Published: April, 2021
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Naples, Florida

Naples checks a lot of boxes for accessibility, great weather, delicious restaurants and fun shopping. It's the kind of town you want to rinse and repeat!
— Cynthia Pillsbury
  • More about your oliver guide:
  • Trip type: Adult, Family, Group getaway, Beach
  • Activity level: moderate
  • Ideal length of trip: A weekend escape or a week long Beach vacation, Naples is an ideal locale!

to & from

Fly into Fort Myers (RSW) and rent a car or uber south to Naples (about 45 minutes). You will most likely want a car, unless you are staying near downtown (5th Ave or 3rd Street) which means you can walk to the beach, restaurants and shops!

Where to Stay

While I am sure there are great VRBO’s, we always stay with family. However, there are lots of hotel options depending on your budget and where you want to stay.

La Playa – High end, small and right on the beach in North Naples. It’s about a 20 minute drive to Old Naples/downtown where most of the shops/restaurants are located, but La Playa is special!
Ritz Carleton- Typical big luxe hotel, on the beach, great vibe and service and has a sister property (Ritz Carleton, Tiburon) that has a golf course.
Inn on 5th- Great boutique hotel right in the center of downtown.
The Edgewater Beach Hotel and Club– Beachside hotel, not in the middle of the hustle and bustle of downtown, great amenities.
The Capri Inn-  Slightly more affordable and lovely hotel near downtown.

Where to Eat and Drink

Naples is the most sophisticated “city” on the Gulf (west) side of Florida; full of amazing restaurants (with a strong European influence) charming shops and lovely beaches. While there is a hustle-bustle vibe to the town, it’s a slower pace than the East Coast of FL. There are SOOOO many delicious restaurants, it’s hard to include them all, but here are some of our favorites!

Chez Boët– Very French and chic with a Moroccan influence… you almost feel like you are in Paris. The food is delicious, decor very special and service. wonderful. Yummy cocktails (French 75) and they are known for Tangines.
Dolce & Salato– Very authentic Italian off of 5th Ave. Take a break from the beach and enjoy a lovely lunch on their patio. You do really feel like you are in Italy. We loved their salads and ròse!
Amore- Sophisticated and delicious Italian located off of Highway 41 (not Old Naples). The Calamari is amazing, as is the pasta and veal piccata, it’s fun scene!
Bleu Provence– Lovely French restaurant in fare and atmosphere.
Campiello– Located in the heart of 3rd street, this has probably the best patio dining in town and the food is great too!
Mediterrano– Delicious Mediterranean cuisine served on a patio full of blooming flowers a block off of 3rd street.
Turtle Club– Beachside dining in North Naples, delicious food. No reservations so arrive when they open!
Swan River Seafood Market and Restaurant– The location is not so sexy, in a strip mall off of Highway 41, it has a fun marine vibe and the their crab cakes are the best I have EVER had!
Food Trucks in Celebration Park in the newly minted Arts District – just 5 minutes east of downtown. The Greek and Seafood Trucks were our favorites!

What to Do

Head to the beach- avoid the areas near the pier– too crowded. The water is clear, sandy bottom and perfect temperature in March and April.

Rent a boat with captain and check out the lovely homes in Port Royal or head into the gulf for a glimpse at dolphins at play, they also offer sunset cruises on a catamaran… Sweet Liberty

Head to the Everglades (only about 30 minutes from Naples) for a chance to see alligators and more. Fast moving airboat (yes, you are in the air and water) flying through the Everglades makes for a very fun half (or full day) day activity. Everglades Excursions and Captain Jack’s are the two providers we have used.

Golf… if you like to golf there are hundreds of private clubs, a few public and a few hotel-connected courses.

Art Galleries along Broad Street- IN normal years they host a Wednesday pm art gallery event, but even without the nibbles and wine, the galleries are still worth checking out!
Favorites include:
Quidley & Company Fine Art– With galleries in Naples, Nantucket and Westport we felt very much at home in this FUN art gallery that had a range of style and prices.
Gardner Colby Gallery– More traditional, lovely gallery that has a great range of artists.

Shop… the stores are pretty amazing, both for apparel and home. I prefer the shops on/along 3rd Street and 5th Avenue, and also usually make a stop at Waterside (more mall type shops, but the Saks Fifth Avenue is especially great) and Venetian Village on the Bay has nice shops and restaurants.
Favorite, don’t miss shops include:
A Mano– Off of 3rd Street, lovely dresses, jewelry, beautiful tabletop and the most cleaver hand stitched linen napkins I have ever seen!
Monogram Goods– Incredible clothing/shoe brands, fun tabletop and gifts items.
Marissa Collection– High women’s clothing shop with a somewhat serious vibe.
Patina Collection– Beautiful home store, full of unique finds, both vintage and new. Lovely driftwood sculptures from Italy, pillows, dishes, one of a kind accent furniture.
Jett Thompson Home– Lovely home decor shop, amazing collection of coffee table books, art furniture, jewelry…I could move in!

inside scoop

If you are going to Naples in the high season (Holidays and March) make dinner reservations in advance! The weather is not fool proof over Christmas– I prefer to go in Spring.

skip it

Tin City, super touristy.

What to Pack

You can step up your fashion game when in Naples. It’s fun to break out your sandles and dressy sundresses for nights out and of course don’t forget your sun hat!

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