Well, it’s official. You survived another holiday season without totally going insane, and even if it was close, now that you have crossed the bridge from 2023 to 2024, it is time to start planning a vacation that will kick off the new year the right way, perhaps with a getaway to the white sand beaches of Siesta Key. If your early winter journey has you visiting our island paradise and staying in our Rent Siesta Key escapes, this guide to doing it right will help you make the happiest of memories during your 2024 in Siesta Key!

Sunrise, Sunset

Mother Nature has perfected at least two things over the millennia, and here in Florida, those two items are, of course, the sunrise and the sunset. If your visit lasts through an entire weekend, we invite you to explore the Sunday evening Siesta Key Drum Circle, celebrating the beauty of a Siesta Key sunset with music, companionship, and love. We’ve talked about the Drum Circle many times over the years, so we won’t go into much detail other than to say it starts about an hour before sunset, and it is an experience you will never forget. The sunrise, however, is one of those things that while equally worthy, may take a little more convincing due to the early hour, but we have just one thing to say about that: Go back to bed after the sun has completed its morning journey and dream happy dreams about the fiery colors that took over the sky!

Siesta Key Wine Bar, 5138 Ocean Boulevard Suite C

Believe it or not, the peace you are feeling from leaving the chaos of the holidays behind and waking up every day in the comfort of our Rent Siesta Key seasonal sanctuaries can be enhanced quite easily with a visit to the Siesta Key Wine Bar. Offering wines from all over the world, it is difficult to find a more relaxing, more soul soothing activity than by sitting at the wood tables on a cool winter’s night, (it’s open until 10 every night except Sundays and Wednesdays) sipping silky wines and savoring the company of your favorite traveling partner. Offering wine flights for sampling, the Siesta Key Wine Bar focuses on relaxation. Can you think of anything you need more?

Take a Tour of the Key

The beauty of Siesta Key will never let you down and with the weather in the winter months being so wonderful, enjoying a tour of the Key aboard a Segway will bring a new awareness of all that the area has to offer. Robin Hood Rentals, located at 5255 Ocean Boulevard, is easily found in downtown Siesta Key Village and offers one- and two-hour tours by Segway. Also offering pretty much everything you need to have a great time, including scooters, golf carts, bicycles, kayaks and paddleboards, this one stop shop for fun may bring you your favorite memories of your trip.

Work on Your Tan

With temperatures rarely dropping below 71 degrees in the daytime, a day at the beach may actually be at the top of your itinerary, especially for those who visit from some of our coldest states. In many of our sanctuaries, guests will find all the gear they need to enjoy a day at the beach, including towels, chairs, umbrellas, and even a cooler that just needs to be stocked with your favorite food and drink. Choose the beach you want to visit, (There are three on Siesta Key: Siesta, Crescent, and Turtle) pack your gear and spoil yourself with a day of sun, surf, and white sand.

Sarasota Seafood & Music Festival, January 26-28, JD Hamel Park in Sarasota

Siesta Key isn’t all that large, just over three square miles in size, but that’s ok; it only makes it easier to explore the towns located just off the key. Sarasota, for example, is home to one of our favorite and most delicious festivals, the Sarasota Seafood & Music Festival, taking place the last weekend of the month. Your kick off to 2024 doesn’t have to start at the final strike of the clock at midnight, and if you wait until the end of January to make your journey, you will experience the sweetest seafood, hottest music, and a chance to explore the talents of local artists and crafts people who will be displaying their work for your purchasing pleasure!

Spoil Yourself at Home

After the chaos of the holidays, you may find that your favorite moments on Siesta Key are the ones spent at home, enjoying the luxury amenities and quiet relaxation that come standard in our seasonal sanctuaries. Binge watch your favorite streaming shows on Smart TVs, enjoy a cozy meal prepared in our fully equipped kitchens and devoured in our dining rooms, and experience deep sleep and happy dreams in cloud soft beds anchoring our tranquil bedrooms.

Reserve your favorite escape today and feel pampered, spoiled, and completely at home during your time on Siesta Key!