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Explore 5th Ave In Naples: Must-See Spots On Your Next Trip

Downtown Naples
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Tourists flock to Naples, Florida every year to treat themselves to fine dining and excellent shopping, especially along its unofficial main street: Fifth Avenue. There’s no shortage of places to shop or dine, so we highly recommend that you spend a day here before sightseeing in the rest of this Gulf city.

What are the best things to do here, and where should you go for unique finds? Read our guide to what to do and where to shop on incredible Fifth Avenue!

Tips Before You Start Exploring

Before you set off to window shop and wander, make your visit to Fifth Avenue smoother and more comfortable with these simple ideas.

Book Nearby Accommodations

Exploring Fifth Avenue means a lot of walking as you window shop. Save your feet the extra steps and get a room somewhere cozy nearby, like the Holiday Inn Express and Suites. This allows you to take your time strolling through the neighborhood, and you can quickly go back if you need a break.

Prepare For The Heat

Florida is sunny all year round, so pack sunscreen and sunglasses to protect yourself from the rays. Don’t forget to hydrate regularly by bringing a thermos or ordering refreshments at a nearby cafe.

Make Reservations For Restaurants

While you may be able to get away with walking into some places during the off-season, many Fifth Avenue restaurants fill up quickly. Make sure you get that coveted table for dinner by calling or reserving online. This saves you the hassle of waiting on an empty stomach for a spot to free up.

What To Do: Fun Activities In 5th Avenue

There are plenty of great ways to soak up some culture and entertainment on Fifth Avenue. Whether you’re going solo or catching these sights with a group, we highly recommend that you make these part of your trip.

Watch A Live Theater Performance By The Naples Players

Sugden Community Theatre, 701 5th Ave South, Naples, Florida 34102

Catch a musical or enjoy a comedy performed by the Naples Players at the Sugden Community Theatre’s state-of-the-art stages. The Naples Players are frequently rated as one of the best community theaters in the country, so check out what’s being staged during your visit. It’s also walking distance from Fifth Avenue’s many cafes and restaurants, making it the perfect activity for an evening out!

Warning: tickets sell out fast at this LGBTQ+-friendly attraction, so book well in advance to get good seats. 

Visit Naples Art

585 Park St, Naples, FL 34102

Located just a block away from Fifth Avenue, Naples Art hosts changing art exhibitions, art classes, and workshops. Explore this two-story art center to learn more about Florida art and regional artists. You can browse for souvenirs at its gift shop, or wander through the main exhibition gallery to see what’s new. Admission here is free!

Check Out Monthly Events

Fifth Avenue South regularly hosts fun activities like live musical performances, stand-up comedy shows, and food festivals. Peek at the monthly calendar to see what’s happening during your visit.

One regular highlight is Evening On Fifth. Held on the second Thursday of every month, visitors can look forward to live musical performances as they shop and dine around this main street.

Booking.com

Where To Eat: Grab A Bite At These Local Spots

Fifth Avenue has many upscale and casual options for dining. If you’re famished after a long afternoon of shopping and perusing art galleries, stop by these Naples favorites and try their best-selling dishes.

Sails Restaurant

301 5th Ave South, Naples, Florida 34102

Dress to the nines and treat yourself to a luxurious meal at Sails Restaurant. Renowned for serving French, Italian, and Greek dishes, it’s widely considered one of the best places to eat in Naples. The freshly shucked oysters, lobster ravioli, and wood-grilled seafood are must-tries.

We highly recommend ordering from its extensive craft cocktail menu to complement your dishes. End your night with one of its decadent desserts – the Valrhona chocolate souffle is especially to die for!

Osteria Tulia

466 Fifth Avenue South, Naples, Florida 34102

Famous among locals as Naples’ first osteria, this restaurant serves delicious Italian cuisine inspired by centuries of culinary traditions. Reviews have praised the fresh homemade fennel sausage and burrata at this neighborhood favorite.

