Our Winter Getaway to Naples, Florida

With our baby boy on the way in April, we decided to take one last trip as a family of three.  We had so much fun in Orlando several weeks ago that we wanted to head back to Florida – but this time to a new city: Naples.  

Why Naples?  Since we’ve moved to the midwest it’s a city that seems to pop up all the time as a popular destination for escaping the winter cold and a great spot for families.  

We got super lucky with the weather the week we were gone – it snowed almost a foot in Central Indiana and was very cold.  Southwest Florida was in the upper 70’s (low 80’s) with clear blue skies.  The weather was exactly what we were looking for.  

How we got there:

Direct flight from Indianapolis to Regional Southwest International Airport (RSW) just outside of Fort Myers.  We rented a car (which I’d highly recommend as there was a lot during this trip that we used it for) and drove about 35-40 minutes south towards Naples.  As far as a carseat goes, we rented one with the vehicle for Eloise so that it was one less thing we had to travel with. 


Where we stayed: Naples Grande Beach Resort

Having never been to Naples before, we did a lot of research before picking a place to stay.  Our most important/deciding factors were: clean, a couple of food options on site, big pool with a kid friendly section, easy beach access, and generally positive reviews.  The last one is almost impossible in any hotel search – most people don’t log on to travel sites to say “nice things” about hotels they have stayed at, which is unfortunate. (Something we’ve definitely learned through all of our travels!).  End of the day, we were comfortable with the location and amenities that the Naples Grande offered and we were generally very happy with everything upon arrival.

The valet and front desk staff were very welcoming and helpful.  The lobby is beautiful with some great areas to sit and get some work done or enjoy a coffee or a glass of wine.  There’s a small market next to the front desk with groceries and just about anything you may need for a trip to the beach or a midnight snack.  

Our room was huge! Very clean, plenty of space and some incredible views of the ocean one way and inland towards the city the other way.  Had there not been a beach or pool, we could have easily spent a full afternoon just relaxing on the patio!

It’s up to you how often you want your room cleaned – we chose to not have our room cleaned during our stay as we really don’t make too much of a mess.  We gather trash as we go and leave it outside for the cleaning staff.  We requested new towels about halfway through and some extra water – otherwise, the room was absolutely up to our standards of clean.  We felt very comfortable.

One of the best parts about staying in this hotel is the beach access.  They have golf carts that operate as shuttles and take people to and from the beach all day.  There’s a pickup spot just beyond the pool and the shuttles come by every few minutes. Takes about 5 minutes in the shuttle or about a 20 minute walk to get to the beach.  Once you get to the beach there is a desk where you can rent chairs, umbrellas, or day beds.  The staff sets up the whole thing for you which is incredibly nice to skip that step of beach set up and take down.  Makes for a very relaxing experience.  There are shovels, buckets, and sand toys available for the kids to play with (no charge) and Eloise had a blast!

The beach is beautiful, but did get pretty crowded the second day we were there as the weather was perfect.  My recommendation would be to head down to the beach early and reserve your spot.  We were lucky to get a spot and we were there shortly after noon.  

There is a restaurant that serves food right above the beach.  Mostly salads and sandwiches which were great for a day at the beach and saved us having to pack them.  There’s also a restroom right there so no need to worry about heading all the way back to the hotel.  


Covid Precautions:

Before we go much further here, let’s get the Covid portion of this blog post out of the way.  The law in Collier County (Naples) during our trip was that you must wear a face covering while inside at any public building or business or outside when it is not possible to maintain 6 feet of social distance.  As always with these posts, I’m not here to give you an opinion, but just to tell you what we experienced.  

I’ll keep this pretty short and sweet: If you are one who is very cautious about wearing your mask at all times and is uneasy about others not wearing their mask – this should probably not be at the top of your list of current vacation spots.  

Downtown Naples was busy for dinner every night we were there and it was probably the busiest spot we’ve traveled too during Covid so far. With that being said, people respected the social distancing guidelines and did wear masks inside and while walking to their table at restaurants. Once again, we felt very comfortable and safe. 



Where We Ate:

Osteria Tulia – Delicious italian food, right in the heart of downtown.  We had dinner here and were very happy with everything we ordered.  The apple salad was delicious and all of the pastas looked incredible.  We shared the bucatini and the ravioli.  Great wine list and very comfortable atmosphere.  The patio was full, but they also have a more spaced out outdoor garden area if you prefer.  We’d absolutely eat here again.

HobNob – Also on 5th Avenue, downtown Naples.  Cool spot with a great list of cocktails and fun menu items.  Seafood, steaks and lots of fun appetizers to share.  There are only about 4 tables outside so if you are looking for outdoor dining, this might not be the best spot for you, but the atmosphere inside is very fun!

Ice Cream – No shortage of fun ice cream/gelato shops in Naples.  Our two favorites were Kilwin’s Ice Cream shop and Gelato & Co.  Kilwin’s is a little bit of a throwback/classic ice cream shop where you want to eat everything in the place.  So delicious!  Gelato & Co is a bit more modern with tons of fun treats and great spots to sit in or outside.  

Matra – Located next to the hotel lobby/front desk, we had dinner here the first night.  Food was good, but nothing out of this world spectacular.  The convenience of this being downstairs and having to go anywhere after a day of travel was awesome.  Right next to this is a small coffee bar called Spressi.  They have coffee, snacks, pizza, and gelato. This was Eloise’s favorite food spot at the hotel!  There’s a full bar next to the main pool that also serves food (nachos, quesadillas, salads, etc) and the bartenders made a great margarita for Bryan and some fun mocktails for me!

True Food Kitchen – we hadn’t eaten at TFK since we lived in Northern CA and we both love their menu.  Very healthy food, but you’d never know it as it tastes so good.  Bryan absolutely loves their gluten free lasagne & we ALWAYS start with the hummus appetizer…a MUST!

PS. Over by True Food Kitchen is a beautiful outdoor mall called the Waterside Shops with some of our favorite stores, Gucci, Lululemon, Tory Burch, Free People, Louis Vuitton, etc. We went there twice to just walk around and browse. A great spot if you are looking for some shopping!


(HOBNOB deviled eggs and charcuterie board)


What We Wore:

All items I  styled and wore on this trip can be found by clicking the images directly below!

(I was 7 months pregnant on this trip and all of these bathing suits worked perfectly for a bump!)


All in all, it was a great trip to Naples!  It’s a city we’d definitely head back to and will look forward to exploring it even more next time around. Highly recommend if you haven’t been yet and hopefully this post gives you some great ideas on where to start when you visit!

1 Comment

  1. Charles berry
    April 4, 2021 / 6:31 am

    Well-written. A short and concise description of key points on Naples. So much more could be experienced with a longer stay.
    Hopefully, a follow-up article after a longer stay?

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