A Local’s Guide to the Best of Naples, Florida

Old Naples: Charm and coastal elegance

Old Naples is the charming, historic heart of Naples, Florida, where timeless coastal elegance meets laid-back Gulf Coast living. My favorite destinations in Old Naples each offer a unique experience that truly embodies the coastal charm of Naples.

Fifth Avenue South

The city’s iconic main street, filled with boutiques, art galleries, cafés, and restaurants. It’s perfect for afternoon shopping and evening cocktails. Be sure to stroll Fifth Avenue in the evening, when it is illuminated by twinkling cafe lights—giving the street a truly magical feel.

Third Street South

A charming, garden-lined district with luxury shops, cafés, and one of the best weekend farmers markets in Florida. Be sure to walk through the historic neighborhoods surrounding Third Street South where you’ll find banyan trees, charming cottages, hidden gardens, and some of the city’s oldest homes. Make a stop to tour Palm Cottage, the oldest surviving house in Naples, where you’ll gain insight into the area’s early history.

Naples Pier & Beach

One of Old Naples’ most beloved landmarks is the historic Naples Pier, where a pristine stretch of white-sand beach provides the perfect setting for beach days, dolphin sightings, and gorgeous sunsets. Unfortunately, Hurricane Ian destroyed the pier and it is currently being rebuilt, with an expected reopening midyear 2027. The beach remains open and is still a highlight not to miss.

Crayton Cove

A waterfront enclave in Old Naples that captures the area’s relaxed, nautical spirit. Nestled along Naples Bay, this picturesque neighborhood is home to colorful art galleries, locally owned boutiques, waterfront restaurants, and the historic City Dock. Stroll the palm-lined streets, watch yachts and fishing boats glide through the harbor, or enjoy fresh seafood with views of the marina. With its laid-back atmosphere and authentic Old Florida character, Crayton Cove offers a quieter, more intimate side of Naples.

Tin City

The historic waterfront district offers a glimpse of Old Florida and serves as a departure point for sightseeing cruises, sunset and dinner cruises, and fishing charters. You’ll feel like you stepped back in time as you explore the unique contrast to the upscale style of Fifth Avenue. Tin City is filled with locally owned boutiques, seafood restaurants, and specialty shops.

A visit to Old Naples isn’t complete without enjoying the area’s parks. Cambier Park is a popular downtown park that features tennis courts, a playground, and band shell. Naples Preserver is just east of Old Naples and is a 9-acre nature preserve with boardwalks that wind through freshwater marshes, mangroves, and coastal habitats. It is a great way to experience some of the wildlife of southwest Florida and is truly a hidden gem that remains quiet and uncrowded.

Nearby, you can also walk or bike the scenic trails and boardwalks at Gordon River Greenway. This is one of the best places in the city for birdwatching and spotting native wildlife as you go through protected wetlands, mangrove forests, and native Florida habitats along the Gordon River. It is a great way for nature lovers to join the locals and escape the beaches and downtown streets.

North Naples: Sun, shopping, and sophisticated living

North Naples offers a more contemporary side of Naples that blends pristine beaches, upscale shopping, and vibrant dining. Stretching along the coast north of Old Naples, this region is known for its stunning waterfront communities, including Vanderbilt Beach and Pelican Bay, where visitors can enjoy soft white sands, breathtaking sunsets, and easy access to some of Naples’ most scenic natural areas.

Grab a beach chair, umbrella, and plenty of water to hit up one of the local beaches. Swim, read, go shelling, and simply enjoy the Gulf views. A few of my favorite beaches in North Naples are:

• Vanderbilt Beach: Perfect if you want a popular and lively beach with easy access to restaurants.

• Clam Pass Beach: Perfect if you want a more secluded beach that is surrounded and protected by mangroves; you’ll ride a complimentary golf cart shuttle over a boardwalk to the beach.

• Delnor-Wiggines Pass State Park: Perfect if you want natural shorelines, excellent shelling, and clear blue waters.

