Welcome to your perfect weekend in Naples, Florida, where relaxation meets excitement in the Sunshine State. As someone who lives here, Naples offers a perfect blend of sandy white beaches, scenic nature trails, cultural activities, championship golf courses, and lots of retail therapy.
Whether you are strolling along upscale 5th Avenue South, soaking up the sun near Naples Pier, or enjoying a delicious meal outdoors, this weekend escape promises a laid-back atmosphere with a touch of sophistication.
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Side Note: This post was written by Janet, a local of Naples. This way, you can ensure you are reading the BEST and most accurate one weekend in Naples itinerary. Locals know best! Read more about Janet in the Author’s Bio at the end of this post!
Table of Contents
How do I get to Naples?
The closest airport to Naples, Florida, is the Southwest Florida International Airport (RSW) in Fort Myers, located approximately 45 minutes north of the city. If you are planning on staying at a resort and have no intention of exploring the area, then an Uber from the airport will work. But if you want to get to know Naples and the surrounding area, then you will need to rent a car at RSW.
An alternative airport is the Fort Lauderdale-Hollywood International Airport (FLL), 90 minutes east of Naples. Depending on your origin, FLL may offer more direct flight options for your travels. From FLL, you will need to rent a car and drive across Alligator Alley (I-75).
Tip! Check out DiscoverCars search engine to find the best deals on rental cars at RSW!
When is the best time to visit Naples?
The best time to visit is typically during the winter and early spring months, from December to April. This period offers pleasant weather with lower humidity, milder temperatures, and minimal rainfall. I prefer March to May in Naples since it is warmer. It is a good time for outdoor activities, beach outings, and exploring the natural beauty of the area.
Keep in mind, that this is also the peak tourist season, so accommodations and attractions may be more crowded, and prices may be higher. If you prefer a quieter experience and are willing to tolerate warmer temperatures, late fall and early summer can also be good times to visit. However, be aware that the summer months can bring higher humidity, an increased chance of afternoon showers, and an unexpected hurricane.
There is always something happening in Naples! If you are a car aficionado, you may want to attend the Cars on 5th one-day show. It is an annual event, held in February on 5th Avenue South, showcasing over 700 classic and exotic automobiles. You will need to purchase an admission wristband online or at the event. Naples is known for their fancy and exotic cars on 5th Avenue South!
Average Naples Weather by Season
- Winter (Dec-Feb): 75/57 (2-3 days of rain)
- Spring (March-May): 83/65 (4-5 days of rain)
- Summer (June-Aug): 90/75 (14 days of rain)
- Fall (Sept-Nov): 85/65 (12 days in Sept, 5 in October, 2 in November)
Practical Tip: Hurricane season is from June 1st to November 30th, with September being the peak month for storms.
Where should I stay in Naples?
This really depends on what you want to do. If you want to play golf for the weekend, then a resort like the Ritz-Carlton Tiburon would be an option. If you want to sit on the beach and play some golf, then La Playa Beach and Golf Resort or Naples Grande Beach Resort would fit the bill.
If you’re looking for a beachfront hotel, explore options like the Edgewater Beach Hotel near Lowdermilk Park, or the Vanderbilt Beach Resort, a charming family-owned retreat. Along Tamiami Trail, Naples’ main thoroughfare, you’ll also find numerous chain hotel choices.
There are many places to stay in Naples, but I would recommend the downtown area near 5th Avenue South. In downtown Naples, you can easily walk to restaurants, shopping, and the beach. Staying downtown is fun and will give you a chance to really get to know the heart of Naples.
If you are visiting during peak season, due to demand, pricing will be on the higher side. The area will be very busy and there will be increased traffic. Some of the hotels provide complimentary shuttle service to 5th Avenue and the beaches. If you are looking for more budget-friendly options, consider visiting in the spring, summer, or fall.
My Personal Recommendations:
- Budget-friendly Option: Holiday Inn Express & Suites Naples Downtown – 5th Avenue – In walking distance to 5th Avenue South, Tin City, and lots of restaurants. Provides comfort and convenience with free parking, a pool, and daily breakfast.
