I love traditions. One of my favorite family traditions is the annual road trip I take with my two daughters and a couple of their friends every summer. That’s when I load up the minivan with these four teenagers and all their “necessities” to hit the open road looking for adventure (and plenty of Hampton Inn waffles and takeout pizza).
I call it the “Endless Road Trip.”
Last summer, we zigged and zagged our way through Florida — on a road trip from east to west and north to south — before turning the car back toward New Jersey just days before Hurricane Irma arrived.
Here’s what happened on our latest road trip adventure.
Editor’s note: This article comes from my archives. I first published it in 2018. Since then, my girls have grown up, and we’ve taken seven more adventures — and added another 60,000 miles under our belts.
In 2024, we celebrated our 20th annual Endless Road Trip. Stay tuned for that adventure…
First stop on this Road trip: Savannah
The first stop: Savannah.
After checking into the newly opened Homewood Suites at the riverfront (its rooftop pool is not to be missed, by the way), we headed to my crowd’s favorite place in Savannah: The Savannah Candy Kitchen.
The Savannah Candy Kitchen is a colorful candy store located directly along the riverfront where you can watch the various confections being freshly made. Pecan pralines are the specialty, but you can find almost any treat imaginable here — including sour cream and onion crickets.
Of course, there are many things to do in Savannah to occupy teenagers besides eating candy. My girls enjoy cruising down the Savannah River at sunset on the Georgia Queen.
And if your time isn’t limited during your visit, a short drive to Tybee Island can be a fun diversion. Here, you can spend the day at the beach, see Georgia’s oldest and tallest lighthouse, eat some great seafood, and even feed alligators at the Crab Shack– if that’s your thing. It’s my girls’ thing.
These road trip teenagers love Sanibel Island
Traveling 500 miles south, we made it to Sanibel Island, Florida. This island, known by many as the Seashell Capital of the United States, certainly lives up to that nickname.
There is an endless supply of beautiful seashells that wash up on almost any beach you happen upon in Sanibel. Live shelling is prohibited here. So make sure to check for living inhabitants before taking any shells.
An important tip: Don’t forget bug spray on your road trip
The “no-see-ums” (sandflies) are here, especially at dusk. And even though you won’t “see um” — you will feel them. I guarantee it. We spent one uncomfortable night walking on the beach without any bug repellent.
My first stop the next morning? Bailey’s General Store to pick up the critical item and hydrocortisone for the damage that had been done the night before. I also used Bailey’s for grocery delivery to our condo. I ordered everything we needed online, and Bailey’s delivered it before we even arrived on Sanibel. Perfect!
If you love to be active, Sanibel Island is the place to be. There is a bike trail that encompasses the entire island, and you don’t need to bring your own equipment. We used Billy’s Sanibel Rentals — which will even deliver a bike directly to your condo or hotel if you prefer.
Teenagers love Tarpon Bay — as long as the activity is late in the day
Another favorite past-time in Sanibel is kayaking on Tarpon Bay. I would love to say that we had a great time kayaking with Tarpon Bay Explorers Nature Tours.
Unfortunately, I can’t.
While traveling with my particular configuration of sometimes-fickle teenage road trip adventurers who love to sleep in, we missed all the morning kayak trips during our stay in Sanibel. And since the unforgiving southern Florida sun makes an afternoon trip unbearable, the helpful nature center guides recommended a sunset boat tour, which included an educational presentation about the wildlife in and around the bay.
A minor road trip emergency
With our time in Sanibel coming to a close, we packed up and put this road trip back on the highway. But not before a small crisis waylaid us. About 2 hours into our journey, my 15-year-old realized to her horror that she had left her lifelong favorite stuffed animal “Pink Elephant” in our condo in Sanibel.
Suddenly my cool and confident teenage daughter turned into a crumbling mess of emotion. I was forced to pull the car over and straighten this emergency out immediately. I made some calls from the side of the road. Luckily, Pink Elephant was found safe and sound. The manager of The Sanibel Arms West assured us that my daughter’s fluffy friend would be waiting for us courtesy of Federal Express at our hotel in Key West.
With that problem solved, we turned our road trip east across the sunshine state.
The Everglades
Traveling on I-75 between Naples and Ft. Lauderdale is the road known as Alligator Alley — and it cuts straight through the Everglades. There are plenty of companies that will take you on an airboat tour to zip through the marshes in search of alligators in the wild.
Checking reviews on TripAdvisor, Wooten’s Everglades Airboat Tours fit the bill for me — many satisfied customers, and it was located directly along my planned route.
In between speeding through the open areas of the wetlands, Captain Carl answered any questions about the ecosystem of The Everglades.
Important tip: Make sure to bring a beach towel to sit on for your ride. These airboats are made of metal with no roof. And the broiling sun heats the entire frame to a scorching point. A steady stream of unsuspecting guests plopped themselves down on these seats only to instantaneously be returned to the upright position amidst screams of “ouch!” (Yes, this happened to me.)
