The Ultimate Itinerary to Experience Paradise in Every Sense
What makes Naples, Marco Island and the Everglades such an unforgettable destination? It all comes down to what you’ll experience here—and with so much to see, hear, smell, taste, and feel, it’s hard to know exactly where to start. That’s why we’ve put together this ultimate itinerary to enjoy Paradise in Every Sense.
Over three days, you’ll move between Gulf beaches, rooftop cocktails, tropical gardens, waterfront dining, seaplane flights, spa rituals, and some of the most scenic corners of Southwest Florida—all while keeping the focus on the exquisite sensory details that make this destination unlike anywhere else you’ve ever been.
Day 1: Arrival, Cocktails, and Dinner in Naples
Arrive in Naples and Check Into The Escalante
For visitors who love cars—or simply want the feeling of driving something extraordinary for a few days—don’t miss the chance to pick up a luxury vehicle from Cloud 9 Exotics. This family-owned company offers Ferraris, Lamborghinis, McLarens, Bentleys, Rolls-Royces, and other exotic vehicles you can rent for the weekend.
After arriving in Old Naples, check into The Escalante, an 11-bungalow boutique hotel tucked between 5th Avenue South and Third Street South. Spend the afternoon settling into the property beside the courtyard pool, where fountains, tropical greenery, shaded pergolas, and poolside cocktails create a quieter contrast to the busy streets only steps away.
Walk 5th Avenue South and Enjoy Pre-Dinner Drinks at The Vine Room
As evening approaches, make the short walk toward 5th Avenue South, where restaurants, galleries, cocktail lounges, and boutiques stretch several blocks toward the Gulf.
Before dinner, stop into The Vine Room, considered one of the best cocktail lounges in Naples. Hidden behind a vine-covered exterior, this speakeasy-inspired lounge serves cocktails finished with smoke-filled bubbles, ocean foam, treasure chests, and other theatrical details prepared directly at the bar. Don’t forget to make a reservation!
Dinner at Tigress Rooftop Bar
After changing for dinner back at The Escalante (you’ll be a four-minute walk away), head toward Tigress Restaurant & Rooftop Bar inside The Perry Hotel Naples.
Overlooking the Cocohatchee River, this rooftop restaurant blends Cantonese cooking with American influences under Chef Dale Talde. Blue crab fried rice, seafood towers, dry-aged duck, and cocktails arrive beside panoramic waterfront views while boats move through the marina below.
Day 2: Beach, Adventure, and Spa Rituals
Spend the Morning on the Beach
Day two is going to be packed with adventure, so let’s start the morning with a more relaxed experience. The Escalante will directly transport you (via golf cart) to nearby Naples Beach, where chairs, towels, umbrellas, and space beside the Gulf are already waiting.
Fly Above the Ten Thousand Islands
Later that morning, drive toward the Marco Island Airport for a flight with Salt Island Seaplanes.
Passengers board a Cessna 206 amphibious seaplane before lifting directly off the water and flying above Marco Island, Naples, the Gulf, and the Ten Thousand Islands. During the flight, you can see mangrove estuaries, barrier islands, shallow turquoise waters, and winding coastal channels while the pilot points out landmarks such as Cape Romano, White Horse Key, and remote stretches of shoreline accessible only by boat.
Reset at Naples Beach Club, A Four Seasons Resort
After your morning flight, it’s time to feel rested and restored at the newly opened Naples Beach Club, A Four Seasons Resort.
Inside The Sanctuary Spa, guests move through thermal circuits featuring heated whirlpools, cooling therapies, experiential showers, steam rooms, saunas, and quiet lounges overlooking the Gulf.
As sunset approaches, head toward Sunset Bar beside the beach for cocktails, ceviche, coastal tacos, and live music beside the Gulf. Each evening, a conch shell signals sunset while guests gather along the shoreline to watch the sky change color over the water.
Dinner afterward at HB’s continues the waterfront experience with grilled Gulf grouper, tuna carpaccio, seafood towers, and raw bar selections, all served just steps from the sand.
Day 3: Gardens, Art, and a Slower Final Day
Begin the Morning at The Escalante
Your final full day begins back at The Escalante with coffee and breakfast served beside the courtyard pool or on the terrace outside your bungalow. After several days spent moving between beaches, restaurants, and excursions, a quieter start feels especially welcome. You may also want to squeeze in one final morning walk along the beach!
Feel Inspired at The Baker Museum
Late morning, make the short drive to The Baker Museum, Artis—Naples. As the foremost fine art museum in Southwest Florida, this museum features rotating contemporary exhibitions, sculpture installations, and works from its permanent collections. Art this incredible will touch your soul.
Stop and Smell the Flowers at Naples Botanical Garden
Next stop? Naples Botanical Garden. See waterfalls, orchid collections, bamboo groves, flowering trees, and tropical pathways as you move from one section of the garden to another. During select Saturdays from October through June, you won’t want to miss the Music in the Garden performances on The Hoffmann Lawn.
End the Trip with Dinner at Veranda E
Return to The Escalante for a final dinner at Veranda E, the hotel’s private on-property restaurant open only to hotel guests, friends, and members. It’s also the only fine dining restaurant in Naples with its own on-premise sustainable organic garden, which influences the seasonal menus served at breakfast, lunch, and dinner.
After your three days experiencing the best of what Naples, Marco Island and the Everglades has to offer, you should have a clear understanding of why this place can best described as Paradise in Every Sense. We hope you leave feeling refreshed, rejuvenated, and ready to plan your next visit.