- Mid-range Option: Naples Bay Resort & Marina – This is where we stayed on our first trip to Naples before we purchased our home. It is a wonderful resort with plenty of amenities like a lazy river, tennis, and water sports since it is right on Naples Bay. You can walk to 5th Avenue and Tin City, and they provide shuttle service to the beach and downtown.
- Luxury Option: Hotel Escalante – Located near 5th Avenue and 2 blocks from the beach. This is a luxurious boutique hotel in a private oasis setting. There is golf cart shuttle service to the beach and to the shops. Everything you need for the beach is provided. You will be pampered here!
- Dog-friendly Stay: La Quinta by Wyndham Naples Downtown – This is a pet-friendly property within walking distance to 5th Avenue and Tin City. They have an outdoor pool and provide a free daily breakfast. Rooms are clean and comfortable.
- Unique Option: The Gondolier Inn – For those nostalgic for the past, this retro 1950’s motel is worth a visit. It has a terrific location right in the heart of Old Naples in walking distance to the beach and 5th Avenue. Each unit comes with a kitchenette and parking. Laundry services are also available.
3-Day Naples Weekend Itinerary
Get ready to embark on a 3-day journey through the heart of Naples designed by a local who loves all that Naples has to offer. In my not-so-biased opinion, it’s the best way to spend one weekend in Naples, Florida!
Day 1: Naples Botanical Gardens, Tin City, & Sunset Cruise
Morning:
Just a few miles from downtown Naples is the Naples Botanical Gardens. It is a great way to start your day exploring the beauty of nature. Upon arrival, sign up for a staff-led tour (free) which provides in-depth insights into the various plant collections and ecosystems within the gardens.
I love wandering through the preserve and around the lake, on a paved path. which is over a mile long. You will get your steps in during this visit. Make sure you see the orchid garden which is stunning!
Lunch at the Fogg Café in the garden. It’s a perfect place for a break and a good meal. I highly recommend the Hand Cut Fries; they are delicious and addictive!
Afternoon:
After your visit to the gardens, head to Tin City in downtown Naples. This waterfront shopping district captures the essence of Old Florida, featuring colorful, repurposed tin-roofed buildings that house an eclectic mix of boutiques, restaurants, and galleries. This is a nice place to walk around and get some souvenirs.
When my boys were younger, we would stop to get Mon “Key” Buntz at the Monkey Bread Factory. Nice and gooey! There are several places for sugary sweets, but I would recommend getting a late afternoon drink at the Riverwalk or Pinchers. You can sit outside and enjoy the views of the Gordon River.
Evening:
After you finish your cocktail, it will be time to board your Sunset Cruise by Pure Florida. This is a 90-minute trip around Naples Bay and Clam Pass out to the Gulf of Mexico to watch the stunning sunset. It is a narrated tour through the back waterways highlighting the impressive mansions in Port Royale. A Naples version of the Lifestyles of the Rich and Famous!
The vessel has a bar for drinks and snacks. It is a fun way to see Naples from the water. It’s important to plan ahead as reservations are required for the sunset cruises.
Upon return to the dock, you can walk to 5th Avenue South. The evening is the best time to see 5th Avenue in action. The street is lined with palm trees wrapped in white lights and luxury cars cruise up and down.
5th Avenue has lots of diverse restaurants, from fine dining to casual while eating under the stars. Some of our favorites are Bistro 821 and Pazzo! Cucina Italiana, and Chops City Grill. While in season, it is necessary to make reservations.
Day 2: Third Street South, Palm Cottage, & Naples Pier
Morning:
Start the day in the historic heart of Naples, Third Street South, renowned as the birthplace of the city. Immerse yourself in the charm of this area with upscale shops, picturesque courtyards, inviting fountains, and an array of enticing restaurants.
