Do you ever feel like you need a vacation from your vacation? Ouff, I sure do. My notorious over-packing doesn't just apply to my carry-on bag — it manages to trickle its way into my trip itineraries too, leaving me exhausted and drained from my "holiday." Naples couldn't have come at a better time. After battling burnout, being horizontal in southwest Florida for two weeks was like a jolt to the system. 

While other parts of Florida, like bumping Miami and the laid-back Florida Keys, spoke to us too, I was looking to live my best coastal grandma life, and Naples fit the bill perfectly. The population (with a median age of 65 years old) swells in the winter months with snowbirds flocking to warmer temps, early retirement and pickle ball courts. 

It's a place where the lawns are so perfectly manicured, the grass looks likes it's airbrushed; where gated communities come with names like Orange Blossom Drive; and people don't just talk about politics, they plaster their "freedom picks" onto their private yachts. Yet, it is a friendly town — despite the, ahem, questionable driving (p.s. you'll need to rent a car here). The people who call Naples home, even for a few months of the year, are happy to chat with you in the grocery aisle, ask how your day is going (wonderful!) and offer parking hacks for the best spot on their world-class beaches

They'll show you where to find the rarest shells, save your seat by the pool and tell you to go beyond the twinkling lights of 5th Avenue South and Third Street South to really discover the best things to do in Naples. But, they won't blame you for doing absolutely nothing at all. 

What to do in Naples, Florida

Naples Princess Cruises

Naples has its fair share of private yachts, but if you don’t have a cool million to spare, an afternoon on the public Naples Princess is a real treat. Hop aboard any of their daily cruises and explore the serene Naples Bay and Gulf of Mexico from the comfort of your luxe three-story ship. Their Sunset Dinner Cruise was one of the highlights of our trip. The experience took about two hours and we spent most of it spying on Port-Royal’s multi-million dollar homes while eating prime rib and drinking wine. Bonus: We got a killer sunset and spotted dolphins jumping in the waves.

Naples Botanical Garden

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Immersing yourself in nature is perhaps the simplest way to lower stress levels, and there's plenty of serotonin to go around at the Naples Botanical Garden. It's USD $25 for general admission, but I think the 170 acres of tropical tranquility are totally worth it. The lush gardens are expertly designed, perfectly manicured and bursting with colour. You'll question your ability to keep a single house plant alive, but it makes for a relaxing and visually stimulating way to spend a couple hours away from your phone screen.

Celebration Park Naples

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Yes, we love a beach sunset, but I recommend heading to Celebration Park in the Bayshore District for sundown with a side of live music right on the water. It's a popular place, so go with a small group on a weekday if you can. Have some friends line up for snacks at the food trucks while you post up at the waterfront bar and watch the boats dock. Live music starts at 6 p.m. every day, and the park closes at 9 p.m., because, well, Naples.

Where to eat and drink in Naples, Florida

Andre’s Steakhouse

Andre's was our favourite meal in Naples, hands down. The classic American chop house came to the south all the way from New York City in the 90s, and it looks like it hasn't changed since then. They do steaks right here. The house specialties (N.Y. strip, Porterhouse or T-Bone) are dry-aged for an "undisclosed time" (I tried to get it out of our waiter, but he wouldn't budge) and served rare on a sizzling hot platter.

The kitchen has the honour of cutting up the perfect steak for the table, so all you have to do is sit back and enjoy the best bites of your life. Do yourself a favour and get the side of fried shoestring onions. Ask for a dessert menu, and you'll get a silver platter filled with "desserts of the day" to choose from.


You certainly can't miss the blaring BEST RIBS IN AMERICA sign on the outside of this legendary, laid-back smokehouse. While the big ass sign makes quite the statement, the slow-smoked ribs pack some big flavours. Their baby back ribs are imported all the way from Denmark — and, boy are they tender, juicy and slathered in an award-winning sauce that you'll be licking off your fingers for hours. You get all the fixings too like baked beans, creamy coleslaw and garlic toast. But the real treat is the price — one full rack with sides is less than $20. Get here before 5 p.m. for cheeky early bird deals. We came, we ate, we bought the t-shirt.

21 Spices

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We followed the mouth-watering scent of smoking tandoori and steaming biryanis all the way to 21 Spices glowing patio. After spending a few days filling our faces with steak and seafood, the contemporary Indian dishes by chef Asif Syed were a welcome change. Their vegan menu more than satisfied our cravings for vegetables with dishes like spiced potato and green pea samosas and fragrant Punjabi daal with a kick of red chili. For mains, we had to do the Chef Asif Special Biryani: tender lamb, tandoori chicken and shrimp with aromatic rice and a fluffy potli naan. 


Seed to Table

I couldn't figure out why so many locals insisted we go to Seed to Table, a grocery store, during our visit. It took us pulling into the overflowing parking lot — with valet service — to realize this is not your average supermarket. The 75,000-square-foot mega store is like an indoor food theme park. It felt like we had walked into a sitcom with rows of perfectly stacked colour-coded produce and shoppers sipping and cheersing glasses of wine in the aisles — the carts even have cup holders!

There are four bars inside the fully-licensed store, along with food counters where you can order anything from fresh tacos to lobster rolls. The coolest part: You can choose an item from their meat or seafood department and they'll cook it to order.

Swan River Seafood

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You haven't had a crab cake until you've tried Swan River's beauties. The pure jumbo crab patties are broiled to a golden brown — not overly battered or fried — and served with their cajun remoulade sauce and fresh tartar sauce (if you ask nicely). I could have ordered seven for dinner, but it would be a shame to miss out on Florida seafood specialties like yellowtail snapper or black grouper. You can choose how you want your fish cooked (grilled, blackened, broiled or lightly fried), plus two sides. Save room, if you can, for a slice of key lime pie for dessert.

Where to stay in Naples, Florida

Naples Grande Beach Resort

It's easy to see how the Naples Grande Beach Resort got its name — it's huge. But, hey, you get more space to sprawl out across its 23 waterfront acres. Pool people will love the various watering holes (complete with slides) and decks for lounging. Just don't go in the pond because there's an alligator in there, OK?

If you're keen for the beach, take the hotel shuttle along the boardwalk overlooking protected mangroves to beautiful Clam Pass Park. Hotel guests have access to the comfy beds, towels and beach chairs all day. After nursing some cocktails on the bone-white sandy beach, we popped into the spa for a quick 50-minute recovery facial and quiet escape in the serene meditation garden. Then, we ended our evening with craft cocktails and fresh sushi in their lively lobby lounge, Mantra.