Fort Myers Family Staycation Itinerary for Under $2,500

The Culbertson Agency likes to give back to our surrounding community and one of the ways that we like to do that is by helping you explore the possibilities for recreation and relaxation that’s available to us right here in our own backyard.

Since most people don’t vacation as single adults, this guide is assuming that you have a spouse or significant other with or without 1 to 3 children of any age.

This itinerary is for one week from Sunday to Saturday and allows you to experience a lot of what Fort Myers has to offer as a vacation or staycation destination. Bear in mind too that this itinerary may be modified to your budget and your liking. If you don’t want to spend 5 nights somewhere, go for at least 3 instead (in order to get the discounted rates). If you don’t really care to do something on this itinerary, by all means, replace or skip it.

Part 1 – A Day in Historic Downtown

Sunday: You’ll stay at a hotel downtown so you can walk (if you want; I’d recommend walking because parking downtown can be a bit trying). Even if you live nearby, staying in a local hotel has certain advantages. For one, you’re on vacation, so act like it! Secondly, this will allow you to experience more in the day without having to worry about facing traffic and getting home and what you’ll do once you get home with all the chores that await you there.

The first thing you and your spouse/family will be doing is the Edison & Ford Winter Estates. I’d recommend going in the early afternoon just after lunch. Even if you’ve been here before, you’ll be sure to find something that you’ve either forgotten or never noticed before. This is especially fun if at least one of you is a history buff. My wife loves to visit historic sites and I was excited to share this quaint, interesting, and—at times—bizarre little museum/home with her.

Monday Morning: It’s time to check-out from your downtown hotel and get ready to head south, with a couple of stops along the way. While you’re downtown, I’d suggest a short trip to Bennet’s Fresh Roast for breakfast. This is a favorite morning breakfast/brunch place for local Fort Myers people that’s not a chain or a giant franchise, but still a small, local place famous for their doughnuts and coffee.

Part 2 – Pause for Mini Golf & Ice Cream

Monday: This part is somewhat optional since it’s just a short stop and we realize that mini-golf isn’t for everyone, but it could be a good way to break up the longer trip out to your next stay (which could take a half-hour to an hour depending on traffic). However, the reason for this “pause” is that as you’re heading from Downtown Fort Myers to Sanibel is to kill some time because you may not be able to check-in at your next stay until 3 or 4 in the afternoon. The idea is: check-out downtown at 11 am, grab some lunch, head south and take a break with some mini-golf before you head out on a long one-lane road out to an island resort.

There’s a couple of mini-golf places on your way to the beach, Smuggler’s Cove and Jungle Golf. Mini golf is usually a fun time whether you have a family and kids or if it’s just the two of you. It’s about $10-$13 per person and kids under 12 are usually about $10. Jungle Golf tends to be cheaper between the two.

Also, while you’re on your way to the beach, take a few minutes to stop and try Love Boat Ice Cream. It’s a local favorite and arguably the best ice cream in town (or anywhere, as far as many are concerned). It’s got over 20 or 30 flavors of home-made ice cream and they get busy with a line out the door and around the side of the building in the evenings, but if you go in the afternoon, it should be quick.

Part 3 – Sanibel-Captiva Island Relaxation

Monday Evening: For the rest of your staycation, you will be staying on Sanibel Island at either Jensen’s Beach Resort or you can stay at the Tween Waters resort using their “3-Night Delight Package” where the rates are discounted from $205 to $320 per night depending on your room size. The 3-Night Delight Package just means you need a minimum of 3 nights to enjoy the lower rate; minimum stays are common on Sanibel. Please note that there are only 7 cottages at Jensen’s and their pricing is a little more affordable than Tween Waters, so make sure to give yourself plenty of time for a reservation. With the discounted rate at Tween Waters, you can expect $1025 to $1600 for a five-night stay. If you’re thinking that’s a lot of money, it’s certainly a chunk of change, but let’s put this in perspective: staying at a Walt Disney World resort could cost about $1,000 to $1,500 for two nights (resort, not just a hotel).

One optional thing that you might want to do is take advantage of Billy’s Bike Rentals (which you passed on the way into either Tween Waters or Jensen’s). Once you experience the limited number of roads and the amount of traffic that can accumulate on Sanibel, you may want to use bikes to get around the island in a more enjoyable way.

Bike Rental Estimated Prices: $25-$35 per bike for 3 days.

Once you’re settled into your beachfront resort stay, there’s a lot of options to keep you entertained during the rest of the week. Check out Beach Bum Boat Rentals if you’d like to rent a boat for the day. Boating and fishing are one of the best things to do in Fort Myers on a staycation with all of the waterways and places you can go. Speaking of fishing, there’s also a half dozen charter services within walking distance of Tween Waters. Make sure you check out The Bubble Room restaurant and many of the other great restaurants that are in the area. Take advantage of being able to walk to the beach, walk to lunch, and just relax and enjoy your time on this less-touristy part of the island. From here on out, enjoy the sun, the sand, and the slow pace of life. Go for a walk, take a nap, or do whatever else you want to do. It’s your vacation after all!