When you arrive into Naples, head straight for the downtown district — it’s lunchtime, after all. Fifth Avenue South is known not only for its pedestrian-friendly walkways and eclectic collection of boutiques and art galleries, but for its sidewalk seating at nearly all of the 30 restaurants and bars that line the avenue.
For more dining options, travel a bit further to Third Street South and The Avenues Shopping District where you’ll find award-winning restaurants like Campiello, Barbatella, and Jane’s Cafe.
On-street parking spot is free in Naples 24/7, so keep an eye out to snag a spot.

A longtime Naples staple is Campiello Ristorante & Bar on 3rd Street South. If the weather’s nice, ask for an outside table shielded from the Florida sun by an umbrella. The lunch menu here features wood-fire pizzas and house-made pasta alongside paninis and tempting entrees, all of which are fabulous.
Once you decide on what to have, sit back and take your time to linger over lunch. The European vibe here means that there’s no rush, and you’re welcome to stay as long as you’d like.

After lunch, walk back over to 5th Avenue South and pop into Marilyn’s, a fashion house curated by owner Marilyn Hellman. Inside you’ll find a showroom not only filled with some of the most beautiful pieces you’ve seen outside of Paris and Milan, but blouses, dresses, and pants under Marilyn’s own label, inspired by her annual buying trips to Europe.
Note: Marilyn's is open 10 am to 5 pm Mondays through Saturdays, closed Sundays.

Stop into Emillions Art, also on 5th Avenue South, and you may be wowed by the artwork on exhibit. The gallery works with established and emerging artists, as well as beginning and longtime collectors, to find the right fit for everyone. Be sure and check out the featured artist and artwork.
Note: Emillions Art is open Mondays through Thursdays 10 am to 5 pm, and Fridays and Saturdays 9 am to 5 pm; the gallery is closed Sundays.

There’s something for everyone when it comes to shopping in Naples, and one boutique to check out is Audrey’s of Naples, a high-end consignment shop that houses one of the largest collections of vintage apparel in south Florida. Browse designer clothes and handbags, and estate and costume jewelry, and you may just find something you can’t live without.
The real prize? Prices could be as low as 10% of what the original buyers paid; many of the shop’s items have the original price tags still attached.
Note: Audrey's is open Tuesdays through Saturdays 10 am to 5 pm, and is closed on Sundays and Mondays. Hours may vary seasonally; check the website for current hours.

Walking back to your car, there's still plenty of opportunities to do some window shopping along the way. Who knows, you may even find a few more boutiques to pop into!

After you’re finished shopping, call ahead and make a reservation at The Turtle Club in hopes of snagging a table on the beach so you can enjoy dinner with your toes in the sand as the sun sets over the Gulf of Mexico. As stunning as the setting is, the menu has to be spectacular. You’re in luck — it is.

If you need a quick stop on your way back to Miami to stretch your legs, use the bathroom, or grab a cup of coffee, stop at the new Miccosukee Service Plaza. There isn't much on this stretch of Alligator Alley, but this 24-hour spot has everything you need to get you to your final destination.