Select Page

Earlier this month, our family took a Florida trip for spring break.  This has become somewhat of a tradition for us.  It's our third year in a row staying there.  We look forward to it, and have lots of great memories to add from this year's adventure.  I thought I'd share some of the highlights of our Madeira Beach trip.


We decided once again to drive.  Two years ago we were able to fly, but the costs have been fairly prohibitive.  Even when we did fly down, we had to drive for over four hours to Columbus, where flights were cheaper.  We did not enjoy that drive at all.  In the future, we will either fly out of Detroit or a closer airport, perhaps Cleveland.

The drive took around 20 hours from when we left to when we arrived.  This was true both coming there and back.

driving road trip family

Road trip down to Madeira Beach

We drive straight through.  My wife and I take turns sleeping and driving through the night.  Each shift is about 3-4 hours.  We'll stop, stretch, go to the bathroom, and fill up.  We also make longer stops for breakfast and dinner.  If the driver is tired, we'll stop and make a switch.  Last year, my wife called for a couple of switches.  This year, I took a turn asking for a switch on the way back.

The kids do OK sleeping.  On the way back, they slept much better, probably because they were tired.  As far as my wife and I, we get sleep while the other is driving.  It isn't exactly restful.  The first night after the drive is a great night of sleep for everybody!


We have stayed in the same condo for three years now.  We stay at a place right near a boardwalk area called John's Pass.  There are a lot of great restaurants and shops.  The condo is clean, fairly modern, and well maintained.  The building has been under construction for the past two stays.  This has been annoying.  Last year they were replacing rebar in the concrete.  This year, they were updating balconies with new flooring and door walls.

We've already booked a stay at the same condo for next year.  We are keeping our fingers crossed that it's construction free!


We have established some favorite places to eat and enjoy adult beverages while we're down there.  Of course, we look to make new favorites every year.  Here are some of our highlights.


We love Gators.  They boast the longest outdoor bar in the world.  Whether that's true or not, it's a great place.  It's right on the water over an inlet to the bay. We see boats come through, which has a drawbridge that's fun to watch.  We'll often see dolphins swimming as we sit along the water.  They have great rum runners, enjoyable food, and a fun atmosphere.

Sloppy Joe's

Over in Treasure Island is one of our favorite places to eat, called Sloppy Joe's.  It's about a 30 minute walk, which is great for a cloudy day.  They serve Caribbean themed food, and we have a salad / bowl that we both look forward to every year.  My mouth is watering just thinking about it.   This year we enjoyed our time on a covered patio, which was good because a rainstorm came in during our meal.

We've realized that lunch is the way to go.  Last year we went during dinner.  While the food was just as good, it was crowded and we had to wait much longer than we anticipated.  Lunch is more laid back and less rushed.  In fact, we realized that lunch is a better time to have our big meal of the day.

Boardwalk Grill

Over in John's Pass is a little hole in the wall place called Boardwalk Grill. They have the best food ever.  No matter what we've had it's amazing.  The fish tacos, onion rings, hot dogs, and fries are our favorites.  We get carry out and enjoy this back on our condo balcony after a day in sun.

Angry Pepper

We were disappointed when Castaway's, a small Mexican restaurant nearby, was no longer in business.  We'd loved going the past two years.   So, we asked around and looked online and found a place called the Angry Pepper.  The food was centered around smoked meat that they made onsite every day.  I have to tell you, it was great.  Again we went around lunchtime, where it was very relaxed.  The waitress was great.  Food was amazing (and we got to watch the meat being smoked).

It's the opposite of fancy, but we would highly recommend it.

Keeping Busy

Beach and Pool

It wouldn't be a Madeira Beach trip without water and sun!  Our family is definitely fine with relaxing and enjoying the pool.  Our kids could play in the pool or ocean all day, every day.  That took up a lot of our trip, and we love it.  Our kids met other kids along the way.  In fact, there's another family that stays every year, and their son has gotten to be friends with our kids over the years.  There were other kids as well.

The condo has a great pool and we'd also go down to the ocean.  Every year the kids get more adventurous in the water.  We also spent almost an entire afternoon playing catch in the water.  This is one of my favorite memories.

madeira beach

Madeira Beach is one of our favorite places in the world!

We had been worried about red tide affecting our vacation.  Red tide is an algae that smells bad and gives rashes to swimmers.  It was very prevelent during the summer and fall of 2018.  However, I'm happy to say that it seems to be gone for now.  We had no issues!

Mix this in with some long beach walks in the morning or later in the afternoon, and it was just about perfect.

Photo Shoot

My wife has dreamed of getting family pictures while on vacation.  Two years ago, we setup a session with a local photographer.  Unfortunately it didn't work out.  The day she was available was extremely windy.  Try as we might, there was just no way it could work.  Last year, we decided to hold off because we had shortened the beach part of our vacation so that we could also go to Disney.  This year, we decided to try again.  We contacted the photographer, and setup a time.  It was perfect.  We got some amazing photos that we will cherish forever.

If you're down in that area, I'd highly recommend Sister Sweet Photo.  Nina does amazing work and is worth every penny she charges.


There was one day that predicted cooler temperatures and rain.  My wife convinced me that a day trip to Disney World was in order.  So, off we went.  It was around a two hour drive each way, so very manageable.  We were able to do a brunch meal, walk around some of our favorite resorts, and spend a few hours in Disney Springs, their shopping area. We also rode the monorail around.  It's too expensive to go to a park for a one-day trip, but we found other ways to really enjoy ourselves.

In short, we had a great time. We stayed for just over a week.  Our family was exhausted when we got home.  But we all had amazing tans, great stories, and smiles on our faces.  We are already looking forward to another Madeira Beach trip for #SpringBreak2020.

Readers, what are some of your favorite family vacation memories?