Follow Your Compass to Sun, Sand, and Sea: Winter Escapes in Florida

Discover Florida’s Best Winter Getaways at Compass Hotels

When the cool winds start rolling in up north, the Sunshine State is calling. Picture yourself trading snow boots for flip flops, frosty mornings for frozen concoctions, and gray skies for the bright blue horizon of the Sunshine State. Winter here is more than just warm weather, it’s about rediscovering your sunshine state of mind.  

That’s where Compass Hotels by Margaritaville come in: boutique charm, laid-back vibes, and thoughtful amenities that make the perfect home base to live more Floridays. Whether you’re traveling solo, planning a romantic retreat, or organizing a family adventure, you’ll find your slice of paradise at one of our three featured destinations: Anna Maria Sound, Flagler Beach, and Naples. 

Why Florida is the Ultimate Cold-Weather Getaway Escape 

The best time to visit Florida runs from December through March, when the weather is mild, the skies are bright, and the event calendars are packed. Their coastal towns offer more than sun and sand—they come alive with holiday light displays, fresh seafood festivals, local art shows, and one-of-a-kind cultural events that showcase the spirit of each destination.  

From coastal traditions to hidden gems, every stop has its own seasonal flavor. And with pet-friendly accommodations, spacious suites, complimentary Sunrise at Compass breakfast, and welcoming gathering spaces, Compass Hotels make it easy to relax, reconnect, and feel right at home while soaking up the sunshine. 

Compass Hotel Anna Maria Sound: Secluded Serenity on the Gulf Coast 

Tucked at the gateway to Anna Maria Island, Compass Hotel Anna Maria Sound is your ticket to a Gulf Coast holiday escape. With views of the Neal Preserve on one side and a bustling marina on the other, the setting strikes the perfect balance between secluded serenity and convenient access to coastal fun. 

Wake up with the complimentary Sunrise at Compass breakfast, then spend the day exploring. Kayak through mangroves, stroll Anna Maria’s historic piers, or savor freshly caught seafood at local favorites. Back at the hotel, lounge by the sparkling pool with a drink from Floridays, or watch dolphins play in the marina from your private balcony. 

Why stay here this winter: 

• Boutique-style accommodations with Gulf Coast charm. 
• Easy access to Sarasota, St. Petersburg, and Tampa’s cultural and seasonal events. 
• Pet-friendly rooms so the whole family can come along. 

Compass Hotel Flagler Beach: Charming Coastal Escape 

For those who prefer the Atlantic side, Compass Hotel Flagler Beach delivers laid-back vibes with a dose of small-town charm. Known for its surfer-friendly waves and welcoming community, Flagler Beach is an unspoiled stretch of Florida’s coastline where life moves a little slower. 

Here, spend mornings walking along the beach just steps from the hotel, afternoons exploring local shops and cafes, and evenings unwinding with a cocktail by the outdoor rooftop pool. The surf-town energy makes this a favorite for families, couples, and anyone craving an authentic beach-town experience. 

Why stay here this winter: 

• 100-room boutique property with ocean-inspired décor. 
• Walkable access to Flagler Beach’s sand, shops, and dining. 
• Perfect mix of relaxation and local culture, with holiday festivals and community events nearby. 

Compass Hotel Naples: A Spacious Winter Retreat 

This all-suite property offers the extra space and comfort you need for longer stays, while still embracing Margaritaville’s signature laid-back lifestyle. 

Naples is known for its upscale shopping, cultural experiences, and beautiful Gulf beaches, and Compass Hotel Naples puts you close to it all. Start with a hearty Sunrise at Compass breakfast, then enjoy a round of golf, a stroll along Fifth Avenue South, or a holiday festival at Artis. Evenings are best spent around the hotel’s backyard firepits enjoying live music and a frozen concoction from the lively 5 o’Clock Somewhere Bar & Grill. 

Why stay here this winter: 

• Spacious suites, ideal for snowbirds and families. 
• Access to Naples’ arts, dining, and seasonal events. 
• Poolside relaxation and firepits to keep the evenings cozy. 

Book Your Spot in the Sunshine 

Winter can mean more than cold winds and gray skies. Down South, it’s a season of sunshine, fresh air, and time well spent with the people you love. With three unique destinations, Anna Maria Sound, Flagler Beach, and Naples, Compass Hotels by Margaritaville make it easy to find your perfect seasonal escape. 

🌴 Reset your compass this holiday season and discover sun, sand, and sea at Compass Hotels in Florida. Start planning your getaway today and make memories that last a lifetime.