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Sara & Katie

Family Vacation to Fort Myers Beach, Florida

December 28, 2019

Family Vacation to Fort Myers Beach, Florida

December 28, 2019

[Photo heavy post – we’ve got many years of photos from our trips here!]

Sara here – coming at you with some warm weather memories during the dreary winter months here in Wisconsin. The holidays are over, and while the days are shorter, these months can draaaaag. Katie and I, along with our families, have a beach vacation coming up in a couple months so thought we’d share a past trip to get the ball rolling on planning. We’ve got our location, lodging and transportation planned, but hoping the next couple months of researching and preparing will help get us through the winter!

Justin and I have vacationed many times in Fort Myers Beach, Florida together, as this is a place he grew up going for family vacations and his grandpa now winters in the area. We’ve done this trip as poor college students on a budget and with our kids as a family vacation. For as long as Justin can remember, his family spent their Spring Break week in FMB, so it’s a nostalgic place and fun to bring the kids and make their own memories.

about Fort Myers / Fort Myers Beach:

Fort Myers is a city located in Southwest Florida, on the Gulf of Mexico. Fort Myers Beach is a town located on Estero Island, which is reached by crossing a bridge that connects the mainland to the island. It’s also near the islands of Sanibel and Captiva, which are other popular vacation destinations.

San Carlos Bridge that connects Fort Myers to Estero Island (Fort Myers Beach)

FMB is about a 7 mile long barrier island with very wide white sand beaches, a variety of restaurants, watersports, and lodging for many budgets.

In order get more out of your vacation rental or hotel in FMB, it’s important to understand the layout of the island to figure out what is important for you. Times Square is considered the “center” or hub of the activity – it has a large public beach, shops and restaurants and is used as a point of reference for the island.

  • North of Times Square
    • Quieter and less crowded
    • Mostly hotels/condos and vacation rental homes
    • Limited restaurants and dining options
    • Bowditch Point Park
  • Times Square
    • Busy area with the public beach
    • Variety of dining options
    • Lots of activity – live music on the boardwalk restaurants, ice cream shops, street performers, etc.
  • Southern End


The closest airport is Southwest Florida International Airport (RSW), about 30 minutes from Fort Myers Beach (note: traffic across the bridge can be VERY slow during peak times). A smaller airport, about 1 hour away, is located in Punta Gorda, FL (PGD).

We’ve used various methods of transportation to arrive at the beach. The easiest and cheapest is Justin’s grandpa picking us up 🙂 Many years ago, before kids and Uber existed, we took a $50 taxi each way from the airport to the beach. We also used the Lee County Transit bus system on another trip. We got lucky one year with a really affordable car rental through Costco Travel and rented an SUV at the airport.

One of the great things about FMB is easy and affordable transportation once you’re on the island. A car is completely unnecessary – there is a free tram and an inexpensive trolley that runs up and down the island, which seems to be about every 15-30 minutes depending on time of day (note, this is seasonal – check the website for schedules before you go). Alternative options for transportation are bike rentals, as there are many locations for this. Even on trips with a car rental, we’ve only used it for groceries (note: Publix also has grocery delivery, which we took advantage of on our most recent trip when we didn’t have a rental car).

Free tram to get around the island
So many places within walking distance
Old photo from 2007, but the San Carlos Bridge is easy to cross on foot


FMB has a good mix of lodging options for a variety of budgets. Do your own research depending on your price point and wants/needs, but listed below are a few places we’ve stayed.

Outrigger Beach Resort
We stayed here in 2010 before kids and were on a budget. It wasn’t anything fancy at the time, but had a nice tiki bar on grounds and a good restaurant. The beach was huge and had watersport and beach chair rentals next door. This was the furthest south we have stayed, and while the beach frontage was nice, it wasn’t my favorite location – I prefer to be closer to or north of Times Square.

Outrigger Beach Resort in 2010

Vacation Rental Home on VRBO – “Sunny Daze”
This was our favorite place that we’ve stayed – this was in December 2016 with two kids (age 1, 3). There was one house between the beach and our rental home, so it was a very short walk (30 footsteps to the sand) and was very convenient for going back and forth with young kids. The rental also included beach chairs, umbrella, and a wagon that proved to be SO helpful that trip. In mid-December, we were literally the only people on the beach except for people walking by. This is on the north end, so it was a good 15-minute walk (made significantly easier with our wagon) to Times Square but we appreciated the quietness no crowds. The price is also slashed if vacationing prior to the peak winter months, so we got a good rate and the weather was still in the 80s.

Some pretty good memories were made here during this trip!
Huge stretches of beach all to ourselves in mid-December

Estero Island Beach Club
We stayed here in March 2019 with two kids (age 3, 5) over Spring Break. This is an older resort and could use a bit of updating on the property, (Justin’s family actually stayed here when he was a kid) but has two pools, hot tubs, shuffleboard, a great stretch of beach, and location near many restaurants. It was so nice to move around from pool, beach, repeat. Many of these are long-term rentals (so it’s an older crowd) and can be hard to get weekly rentals but there may be some weeks that open up on their site. We were able to get a deal through Justin’s grandpa who is an owner, making it very affordable for us that year.

