My Guide To The Perfect Long Weekend In Naples, Florida

Updated 01/11/2022

I sometimes get asked why I return to Naples over and over again when Florida offers so many great oceanside towns. The curiosity of the question stems from the fact that many travelers don't give much thought to the Sunshine State's West Coast, instead planning their vacations along the Atlantic in hot spots such as Miami or Palm Beach. To them, the Gulf Coast is the sleepy (dare I say boring) cousin to the East, but the towns lining this stretch of unspoiled coastline are not to be overlooked.

The truth of the matter is, I return over and over because my in-laws have a home there. But, how lucky for me as Naples really is such great place to visit! Downtown, pristine white sand beaches rub shoulders against charming avenues lined with countless shopping and dining options. Not far away, adventure is to be had in the Everglades and mangrove forests. Yes, it's an upscale beach town with a quiet side, but don't let its affluent status steer you away. Whether you're looking for a laid-back family getaway or a momcation, you'll find Naples offers something for everyone.

Since I was fortunate to both start and end January in Naples, all my favorite spots are fresh on my mind, so I thought I'd do a city guide broken down into a 72-hour itinerary, as a long weekend is the perfect amount of time to visit. Plus, I’ve included plenty of other suggestions if your stay extends past the weekend!

Friday Afternoon

It’s always wonderful to touch down in the Sunshine State! To get to Naples, your best option is to fly into either Fort Myers (RSW) or Fort Lauderdale (FLL) and rent a car, which you’ll want anyways for a full weekend of exploring. While Fort Myers is only a 40 minute drive compared to the 90 minutes it will take you from Fort Lauderdale, it’s worth checking out flights into FLL as it offers more nonstop options, and often, at better prices.
Though I cannot speak from experience, these are a few of the hotels in Naples worth checking out: For a tried and true stay, book a room at the beachfront **Ritz-Carlton** located along Vanderbilt Beach; Naples' other highly-recommended oceanfront haven is **La Playa Beach and Golf Resort**, which has been recently renovated and offers some of the best waterfront dining in town; Or, if accessibility is your priority, **The Inn on Fifth** is the place for you. Its prime location in Old Town Naples provides easy access to the city's best dining and shopping, as well as a short walk to the beach. Given the town’s limited resort options, consider renting a condo or home, especially if traveling with a large group.

Friday Evening

You'll quickly discover that the heartbeat of Naples is felt strongest on 5th Avenue South. So, to get a lay of the land and a sense of what there is to see and do, start your weekend by heading downtown.
For dinner, book a table at **Bha! Bha! Persian Bistro**. It may not be the meal you thought you'd be eating your first night in Florida, but after a bite or two of dolmeh (stuffed grape leaves) you won't give that fried shrimp basket a second thought. Fragrant spices and bold flavors are found in Middle Eastern dishes such as turmeric dusted red snapper and Persian style seafood paella. This intimate restaurant located at the near end of 5th Avenue makes the perfect spot to start your leisurely after-dinner stroll down the palm lined avenue, which is most beautiful at night when said palms are lit up with a golden glow. High-end art, souvenirs made of seashells and everything in between can be found in a variety of stores, which during high season (December - April) are open late. Top the night off with a scoop or two of ice cream from Kilwin's, which won't be hard to find - simply follow the heavenly scent.

Saturday Morning

While last night was all about discovering 5th Avenue, this morning is all about exploring downtown's other popular neighborhood, Third Avenue South.
First things first, it's time to eat. Head to breakfast at **Jane's Cafe on 3rd** before the crowds get there (they open at 8am). I recommend the Eggs Benedict (there are 7 variations offered) and a glass of the fresh squeezed strawberry orange juice, though I have yet to order anything I didn’t like. Possibly more noteworthy than the food is the garden courtyard setting where red table umbrellas pop against lush greenery, evoking images of a European cafe.
From breakfast, stroll the surrounding blocks to do a bit of shopping. A few of my favorite stores are **Patina Collection** for thoughtfully curated clothing, home goods and accessories collected from all over the world; **Gattles** for home linens and sleepwear; and **Monogrammed Goods**. Don't let the name of the latter deter you if you're not one to put your initials on anything and everything. While the store does offer a large selection of products to be monogrammed, the majority of the store is youthful women's resort wear.
Before moving on with your day, take time to peruse the **Third Street Farmer's Market**. Every Saturday from 7:30-11:30am you'll find dozens of local vendors selling fresh produce and goods. Pick up a couple snacks for the next part of your day - the beach!

