5th Avenue – Naples, Florida: A Guide to Shopping, Dining & Entertainment

Fifth Avenue is a popular destination in Naples, Florida, known for its upscale shopping, dining and entertainment venues.  The street stretches from Tamiami Trail to the Gulf of Mexico in Old Naples, making it one of the most exclusive addresses in the nation. 

One of the main draws of Fifth Avenue is its selection of fine dining options. From Italian to seafood to American cuisine, there is something for everyone on this iconic avenue. Visitors can indulge in a romantic dinner for two or enjoy a casual lunch with friends while taking in the sights and sounds of the street.  In addition to dining, Fifth Avenue also offers a variety of entertainment options, including live music and theater performances.

For those looking for fine shopping, Fifth Avenue has a range of boutiques and specialty shops that offer one-of-a-kind gifts, artwork and home décor.  Overall, Fifth Avenue in Naples is a must-visit destination for anyone looking to experience the best that the city has to offer.

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About 5th Avenue

Fifth Avenue has a rich history that dates back to the 1920s, when it was first established as an unofficial “Main Street” in the city.

Over the decades, Fifth Avenue has undergone several transformations, evolving from a strip mall to a bustling hub of activity. Despite these changes, it has remained the heart and soul of Naples, serving as a gathering place for both locals and tourists.

One of the most notable features of Fifth Avenue is its unique architecture. Each structure is distinct, featuring columns, archways, and recessed plazas that add to the avenue’s charm and character. The Naples Women’s Club, located on Park Street, off Fifth Avenue, is one of the historic buildings that still stands today.

Today, Fifth Avenue offers a wide range of shopping, dining, and entertainment options. Visitors can explore the many boutiques, art galleries, and specialty shops that line the avenue, or enjoy a meal at one of the many restaurants that offer everything from casual fare to fine dining. 

Shopping on 5th Avenue

5th Avenue South is a shopper’s paradise, offering a wide variety of upscale shops, boutiques, and galleries. Visitors can find everything from designer clothing and jewelry to unique gifts and home décor.

Many of the businesses on 5th Avenue South have been here for decades and are locally owned and operated, adding to the charm and character of the shopping district. Some of the popular shops include:

  • Best of Everything
  • Back of the Bay Boutique
  • Regatta
  • La Vie En rose
  • Marylyn’s
  • Petunias of Naples
  • The Blue Mussel
  • Chico’s
  • White House Black Market
  • Alice Simone Shop
  • Kay’s on the Beach
  • Giggle Moon
  • Brandy Melville

Dining on 5th Avenue

Fifth Avenue South is a culinary destination, offering a wide range of dining options to choose from. Whether you’re in the mood for casual or upscale dining, traditional Italian cuisine, or fresh seafood, there is something to suit every taste and budget.

Some of the restaurants and bars include:

  • Aqua Seafood & Steaks
  • Bice Ristorante
  • Chops City Grill
  • Bistro 821
  • KJ Sushi & Asian Bistro
  • La Trattoria
  • The Vine Room
  • The Cafe
  • Osteria Tulia
  • The French
  • Truluck’s Ocean’s Finest Seafood & Crab
  • Ocean Prime

No matter what your taste buds are craving, Fifth Avenue South has something to offer. With its diverse range of dining options, it’s no wonder it’s a top destination for foodies visiting Naples, Florida.

Art and Culture on 5th Avenue

5th Avenue South in Naples, Florida, is not only known for its high-end shopping and dining but also for its thriving art and culture scene. The avenue is home to several art galleries, theaters, and cultural centers that showcase the best of local and international talent.

The Emily James Gallery is one of the most popular art galleries on 5th Avenue. It features contemporary art pieces from renowned artists such as Emily James, Paul Arsenault, and Cheryl Fausel. The gallery offers a diverse collection of paintings, sculptures, and mixed media pieces that are thought-provoking and visually stunning.

For theater enthusiasts, the Gulfshore Playhouse is a must-visit destination. The theater company produces professional plays and musicals that are both entertaining and thought-provoking. The venue is intimate, with only 250 seats, allowing for an immersive theater experience. 

There is also The Naples Players theatre which was founding in 1986 but moved to Fifth Avenue in 1998.

In addition to art galleries and theaters, 5th Avenue South also hosts several cultural events throughout the year. The Naples Downtown Art Show is one of the most popular events, featuring works by over 200 artists from across the country. The event is held in February and attracts thousands of visitors each year.

Overall, 5th Avenue is a hub of art and culture in Naples, Florida. With its diverse collection of art galleries, theaters, and cultural centers, the avenue offers something for everyone.

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Hotels & Overnight Accommodations

Naples, Florida, has a wide range of accommodation options to suit all budgets and preferences. Whether you’re looking for a luxury hotel or a cozy bed and breakfast, you’ll find it on or near 5th Avenue South.


