San Marco Island: A Florida Family Vacation - Cleveland East Side Moms
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by | Mar 14, 2019 | Travel

This past month our little family of three boarded a flight in 20 degree weather and stepped out the other side into a delightfully warm 75 degree night.  We had arrived.  On our first family vacation and on San Marco Island, FL.



We started planning this trip back when Theo was only a few months old and therefore had no idea what his sleep/nap schedule would be like at this time.  So we ended up making our vacation decisions based on the following criteria:


The Trip Parameters


  1. It had to be a direct flight into the same time zone. Seeing as it was Theo’s first time flying, we wanted to minimize as much stress as possible and this seemed like a good way to do it. We also wanted to keep to his schedule as much as possible so staying in the same time zone was a no brainer.
  2. Whatever the destination, we had to stay at a Marriott. I say ‘had’ like it’s a bad thing.  The Marriott resort we stayed at was amazing.  There are some downsides to a spouse that travels but one perk is definitely all those travel points.
  3. We needed to go somewhere warm. And apparently so did everyone else.  Because every person who we met down there that didn’t live there was from Ohio.


The JW Marriott on San Marco Island fell neatly into those parameters, and so it was. Our timeline was four full days bookended by travel days. The vacations I grew up on and all the travel I did pre-kids were always pretty much packed to the brim in terms of itinerary. But we really wanted this to be low key with Theo being so young still and this turned out to be the perfect place and plan.


I’ve never heard of San Marco Island but thanks to Google we quickly became familiar with it. We learned that Naples and the Everglades were close by and decided to spend two of our days doing day trips to those areas and the other two just hanging around close to where we were staying.  A quick look at our itinerary is below.


The Itinerary

Day 1: Travel day, check in, quick dinner from hotel at Quinn’s

Day 2: hang out day, breakfast, nap, pool time, nap, Snook Inn for dinner

Day 3: Naples day trip, lunch at Another Broken Egg Café, Tigertail Beach park playground & lookout on the way home, take out sushi for dinner

Day 4: Everglades day trip, lunch at Havana Café of the Everglades on the way to Shark Valley Tram Tour 2PM-4PM, take out dinner from Quinn’s

Day 5: beach & pool day, date night dinner at The Oyster Society

Day 6: Travel home



The Resort: JW Marriott Marco Island

So, like I was saying, on our lounge days we just hung around the hotel. And by hotel, I mean resort, which for those traveling with kids actually makes a huge difference, I think. They have three pools, a ton of daily programming that’s kid friendly (they give you a brochure with all of this laid out by day when you check in) and a handful of restaurants on site. It’s truly a place you don’t have to leave if you don’t want to.



Oh, and you’re basically five steps away from the beach, as in the resort is on the beach. Every night they have a fire dancer who dances at sunset which seems to be a draw for all the kiddos and they can get their picture taken with him after the show. They give you cards that you can exchange for beach towels and you can throw your towels down on some pool chairs in the morning to reserve a spot before everyone starts camping out for the day.



One other thing to note about this resort is that they have an entire tower that is adults only with an adults only restaurant and an adults only part of the beach. I went to check out that area one day and it looked pretty inviting. Oh, and there’s a spa pool too where I took part in a floating yoga class (this is part of the free daily programming on offer; see pic below!) that’s also adults only, I believe. So kid friendly vacation or romantic getaway for two, the JW Marriott San Marco has got you covered.



Day Trips:


Naples is a quick 30 minute or so drive north of San Marco Island. We originally heard a lot about Tin City as a place to go but upon arriving quickly realized it was a tourist trap and got out of there. We ended up parking in a garage around 5thstreet and just walked around Old Naples. I really wanted to go to Café Nutrients for lunch and we walked all the way there to discover they had closed for the day do to unforeseen circumstances. But it looked so cute inside and with healthy fare I’d definitely recommend going to try it out if you find yourself in the area.


