We had just moved to Florida, started new jobs, and could’ve played it safe with something simple and close to home. Instead, we pointed the car toward the Keys, added a seaplane, a submarine, a Southern Caribbean cruise, and a few stories we’re still laughing about.

Here’s how it all adds up.

Trip Snapshot

• Dates: October 24 – November 9, 2024
• Route: Clermont → Florida Keys → Fort Lauderdale → Southern Caribbean cruise → Miami / South Beach → home
• Days away: 17
• Transportation: Road trip, seaplane, cruise ship, submarine, bikes, and a few very fast walks back to the ship
• Luggage: 2 carry-ons and a backpack.

By the Numbers

• 1,000+ miles driven through the Florida Keys, Fort Lauderdale, and Miami, then back home
• 140 miles flown on 1 seaplane
• 139 feet below the surface in a submarine
• 4 dolphins spotted (including one unforgettable Superman-style launch)
• 2,768 nautical miles sailed across 1 sea and 1 ocean on a Southern Caribbean cruise
• 4 countries visited: British Virgin Islands, Barbados, Saint Lucia, and Saint Kitts & Nevis
• 10 cities and island towns stepped into: Key West, Key Largo, Plantation Key, Tavernier, Dry Tortugas National Park, Marathon, Islamorada, Fort Lauderdale, Miami, and South Beach
• 4 hotels
• 3.5 miles cycled
• 252,378 steps walked together (about 114.7 miles on foot)
• 2 carry ons, no checked bags, and zero desire to go back to hauling suitcases

The Highlights Reel

• Seaplane to Dry Tortugas: Taking off and landing on water, watching the color of the ocean shift beneath us, and seeing the fort appear from the air like a brick hexagon in the middle of the gulf. Sitting in the co-pilot’s seat was the icing on an already great cake.

• Key Largo “Christ of the Abyss” attempt: We booked the trip hoping to get back in the water after years away—even if it was just snorkeling. The conditions had other plans. We lasted about five minutes before retreating to the deck, where we spent the rest of the time flat on our backs, eyes closed, riding out some of the roughest water we’ve ever been in. The captain eventually called it due to the weather. We never saw the statue, and somehow, it’s still one of the stories we laugh about the most.

Islamorada insomnia: One night in a hotel room with a bed that squeaked so loudly neither of us could move without setting it off. Every tiny shift sounded like a cartoon sound effect—very little sleep, plenty of resigned laughter.

Submarine dive: Dropping 139 feet below the surface—past my previous deepest scuba dive of 127 feet—and watching the undersea world slide by from a tiny window. No tank, no fins, just the quiet hum and the feeling of being somewhere most people never see.

Dolphin Superman: Forty-five minutes in the water with dolphins in St. Kitts, capped off by one very enthusiastic Superman-style launch that left me airborne, slightly limping, and grinning like a kid. Still no photo of the best part. Still zero regrets.

“Plenty of time” tour: After the dolphins, we trusted a local island tour that promised to get us back to the ship with “plenty of time to spare.” We saw the island, loved the views, and spent the last stretch quietly wondering if we were about to test out our sprinting form on the pier. We made it—but their definition of “plenty” and ours were clearly not the same.

Pitons by catamaran: Sailing along the coast of Saint Lucia, stopping to swim, and then watching the Pitons rise up out of the water like something painted onto the horizon. Warm breeze, music on the boat, and one of the prettiest backdrops we’ve ever floated past.

South Beach spin: Trading ship decks for palm trees and bike paths, renting bikes and cruising along the beach with a salty headwind and that “we’re not in a hurry anymore” feeling.

Seventeen days, one “stay closer to home” plan that still managed to include planes, ships, submarines, and seasickness—and honestly, exactly the kind of getaway we needed.