Between the easy access to the beach and the full lineup of fine dining, high-end shopping and outdoor activities ranging from the tame to the adventurous, Naples, FL has no shortage of romantic destinations. That means the pressure cooker sure starts to turn up the second you’ve asked out that “special someone.”
Suddenly, you find yourself drawing a complete blank when faced with planning that perfect date.
Whether you’re aiming to impress a long-term crush you’ve always admired from afar, tackling the nerves that come along with meeting someone face-to-face that you’ve only spoken with online, or you’re looking to show your longtime love a new, romantic side of yourself, dating is hard. Plain and simple.
Since we feel your pain, we’ve put together a guide to the best date ideas in Naples, Florida that are sure to impress the object of your affection. Whether this is your first date or you’re celebrating a milestone anniversary, let’s get prepared for the best date of your life.
First things first: if it’s a first date, you should keep some simple rules in mind (or perhaps you’re due for a refresher). While we’re confident you’re suave and smooth and you’ve got this stuff down, it’s good to have a reminder from time to time. Here are a few things you should keep in mind when prepping for the big night:
- Be There on Time — Leaving someone waiting is a sure way to start the romance off on the wrong foot. Show up a little early to allow for traffic, parking challenges and more. Aside from showing up on time, be mindful of the other person’s schedule. Rescheduling plans a couple hours before the date is disappointing for the other person and may not give them sufficient time to make other plans for the evening.
- Consider the Dress Code — While it should be a no-brainer, if you’re going to a nice restaurant, dress accordingly. Men should wear a nice shirt, slacks and dress shoes, while women can opt for a dress or nice pants and a top.
On the opposite end of the spectrum, there’s no need to go all-out if you’re going to the beach or the farmer’s market. When in doubt, do a quick internet search before you get dressed and you’ll be sure to match the setting.
- Don’t Make the Conversation All About You — Look, as human beings, we all love to hear the sound of our own voice. It’s a biological fact, and when first date jitters enter the mix, all bets are off. But we also like to know that people want to hear what we have to say. Be an active listener and take turns talking with your date. You just might like what you hear.
- Don’t Act Like it’s a Job Interview — While it’s great to ask questions, everyone has been on at least one first date where the other person more or less grills them over dinner. Treat your date as you would a friend. You can ask about work or where they went to college, but it’s better to create a sense of fun, rather than a sense that they have to prove themselves.
- Be Yourself — Yes, this is just about as clichéd as it gets, but it’s always good to remember to stay true to yourself. Don’t pretend you like something you hate, or that you follow a strict vegan diet just because your date does. If the person you go out with falls for that fake version of yourself, you’re just prolonging the amount of time it takes before they realize you’ve been lying. It’s never good to start off on a lie, after all.
While these things seem like common sense, it’s easy to forget basic manners the second pre-date jitters enter the fold.
Now that that’s out of the way, it’s time to start planning! First, determine what kind of date you’d like to go on, and try and gauge whether you think the other person is up for the same. It’s always good to have a few suggestions in your back pocket in case you’ve miscalculated.
Whether you’re up for brunch, beach or a nice dinner, here’s a look at some romantic things to do in Naples.
Start the Day With a Brunch Date
Wake up and go to brunch. Sure, we tend to think of dinner as being the most romantic meal to eat with a loved one, but a brunch with the works — we’re talking bottomless mimosas, thick-cut bacon and perhaps a hearty side of pancakes — can be a truly wonderful date option.
Here are a couple recommendations if you’re looking for a spot to take your sweetheart.
- Le Lafayette — A fine dining brunch experience, Le Lafayette features a solid lineup of French Cuisine, a custom omelet station and more. Celebrate the day early with champagne, and take some time to appreciate the local scenery.
- 7th Avenue Social — Priding itself on its Modern Southern menu, 7th Avenue Social features a fantastic Sunday brunch that elevates the basics. Try Duck Confit and Waffles or the Cotija Cheese Quiche, and don’t forget the drinks! Bottomless mimosas and bloody Marys will wash down all those rich breakfast foods beautifully.
Go for a Walk
Alright before you accuse us of failing to plan for our date planning guide, hear us out. Naples is the territory of pristine beaches, amazing sunsets and miles of gorgeous scenery. No movie can compete with what our beautiful city has to offer in the flesh.
Here’s a few of our favorite places to walk around:
- Naples Pier — Located right off the 12th Street beach, the Naples Pier is the perfect place to take a walk in the morning with a cup of coffee in hand, or to venture out just in time for sunset. In addition to the ability to walk out over a vast stretch of the Gulf of Mexico, the pier is a known spot for fishing, bird watching and dolphin sightings.
Sometimes it’s good to go with what works, and a Naples sunset always delivers.
- Naples Botanical Garden — A lush, idyllic garden that also focuses on green issues, the Naples Botanical Garden is the perfect place to walk around and get to know your date a little better. Take in the diverse collection of flora and just settle in for a good chat.
- Palm Cottage — If you’re looking for something a little different than the beach, Historic Palm Cottage features guided tours of the oldest house in Naples. Made from sand, shells and more, Palm Cottage makes for a great date spot for anyone who’s interested in history or architecture, or who just wants to get to know the city a little better.
Get Ready for an Adventure
If you and your date are the adventurous types, you’ll likely want to try something a little more intense than the botanical garden. With the sea literally at your fingertips, think outside the box for the perfect day at the beach.
