Naples, FL: What To Do (And Wear)


As Spring Break approaches I find myself a leetle regretful that I didn’t plan a warm weather trip for us this year. I mean, we’re so much closer to Hawaii here in Portland and we still haven’t been…next year maybe I can write a travel post on that trip! (Pinky, are you reading…)

We were fortunate enough to get to visit my parents in February in South Florida this year, though, for some sunshine. (You may have seen a few pics on my Instagram account @elletrain) The weather was in the low 80’s for at least half of our trip and it was lovely. We got a date night, I got some mama time and of course we had some trips to the beach while we were there. I did a little run-down here of some of our favorite activities and some suggestions on what to wear and pack if you’re planning a trip to the Sunshine State.

The Location

Naples is on the southwest coast of southern Florida, just south of Fort Meyers (the closest airport). It’s quite close to the Keys and stays warm year round. It’s been a popular retirement location for years, as are many places in the state, but we’ve noticed a growing younger crowd lately and with that fun attractions for families. Here are a few of my favorite places around town and some well-tested suggestions from my newly-localite mom, too. (Thanks, mom!)





The To-Do List


Naples has a beautiful downtown area that locals refer to as Old Naples. The architecture is stunning and it’s fun just to walk around and check out the gorgeous buildings and homes.  There are fancy shops, art galleries and many great restaurants for brunch and beyond. Some of our favorites are Ridgeway Bar & Grill for brunch/lunch (and ask for the patio area!), Jane’s (breakfast/brunch – disregard the website, the food is excellent), Bleu Provence, Tulia (one of my faves), Sea Salt for oysters and delish fancy seafood, and Chops.


Striped dress – Faithful the Brand Phoebe Dress – This is adorable and so beach perfect. Wear with sandals or sneakers for a great day or night outfit.

Woven clutchKayu Pineapple Woven Straw Clutch – Such a cute pattern and perfectly beachy.

Sandals (same pair I’m wearing) –  Avarcas Pons Classic in Taupe (c/0) – I really love these and have had a few pairs for years. They’re comfy and break in nicely and the leather is super smooth so I haven’t had a problem with blisters or rubbing. Only in whole sizes and they stretch, as good leather should, so if you’re between sizes, size down.

Sienna’s dress – (Cat & Jack sold out) Old Navy Striped Swing Dress – insanely cute!

Sienna’s sandalsAvarcas Frailera Sandal (c/0) Sienna wore these everyday for a week when we got them 🙂 And that color!



The beaches in the area are gorgeous – white sand and full of pretty shells. The Gulf of Mexico waters are warm and pretty calm. It was a little too cold for swimming in regular suits when we were there in early February, but it was still nice on the beach and warm enough for sunbathing and shell hunting. The sunsets are seriously not to miss. Go to La Playa for dinner and sunset watching. Many of the beach clubs also have dining with gorgeous end-of-day views. Also take a walk on the boardwalk through the estuary in Pelican Bay. It’s a great walk and you can see some interesting wild life (yes, watch out for gators).


Swim top (similar) Coco Rave Tatum Fringe Bikini Top – Fringe (and high neck) are my new favorite swim top style. Mine is sadly sold out, but loving this one from Macy’s.

Swim bottoms Gap Classic Bikini Bottoms Go-to bottoms that cover and go with most every top. Wearing size Medium, for reference.

Cover-up (not pictured) Spaghetti Strap Loose Fit Harem Jumpsuit – I have one similar to this that I adore for warm weather. It’s perfect as a coverup and an easy, cool, no-brainer piece to wear anywhere really.

To Bring – SunglassesHalfmoon Magic Cat Eye Sunglasses – I love these fancy sun goddess gold and pink sunnies!

To Bring – Towel – Turkish Beach Towel – These are the best towels. They dry quickly, are lightweight and easy to pack and can double as a sarong.



