A Weekend in Naples, Florida | Ultimate Romantic Itinerary
Planning a long weekend in Naples, Florida? Sunshine, beaches, and bliss are calling… don’t leave them on hold! Sure, there are lots of itineraries out there, but finding a perfect romantic getaway for couples isn’t as easy.
Here, we’ll help you explore the best of Naples, without the planning pains.
From sun-kissed beaches to fun activities to delicious dining options, we’ve got all the best recs straight from our personal experience. Get ready for a sprinkle some rose-colored magic on your time in Florida’s paradise coast! Naples city is about to be your own little playground of charm and sunshine.
History & Facts
Naples, Florida, is a picturesque coastal city known for its pristine beaches, upscale lifestyle, and fascinating history. Sitting along the Gulf of Mexico, Naples traces its roots back to the ancestral lands of the Calusa people before evolving into a world-renowned premier winter retreat. Today, it’s celebrated for its luxury vibe, world-class golf courses, and lively cultural scene.
Here are some fun facts and highlights from Naples’ history:
- The Calusa Indians thrived in the area for thousands of years before Spanish colonization began in the 16th century.
- The modern city was established in 1886 by former Confederate General John Stuart Williams and publisher Walter N. Haldeman, who developed it into a winter retreat.
- The Naples Company turned the city into a thriving tourist spot, drawing in wealthy visitors with its stunning beaches and bay.
- Built in 1888, the Naples Pier was key to the town’s early growth and remains a beloved landmark today.
- The Naples Airport (formerly a U.S. Army Air Field) trained combat pilots during World War II.
- Naples is home to one of the highest concentrations of millionaires in the U.S., making it one of the wealthiest cities in the country.
- Naples is known as the “Golf Capital of the World,” with more golf holes per capita than anywhere else in the U.S.
When to Visit
The best time to visit Naples is between November and April. During this time, temperatures usually hover around 70-86°F, with cooler days in the 60s and nights dipping into the 50s. The coldest stretch is usually in February and March, when daytime temps can drop to the low 50s for a couple of weeks.
Hotel recommendation
LaPlaya Beach & Golf Resort
If you’re looking for a relaxing escape, LaPlaya Beach & Golf Resort is the place to be! The views of the ocean and bay are absolutely stunning, and the rooms are super spacious. Their beachfront restaurant, BALEEN, is the perfect spot for a sunset dinner with your toes in the sand. Into golf? The courses are amazing, and the spa is next level with poolside massages.
Want to explore more romantic hotels? Check out these 7 Most Romantic Hotels in Naples, Florida.
How to Get There
The easiest and most convenient way to reach Naples, Florida, is by flying into Southwest Florida International Airport (RSW) in Fort Myers, located just 30 to 40 minutes away by car. If you’re driving, Interstate 75 is your main route, whether you’re coming from the north, east, or even Miami.
A Weekend in Naples, Florida – 3 Day Itinerary
Gallivanting through the Naples area for a romantic weekend getaway is just enough time to experience all this beautiful city has to offer. In this itinerary, we’ll share all our favorite spots, mixing iconic tourist must-sees with hidden local treasures.
Day 1:
On your first day in Naples, start with breakfast at The Rooster, a popular spot among locals. Their bananas foster French toast is heavenly, and the biscuits are legendary.
Visit Vanderbilt Beach
Vanderbilt Beach is a must for that classic Naples experience. Going in the morning will give you the best chance to find a good spot with fewer people around. Sink your toes into the powdery white sands, soak up the sun, and take a dip in the clear waters. You can rent beach chairs and umbrellas, or simply spread out a towel and relax.
Explore Downtown Naples
Head over to Fifth Avenue South to wander through the many boutiques and galleries. Tin City is East of here, which has more quirky waterfront shops to peruse. Grab lunch while you’re in the area. We loved The Cafe on 5th with its smoothie bar and trendy decor.
Walk Naples Pier
After lunch, head over to one of the most romantic places, the Naples Pier, for a sunset stroll (just double-check if it’s open since there’s been some construction) and see if you can spot some dolphins!
Wrap up your first night in style at Tommy Bahama’s, where live music and tropical vibes make for a fun, laid-back atmosphere. Cheers to a great start in paradise!
Day 2:
Your second day in Naples is all about adventure and exploring the fascinating ecological wonders that make Florida so special. Start your morning with a quick breakfast at your hotel. You’ll want to head out nice and early to make the most of your day of adventure.
Hike Through Corkscrew Swamp Sanctuary
Corkscrew Swamp Sanctuary is about 20 minutes east of Naples. Take a sunrise hike along its iconic 2.25-mile boardwalk. If you’re a nature lover (um, who isn’t?), you’ll love the ancient cypress trees, wading birds, and maybe even an alligator in this pristine wetland.