After the beach, Mercato is a vibrant open-air destination that brings together upscale shopping, exceptional dining, and lively entertainment in a stylish, walkable setting. The beautifully designed district features boutique shops, chef-driven restaurants, wine bars, and outdoor spaces that create a welcoming atmosphere from day to night. Bring a chair or blanket, grab dinner or a drink from one of the nearby restaurants, and settle in for an evening of outdoor movies, live music, and coastal community vibes. Mercato is one of Naples’ favorite spots for an evening out for locals and tourists.

Park Shore: Coastal chic

Park Shore is one of Naples’ most scenic and polished waterfront neighborhoods, known for its beautiful Gulf views, elegant homes, and relaxed coastal atmosphere. Located between Old Naples and North Naples, this upscale community features a picturesque shoreline, luxury condominiums, and the charming Venetian Village, a waterfront destination overlooking Venetian Bay. Venetian Village is a great choice for a casual waterfront lunch and afternoon of boutique shopping.

Nearby experiences worth exploring

• Keewaydin Island: Accessible only by boat, Keewaydin Island offers a true escape from the crowds with miles of undeveloped shoreline, excellent shelling, and a chance to see dolphins along the way. You can either book a boat excursion or rent a private boat for a day.

• Rookery Bay: Book a kayak or boat tour through Rookery Bay National Estuarine Research Reserve. This is one of the best ways to experience Southwest Florida’s mangrove ecosystems.

• Naples Botanical Garden: For a relaxing way to spend a morning or afternoon, stroll Naples Botanical Garden. It is a beautifully designed garden featuring plants from around the world, themed landscapes, water features, walking paths, and seasonal exhibits.

• Naples Zoo: Explore the Naples Zoo for a unique wildlife experience surrounded by lush tropical landscapes and historic botanical gardens. Highlights include a guided boat ride through islands where primates and other animals can be observed in naturalistic habitats, giraffe feedings, wildlife presentations, and opportunities to learn about conservation efforts.

• Corkscrew Swamp Sanctuary: An easy-to-walk boardwalk trail that is a 2.25 mile loop that takes you through pine flatwoods, wet prairie, marsh, and the famous bald cypress trees and offers opportunities to see alligators, birds, deer, and more.

• Everglades National Park: Join a tour or do a self-guided drive to Everglades National Park. There are three entrances to the park, but the closest is in Everglades City. Everglades City is a charming Old Florida fishing village that is full of history, fresh stone crab, and a laid-back waterfront vibe. Triad Seafood, and its grouper sandwich, is worth the drive. Walk the boardwalk, take an airboat tour through the Everglades, or a boat excursion to the Ten Thousand Islands for a fun-filled afternoon. You can also make a stop at Fakahatchee Strand Preserve State Park, known as the “Amazon of North America.” This vast preserve is famous for its wildlife, rare orchids, and remote swamp landscapes.

Naples boasts an exceptional restaurant scene, with memorable dining experiences around every corner. But here are a few of my favorites:

• Sails Restaurant: One of Naples’ most elegant dining experiences on Fifth Avenue with exceptional seafood and steaks—I love going here for brunch

• Osteria Tulia: popular Fifth Avenue choice for its elevated yet rustic, classic Italian menu in a warm, intimate setting

• Captain & Krewe: Just off Fifth Avenue, this is a neighborhood seafood market and restaurant with casual dining and great happy hour specials

• The Syren Oyster Bar: A stylish waterfront restaurant on Naples Bay that centers around seafood and creative cocktails—the Dirty Syren and oysters are always a good pick.

• Campiello: Lively, upscale, Italian restaurant on Third Street with a stunning courtyard—my favorite dish is the Tagliatelle Frutti di Mare.

• Bar Tulia: My favorite restaurant in Mercato, featuring a lively, social atmosphere, Italian menu with excellent craft cocktails—their wood-fired pizzas are outstanding.

• Tigress Restaurant & Rooftop Bar: Rooftop setting with spectacular views of the Cocohatchee River, mangroves, and Gulf that features elevated dining with Asian-inspired flavors—making a reservation at sunset is highly recommended.

• Blackbird Modern Asian: Located on Naples Bay, this modern restaurant provides a bold and contemporary take on Asian cuisine, blending traditional flavors with modern techniques and dramatic presentation - great shareable plates, including the smoked salmon rangoons.