Everglades National Park

I grew up on National Parks and absolutely love visiting them, so going to the Everglades was a must. It would also be Theo’s first National Park which just made me happy. When people talk about the Everglades, I think a lot of people think about the airboats, but upon further research I learned that airboats actually aren’t allowed in the Everglades because they’re so disruptive.  So you see them on the outskirts of the park. We were trying to decide between a tram tour and a boat tour and ultimately decided on the tram tour because it was just a safer bet with a baby. I also think, looking back on it, being on a boat for 2 hours in the scorching sun really isn’t my idea of fun. At least the tram had a roof for some shade.

The tram tour was nice, it was a slow scenic ride through the park with a ranger that guides you through it and points out and teaches you about the wildlife that you see. It’s a much different park than say, the ones out west with their wide sweeping panoramas that take your breath away, but it was beautiful nonetheless. The only bummer was that our tram broke down a mile or two from the end because the engine over-heated and we were stuck for about 20 minutes until someone came to rescue us.  Theo was pretty much at the end of his rope by then so that wasn’t the best. But overall, it was a nice experience and I’d recommend it for anyone looking for an easy way to see the Everglades.


Where We Ate

Quinn’s on the beach – this is one of the resort restaurants and it had the BEST coconut shrimp. Seriously, so good. I got it a couple times. Also, their Miami Vice was a quintessential frozen beach drink that just really hit the spot.


The Oyster Society – this was where we went for our nice date night dinner with Theo in tow. We just went early so Theo was still in a good mood (around 5) and sat out on the patio under an umbrella. Really good food, really attentive service, and kid friendly. Win, win, win.


The Snook Inn – this was heralded by many as a place you just had to go but I’m going to have to disagree. Average food, average service. They have live music and it’s on the water but it’s just not very well done and it was really pricey for what it was. Skip.


Havana Café of the Everglades – this place was so good! It was the halfway point between San Marco and where we were going for the tram tour.  We were able to grab lunch (get the shrimp tostones, SO GOOD) and Theo was able to eat lunch too on the stop which was the plan.  But it got very busy a little while after we got there (around 11) so plan accordingly.


Trip Purchases

Travel Stroller

We bought this travel stroller for the occasion which was nice to run through the airport with after we checked our bags and the car seat at the check-in.  And it was nice for him to be forward facing and see the world as opposed to using the other stroller we have which just clips in his carseat. So this was a nice travel-friendly alternative.

Beach pop up tent

We only actually went down to the beach one time and it was nice to have but ultimately didn’t get much use out of it. I’d think I’d skip it and just rent a large umbrella next time.

Bathing Suit

I got this bathing suit with the Hi Tide Bottom and the Double Scoop Top.  Best. Bathing Suit. Ever.  Especially postpartum.  It is super comfy, very flattering (hello high waisted bottoms!), machine washable, super simple.  I recommend you get you one. Stat.

Snooze Shade

Get yourself a blackout cover for the pack n play. The resort had a pack and play for us so we just took this pack n play cover with us and Theo slept so well I just couldn’t believe it.


We also brought our monitor to bring outside with us while he slept because the balcony door was so thick that you couldn’t hear any noise from inside, outside, or vice versa. This was nice because we didn’t have to keep opening and shutting the door to see if he was awake or not. So we didn’t set it up to see him, although if you wanted too I’m sure you could probably rig something, but hearing him was enough for us.


A note about the balcony on our room.  Traveling with a baby can be tough, mostly because of the organizing things around naptimes and the early bedtimes which basically confine you and your spouse to the room. Having a balcony saved our nights and allowed us to have a space for after Theo went to bed.  If this is an option or if getting a suite is an option so your kiddo can have their own room I’d highly recommend it so your night can continue on after 7PM.


I was actually amazed at how well Theo did and we ended up having such a good time. I’d lie if I said I wasn’t nervous it was going to be a complete disaster. On the way home our flight was overbooked so we opted to take another plane.  Lucky us, we got some travel vouchers out of it so we’re already planning our next adventure for the fall!

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