Dream vacations can come true, you just have to make a little effort. Choosing the right destination (you chose Sarasota, so you can check that off your list!) the right vacation home (again, Rent the Keys was the perfect choice!), and the right activities! (It’s Florida, summer, and you are at the beach; there’s no way to mess that up!) And because Sarasota offers more than the best-tasting seafood you have ever enjoyed and white sand beaches you will never want to leave, we have done a little research and created this list of the top summer events of 2023, knowing that no matter how wonderful your vacation is destined to be, it can always be enhanced! And as you go about your summer days, having fun and relaxing under the Sarasota sun, knowing that you get to come home to our beautiful summer sanctuaries every evening will be the cherry on top of the most delicious vacation sundae ever! 

Sarasota Music Festival, June 16th, Sarasota Opera House, 61 N Pineapple Avenue 

By the time you read this, June 2023 will be over but we want you to know that you have something to look forward to for your 2024 summer visit! The classical music and beach vacations do go hand in hand and this year (next year is sure to be as wonderful!) the musical “subject” will be Appalachian Spring, celebrating the stylings of Mozart, Copland, and Brahms. Lasting 2 hours and offering ticket prices that start at $29 (topping out at $50) this sweet evening of music and class will be remembered fondly for years to come! 

Waves and Wheels Kickoff Party and Fun Run, June 30-July 1, Joyland Live Music Venue 

This fun event is also a benefit for Suncoast Charities for Children so you can combine a great party with a good deed, simply by purchasing tickets! The Kickoff Party for Waves and Wheels begins at 5 PM on the 30th, and provides food, beverages, casino games, and, of course, live music! The fun run is held the next day and if you aren’t into running unless something or someone is chasing you (especially on vacation!) this run is for cars, motorcycles, or boats! Strap yourself in, put on your helmets, and garner your points at each stop along the route! Ticket costs range between $25 to $125 so this worthy event will fit into every traveler’s budget!

Stars, Stripes, and Rooftop Delights, July 4, 100 Marina View Drive 

Happy Birthday to America! 4th of July is our favorite holiday and this rooftop event brings visitors even closer to the best part of the holiday, the fireworks extravaganza! Taking place on the rooftop of the Sarasota Westin (the tallest building in town), there will be a DJ hosting a dance party, stunning views of our beautiful hometown, a barbecue buffet, and of course, all the red, white, and BOOM you can handle! Tickets range from $30 to $100. 

Annual St. Armand’s Circle Art Festival, August 15 through August 19 

St. Armand’s Circle is known for its high-end shops, restaurants, and galleries and every August it is also known for its annual art festival! Offering art created by local artists, crafts created by local craftsmen and women, and always more than a few opportunities to enjoy a good meal! Spend a few hours of your vacation escape wandering through the aisles, finding gifts and souvenirs that you just won’t find anywhere else. Also offering jewelry, pottery, and other artistic pieces, the circle offers festivals multiple times each year, so if a summer visit isn’t on your agenda, check out their schedule to learn when the next one will be! 

Sarasota Slam Fishing Tournament, August 23 through August 27 

The seas that surround our fair city are loaded with the ultimate trophies, the sea creatures that live under the sea and if you are visiting at the end of summer, it is the perfect time to try out one of our state’s more well-known events, the Sarasota Slam Fishing Tournament. Offering a variety of competitions, including fun fishing and junior divisions, the top prize for the professionals participating is $500,000! Also offering a Saturday evening barbecue and a party that honors all that have participated, this event more than most, represents the best part of Florida life! 

Your Summer Vacation 

When you really think about it, couldn’t your annual family vacation be considered an event? Summer is sweeter when spent in our Rent the Keys Sarasota sanctuaries, designed to make the season, and your vacation, feel even more special! Hold family barbecues in the backyards, binge-watch summer-themed movies on a languidly beautiful summer night and celebrate the joys of a family vacation in comfort and luxury. Reserve your favorite escape today!