ISLAMORADA, Fla. — Having somehow failed to visit the Florida Keys when I was young and single and sociable, I approached a school vacation there last spring with a bit of unease: Had I missed my moment? Would a family trip there feel tempting but inappropriate, like a stroll through Mardi Gras with children in tow? Should we just go to Disney World like everybody else?
Happily, no. My husband and I took a chance on the Keys and discovered destinations so ideal that we’re considering an annual return.
The key to our happiness was focusing on the right key. The islands that make up the Florida Keys are many and varied and not all as raucous as the infamous Key West. Since the Keys are also known for shallow water and marine life — not exactly beaches where kids 5 and 8 can spend hours body surfing — we confined our search to hotels with inviting pools near locations where we could try snorkeling.
We settled on Islamorada, a village of four islands not far from the mainland and still 2 hours from Key West. The area felt central and had multitudinous offerings for children.
Our hotel choice — discovered on-line at hotels.com — was the Postcard Inn, and it charmed me like few other places I’ve been. From the road, it looked unremarkable and dated, a roadside hotel. But as we entered, it unfolded into a low-key resort of stylish tranquillity. With several casual restaurants, including a great waterside raw bar, the resort offered easy access to meals without a lot of cost or drama.
When we visited we didn’t see a lot of organized resort-style activities for kids. Then again, we were there to play with them, not send them to summer camp. When we needed a break from the sun, we played Ping-Pong or visited the game room — an adorable space lined floor-to-ceiling with soft fake grass alight with faux fireflies, a climbing wall, and free Pac-Man. Nearby were board games, newspapers, and computer access ... what more could we need for a rainy day? (If we even had one.)
The inn’s rooms featured a carefully thought-out mashup of decor — retro, modern, and nautical. I loved the quixotic quotations stenciled on the walls. (“I went fishing with Salvador Dalí. He was using a dotted line. He caught every other fish,” was credited to S.W., apparently the comedian Steven Wright.)
The place felt so uniquely stylish that I was stunned to discover it’s part of a chain. The Postcard Inn was once the Holiday Isle Resorts & Marina, and it was apparently quite a scene. Slated for reconstruction as some grand condo and hotel complex, it succumbed to the real estate bust and ended up foreclosed and facing demolition in 2009. Investor Starwood Capital reclaimed it and redesigned it, capitalizing on the modest architecture and giving the hallways the look of a stylized boathouse.
During our trip, the resort still felt unfinished and empty, though outfitted for fun, with its “world famous” Tiki Bar at Holiday Isle. Right next door is Rum Runners Island Bar, a fabulous multi-tiered tiki hut that looked, to my children, like a magic treehouse. (It was not. It was a dive bar dominated by salty types who smoked sullenly by the bar, ignoring the spectacular view behind them.)
But we weren’t there for night life, and the relative calm of the resort meant that we owned both pools. Over four days not a single other person was in the pool, meaning my kids got to splash, throw dive sticks, and practice snorkeling with reckless abandon.
We were preparing them for their first open-water snorkel trip, which we scheduled nearby in Key Largo on a glass-bottom boat (so they would be sure to see marine life, even if their snorkeling was short-lived). It was a wise move. The day was windy and the water choppy; two adults on board turned green and one of them got sick. My children snorkeled and saw some gorgeous fish, but the conditions were challenging, so they didn’t last long. We were glad to have the opportunity to do some fish-spotting below the boat, too.
Our water adventures continued back in Islamorada with a delightful trip to Robbie’s Marina, a tucked-away, touristy, but eclectic area with shops and kiosks, a restaurant, and opportunities to rent jet skis or charter fishing boats. There, the kids fed the tarpon, mighty silver fish that hovered just below the docks, and watched hand-fed pelicans spar for their food. Colorful Adirondack chairs line the beach area just around the dock, creating a welcoming spot for a visit.
There are laid-back places like that all over the Keys, and though some are hotly advertised to tourists, they still seem quirky and original. Take the No Name Pub, which was compelling from its name (or lack thereof) to its route. Located on Big Pine Key, it’s nestled in a neighborhood that is roamed by wild deer. (We spotted five on the ride from the highway.)
The pub is covered — and I mean covered — with dollar bills, creating a dim, barnacled look we found amusing but not necessarily appetizing. We preferred the sunny outdoor patio, shaded with palm trees whose signs warned, “I’m alive, No Carving,” and “that means you.”
Our final destination was the place that I regarded with both longing and dread: Key West. It lived up to my expectations. It was the only place I found myself wishing that we had a baby-sitter. We went to the nightly waterfront sunset celebration and saw magicians and foul-mouthed street performers — a scenic and lively event, but not the best spot for little ones. A striking number of the people we passed looked drunk — not one-too-many-tonight drunk, but hopelessly, habitually drunk. I watched my children like a hawk.
The highlight of our Key West stop was a visit to Ernest Hemingway’s house, a sprawling Spanish Colonial that offers a glimpse into his writing space. As any parent knows, house tours are not among children’s favorite activities, so I prepared my kids well. For weeks, I had been talking up the cats to be found on the grounds. Legend has it that a sea captain gave Hemingway the original six-toed tomcat whose descendants still have their run of the place, splaying their unusual paws for visitors and retreating to the elaborate wooden cat houses that dominate the grounds.
My children chased after the poor cats while I studied Hemingway’s writing studio above the pool house. I tried to see the view that Hemingway would have seen, gazing out the windows while he wrote his most enduring works. I was embarrassingly inspired.
Yet I couldn’t imagine how, in a place so near to Sloppy Joe’s Bar, he got anything done.