From kayaking and sailing to a charter boat fishing escape, these dates fall a little outside of the usual “dinner and a movie” box.
- Everglades Area Tours — Show your date a different side of Naples! Look toward Everglades National Park for a closer view of the surrounding swamp lands, which are surprisingly picturesque. Try a kayak tour, which can last anywhere from a few hours to a few days, providing the perfect opportunity to get to know more about the person you’re dating.
Additionally, this company offers a solid lineup of tours that includes charter boat fishing and tours of the islands surrounding the Naples area.
- Sail Away — Head over to New Moon Sailing and climb aboard a 40-foot sailboat. There’s a variety of packages available, from a five-hour tour featuring champagne, a picnic lunch and plenty of dolphin sightings, to a nighttime adventure that departs at sunset and doesn’t return until the sun comes up. Whatever you decide, you’ve got a recipe for romance.
- Keewaydin Island — A popular pit stop for boats, Keewaydin Island is the perfect place for a romantic picnic lunch after a long session on the water. With its white sands, clear waters and easy walking, nothing beats this undeveloped beach island as far as romance is concerned. It’s only accessible by boat, so you’re better off making a day of it.
How About a Luxurious and Romantic Staycation?
Looking for something that feels a bit more special than lunch at your favorite restaurant or a walk to the farmer’s market? Well, we’ve got a few picks that’ll have you feeling like you’ve upgraded your life. From the spa to drinks on the veranda, show your date you appreciate the finer things.
- The Spa at Naples Grande — Granted, a trip to the spa probably isn’t the right setting for a first date, but if you’ve already got a special someone, a relaxing trip to the spa complete with a couples’ massage package is the perfect way to show you care, or to celebrate a birthday or anniversary.
Located right on the beach, the Naples Grande resort is the perfect getaway, whether you live in town or are just visiting for a while.
- Fifth Avenue South — After a recent revamp, Fifth Avenue South has become a bustling destination for locals and tourists alike, featuring a solid lineup of fine dining, shopping and prime people watching opportunities. Make a day of it and take in the sights, from art galleries to local events.
This historic district is a great place to catch a bite to eat, including a variety of rich desserts that are just perfect after a long day of shopping or beach activities.
- La Playa Resort — You don’t need to be a tourist to enjoy the local amenities. Book a cabana for a few hours and kick back poolside. Order some chips and guacamole and a pitcher of margaritas and soak up the sun. Or, live a little and order some wine and chocolate-covered strawberries to up the romance factor.
Either way, nothing beats a day of lounging around in style. This is a much better low-key date option than your typical watch-a-movie-at-home kind of date, if you ask us.
For a Night out on the Town
Sure, it’s a cliché, but dinner and a show is always a good pick — not to mention dancing under the stars or taking in the glorious Naples sunset. If you’re in it for some classic romance, here are a few options that you and your date are sure to fall in love with:
- Mercato — A Naples hub for dining, drinks and more, this is the ideal place to take a date. Whether its cocktails and small bites — Mercato features 15+ restaurants with a daily happy hour — or to try something new, check out First Wednesdays if you’re itching to put on your dancing shoes, or perhaps one of the free concerts if live music is more your speed. In any case, there’s something fun for everyone.
- Silverspot Cinema — A comfy, upscale movie theater located in the Mercato shopping center, Silverspot has the added benefit of serving beer and wine to be enjoyed as you watch. This is the go-to spot to catch the latest flick before going out for a late-night drink or a meal.
- Ristorante Ciao — An Old Naples staple, this glamourous Italian dining spot is the quintessential dinner date with all the works, from seafood pastas to fine wines. The warm and inviting atmosphere provides fertile ground for good conversation to go with the tasty food.
- USS Nemo — Looking for a memorable meal to share with a special someone? USS Nemo is the perfect spot for a little upscale romance. From the classy yet whimsical underwater theme to the impeccably cooked entrees, USS Nemo is sure to help you set the tone for a lasting romance — or, at the very least, a night out to remember.
We certainly hope we’ve helped you narrow down date ideas in Naples, FL! Now you can go ahead and focus on selecting just the right outfit and locking down a time, or perhaps getting a haircut. No matter where you decide to go, stick to the things you like, but also don’t be afraid to step out of your comfort zone, whether that’s by asking out the person you’ve been holding a torch for, or trying an activity you haven’t thought of before.
While we might be a little bit biased here, we think USS Nemo is an excellent setting for a date, whether it’s the first, second or hundredth. Helmed by Nicolas Mercier, recognized as one of the Best Chefs in America for four years in a row, we’ve got a dish for everyone — whether you’re craving branzino or tuna, steak or something a bit more vegetarian.
We can only seat complete parties for reserved tables. Please be sure your entire party has arrived before checking in with our hostess.
"With its subtle submarine motif and obvious seafood obsession, USS Nemo (239-261-6366) is among the most original restaurants on the Naples dining scene these days, and it has the fan base to prove it."
Chelle Koster Walton
"The miso broiled sea bass with citrus-ginger butter sauce is almost worth a trip to Naples in and of itself."
The New York Times
"I can tell you without hesitation, this is THE BEST and most consistent restaurant in Naples. I can guarantee you will not be disappointed!"
"Most consistently great restaurant in Naples!"
Monday-Thursday 4:30-9:30 pm
Friday & Saturday 4:30-10:00 pm
Sunday 4:30-9:30 pm