Tucked along Florida’s southwest coast, Naples is a gem that blends upscale elegance with natural beauty. With its powdery beaches, world-class dining, art galleries, and laid-back charm, this coastal town offers something for beach lovers, foodies, and nature seekers alike. Whether you’re planning a romantic retreat, a solo recharge, or a family-friendly weekend, this 3-day itinerary will help you make the most of your time in sunny Naples, Florida.

See my Naples adventures here: The Honest Passport

Day 1: Arrive, Unwind, and Explore Old Naples

Check-In

Choose a centrally located hotel or resort:

Inn on Fifth – boutique luxury in the heart of downtown
Edgewater Beach Hotel – beachfront with stunning sunset views
Bellasera Resort – Mediterranean-style suites with resort amenities

Afternoon: Stroll & Shop in Old Naples

Head to Fifth Avenue South and Third Street South, where brick sidewalks and lush landscaping line rows of chic boutiques, art galleries, and cafés. Stop for a cold drink or gelato, and soak up the sophisticated, walkable charm of downtown.

Dinner:

Campiello – Tuscan-style cuisine in a romantic courtyard
The Continental – upscale steakhouse with live music and a stunning garden bar

Evening: Naples Pier Sunset

Wrap up the evening with a walk down the historic Naples Pier. Watch pelicans dive for dinner, spot dolphins playing in the surf, and enjoy one of the most breathtaking sunsets in Florida.

Day 2: Beach Bliss & Nature Exploration

☕ Breakfast:

Jane’s Café on 3rd – colorful, cozy, and great for al fresco dining
Blueberry’s Cafe – a local favorite for pancakes and hearty morning fare

🏖️ Morning: Beach Day

Lowdermilk Park – white sands, calm waters, and family-friendly facilities
Delnor-Wiggins Pass State Park – ideal for swimming, snorkeling, and nature walks
Rent chairs or bring your own, and don’t forget sunscreen and a good book!

🛶 Afternoon: Outdoor Adventure

Kayak or paddleboard through mangroves at Rookery Bay Reserve
Or take an eco-cruise to Keewaydin Island, a pristine barrier island accessible only by boat

🍤 Dinner:

The Turtle Club – beachfront dining with fresh seafood and unbeatable sunset views
Sea Salt – sophisticated seafood with a focus on global flavors and local ingredients

Day 3: Culture, Relaxation & a Taste of the Everglades

🎭 Morning: Art & Culture

Visit The Baker Museum at Artis—Naples for modern and contemporary art
Or explore the Naples Botanical Garden, a lush, 170-acre tropical paradise

🍽️ Brunch:

The French – classic Parisian bistro fare with a tropical twist
Ridgway Bar & Grill – beloved brunch spot with garden seating

🐊 Optional Afternoon: Everglades Excursion

Take a short drive east to Everglades City or Big Cypress National Preserve:

Book an airboat tour or swamp buggy ride to see gators, birds, and the wild beauty of the Everglades
Visit the Smallwood Store for a glimpse into Old Florida history

🍷 Final Dinner:

Truluck’s – upscale seafood and steak with a refined atmosphere
Bar Tulia – cozy gastro-pub with creative small plates and craft cocktails

💡 Tips for Visiting Naples:

Best time to visit: November through April (dry season with cooler temps)
Getting around: Rent a bike or use the Naples Trolley for easy sightseeing
Dress code: Casual chic by day, resort elegant by night

🏖️ In Summary

Naples is more than a beach town—it’s a coastal lifestyle experience. Here, mornings begin with seashells and espresso, afternoons bring art walks and mangrove paddles, and evenings end with fresh seafood and golden sunsets. Whether you're in search of relaxation, adventure, or just a beautiful change of scenery, Naples offers it all with a touch of class.

So pack your sandals and a sundress (or linen shirt), and get ready to fall in love with the easy elegance of Naples, Florida.

Naples Florida Itinerary