A Romantic 3-Day Weekend in Naples, Florida

Afternoon: Arrival & check-in

Arrive in Naples, check into your hotel or rental, and take a moment to settle in. Kick off your shoes and shift into vacation mode.

Late Afternoon: Stroll on Fifth Avenue South

Begin your exploration with a leisurely walk down iconic Fifth Avenue South. This is the heart of Naples, lined with beautiful architecture, upscale boutiques, art galleries, and enchanting courtyards. It’s the perfect place to hold hands, window shop, and soak in the city’s elegant atmosphere.

Evening: Sunset at the Naples Pier

A short walk or drive from Fifth Avenue will take you to the historic Naples Pier. This is a quintessential Naples experience. Stroll to the end of the pier, watch the pelicans, and look for dolphins playing in the surf. Find a spot on the sand to witness a breathtaking sunset over the Gulf of Mexico, an unforgettable and romantic start to your weekend.

Dinner: Downtown dining

Head back toward Fifth Avenue area for dinner. For a classic and romantic setting, consider The French Brasserie Rustique, offering authentic Parisian ambiance and cuisine. Alternatively, Osteria Tulia serves rustic Italian fare in a beautifully designed, lively setting.

Morning: Keewaydin Island shelling cruise

Begin your day on the water with a beach and shelling tour aboard the Sweet Liberty, a 53-foot sailing catamaran. This delightful cruise will take you through the gorgeous waterfront homes of Port Royal before heading out to the Gulf. The destination is Keewaydin Island, a pristine barrier island accessible only by boat, famous for its incredible shelling and natural beauty. You’ll have time to walk the secluded beach, collect unique shells, and take a dip in the turquoise water.

Lunch: Toes-in-the-sand lunch

After the gardens, drive to Vanderbilt Beach and treat yourselves to a memorable lunch at The Turtle Club. This beloved restaurant offers exquisite dining directly on the sand. There’s nothing quite like enjoying fresh seafood with your feet in the sand and the sound of the waves just steps away. Be sure to make a reservation well in advance.

Afternoon: Beach relaxation or art exploration

You have two great options for the afternoon. You can either find a spot to relax on the soft white sands of Vanderbilt Beach, or for a dose of culture, visit The Baker Museum at Artis—Naples, which features a diverse collection of modern and contemporary art.

Evening: Sunset dinner cruise

For a truly magical evening, embark on a sunset dinner cruise aboard the Naples Princess. Boarding from the Port-O-Call Marina, this cruise will take you through Naples Bay, past the luxurious mansions of Port Royal, and out into the Gulf of Mexico. Enjoy a delicious buffet dinner and cocktails from the bar as you watch the sky erupt in color during a spectacular Florida sunset from the best vantage point possible: the water.

Morning: Naples Trolley Tour

See the best of the city in comfort and style on the Naples Trolley Tour. This hop-on, hop-off tour is a fun and relaxing way to get a comprehensive overview of Naples’ most famous landmarks. You can do a full two-hour loop to hear the narration and history, seeing everything from the upscale shops of Fifth Avenue South to the historic homes of Port Royal, before hopping off near your brunch spot.

Brunch: Brunch at Venetian Bay

For your farewell meal, head to the beautiful Village Shops on Venetian Bay, an upscale, open-air marketplace with stunning waterfront views. Enjoy a fantastic brunch at Bayside Seafood Grill & Bar, a local favorite known for its delicious food and panoramic views of the bay. Afterward, take a few minutes to stroll through the Mediterranean-inspired village and browse the lovely boutiques.

Afternoon: One last walk

If time allows before your departure, take one final walk on the beach. Lowdermilk Park is an excellent option, with easy access, beautiful sand, and facilities. It’s the perfect way to say goodbye to the Gulf Coast before heading home, feeling relaxed and reconnected.