One of two pools at Estero Island Beach Club
Night swims at the resort

Pink Shell Resort
We didn’t stay here, but our good friends had a week rental and we were able to visit the resort and spend the day at the pool with them. This place was amazing! However, you pay the price for amazing, as it’s not cheap. Had it been in our budget, it would’ve been fun to stay here for all the kid-friendly options – great pools and nice quiet beach, plus the adult-friendly options like a poolside bar with delicious rum runners and outdoor dining. During peak time, like the Spring Break week we were there, they have a lot of fun activities for the families visiting so check it out!

Pool + Rum Runners at Pink Shell Resort

dining and restaurants

There are way too many restaurant options to mention, but you can’t really go wrong. We like to mix some easy home-cooked meals, cheaper snack shops & cafes, and a couple nice dinners out. Here’s a few of our favorites over the years:


  • Heavenly Biscuit
    • A must-do! The cinnamon rolls are delicious! It does get very busy and is a small place, so we usually grab cinnamon rolls to go. Cash only!
  • Reese’s Restaurant
    • Sit-down family restaurant. Also can get pretty busy.
  • Tuckaway Cafe
    • They’ve moved locations so we haven’t been to the new spot. Great place for yummy waffles and breakfast sandwiches, plus coffee drinks and smoothies.
  • Ray’s Pizza
    • We’ve had pizza delivered a couple of times from here
Smoothie break at Tuckaway Cafe (former location)
Sunset pizza party from Ray’s Pizza on the beach


San Carlos Island (either walk, bike, or bus across the bridge):

  • Doc Ford’s Rum Bar & Grill
    • Our favorite in the FMB area! Best food and atmosphere. Waterfront indoor or outdoor dining on a huge dock with live music, delicious seafood and drinks
  • Dixie Fish Company
    • We haven’t eaten here and only recently heard of this, but it’s supposed to be an amazing old-Florida style fishouse.
Celebrating a birthday at Doc Ford’s Rum Bar & Grill

Sit Down Restaurants on the Island (all near Times Square)

  • Mantanza’s on the Bay
    • Different dining options – Dockside Pizza, Upper Deck, and main level (all have different menus)
  • Nervous Nellie’s
    • Fun bayfront restaurant
  • The Whale
    • Haven’t eaten here in years, but seafood restaurant that’s been around a long time. Upper deck is great!
  • Smokin’ Oyster Brewery
    • Again, haven’t been here in years but beach-style dive bar with daily live music

Quick Bites / Takeout Options

What to Do

We’re probably not the best people to talk about all the fun activities and places to visit in the Fort Myers area because we are perfectly content to plop ourselves in a beach chair and spend an entire day doing nothing but playing in the ocean and the sand. However, here’s a few small activities we’ve done:

Lover’s Key State Park
$8 entrance fee
The beach is pristine and quiet here at the far tip of the island, as it’s a protected natural area. The kids had fun watching the crabs make their way around the sand and seeing some of the sealife. There is supposed to be some good shelling here as well, but check the rules first.

Lover’s Key State Park

Salty Sam’s Pirate Ship Cruise
We bought tickets a month or two in advance online because we wanted the 6:30pm cruise which was offered infrequently. We loved this cruise time because we could have fun in the sun all day, then grabbed dinner with friends and boarded the ship to see the sunset. The kids had a blast – the pirates were very engaged and entertaining and would highly recommend. Also, there was a bar on the ship with signature cocktails for the adults. 🙂

Limbo party aboard the pirate ship!

There are a variety of beachy, touristy shops in Times Square and scattered throughout the island. Unlike some Florida cities, like Miami and Naples, there are no fancy shops here! We usually save shopping for a rainy day and just wander in and out to keep occupied.

The Pier
Also known as Pelican Pier, it’s a fun place to grab some ice cream at the little shop mid-pier and watch people fishing. The pelicans hang around here too, which are fun for the kids to watch. You can rent a rod and reel (without needing a fishing license) for around $10. At sunset, people line the pier to get a good view.

Ft. Myers Beach Pier
Pier in background at Pierside Grill in 2008

Times Square

Located in the heart of Estero Island, Times Square is a good place to spend some time at different parts of the day. We like to walk down here in the late afternoon to grab ice cream, appetizers and drinks at one of the open-air restaurants on the boardwalk and then head back later for some more ice cream (hehe!) and watch the street performers and night activities.

Beach activities
The simple stuff – sandcastles and seashells and playing catch. It’s free (or very cheap) and provides hours of entertainment on a nice day. Hands down, our favorite kind of day.

Watersports – there are a few vendors scattered throughout the island to do some water adventures and watersport rentals.

Even on the not-so-nice days, the kids still enjoyed the same beach activities.

Looking for seashells on a chilly, cloudy day
Wandering around the condo at night with flashlights
(*Note: flashlights on the actual beaches at night are discouraged, as nesting turtles could abandon their eggs!)

…and as with any beach vacation, make sure to catch the sunsets!

We’ve got a new location in Florida planned this spring and cannot wait to get back to our happy place at the beach. We’ll still be on the Gulf of Mexico and will be interesting to compare it to Fort Myers Beach. It’ll always be a special place to us – the first vacation that Justin and I ever took together, along with the first family vacation for our kids (and their first time in the ocean!). As always, feel free to ask any questions or share your own favorite places and things to do in Fort Myers, Florida!

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