Begin your morning at the Third Street Farmers Market, a lively outdoor market held on Saturday mornings. Featuring a diverse selection of fresh produce, artisanal goods, and local crafts, the winter market spans from Third Street South to 13th Street, while the summer market is in the parking lot behind Tommy Bahamas.
After a short walk from the market, you will want to have brunch at Jane’s Café on 3rd. Everything on the menu is delicious and I love the French toast with berries. Most of the seating is outside around the fountain, which is lovely. They do not take reservations, and seating is first come, first served. They always win the best brunch award!
Afternoon:
Just a couple of blocks from Third Street South, you’ll find the historic Palm Cottage, built back in 1895, making it Naples’ oldest home. The Cottage opens its doors for tours every Tuesday through Saturday, from 12:00 pm to 4:00 pm.
Opting for the docent-led tour is a good call – it sheds light on the lives of the early settlers and the development of Naples. The tour itself takes 45 minutes, and your ticket covers access to the Norris Gardens and the Viewing Center, featuring a 24-minute video. I’d suggest securing reservations for the tour.
Your next stop will be the Naples Pier, just one block from Palm Cottage. Built in 1888, the pier stands as a symbol for the city and is frequently featured in photographs. Extending 1,000 feet into the Gulf of Mexico, the pier is popular for fishing and leisurely walks. You can often see dolphins and pelicans in the area.
Now is your opportunity to take a walk along the beach. Next to the Naples Pier, there’s a section along the beach known as Millionaires Row, showcasing beachfront homes built by wealthy and influential individuals. The walk is beautiful along the Gulf of Mexico, with white sand and lots of shells. My shell collection continually grows!
Practical Tip: Unfortunately, Hurricane Ian in 2022 inflicted substantial damage on the pier. At present, only the nearest 100 feet from the shore are open to the public. Based on available information, it is anticipated that the restoration work will be hopefully completed by 2025.
Evening:
Wrap up your Old Naples visit with dinner on Third Street South. With numerous dining options available, consider Tommy Bahamas Restaurant or Sea Salt if you fancy live music. Both offer patio seating, providing a great vantage point for people and car-watching. Reservations are advisable, especially during peak seasons.
Day 3: Audubon Corkscrew Swamp Sanctuary & Lowdermilk Park
Morning:
Today, you are venturing out of downtown Naples to the Audubon Corkscrew Swamp Sanctuary which is approximately 45 minutes east. If you like nature, then you will enjoy this walk through the sanctuary. The extensive boardwalks, spanning 2.25 miles, guide you through diverse ecosystems. You will see bald cypress trees, wading birds, and vibrant flora.
Spot wildlife, including alligators, Red-Shouldered Hawks, and maybe the elusive Painted Buntings, making it a birdwatcher’s paradise. The sanctuary also offers educational programs and guided tours. It is open from 8am to 3pm, with the last entry at 1pm. The walk takes about 2 hours. During the peak season, tickets need to be purchased in advance. Remember to bring your water bottles!
Afternoon:
Head back to downtown Naples and go to the Lowdermilk Park for an afternoon at the beach. This is a beachfront park where you can rent beach chairs and settle into an afternoon of sunshine on the Gulf of Mexico.
Have lunch or a snack along with a cocktail at Flip Flops Beach Bar & Grill while enjoying the beach. The beachfront park has sand volleyball courts, a children’s playground, gazebos, restrooms, and showers. There is pay-by-space parking, and, at times, it can be challenging to find a spot.
Evening:
A perfect end to your day is having cocktails at Limon Rooftop Bar. Limon is in the AC Hotel Naples 5th Avenue, and recently opened in December 2023. It has a Mediterranean vibe and beautiful views of the area.
For dinner, head to Kelly’s Fish House Dining Room Naples. It is the oldest seafood restaurant in Naples, opening in 1952. Kelly’s is on the water across from Tin City. It is known for its traditional seafood offerings, including Stone Crab Claws. I am a big fan of their slaw salad and hush puppies!
Practical Tip: Kelly’s has a parking lot and they do not take reservations. Stone Crab Claw season runs from October 15 to May 15.