Start with the complimentary bread and eggplant spread before tucking into the hearty pasta dishes. Cap it off with its rich hazelnut torte for an unforgettable meal in Naples.

Regina’s Ice Cream

824 5th Avenue South, Naples, Florida 34102

Take a trip back in time at Regina’s Ice Cream, a local retro-inspired spot famous for old-fashioned malts, egg creams, and ice cream sodas. With over 50 flavors to choose from, there’s something to satisfy every sweet tooth. 

Get your daily dose of caffeine from its blended coffees, or try its signature flavors on a homemade waffle cone. Visitors sing praises about the Naples Special Butter Pecan, Port Royal Praline, and soft-serve frozen custard.

Where To Shop: Great Places For Retail Therapy

Looking for something special? Shop for classy home furnishings, souvenirs, or new additions to your closet at these Fifth Avenue stores.

Marilyn’s

375 5th Avenue South, Naples, Florida 34102

Looking for a well-made, unique pair of shoes or some jewelry to complete your look? Marilyn’s stocks unique French and Italian women’s fashions that will add flair to your wardrobe. Owner Marilyn Hellman has cultivated warm relationships with many European designers over the years, allowing her to continuously offer exciting new collections.

One item we highly recommend you get from this chic boutique? The couture handbags are a must if you’re willing to splash some cash on a special gift!

Blue Mussel

757 5th Avenue South, Naples, Florida, 34102

Blue Mussel has been selling quality home decor, handcrafted gifts, and jewelry since it first opened in 1962. Browse through its selection of unique shells, decorative coral, and nautical accessories. You can score pretty sea glass rings and fun wooden signs at a great price here.

Not sure what to get as souvenirs for your loved ones back home? Don’t be afraid to ask the friendly owners for recommendations. They can help you find the perfect beachy crafts for your budget.

The Wind In The Willows

793 5th Avenue South, Naples, Florida, 34102

Stop by The Wind In The Willows for one-of-a-kind clothes and accessories. This whimsical store is known for its mannequins with animal heads displaying the store’s latest finds.

Must-buys here include hand-tooled boots and custom jackets. While browsing its nooks for a unique gift, feel free to pet any of the three beribboned Persian cats that call this store home.

Naples Soap Company

1200 Fifth Avenue South, Naples, Florida 34102

Pamper yourself with skincare products from this beloved Naples establishment. Naples Soap Company’s natural, organic products are great for those with sensitive skin. Best of all, its items are vegan, gluten-free, eco-friendly, and cruelty-free!

Try one of the shampoo bars and lotions in special scent blends, or grab some luxe gift sets to take home. Don’t be shy about stocking up, as it offers bundle discounts if you get more items!

Put These Activities And Places On Your Naples Bucket List!

Fifth Avenue is a premier shopping and dining destination in Naples. Thousands of tourists flock here every year to immerse themselves in this bustling business district. If you’re not sure where to shop or what to do, don’t worry! Try our suggestions to plan a fun-filled day at Fifth Avenue.


**Disclaimer: There is a good chance that this post contains affiliate or sponsor links. If you make a purchase through them, we may receive a small commission at no extra cost to you (for which we are extremely grateful).

Also, while we do our best to highlight LGBTQ-friendly destinations and businesses, info provided is based solely on personal experience and recommendations by community partners. We hope that nobody experiences discrimination or homophobia while visiting Florida, but we make no guarantees. Please inform us if you experience discrimination or homophobia while visiting any destination so we can make updates to our recommendations.

Written by Rachel Covello

Rachel Covello is an award-winning speaker, writer, diversity consultant, and LGBT advocate. She was the Founder of LGBT Equality Alliance, a Chester County, PA nonprofit organization. She is currently the Publisher of OutCoast.com and Producer of the OutCoast TV YouTube Channel, both of which highlight LGBTQ welcoming destinations in Florida.


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