Sunshine Craft Beer Festival- This festival will take place on Saturday October 29th, 2016 starting at 12pm for VIP ticket holders and 1pm for regular ticket holders and lasts until 9pm. Tickets range from $35-$100 and are available online. The event exclusively features Florida craft breweries and a concert event at Sundown Session, where food and drinks will be available.

Spooky Activities

Haunted Trails at Oscar Scherer Park- This year will be the 4th Annual Haunted Trails at Oscar Scherer Park. This family-friendly event takes place on Friday October 21st and Saturday October 22nd, 2016 from 8-10pm. There is a scary haunted trail for those looking to be spooked and a not-so-scary trail for those who don’t want to be scared. There will also be kids activities, costume contests and more. Tickets are available online.

Boofest on Main Street at Lakewood Ranch- Boofest will take place on Friday October 28th, 2016 from 6pm to 9pm. The event is free and open to the public. This year’s Boofest will be Wizard of Oz themed to celebrate the 10th anniversary of the event. There will be plenty of activities this year to enjoy: haunted trolley rides with ghost stories, costume contest, trick-or-treating, inflatable dark maze, haunted trail, kids play zone, live DJ, merchant window painting contest, wandering Wizard of Oz characters, photo booth, balloon artist and face painting.

Year-Round Events

Throughout the year there are many recurring events in Sarasota that feature live music, food and culture of the area. If you’re looking for something to do for an evening, Sarasota has several options for you to choose from:

Ringling Underground

The Ringling Museum hosts Ringling Underground on select nights throughout the year. Band schedules are announced on their website. There will be a mix of local and regional live music and art in the courtyard from 8 pm to 11 pm. Some of the upcoming dates are: September 1st, October 6th, November 3rd, 2016, February 2nd, March 2nd and April 6th, 2017.

Music on Main Lakewood Ranch

Music on Main is a free concert series and block party hosted on the first Friday of every month. This event takes place on Main Street on Lakewood Ranch from 6 pm to 9 pm. There will be food vendors, beer trucks, sponsor booths and kid-friendly rides and activities.

Live from Downtown its Friday Nights

Live from Downtown occurs every Friday night in downtown Sarasota from 6 pm to 9 pm. There will be live street performances: live music, dancing and more. Many businesses will be open extended hours so visitors can continue shopping during the event. Admission is free.

Art Walks on Palm Avenue

Art Walks on Palm Avenue happen every first Friday of the month from 6 pm to 9 pm. Local galleries will be open for the public to admire and talk with the artists. There will also be dining, antiques, specialty shops, refreshments and live performances.

Places to Eat – in Siesta Key and the Surrounding Sarasota Area

Entrepreneurs from all over the nation and the world come to Sarasota and open up their restaurants. Consequently, there is a lot of variety in restaurant options in the Siesta Key/Sarasota area. From breakfast and brunch, lunch, and dinner to international food, coffee shops and snack options; this area offers many wonderful choices for places to eat. Here are just a few alternatives for you to choose from:


Sun Garden Cafe* – known for its great atmosphere, tasty food and kind staff

Another Broken Egg Cafe* – food that is as delicious as it is photogenic

Toasted Mango Cafe* – great breakfast spot—wonderful food and service


Corkscrew Deli – one of the top delis in the area, known for the “Best Cuban” in Sarasota

3.14 Pi Craft Beer and Spirit* – amazing pizza served in a unique and laid-back atmosphere

Siesta Key Oyster Bar* – if you’re in the mood for fresh seafood—this is the place to go

Pride of the South BBQ – incredible 5 star barbecue experience

Nutritious You* – a great vegan/gluten-free restaurant


Big Water Fish Market* – BYOB style seafood market with a nice selection

Clayton’s Siesta Grille* – fantastic restaurant for dinner with lots of options

Flavio’s Brick Oven Pizza and Bar*- a nice Italian restaurant with gluten-free options

The Cottage* – fresh ingredients, tasty drinks, and great ambiance

International Food

Isan Thai Restaurant – a great Thai restaurant, a short drive from Siesta Key

PHO 101 Noodle House – really good Vietnamese food, also serves taro boba tea

A Taste of Germany* – amazing German breakfast/brunch restaurant located on Siesta

Opa Opa – an authentic Greek restaurant less than a ten minute drive from Siesta

El Toro Bravo – serves some of the best Mexican food in town


Lelu Coffee Lounge* – in addition to their coffee, expresso, and pastries, Lelu also serves breakfast and lunch

Simon’s Coffee House – serves breakfast and lunch, teas, juices, and coffee options

The Local Bean* – great locally run coffee shop with locally roasted beans, homemade syrups, organic milks and gluten-free treats

The Clever Cup Coffee Shop – enjoy some coffee, hot chocolate, pastries or pie at this cozy shop


Meaney’s Mini Donuts* – fresh, hot, delicious mini donuts and coffee

SubZero Ice Cream and Yogurt* – customize your order and watch as they freeze it in liquid nitrogen

Tropical Shores Popcorn – includes at least 40 different popcorn flavors for you to choose from

Boardwalk Eats and Sweets* – if you’re craving hot dogs or some fried food—this is the place to go


Siesta Key Farmer’s Market* – open Sunday 8am – 1pm, includes live music, a great way to see local art and businesses selling their products

*- the restaurant/shop is located on Siesta Key (others not marked are a quick drive from Siesta Key)

Whatever your food preference, there are plenty options to choose from! From art and activities to tradition, culture and food, Sarasota has so much to offer. Your stay on Siesta Key will be full with all kinds of wonderful experiences. Let us know where in Sarasota or Siesta Key you enjoy eating at the most!