Take an Airboat Tour in The Everglades
Next, drive to Everglades City and hop on an airboat tour at Captain Jack’s for an adrenaline-packed glide through mangrove forests and sawgrass prairies. It’s the perfect opportunity to spot wildlife like alligators, herons, and more. Just be sure to check tour times in advance!
Stroll the Kirby Storter Boardwalk
After your tour, take the scenic Loop Road drive, stopping for short walks at Kirby Storter Boardwalk and the Tree Snail Hammock Trail. Both offer quiet, immersive ways to soak up the Everglades’ wild beauty.
By the afternoon, you’ll probably be ready for some downtime. Chill by the hotel pool with a good book and a cocktail in hand. Later, freshen up for dinner at Jimmy P’s Charred, where you can enjoy Wagyu steaks and creative dishes to end your day on a high note.
Day 3:
Kick off your morning at Jane’s on 3rd, where you can enjoy breakfast all day (their French toast is legendary!). Snag a seat by the koi fountain for the best ambiance. This place is kind of a splurge, but worth it.
Visit Lowdermilk Beach Park
I recommend arriving as early as possible to snag a good spot at the beach. If you’re driving, this is especially important (weekends get packed!). Rent chairs and an umbrella, swim in the Gulf, picnic at the shaded tables, or just lie out like the beach bum you are.
Get Pampered at the Spa
After some fun at the beach, why not unwind some more? It’s your last day, so make it count! Treat yourselves to a couples’ spa treatment at your hotel (if they offer it — check ahead!). If not, the Ritz Carlton Spa is a great option, and you don’t need to be a guest to enjoy it. It’s pure luxury at its best!
Book a Sunset Cruise
For the grand finale, set off on a sunset cruise with Miss Naples catamaran. You’ll glide past Port Royal’s mega-mansions, sip drinks from the cash bar, and soak up the sunset with music.
Cap the night with a fancy dinner at Bistro 821 (modern American) or Lima (upscale Peruvian) — both are perfect for a romantic farewell.
Things You Don’t Want to Miss
- Pack up for a beach picnic and enjoy some quality time together.
- Swing by the historic Rod & Gun Club in Everglades City. It’s full of taxidermy, antiques, and old Naples charm. Grab a drink (but maybe skip the food).
- Catch a live show by The Naples Players at Sugden Community Theatre.
- While you’re at Lowdermilk Park, make sure you go shelling or try water activities like kayaking or paddleboarding!
Best Places to Eat in Naples, FL
Other Things To Do
- Visit Naples Botanical Garden – it has amazing tropical garden displays!
- Rent jet skis at Doc’s for an afternoon of adventure.
- Explore the Naples Zoo at Caribbean Gardens, perfect for animal lovers.
- Go to Marco Island, just a short drive away, for beautiful beaches and a laid-back island atmosphere.
- Check out vintage cars at the Revs Institute.
What to Pack
Clothing:
- Lightweight, breathable outfits (shorts, t-shirts, sundresses)
- Swimwear & cover-ups
- Comfortable walking shoes & flip-flops
- Light jacket or sweater for cooler evenings
- Rain jacket (just in case!)
Gear & Essentials:
- Sun protection: sunscreen, hat, sunglasses
- Insect repellent
- Reusable water bottle
- Small backpack and large tote for beach trips & excursions
Packing tip: Naples is warm year-round, but layers help with breezy evenings or sudden showers!
A Weekend in Naples to Remember
Without a doubt, Naples is sure to give you an unforgettable experience, with luxurious relaxation, jaw-dropping sunsets, and just enough excitement to keep things spicy — perfect for you and your better half.
Looking for more ways to spend your time here? Check out our guide on the Top 5 Most Romantic Things To Do in Naples for extra date ideas!
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Enjoy your romantic weekend in Naples, Florida!
FAQs
How walkable is Naples, Florida?
Naples is so easy to get around! It’s small enough to explore on foot or by bike, so if you’re into walking or cycling, you’re going to love it here. If you ever don’t want to walk, many hotels offer shuttle services to the beaches or downtown areas.
What are the rules for Naples beach?
Planning a visit to Naples Beach? Keep these important rules in mind:
– Glass containers, pets, and fires are not permitted on the beach.
– Parking requires either a Beach Parking Permit or payment at designated spots.
– Only park in marked spaces.
– Parking is prohibited between 11 PM and 5 AM.
When is hurricane season in Naples, FL?
Hurricane season runs from June 1st to November 30th, but the peak time for storms is usually between mid-August and late October. That’s when things really ramp up. Of course, hurricanes don’t always stick to the schedule — they can pop up before or after these dates too.
