Ernest Hemingway and Jimmy Buffet may have had it right. Both men fell in love with the southernmost peninsula of the continental U.S. and for good reason. The slow pace and island vibe are both inviting and relaxing, but this area has a colorful past that was anything but that. Although there are ferries that run down the peninsula giving you more immediate access to the end of highway 1, opt for the drive and take in the miles of bridges and crystal waters as you make your way down to Key West.

If you are a water lover, getting wet in Key Largo is a must. With the largest coral reef in the continental United States, the John Pennekamp Coral Reef State Park offers opportunities for snorkeling among assorted fish, as well as scuba diving on statues and shipwrecks. A quick thirty minute boat ride will have you gearing up to take in all that this area has to offer. Companies like Sundiver Snorkel Tours offer multiple trips a day, and your fee includes equipment rental as well. Reservations are highly recommended, but we managed to walk in and pick up a spot the same day. When you get off the boat, spend the rest of your day like the locals, lounging by the water or paddling on a board or kayak. If you stay at Drift Hotel (top right), use of the dock chairs and stand up paddle boards are included with your visit (top left).

We started out early with breakfast at a nearby establishment known not only for their amazing made to order breakfast burritos and heavenly barista poured lattes, but also for the nursery and gift shop that surround the outdoor eating patio. Be sure not to miss fueling up at Gardenia’s Bistro in Tavernier before heading further south.

In search of the southern most point, we ventured onward taking in the views of the Gulf of Mexico and the Atlantic simultaneously while thinking about the dreamers who once called the Keys their home, including Ernest Hemingway. The Lighthouse Hotel, built in 1858 and our home for the night, sits adjacent to his, now The Ernest Hemingway Home and Museum. It is rumored that some of the many cats that inhabit it are descendants of his six-toed feline, Snow White. The climb to the top of the local lighthouse, also a stone’s throw away, gave us a great overview of this tropical paradise.

After a quick portrait painting and a half an hour spent watching amazing physical feats, we had worked up our appetites. I’m ashamed to say we made it all the way to Key West without visiting Margaritaville, but it’s true. Instead, we opted for dinner at The Flaming Buoy and were treated to an amazing meal and even better nostalgia, as we donned Star Wars helmets and gazed upon the wall behind the bar filled with treasures. Whatever you do, don’t miss the bathroom! Afterwards, we sauntered across the street for a nightcap at Tempt in the Burgundy Bar. The atmosphere and drinks were refined and moody, just the way we like it

Driving the Overseas Highway and standing on the southernmost point of the United States had long been a dream of mine, but as I stood there, leaning against that oversized buoy, I was thinking about Dry Tortugas National Park. Sitting 70 miles off the coast to the west, this seven island, one hundred square mile oasis just didn’t fit into our tightly strung together weekend agenda. Now we’ll know to make reservations well in advance for our next visit. Oh well, as Jimmy Buffet would say, fins up!