The nation is divided on when to start the new school year, with some parts waiting until September to ring the first bell and other parts not seeing anything wrong with starting in the middle of August. But all of the nation is united when it comes to celebrating what is often considered the last big weekend of the summer, and no matter where you hail from, a Labor Day getaway in Sarasota is destined to offer all the ways to celebrate, relax, and feel pampered and spoiled. And that last part is where we at RentTheKeys come into the picture, offering the homes you can’t live without and ensuring that this vacation will be one that helps you get into the swing of things during the crazy school year that is about to begin.

The 76th Annual Labor Day Regatta, September 1 & 2

Sailing regattas may seem a little foreign to those who don’t live near the sea, but for us, they can be an integral part of our everyday life with the 76th Annual Labor Day Regatta being one of our favorite events. You don’t have to be a sailor to enjoy this event sponsored by the Sarasota Sailing Squadron, just being able to watch the graceful vessels skimming across the waters is enough for most people, but if you DO sail and you think you might be interested, we encourage you to check it out. Hundreds of sailors from all over the nation participate in this event that takes place at City Island (1717 Ken Thompson Parkway) and is absolutely free for spectators.

Florida Highwaymen, Selby Gardens, 1534 Mound Street, September 1-15

The Florida Highwaymen were a group that consisted of 26 black artists that specialized in painting Florida land and seascapes starting in the 1950s, and due to the subject matter, it is only fitting that Selby Gardens is offering this exhibition of some of the best of their work. The artists were mostly self-taught and the environment in the nation in the 1950s and 60s kept them from being able to show in local galleries, which meant that most men sold their works from the trunks of their cars. Filled with color and that unique Florida vibe, the Florida Highwaymen artwork is a true complement to the gardens that are always on display.

Venice Craft Festival, September 1, Downtown Venice with Free Parking Offered at Miami Avenue West

The island town of Venice, Florida is located just under 20 miles south of our Sarasota hometown and is home to the Venice Craft Festival. Featuring the works of local artists who work in a variety of genres, including ceramics, jewelry, and stained glass in addition to paint and photography, this wonderful event opens at 10 AM and closes at 4 PM. Offering a  great chance to find some exciting souvenirs, you may want to stay for the entire day, taking some time to check out Caspersen Beach, a beach that has made Venice known as the Shark’s Tooth Capital of the World!”

Savoring a Taste Tour of Sarasota

The best vacations are often remembered not just for the sites visited or the comforts experienced, but also for the foods we devoured during our explorations of the area and Sarasota is also known as a foodie’s paradise. Starting out your day right inside the doors of a brightly painted yellow cottage known as the Breakfast House, located at 1817 Fruitville Road, taking a break from a beautiful beach morning to explore the cuisine at 1592/Wood Fired Kitchen & Cocktails for lunch (1592 Main Street). At dinner, your choices are plentiful in this town where white sand beaches compete for attention with local restaurants, but if we had to choose just one, we would absolutely recommend Indigenous. Located at 239 S Links Avenue, Indigenous is an all-American restaurant serving foods that are, well, indigenous to the area, and although their menu changes regularly (often on a daily basis) we can’t praise their quality, taste, and creativity highly enough.

Relaxing with RentTheKeys

The school year, whether it is just about to begin or has already been in session for a few weeks, is always hectic, crazy, and overscheduled, so why not take this last getaway of the summer to relax and rejoice in the comforts found in our RentTheKeys vacation sanctuaries? Swimming in private pools located in screened-in lanais, playing pool in air-conditioned game rooms, gathering with the family on the comfiest couches in the state watching summer movies on state of the art televisions (Hey 80s movies fans, Eddie Murphy is back in a new Beverly Hills Cop movie and it offers all the magic the first 3 provided all of those years ago) and watching the sunset from cushioned chairs that overlook the sea. All of these experiences will help you relax and prepare for the next 8 months of fun. Contact us and reserve your favorite escape today!