Other things to do in Naples:
One weekend in Naples is definitely not enough to see it all. Here’s a list of more things to do in Naples in case you have some extra time.
There is so much to do in Naples, as well as day trips outside of Naples, and it is hard to pack it all in 3 days. If you have more time, check out more things to do below.
- Car lovers will enjoy a docent-led tour of the Revs Institute, home to over 120 vintage classics to iconic race cars. Reservations are required. Docent tours are on Tuesday, Thursday, and Saturday at 12:30 pm – $30.00 per adult.
- Take a narrated, hop on, hop off tour of Naples on the Naples Trolley. Tickets can be purchased online or in their store – $34.00 per adult, $19.00 per child 11 and under.
- View a variety of animals and botanical gardens, along with a primate expedition cruise, at the Naples Zoo at Caribbean Gardens – pricing ranges from $22.95 to $14.95 depending on age.
- Art aficionados will enjoy a visit to the Baker Museum, home to a collection of contemporary and modern artworks, including works from the classics like Picasso and Monet – $10.00 for 18 and up.
- Sail to Keewaydin Island on Sweet Liberty, a 53” catamaran from the Naples City Dock. The 3-hour morning trip costs $46.80 per adult, $25.00 per child (3 to 12 years). Reservations are required.
See more Naples tours on GetYourGuide or Viator!
Where (else) to Eat in Naples:
Naples boasts an array of restaurants so extensive that you could eat out every day of the year and still leave some unexplored. Just on 5th Avenue South, there are over 30 dining options. Consider adding these additional culinary gems to your must-try list during your 3 days in Naples.
- Baleen Naples – a fine dining venue on the beach, located in the La Playa Beach & Golf Resort. Perfect for a special occasion and for watching the sunset.
- Osteria Tulia – serving upscale Italian meals (known as rustic farmhouse chic) on 5th Avenue South.
- Keewaydin’s on 5th – recently opened in January 2024 on 5th Avenue South. The food is a fusion of Caribbean and Asian flavors, specializing in fish and seafood.
- The Dock at Crayton Cove – a waterfront restaurant serving seafood, overlooking Naples Bay in the Crayton Cove neighborhood in Old Naples.
- Bleu Provence – Classic French bistro serving authentic French cuisine.
- The Bay House – known for their raw bar seafood and fresh fish on the Imperial and Cocohatchee Rivers.
- Old Naples Pub – a casual, burger, and sandwich pub in Old Naples, 2 blocks from Naples Pier. Homemade pickles in a jar are on each table, a treat for all.
- Grouper & Chips – this is an affordable, family-friendly, restaurant serving the freshest grouper in town.
- Celebration Park Naples – if you like the food truck scene, then this waterfront park with an open-air bar is the place to go. Open daily starting at 11 am with live music in the evening.
- EJ’s Bayfront Café – a diner on the water serving breakfast and lunch.
Other Tips to know before visiting Naples:
- Sun Protection: The Florida sun can be intense, during your weekend in Naples it’s essential to use sunscreen, wear a hat, and stay hydrated, especially if you’re spending time outdoors.
- Weather Awareness: Be mindful of the weather, especially during hurricane season (June to November). Stay informed about any potential weather changes and plan accordingly.
- Wildlife Caution: Florida is home to various wildlife, including alligators. Exercise caution near bodies of water and adhere to posted warnings. Enjoy observing wildlife from a safe distance.
- Booking Reservations: Naples is a popular tourist destination, and restaurants can get crowded, especially during peak season. Consider making reservations in advance for popular dining spots.
One Weekend in Naples Map
Here’s a handy dandy map to help plan your perfect weekend in Naples! I’ve included all the stops we discussed above, but feel free to download and make your own changes 🙂
About the Author!
Hi, I’m Janet and I spend my time in Southwest Florida and Southern Italy, from Naples to Napoli! I provide travel tips, trip planning expertise, and updates on where I live and places I have explored. To learn more, check out my website, Practical Travel Concepts or follow me on Facebook.
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