Uncertain schedules meant we couldn’t book months in advance for Spring Break this year and had to travel on the fly (OTF). Luckily, the approach worked out well and the whole family wound up with a strong appreciation for both the Florida Keys and OTF adventuring. 

I’m usually diligent about planning our trips—nailing down travel plans well ahead of time and creating detailed daily agendas, even visual guides—because our adventures provide content for travel books. And there are definite advantages to being buttoned up about it, namely, reduced anxiety at the outset and sometimes spending less money.

But OTF travel also has its advantages. Determining our destination through searching last-minute travel deals and figuring out our daily plans by talking with locals on the ground allowed us to be more guided by our curiosity and able to learn about and experience things, from food to activities and sites, like locals might. 

Here are five tips to help you and yours have your own positive OTF adventures: 

Consider Credible Apps for Last-Minute Bookings

There are some apps—such as Hopper, Skyscanner, Google Flights and Airbnb—that allow you to book one aspect of your travel and others that let you book all parts (flights, lodging and car) through bundled deals. We chose the latter, searching Travelocity, Booking.com and Expedia, and ultimately booking a deal through Expedia that included five nights at a resort in the middle of Marathon Key, as well as flights and a minivan for use throughout our trip. The deal worked out well, with no surprises except for an additional daily resort fee we weren’t expecting, and the resort was perfect for a family, offering villas with multiple bedrooms and a kitchen, beach volleyball, life-size chess, multiple putting greens, a lagoon-style beach and three heated pools all for a reasonable price.

Be Flexible With Destinations

Our original intention was to visit Paris, but the cost would have been exorbitant. We’d agreed on a budget and the available places of interest that fit within that included Costa Rica, Jordan, Peru, Chicago and the Florida Keys. But after a deeper dig into the details of each deal, and a family discussion that unearthed a unanimous desire for more beach time and less travel time, the Florida Keys rose to the top of the list.

Have Travel Documents and Payment Ready

To be honest, we might have more seriously considered Jordan or Costa Rica if I’d had a valid passport. But it was expired, we had two weeks before Spring Break and I didn’t want to pay the expediting costs for getting a new one quickly. 

I also didn’t have a Real ID, but because our trip took place before May 7, that wasn’t an issue. A TSA agent reminded me that after May 7, I would either need a valid passport (or one that was less than a year expired) or a Real ID.

For payment, I opted for a payment plan offered through Expedia, which allowed us to pay a portion of the cost of the trip as a down payment and the rest over a year. Surprisingly, the fees for this plan were more advantageous than putting the full trip on a credit card.

Seek Suggestions from Locals 

We built our plans primarily by seeking advice from restaurant, resort and tourist attraction staff, and supplementing with online research. 

In Key West, Google Maps led us to an excellent seafood restaurant on Duval St., to Truman’s Little White House, writer Ernest Hemingway’s house and to the site marking the southernmost point in the U.S., which looks out toward Cuba, a mere 90 miles away. 

A conversation with our waitress at the seafood restaurant in Key West led us to Sunset Grill, which sits at the end of the historic 7 Mile Bridge and offers vantage points for spectacular sunsets, and to the various wonderful sites of Islamorada, including the Theater of the Sea for dolphin and sea lion shows, Anne’s Beach to watch parasailers gliding on the ocean and air and Robbie’s for fried conch and giant tarpon feeding. 

A staff member at our resort suggested we visit the nearby Turtle Hospital and Bahia Honda State Park, both of which were highlights of our trip. He recommended Bahia Honda, which hadn’t come up in our online searches of best beaches on Marathon Key, over other nearby beaches and it was one of the most beautiful beaches any of us had ever seen, with its long stretch of aquamarine colored ocean and warm, shallow natural wading pools.

Stay Connected

Make sure to bring your smartphone and travel charger with you for easy access to your travel reservation details and confirmations, driving direction apps (e.g., Google Maps and Waze), online travel guides, weather apps and search and excursion booking apps (e.g., Viator and Tripadvisor) for researching and confirming activities. 

For international travel, enable international roaming or get a local eSIM/SIM via apps like Airalo.