The Best Snowbird Hotel in Naples—Compass by Margaritaville

Winter Guide for Snowbirds: Compass Hotel Naples

Fall and early winter bring a sunshine-fueled migration to Naples, Florida, where snowbirds swap parkas for pool towels and enjoy months of warmth and endless relaxation. At Compass Hotel Naples, this season is all about enjoying life like a local: soaking up the best events, exploring vibrant neighborhoods, and unwinding in the heart of paradise. 

Below is a curated calendar of festivals and signature happenings to make the most of your stay, plus the top reasons Compass Hotel Naples is the ultimate home base for snowbirds ready to turn vacation into lifestyle. 

October: Festivals, Film & Fast Cars 

• Halloween Spooktacular on 5th Avenue South (October 25): Enjoy a lively evening filled with musical performances, festive dining, boutique shopping, and entertainment along one of Naples’ most iconic streets. 
• Naples International Film Festival (October 23–26): Hosted by Artis—Naples, this acclaimed festival features independent films, Q&As with filmmakers, and a glamorous opening night gala. 
• 15th Annual Stone Crab Festival (October 24–26): A true Naples tradition, the Stone Crab Festival at Tin City and the Naples Waterfront serves up fresh seafood, live music, boat tours, and waterfront views. 

November–December: Holiday Magic & Cultural Charm 

• Third Street South Farmers Market (Mid-November – April): From fresh produce and seafood to baked goods, flowers, and artisanal treats, this bustling market is a favorite for snowbirds and residents alike. 
• Cars & Coffee 239 at Mercato (November 16 & December 21): Kick off the season with a laid-back Sunday morning featuring luxury and classic cars, community vendors, and, of course, plenty of coffee. 
• Johnsonville Night Lights in the Garden (November 28 – January 4): Experience the Naples Botanical Garden transformed into a tropical winter wonderland with thousands of lights, festive photo ops, live music, and holiday treats. 
• Christmas Walk & Tree Lighting on 5th Avenue South (December 5): Celebrate the season with sparkling lights, faux snow, live carolers, and extended shopping and dining hours along Naples’ most festive street.  
• Trees & Teas Festival at The Naples Players (Nov 18 – Dec 21): Stroll through a festive wonderland of artist-decorated trees and indulge in holiday teas and treats, a favorite tradition for all ages. 
• “Little Women: The Musical” at The Naples Players (Nov 19–Dec 21): for Broadway-style holiday entertainment. 
• Christmas Club Popup Bar (Late November – Early January): Naples’ original holiday bar offers themed cocktails, daily food specials, and photo-worthy decorations; no tickets required, just pure holiday fun. 

Local Fall Favorites for Snowbirds 

• Fall kayaking and paddleboard eco-tours, spot manatees or dolphins along the Gordon River Greenway or in the Ten Thousand Islands. 
• Explore Corkscrew Swamp Sanctuary, hikes among ancient cypress, rare birdlife, and serene trails are prime for cool weather exploring. 
• Fall food and wine tastings at top Naple's restaurants, look for pairing dinners and events at standout spots like The French and Bleu Provence. 

Why Compass Hotel Naples Is the Ultimate Snowbird HQ 

1. Central, Intimate Boutique Charm 

Compass Hotel Naples is an intimate, all-suite boutique that channels Margaritaville's laid-back vibe. Studio, one-bedroom, and two-bedroom suites provide comfortable sanctuaries, complete with plush bedding, custom-designed furnishings, separate living areas, and fully equipped kitchenettes. The setting feels both fresh and familiar, with just-right amenities, pet-friendly accommodations, and pristine housekeeping that keeps relaxation on the agenda from check-in to check-out. 

This prime Naples location surrounds guests with authentic energy, dozens of top-rated restaurants, chic boutiques, and trendy art galleries. From Compass Hotel Naples, iconic spots like Clam Pass Beach, 5th Avenue South, Mercato, and farmers markets are just a quick 10-minute drive or Uber away. Fishermen, foodies and shoppers will all find it easy to plan the perfect day out, with the Compass staff always ready to recommend local favorites and insider spots. 

2. Backyard Relaxing & Culinary Offerings 

Whether savoring a tasty breakfast, sipping poolside cocktails, or grooving to town musicians, the backyard oasis at Compass Hotel Naples rivals any local hotspot.   

Fuel up each morning with the Sunrise at Compass complimentary breakfast, an elevated spread of hot and cold classics, fresh fruit, neighborhood pastries, and rotating chef specialties. This hearty start ensures energy for every adventure. 

The Welcome Cabana in the lobby offers complimentary refreshments all day. Enjoy fruit-infused water, premium coffee, and an array of light snacks and desserts like fresh baked cookies and tropical bites.  

Dining and drinks take center stage at the 5 o’Clock Somewhere Bar & Grill. This lively, island-inspired spot features a full menu of coastal favorites: shrimp tacos, gourmet burgers, and fresh local seafood, plus signature margaritas, crafted cocktails, and frozen concoctions.  

Live entertainment is woven into the Compass experience, transforming The Backyard into one of Naples’ go-to gathering places for guests and locals alike. Nightly entertainment brings in community acts and acoustic sets, creating a soundtrack that gives equal parts vacation and paradise. The result is a space that offers every guest the full flavor of Naples and endless Happy Hours.  

3. Personalized, Heartfelt Service 

Compass Hotel Naples is your home away from home for long stays, family vacations, and couples’ retreats, with personalized service and a seamless experience. Travelers rave about the hotel’s attentive service, from smooth check-in and check-out and quick front desk assistance to poolside conversations with the servers and bartenders. 

Start Dreaming of Your Sun-Kissed Escape 

Experience the best of Florida’s Paradise Coast this snowbird season with a fall or winter escape to Compass Hotel by Margaritaville Naples, where warm weather, Gulf Coast sunsets, and spacious all-suite accommodations meet easy access to Naples’ top winter events and attractions. 

Booking direct at Compass Hotel Naples guarantees value, exclusive offers, and access to one of the friendliest intimate accommodations along Florida’s west coast. So, share this snowbird guide with your travel crew and start planning your Naples escape - adventure awaits.