Saturday Afternoon

A few blocks over from Third Avenue lies **Naples Beach and Pier**. Plan on spending the afternoon relaxing in the sun. After all, this is the reason you came to the Sunshine State! Since the majority of this stretch of coastline belongs to private residences instead of resorts, most days the beach lends towards the quiet side with plenty of room to spread out. Note that the pier is the only place along this stretch of beach with restroom access, so you may want to set up camp closer than not if you plan on spending all day here.

bycourtneybrownnaplesflguide5 — Saturday Evening

Tonight you're back on Fifth Avenue but this time for a little bit of indulgence and culture. Make a reservation for dinner at **Sails**. First impressions aren't everything, but Sails sure knows how to make a good one, starting with the servers resembling well-appointed ship's hands in all-white uniforms. The candle lit dining room is beautiful and features a white marble bar and Italian leather button-tufted banquettes, all very timeless yet modern. Given your proximity to the ocean, make sure to start your meal with a selection from the extensive raw bar, but don't over order, as you'll want to save room for tempting dishes such as crab lasagna and sticky toffee pudding.
After dinner, make your way down the palm tree lined avenue to **Artis - Naples** where you'll spend the rest of the evening taking in a show. The Philharmonic Center hosts over 400 events a year including world-class theater, dance, comedy, classical and popular music. Check out the calendar in advance to see what's playing during your visit.

Sunday Morning

Sunday will be a bit more adventurous, but in keeping with the spirit of Naples, all very low-key. Start your morning with a fresh smoothie or acai bowl at **The Bowl** before heading to the day's first activity: **a kayak trip through the mangrove forests**. Over 90% of Florida's "Tree of Life" (as this unique ecosystem is known) is located in the counties surrounding Naples. The experience not only gets you on the water but provides wildlife viewing of birds and fish, and if you're lucky, dolphins and monkeys. There are plenty of places to launch your kayak, but companies worth checking out for rentals and tours are Naples Kayak Adventures and Up A Creek Kayak Tours.
If kayaking isn't your thing, another great family activity would be spending the morning at the **Naples Zoo at Caribbean Gardens**.

Sunday Afternoon

This afternoon, you’re trading waterway for motorway (of sorts). But before you hit the road, make a pit stop at **Turco Taco** for a quick lunch. This casual eatery offers a Baja Coastal vibe that's just as fresh as the food being served (all organic locally grown produce with hormone and antibiotic free meats). Both the quesadillas and tacos are noteworthy, and be sure to order a side (or two!) of Mexican corn.
Once done eating, walk around the block to **Beach Bugz** to pick up your new wheels: a sporty Vespa for some afternoon cruisin'. No trip to Naples is complete without a drive along the town's mansion lined streets, and what better way to sightsee then on a Vespa ($65 for 4 hours). Be sure to cruise down Gulf Shore Blvd S and Gordon Dr (which run parallel to each other), but beware - home envy is near inevitable!

Sunday Evening

If there's one thing Naples is known for it's the sunsets, so tonight be front and center for the show. Before making your way to the water, grab a blanket and place a pickup order at **Sushi Thai Too** for a beach picnic. While there's not a bad seat in the house, I recommend heading for the Naples Pier as the concession stand serves beer and wine, so you can toast another wonderful day spent in paradise. And, if you want to do a little ocean fishing while in Florida, this is a great place to do so. Note that visitors don't have to have a special fishing license.
If you’re not ready to call it a night, head over to **La Playa Beach Resort** and snag a seat around one of their beach fire pits. Between the flickering glow of the fire and the sound of the waves softly crashing upon the shore, it’s the perfect spot to savor your last night in paradise.

If You’re Staying PAST THE WEEKEND…

Home

Mar 1, 2019

Insider’s Guide to Sarasota, Florida

Mar 1, 2019

Jul 1, 2018

Hotel Spotlight: Miami Beach EDITION

Jul 1, 2018