Skip to main content

72 Hours in Naples

Kick back in the beachside town of Naples, Florida with this relaxation-filled itinerary for a three-day weekend with the entire family.

The quaint beach town of Naples, Florida calls those wishing for a relaxing retreat away from it all. Forget your watch and tell time by the sun, drifting from the sugar sand beach back to your residence fit with a private pool and plenty of space to kick back in. Revel in family time, wander the quaint streets of boutiques and art galleries, and enjoy everything within a mere five- to ten-minute golf cart ride away. Welcome to paradise.

What To Do


9 a.m. | Start your day at Jane’s Café on 3rd. Their extensive menu serves up breakfast all day, including a long list of breakfast sandwiches to choose from and a variety of egg scramblers. Kick it off with a French toast appetizer—you won’t be disappointed.

11 a.m. | Walk the beach from Naples Pier to Lowdermilk Park, taking in the sights of magnificent homes and mangroves galore, and maybe spot a dolphin or two! Pick a spot on the beach to soak up some sun and play in the gentle waves.

2 p.m. | Refresh yourself after the beach with an acai bowl at The Bowl. Their menu features organic acai and pitaya bowls and smoothies topped with fresh fruits and homemade granola. They even serve up coconut water by popping a straw in a fresh cracked Thai coconut.

4 p.m. | Back at your residence, take a plunge in your private backyard pool to cool off and wash your cares away.

7 p.m. | Take the night to relax and enjoy a meal prepared in your own private vacation home by Member-favorite private Chef Jay Wolfson. Dine on fresh surf and turf options outside on the patio.


10 a.m. | Cruise the warm Gulf waters off of Naples with a full-day yacht charter from Naples Nantucket Yacht Charters. A variety of fully crewed yachts are prepared to cater to your every whim while sailing along the beautiful Florida coastline. It’s a once-in-a-lifetime travel adventure you and your loved ones won’t forget.

5 p.m. | Begin date night out with happy hour drinks at The Bevy, an American eatery serving up happy hour cocktails nightly from 3-4:45 p.m. Their extensive menu of signature drinks features favorites including frosé, a prickly pear margarita, and a cedar fire old fashioned garnished with candied bacon.

7 p.m. | Continue date night with dinner at Campiello, a contemporary Italian restaurant inspired by traditional Tuscan country cooking—think savory meats cooked over an open fire, traditional pizzas baked in a wood-burning oven, and modern interpretations of classic Italian favorites.

Naples Beach
3rd Street South Shopping


9 a.m. | Stroll along the sugar-soft sand just a couple of blocks from your residence and revel in the peace of the beach.

11 a.m. | Continue your relaxing morning with in-residence massages. Choose from Swedish or deep tissue options and let Kris or JJ pamper you for a blissful wellness experience in the comfort of your own luxury vacation residence.

2 p.m. | Stroll and shop along the chic boutiques and art galleries of 3rd Street South. This historic street is brimming with clothing selections for both women and men, home and garden décor, jewelry shops and art galleries to peruse to your heart’s content. Enjoy the courtyards, colorful landscaping, and fountains along this quaint area.

6 p.m. | Cheers to a weekend well-lived! Dine while enjoying live music at Tommy Bahama. With menu selections for the entire family, nobody will leave disappointed. Start off with ahi tuna tacos and finish with their famous piña colada cake. Don’t forget to order the coconut shrimp, a classic favorite.

Where To Stay

Beach lovers will adore our luxury vacation residences in Naples, Florida. All are no more than seven blocks from the beach within Old Naples, which has plenty to see and do. Shop or dine nearby on 5th Avenue South, which features hotspots such as Hob Nob, Pazzo!, and Bistro 821, or visit the chic boutiques and art galleries on 3rd Street South. The Naples Pier, yacht club, and marina provide access to water adventures just minutes away. It’s popular to rent street-legal golf carts to navigate this little beach community; your Concierge can arrange this at your request. Everything in Old Naples is within a five- to ten-minute drive.