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Plan a Winter Journey to Siesta Key

HomeJourneys to Siesta KeyPlan a Winter Journey to Siesta Key

There’s nothing more exciting or refreshing than knowing you have time set aside to enjoy a well-deserved getaway. Even if you only have a few days to spare in the name of fun, a vacation somewhere sunny, scenic, and thrilling can make all the difference. This winter, plan on setting your travel sights on Siesta Key where the sun shines year-round and summer activities are accessible no matter what time you arrive! The following is a three-day itinerary to consider when you can’t wait to pack your bags and head towards the Florida Keys winter adventure you deserve.

Day 1: Beach Hopping and On-The-Water Fun

The first morning of your three-day winter getaway to Siesta Key begins with a filling breakfast enjoyed at Village Café. Found at 5133 Ocean Boulevard, this popular breakfast stop is a great place to fuel up for a day of fun in colorful surroundings enjoying everything from breakfast burritos and pancakes to waffles, smoothies, and French toast. Once you’ve had your fill, head over to iconic Siesta Key Beach! Yes, even in the winter months, the beach is very much an option when you head this way and travelers should take time to enjoy every moment possible. Siesta Key Beach is a beautiful and popular stretch of shoreline that includes access to playground equipment for little ones, a snack bar, picnic areas, and gazebos galore. When you’ve had time to savor the sun and sand, renting a paddleboard and getting out on the water is always a good follow-up idea. It’s a good way to get exercise and also have a unique perspective on the tropical fish that swim in the waters below your feet. Tonight, choose to dine at The Cottage on Avenida Messina where you can enjoy a delightful dinner featuring American favorites and Japanese-inspired fare as well!

Day 2: Take Your Florida Keys Winter Trip Sky High

Day two of your adventure begins with a well-deserved and European-inspired breakfast at Restaurant Bonjour French Café. This quaint and inviting eatery is located on Ocean Boulevard and offers guests a chance to start their day on a sweet or savory note with menu selections like crepes, croissants, sandwiches, and espresso available in abundance! When you’re feeling fueled up and ready to go, Turtle Beach is your first stop of the day. This is another one of Siesta Key’s three main beaches and well-worth checking out when you’re filling your winter escape with time on the sand. Once you’ve had time to admire shorebirds and watch the blue waves roll in, it’s time to take your adventure to a new, sky-high level by booking a parasailing trip this afternoon. There are several local companies to choose from that will help you enjoy a new vantage point on this incredible Siesta Key scenery! When you make your way from sky to ground once more, enjoy dinner at Summer House Steak & Seafood on Avenida Messina. The menu here is robust and features everything from New York Strip to Grouper, both perfectly paired with wine selected from the restaurant’s extensive beverage menu.

Day 3: Sightseeing on the Water

The third and final day of your Siesta Key winter getaway begins with a breakfast at Another Broken Egg Café on Avenida Messina. This casual eatery is a great place for the entire family to dine on omelets, French toast, hash, and beyond! Once you’ve enjoyed the last drop of your coffee, head over to Crescent Beach. This is the third of three beaches Siesta Key hosts and a great place to start your day with some tranquil and scenic time enjoyed on the sand. When you’re ready for the adventure to continue, make your way to the iconic landmark known as Point of Rocks which sits just as the southern end of this stretch of shoreline. You’ll have to walk some stairs to reach the area where you choose to snorkel, go shelling or simply spend some time admiring the many tide pools and marine life that thrive within. The last activity of the day will be a dolphin cruise. Siesta Key is home to a vast number of dolphins and booking your place on a local cruise is a great way to admire them in their natural habitats. Dine at Island House Tap and Grill this evening over a Latin-inspired dish and take time to reminisce about all of your vacation fun in the Florida Keys in winter!

Book Your Siesta Key Getaway Today

There’s no reason to wait when you’re excited to plan a scenic and fun winter getaway to Siesta Key. When you need accommodations to match your journey to Florida Keys in winter, the team at Rent Siesta Key is here to help. We’ll make sure you’re settled into a rental that meets your needs and exceeds expectations too. Reach out today to learn more about our many property options and to begin planning your next adventure. We can’t wait to see you in Siesta Key soon!