Downtown Naples: Where to Sip, Snack, and Unwind
Downtown Naples isn’t just about boutiques, art galleries, and sunsets — it’s also home to some of the best happy hour spots in Southwest Florida. Whether you’re winding down after work, meeting friends, or enjoying a seasonal getaway, these spots offer great drinks, bites, and a lively atmosphere.
Here are some of the top happy hour destinations in downtown Naples:
Sunset Bar at the Four Seasons (NEW) – Sophisticated Cocktails with a View
The Sunset Bar at the Four Seasons is a must-visit for those seeking a chic, elevated experience. Enjoy expertly crafted cocktails while taking in the stunning views of the Gulf of Mexico. Their curated wine and champagne selections make it perfect for a special evening or sunset toast.
Highlights: Upscale atmosphere, craft cocktails, scenic outdoor seating
Tommy Bahama – Island Vibes & Tropical Drinks
For a laid-back, island-inspired time, Tommy Bahama hits the spot. Sip tropical cocktails like their signature coconut cloud martini while enjoying small bites in a relaxed setting. It’s casual, fun, and quintessentially Naples.
Highlights: Tropical cocktails, casual outdoor seating, island-inspired menu
Sails Restaurant – Upscale Coastal Dining & Drinks
Known for its quality seafood, live music, and elegant coastal ambiance, Sails is always a good choice for a chic night out with friends or a date night. Enjoy fresh oysters, artisanal cocktails, and specialty wine at their iconic marble bar.
Highlights: Fresh seafood bites, refined cocktails, stylish interior
The Continental – Modern Lounge & Classic Cocktails
The Continental is a downtown favorite for those who love expertly crafted cocktails and a modern, vibrant atmosphere. Their menu features caviar, amazing steaks, and small plates, perfect for sharing with friends. When you see the koi pond and overflowing fresh flowers at the entrance, you know you made it.
Highlights: Craft cocktails, modern lounge atmosphere, small plates
Campiello – Italian Flair & Wine Specials
For classic Italian-style with a twist, Campiello delivers. Enjoy a glass of wine under the trees or a craft cocktail with an oven fired pizza, all while soaking in the vibrant downtown Naples energy. Their homemade pasta selections make it easy to turn happy hour into dinner. Try the squid ink pasta!
Highlights: Italian small plates, wine specials, cozy yet lively environment
Insider Tips for Downtown Naples Happy Hour
Outdoor seating: Downtown Naples shines at sunset, so grab a patio table when possible.
Sharing plates: Many offer small bites perfect for sharing with friends.
New spots: Keep an eye out for new bars and rooftop lounges popping up downtown.