This road trip hits The Florida Keys
Next, we headed to Islamorada, in the Florida Keys. We arrived just in time to have a great dinner at Lazy Days — outside directly on the water, serenaded by a man playing a variety of Jimmy Buffet tunes on his guitar.
We checked into the Amara Cay Resort and got up “early” the next day to go on a snorkeling trip to the John Pennekamp Coral Reef State Park. And when I say early, I mean 11:30 a.m. I’m an early riser, but as I’ve mentioned, these girls — not so much.
What kind of makeup can you wear while snorkeling?
A funny thing about traveling alone with four teenage girls — you hear a lot of silly conversations — like how to keep makeup in place for photos on a snorkeling trip. In the ocean. Underwater.
No.
I made the executive announcement that no makeup would be applied for this excursion. Appealing to the girls’ sense of caring for the earth, I let them know that makeup could harm the delicate coral reef.
Another problem resolved. A makeup-free day for four teenagers. Gasp!
This road trip hits John Pennekamp Coral Reef
The John Pennekamp Coral Reef State Park is located off the coast of Key Largo. I wanted the kids to see it before, as our guides warned us, “it’s gone forever.” Which is currently projected to be only several years in the future.
We boarded our boat for the 30-minute ride out to the reef. The boat was steady, and I completely forgot that I suffer from terrible seasickness. That is, until the end of the trip.
But first the good stuff:
Then the troubles began. We had to wait for several diehard snorkelers who did not want to reboard until the absolute last minute. As a result, the rest of us had to wait on a wildly rocking boat until they returned. My seasickness came on full force — and I wasn’t alone. Four other shipmates had a similar problem.
I am not going to sugarcoat this — it was awful. But the captain said he had a miracle cure. He gave me a cup of ice. I assume this is a placebo, but I did as the captain instructed and ate the ice and counted down the moments until we could take off.
Finally, after multiple warnings, these tardy snorkelers climbed back on the boat. Thankfully we were able to take off.
Back at the Amara Cay, we enjoyed the sunset on the beach. Only 20 feet or so offshore, I could see dolphins. My girls were mesmerized by a stray black cat.
Go figure.
Driving on to Key West
The next day, we headed toward our most southern point of this road trip. In fact, we were heading to the Southernmost Beach Resort in Key West.
At just around two hours, this drive was just a drop in the bucket compared to the long drives that were already under our belt on this road trip.
Key West is a fun little town filled with restaurants, souvenir shops, and boutiques. And I could finally take a break from driving since everything is within walking distance of everything else.
Half of my girls are vegetarians, and they soon discovered The Cafe near our hotel. This place quickly became a crowd favorite with its self-described “chill vibe.” I don’t know what the vibe actually is because I never went inside. But the girls visited four times in four days. So if vegan or vegetarian is your thing, check it out (it’s definitely not my thing). The standout dish according to my older daughter is the vegetarian “chicken” and waffles.
My nonvegetarian daughter and I went in search of other kinds of food. For us, Pinchers was everything we needed. We were able to sit outside on the lanai and watch the (sometimes strange) street scenes pass by while enjoying some great seafood. Yes, street chickens are a thing in Key West.
What can teenagers do on a road trip to Key West?
After seeing a large fish swimming off the pier, my girls quickly scratched swimming in the ocean off their to-do list.
So what else did these road-tripping teens do in Key West?
The Grateful Guitar has a variety of hand-painted unique ukuleles, and since my younger daughter plays, we popped into the store for a look. She was immediately drawn to the wide selection of ukuleles that are hand-painted by local artist and musician Jean Paul. Jean Paul’s art also happens to be featured in The Café’s decor.
With great difficulty, my daughter selected her favorite ukulele, a brightly colored instrument with scenes of Key West. And as you can imagine, the car was never quiet again the rest of this road trip. I re-thought the purchase about 500 miles later.
Of course, Key West is known for its rowdy night-life. Almost none of it appropriate for four teenagers and one mom on a road trip. However, the older girls had heard a frightening tale of a haunted doll that resides in Key West.
Who is Robert the Doll and are teenagers afraid of him?
The curators of the museum where Robert the Doll resides boast that he is “the most haunted doll in the world.” And the three girls wanted to take a night-time ghost tour to see him. So off they went for the 10 p.m., 2 hour Ghost tour with Key West Ghosts and Graveyards.
Were they scared? A little. They reported that Robert did seem quite creepy, but although their guides suggested that paranormal activity was going on — they remained unconvinced.
Our time in Key West came to an end, and I steered this road trip north to the unofficial capital of Florida — Orlando. With Disney World and Universal on the agenda for these teenagers, we spent an active week hitting every rollercoaster we could find.
At the end of the week, it was time to pack up this road trip crew one last time and start the long drive home. And just in the nick of time since Hurricane Irma was heading Florida’s way.
Recently, I checked with each hotel that we visited in the Keys, the hardest-hit area of Florida. The good news is that everything is returning to normal. Florida has reopened for business and would love to have you for a visit, too. VisitFlorida is a great place to get you started with your planning. Happy travels! (Michelle Couch-Friedman, Consumer Rescue)
* Before you go: Check out this amazing Arctic cruise