We had a few fun nights out while we were there. One night we went up to the Mercato shopping area and had a casual dinner and drinks, but on a previous visit we ate at Masa and really enjoyed their food and margaritas. You can catch a movie at Silverspot Theaters, too, where you can enjoy upscale snacks and drinks with your flick.

For Pinky’s early birthday celebration, we did a really fun sunset dinner cruise on the Naples Princess. The dinner is buffet style and actually pretty tasty, but you really go for the views and the sunset (and the occasional dolphin sightings!) Be sure to snag a top deck seat when you first board, grab a drink and enjoy sailing through the canals past all the insanely fabulous homes along the waterways. It sounds like a really cheesy touristy thing…maybe, but it’s so fun and worth it!

Another great date spot for any foodies or fellow crab aficionados is Kelly’s Fishhouse. It’s definitely old-school fish house style and boasts being the oldest seafood restaurant in Naples. Trust me. You go for the stone crab. Florida stone crab are the most delicious things on planet earth. They are unique in that they really only live in this part of the world. They are fished from mid-October to mid-May and only the claws are harvested, not the whole animal (they regrow them!), so they are quite a sustainable seafood. Now I must stop talking about them because I just went to Florida and it’ll be a while before I get back. #sadface


Cold shoulder topAbercrombie Cozy Cold Shoulder Sweatshirt – I adore this fleecy sweatshirt that is still ok for date night. Am I the queen of finding the most comfy things I can get away with besides PJs for a night out? I think the crown goes to me, yes. Wearing a small, for reference.

Lace-up heelsJeffrey Campbell Cors Suede Peep Toe – Current fav badass heels. They are comfy and stay on well due to all the laces. Love.



There is plentiful shopping in Naples and of course the shopping areas are outdoor. My favorite for local shopping is downtown and for a beautiful shopping center experience (think upscale shops and water fountains) Waterside Shops is gorgeous. Gallery perusing would be a great activity for some mama time, too. There is not a shortage of watercolor beach landscapes, to be sure, but I was really impressed with some of the variety of the art there. Get a coffee and stroll through some of the downtown galleries for a fun afternoon and be sure to check out various art events throughout the year.


BlouseGap Split-Neck Long Sleeved Blouse – This is so airy and light and just what you want on a beach vacation. I’d pair it with shorts for sure (I’m a horrible packer even after all these years of traveling a lot and I didn’t bring shorts to Florida – please, learn from my mistakes) Wearing size small, for reference.

JeansMother Denim The Looker Crop Skinny – Mine are a pair sold out at Anthro, but these are the same fit and a cooler, more destructed wash. LOVING Mother denim. The fit is excellent and it’s a good-butt jean.

SandalsCopper Birkenstock Arizona Sandals – I’ve wanted these since last year. Can Birks be chic? I think so.

Kiddo Fun

If you need a break from all the sand in everything and want some kiddo-friendly activities, visit the Children’s Museum of Naples and the Naples Zoo.

The children’s museum is top notch and is great for a rainy afternoon or first thing in the morning because there is coffee available. Thanks CMON. It has a crazy, adorable entranceway that reflects the insanity fun inside.

The Naples Zoo (formerly Jungle Larry’s but we won’t talk about exactly how long ago) is a lovely walk through zoo where you can feed a giraffe, take a boat ride to Monkey Island, or have your face painted like a cheetah (see above for lovely grandmother selfie!) The zoo is one of the top in the country when it comes to donations to conservation efforts worldwide, so your to-zoo or not-to-zoo struggle (mine, always) can feel a little more okay with making this a vacation stop.


What I Packed (and Should Have Packed)



If you’re heading to Naples or have any other recommendations, I’d love to hear about it! I only wish it were much closer to Portland, as does my mom, I’m sure. If you want to check out my new fav taupe booties I picked up while on this trip, follow me on Instagram @elletrain. Happy Spring Breaking everyone and don’t forget to wear sunscreen