Naples Staycation: Top 10 Things to Do Downtown

Nestled on Florida’s Gulf Coast, Downtown Naples offers a charming mix of sophistication, tropical beauty, and a laid-back vibe—making it the perfect staycation destination. Whether you’re a local looking for a relaxing getaway or a visitor seeking to enjoy the best of this coastal gem, Downtown Naples has plenty to offer. From fine dining and boutique shopping to outdoor adventures and artsy escapes, here are the top 10 things to do in Downtown Naples, Florida, for a staycation to remember.

1. Stroll Down Fifth Avenue South

No trip to Downtown Naples is complete without a visit to Fifth Avenue South. This vibrant, palm-lined street is the heart of downtown, offering a mix of upscale shops, art galleries, and award-winning restaurants. Whether you’re in the mood for shopping, people-watching, or enjoying a coffee at a sidewalk café, Fifth Avenue South sets the tone for a perfect day in Naples.

2. Relax at Naples Pier

For a quintessential Naples experience, head to the historic Naples Pier. Originally built in 1888, the pier is a beloved landmark and an ideal spot for fishing, sunset viewing, or simply soaking up the Gulf breezes. Stroll along the pier to spot dolphins, enjoy the panoramic views, or catch a stunning sunset as the day winds down.

3. Explore the Naples Botanical Garden

Take a break from the bustling streets and immerse yourself in nature at the Naples Botanical Garden. Just a short drive from downtown, this lush 170-acre garden features tropical plants, serene walking paths, and beautiful water features. With themed gardens like the Brazilian Garden and the Asian Garden, it’s a peaceful escape that’s perfect for a staycation day trip.

4. Enjoy Fine Dining at Sea Salt

Naples is known for its excellent dining scene, and Sea Salt is one of the best. Located on Third Street South, Sea Salt offers fresh seafood dishes with a creative twist. With an open kitchen, an oyster bar, and an extensive wine list, this elegant restaurant is a great choice for a memorable staycation meal. Be sure to try the signature sea salt-crusted whole fish.

5. Catch a Show at The Naples Players

For a cultural experience, spend an evening at the Naples Players at Sugden Community Theatre. Known for its outstanding productions, this community theater offers a variety of performances, from Broadway musicals to classic plays. It’s a fun and entertaining way to enjoy a night out on your staycation while supporting local talent.

6. Visit The Baker Museum at Artis–Naples

Art lovers will appreciate a trip to The Baker Museum, a cultural gem located at Artis–Naples. This museum houses an impressive collection of modern and contemporary art, alongside rotating exhibitions and installations. It’s a must-see for anyone looking to add a touch of sophistication to their Downtown Naples staycation.

7. Indulge in Ice Cream at Kilwins

No staycation is complete without a sweet treat! Stop by Kilwins, located on Fifth Avenue South, for some handcrafted ice cream, chocolates, and fudge. Whether you’re a fan of classic vanilla or prefer adventurous flavors like salted caramel, Kilwins is the perfect spot to cool off with a scoop or two after a day of exploring.

8. Take a Boat Tour of Naples Bay

One of the best ways to experience the beauty of Naples is from the water. Book a boat tour around Naples Bay to see the stunning waterfront homes, mangroves, and local wildlife, including dolphins and manatees. Companies like Pure Florida offer narrated cruises that highlight the area’s history and natural beauty. It’s a relaxing and scenic way to spend your staycation afternoon.

9. Browse the Third Street South Farmers’ Market

Held every Saturday morning, the Third Street South Farmers’ Market is a favorite among locals. Featuring local vendors selling fresh produce, artisanal goods, flowers, and more, it’s a great way to support small businesses while enjoying the lively atmosphere of Downtown Naples. Grab a coffee, wander the stalls, and pick up some treats to enjoy later.

10. Unwind at Cambier Park

If you’re looking for a peaceful outdoor space to relax, Cambier Park is the perfect place. Situated in the heart of downtown, this park offers beautifully landscaped grounds, shaded picnic areas, and tennis courts. On many weekends, you can catch live music performances at the park’s band shell, adding a lively and fun element to your staycation.

Tips for Planning Your Downtown Naples Staycation

• Book restaurant reservations early: Popular dining spots like Sea Salt and other high-end restaurants in downtown Naples fill up quickly, especially on weekends.
• Go for a sunset stroll: Plan to end your days with a walk along Naples Pier or the beach to catch one of the Gulf Coast’s legendary sunsets.
• Explore on foot: Downtown Naples is a very walkable area, so take advantage of the sidewalks and enjoy the sights at a leisurely pace.

With its mix of culture, outdoor activities, fine dining, and scenic beauty, Downtown Naples offers the perfect setting for a staycation filled with relaxation and local charm. Whether you’re exploring the vibrant streets of Fifth Avenue or unwinding in the natural beauty of the area, there’s no shortage of things to do in this Florida paradise.

Book your Naples Florida staycation rental with Whimstay today!

 Download

Whimstay

Find the best deals on last-minute vacation rentals

Instagram Facebook LinkedIn Pinterest