10 Things to Do for 20 to 30 Somethings: On (and Around) Siesta Key

So, you’re anticipating your stay in sunny Sarasota. You’re probably very excited about starting your vacation; daydreaming about laying on the beach. But, hey, what else is there to do here? (Understandably) You may not have done much research yet besides googling pictures of Siesta Key’s beautiful white sands and blue waters. And now that you’ve secured your vacation lodgings right on the beach, you’re wondering, “What other activities are there to do on Siesta Key?”. Luckily, we’ve put together a list for you. Here are ten ideas for things to do on (and around) Siesta Key as a twenty to thirty-something.

1. Make a Sports Rental

Bikes, boats, kayaks, paddle boards, parasailing, jet-skis, snorkeling…it’s all here. Explore Siesta Key on something other than your own two feet. Whether you prefer your transportation to be land, sea or air, this is a great way to take in the scenery.

Siesta Key Bike & Kayak is family owned and operated and serves Siesta Key and surrounding areas, offering a multitude of products and services including: bike, kayak, paddle boards, scooters, scooter car rentals and eco-tours.

Siesta Key Watersports has been in business for 24 years with a perfect safety record. Their services include: parasailing, jet ski rentals, boat rentals, fishing, dolphin watches and sightseeing cruises.

The Califlorida Surf and Skate Shop has great prices for paddle board, surf board, skim board, body board, longboard and skateboard rentals as well as bike rentals, kayak tours and beach chair and umbrella rentals.

2. Visit St. Armand’s Circle

Take a walk around the circle. Located on Lido Key, St. Armand’s Circle is must-see. Have some seafood and a drink at the Daiquiri Deck. For dessert try some ice cream at Big Olaf’s, and then shop a little…

3. Go Horseback Riding On the Beach

Make an appointment with a local horseback riding company for a one-of-a-kind equestrian experience.

4. Grab Brunch

Who doesn’t like brunch? These restaurants on the Key are known for their fantastic brunches:

Toasted Mango Cafe 

Village Cafe 

Sun Garden Cafe 

Another Broken Egg Cafe

5. Go Wine Tasting

Siesta Key Tropical Wines offers a wide selection of wines to try. The staff are very knowledgable and friendly, guaranteeing a fun and educational experience to end the day.

6. Join the Drum Circle

The drum circle begins every Sunday around sunset and often lasts until the early morning. This Sunday night activity is a great way to tap into your adventurous side. Spend the evening on the beach listening to the beat of the drums, and join in and dance.

7. Take a Beach Yoga Class

Looking for a calming way to start off your day? Siesta Beach offers free beach yoga this summer on Monday, Wednesday, Friday and Saturday mornings from 8:00-9:30 am, just behind the green lifeguard stand.

8. Check Out Siesta Key’s Nightlife

Once the sun sets it’s time to head to Gilligan’s Island Bar & Grill or The Beach Club on Siesta Key. Enjoy some live music and maybe even grab a drink or two.

9. Visit the “Other Two Beaches”

There’s more than one beach on Siesta Key. While Siesta Beach is most famous for its beautiful sand, Turtle Beach and Crescent Beach are two more wonderful beaches in the area; so you should check them out too! Crescent Beach actually shares the same sand as Siesta Beach but with a more relaxed environment. Turtle Beach’s sand is slightly coarser, but still beautiful, and has boating launch access. Generally less crowded, these beaches are great spots to spend a day lounging about.

10. Visit the John and Mable Ringling Museum of Art

While 20 minutes from the heart of Siesta Key, it’s definitely worth the drive. If you’re at all interested in art or history I would highly recommend visiting. The John and Mable Ringling Museum of Art is the state museum of Florida. The Ringling Estate is home to the Cà d’Zan (which overlooks the water), Rose Garden, Circus Museum, Ringling Art Library, “The Wisconsin” and Secret Garden. Every Monday the John and Mable Museum of Art and its special exhibits are free to the public. The exhibits are wonderful and the estate is beautiful; truly an enriching way to spend the day.

*Bonus: The Annual Siesta Key Crystal Classic Sand Sculpting Festival

This year the event takes place on November 11- November 15, 2016. If you’re staying on Siesta Key during these dates you can watch the creation of the sand artwork and maybe create some sand art of your own.
Check out the website for more information:

If you have any additional questions or would like more recommendations for things to do on Siesta Key, please do not hesitate to contact us! Whether you’ve booked your vacation for this summer or later in the season, we’re excited to have you stay with us. And of course, let us know during your visit what activities you end up doing!