Visiting Historic Old Naples — A Comprehensive Guide

Visiting Historic Old Naples — A Comprehensive Guide

Established in 1886, Naples started as a 3,712 acre town that was designed as a winter retreat, reminiscent of the Italian peninsula. That small town is now one of the most popular vacation destinations in America. However, the rich history and charm of that original town can still be found in a captivating district known as Old Naples. Nestled in the heart of Naples, Florida, this beautiful neighborhood invites you to wander through its quaint streets, impressive marinas, beautiful beaches, elegant art galleries, and delicious cafes. This historic area seamlessly blends “Old Florida” with new luxury making it a hot tourist destination. Join us as we explore Old Naples and the unforgettable experiences that lie within.


First, a history lesson.

Florida Everglades

General John S. Williams and Walter Haldeman were the two men who purchased the initial acres for Naples for $11,136, or $3 an acre. The land was between the Gulf of Mexico and Naples Bay and they built homes and the first hotel. Naples Bay is now a popular spot with Tin City and multiple yacht clubs and marinas lining the bay. The early 1900’s brought Ed Crayton to town and he purchased all the land from Haldeman. He brought about a new chapter in Naples as he continued to heavily develop Naples. In 1923, Baron Collier founded Collier County and instilled major economic growth. Simultaneously, The Collier Family still plays a big role in the development and management of Naples today.


Now, a sightseeing guide.

Fifth Avenue South in Old Naples is a vibrant street that offers a delightful blend of boutique shops, art galleries, and diverse dining options. With its stylish storefronts, you can explore unique fashion, jewelry, and home decor. The historic avenue also features a collection of art galleries showcasing local and international talent. From cozy cafes to upscale restaurants, there is something for every taste and budget. Read our Naples Dining Guide to learn more about the local offerings and our recommendations. At night, Fifth Avenue comes alive with musicians lining the street, lit palm trees, and swanky bars perfect for a nightcap. Whether you’re seeking shopping or dining adventures, this bustling avenue is a must-visit destination in Old Naples.

An equally amazing spot for strolling and people watching is Third Street South. Situated just two blocks away from the Naples Pier, this street is quieter than its bustling counterpart yet delivers more understated glamor. The “Old Florida” ambiance and charm is overflowing on Third Street with colorful beach cottages, cascading flowers, fine dining restaurants, and sophisticated shopping. A Saturday morning is well-spent at the weekly farmer’s market on Third. Feel free to bring your four-legged friend as Third Street is one of the most pet-friendly spots in all of Naples!

After the farmer’s market, take a stroll around the neighborhood to be wowed by stunning, beachfront homes and charming coastal cottages. For those interested in learning more about the history of Old Naples, stop by the Historical Society at Palm Cottage (a Landmark in the National Register of Historic Places). This is the oldest home in Naples, built in 1895! There, you can either tour the extensive house museum or partake in a walking tour. Throughout the years, the real estate in Old Naples grew rapidly and steadily in value. Now, many of the homes are sprawling estates that are within steps of the Gulf of Mexico. Take a drive down Gulf Shore Boulevard South to feast your eyes on the impressive real estate that lends Naples to being one of the wealthiest cities in the South.

Old Naples Third StreetA few streets over from Third Street is Crayton Cove which harbors the exclusive Naples Yacht Club, vibrant Naples City Dock, charming Cove Inn on Naples Bay, and a variety of shops and restaurants. A staple in the Naples dining scene is the Dock at Crayton Cove which serves up delicious seafood with stellar views. The Naples City Dock lies at the heart of Crayton Cove and is the go-to spot for fishing charters, water-sports, and beautiful coastal views. If you’re looking for a fun way to explore the bay, the Naples Bay Water Shuttle is a crowd-pleaser.

Most people flock to Naples for the beautiful white sand beaches and Old Naples has some of the best in the area. While the Naples Pier beach is by far the most popular, there are beach access points at the end of each street in Old Naples and they are far less crowded. Parking can be tricky to find since much of the parking is reserved for Collier County residents. However, there is some street parking and a few beach parking lots that are first come, first serve. 

Naples Pier and BeachLastly, we had to recognize the Naples Pier. While Hurricane Ian destroyed the pier, the city is planning to rebuild and they’ve already approved the new design. The pier has always been an iconic part of Old Naples as people from around the world would gather to watch the glorious sunsets over the Gulf of Mexico.

From the vibrant Fifth Avenue South, lined with boutique shops and delightful restaurants, to the iconic Palm Cottage showcasing the rich history of Naples, there’s no shortage of captivating sights to explore. It is no surprise that Old Naples has stolen the hearts of so many people. The idyllic district is a great place to visit and an even better place to live. If you’re interested in buying real estate in Old Naples, our team is here to help. Please contact Taber Tagliasacchi for more information.

 Taber Tagliasacchi · 239-287-0777 ·


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