There are several hotels on or near 5th Avenue South that offer luxurious accommodation and easy access to the area’s attractions. Some of the most popular options include:

  • Inn on Fifth: This award-winning hotel is located in the heart of 5th Avenue South and offers luxurious rooms, a rooftop pool, and a spa.
  • Bellasera Resort: This Mediterranean-style resort is located just a block from 5th Avenue South and offers spacious suites, a pool, and a restaurant.
  • Hyatt House Naples/5th Avenue: This modern hotel is located just a few blocks from 5th Avenue South and offers spacious rooms, a pool, and a fitness center.

Bed and Breakfasts

If you’re looking for a more intimate and cozy accommodation option, there are several bed and breakfasts in the area. Some of the most popular options include:

  • The Capri Inn: Formerly the Trianon Old Naples, this charming bed and breakfast is located just a few blocks from 5th Avenue South and offers comfortable rooms, a pool, and a complimentary breakfast.
  • The Gondolier Inn: This historic bed and breakfast is located just a few blocks from 5th Avenue South and offers charming rooms, a pool, and a complimentary breakfast.

Vacation Rentals

For those who prefer a more independent accommodation option, there are several vacation rentals available in the area. Some of the most popular options include:

  • Naples Florida Vacation Homes: This company offers a wide range of vacation rentals in the area, from cozy apartments to luxurious villas.
  • VRBO: This popular vacation rental website offers a variety of options in the area, from beachfront condos to spacious homes.
  • Airbnb: This popular vacation rental website also offers a variety of options in the area, from cozy apartments to unique and quirky homes.

No matter what your budget or preferences, you’re sure to find the perfect accommodation option on or near 5th Avenue South in Naples, Florida.

If you thinking about staying at this property or any of the amazing hotels in Florida, we would appreciate if you can use our links when making the reservations. Endless Summer is an affiliate with MarriottHilton & Expedia.com, receiving a small commission for each stay that was referred by our website.  

Events and Festivals

5th Avenue South is not just a shopping and dining destination, but also a hub of events and festivals throughout the year. Visitors can take part in various cultural, art, and music events that take place on the avenue.

One of the most popular events is the Naples New Year’s Art Fair, which takes place in January. This fair attracts artists from across the country who showcase their unique creations in various mediums. The event is hosted by the Naples Art Association and held in Cambier Park.

Another major event is the Naples Downtown Art Show, which takes place in March. The event features over 200 artists and visitors can enjoy live music and food while browsing the art exhibits.

Apart from these major events, 5th Avenue South also hosts various smaller events throughout the year. These include the Evening on Fifth, which is a monthly street party that features live music, food, and drinks. The Halloween Spooktacular is another popular event that takes place in October, where visitors can enjoy trick-or-treating and other spooky activities.

Overall, 5th Avenue South offers a variety of events and festivals for visitors to enjoy throughout the year. From art shows to street parties, there is always something happening on the avenue.

Living in Naples, Florida

The Naples, Florida area has been one of the fastest growing areas of the state.  There are many reasons why people choose to live in here which include:

  1. Beautiful beaches: Naples is home to some of the most beautiful beaches in the world, with white sand and crystal-clear water. Living in Naples means you’ll have easy access to these beaches year-round.
  2. Warm weather: Naples has a warm, tropical climate with hot summers and mild winters. If you enjoy warm weather and plenty of sunshine, Naples is the place for you.
  3. Outdoor activities: Naples is a great place for outdoor enthusiasts, with plenty of opportunities for boating, fishing, golfing, and hiking.
  4. Cultural scene: Naples is home to a thriving arts and culture scene, with museums, galleries, and performing arts venues.
  5. Retirement: Naples is a popular retirement destination, with many retirees choosing to spend their golden years in this sunny paradise.
  6. Safety: Naples is consistently ranked as one of the safest cities in Florida, making it a great place to raise a family.
  7. High quality of life: With its beautiful scenery, warm weather, and luxurious lifestyle, Naples offers a high quality of life that is hard to beat.

Overall, living in Naples offers a unique combination of natural beauty, outdoor activities, cultural amenities, and a high quality of life that is hard to find elsewhere.

Homes in Naples typically start from around $500,000 and can exceed $25 million for beachfront estate properties.  If you are interested in click here to contact our preferred real estate advisor.

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Jerry Joyce

Jerry Joyce has been a Florida resident since 1988 and has lived in a variety of places in the South Florida area. Jerry is an avid boater & water sports enthusiast, beach aficionado, a lover of great food, muscle car fan and a theme park annual passholder for many years. Some of his favorite places in Florida include the Florida Keys, Walt Disney World, Cedar Key, the Loxahatchee River, St. Augustine and Ten Thousand islands.

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