by Chelle Koster Walton

In my early Flori-days, a road trip to the Keys meant one thing: party! We’d find a cheap roadside motel or throw together some camping gear and dive equipment and head on across Highway 41 to Krome Avenue, then down the legendary Overseas Highway. In addition to “party,” “cheap” was the operative word in those days, and the Keys greatly obliged with inexpensive dives (that had nothing to do with going underwater), two-buck T-shirts, and ninety-nine-cent breakfasts.

Fast-forward to nowadays. The Keys have matured, and so I have—well, at least when it comes to my taste in travel. These days, I’m looking for a little pampering and poshness with my Keys adventure. I love to make my way down to Key West (okay, I still equate “party” with the Keys) and then work my way up through the pearl-string keys along the luxury route. (Those who want the easy Keys-y luxury route could charter a plane or sailboat to make the trip to Key West, then rent a convertible or exotic car for the ride back.)

Old Town is the place to party in Key West, but if you want to do the Duval Crawl in style, hire a ride from Perfect Pedicab and save your feet. For performance art that’s purely Key West, check out the female-impersonator cabaret shows at LaTeDa on Duval Street.

Key West also has its highbrow side, so once you’ve had your fill of downtown debauchery, check out what’s playing at the Red Barn Theatre on Duval Street (the musical A Christmas Survival Guide will be on stage December 2 to January 2), or escape the bustle and crowds for a show at the Tennessee Williams Theatre on Stock Island, just over the bridge north of Key West.

To spend the night out of earshot from Key West’s famously raucous nightlife scene, there are plenty of options. One of the easiest and most escapist involves a short ferry ride from Old Town to twenty-seven-acre Sunset Key, a prime Westin-owned resort village on its own private island.

The one-, two-, and three-bedroom cottages, done up in Caribbean meets Old Florida style, share the property with sandy beaches, swaying palms, flowering gardens, and a delicious sense of privacy. Baked goods, juice, and a newspaper are delivered each morning; grocery-shopping and private-chef services are available for a fee; and you can use all the facilities at the Westin Key West Resort & Marina in Old Town (where you check in and board the boat shuttle).

In Key West’s New Town, two brand-new resorts let you breathe a sigh of relief at their removal from the downtown scene. Marriott Key West Beachside Hotel’s private, manmade beach and spacious, impeccably decorated, one- to three-bedroom condos extend a feeling of delicious isolation despite its more than two hundred units. Designer cupboards, furnishings, and art reflect the resort’s gulfside stance. Frette linens, china kitchenware, and marble Jacuzzi tubs add touches of luxury. Rooms perch atop closed parking. Those on the first and third floors of the three-floor accommodations sport spiral staircases down to the gardens at ground level or up to the rooftop sundecks.

Not far away, Parrot Key Resort opened in 2008 with one- to three-bedroom townhouses that include a home theater on the third floor equipped with speaker-outfitted rocking chairs. With its front porches and picket fences, it feels like a new-fashioned old-fashioned beach town. Mangroves fringe the manmade beach that edges Florida Bay.

To trade in manmade for a more natural beach setting and new for grande dame historic, Casa Marina Resort is a refreshing step back, in more ways than one. Built in the 1920s, it retains its richly appointed lobby with beamed ceilings, polished pine floor, and original art. Guest rooms, newly renovated in 2008, are stylishly decorated with Italian tiled floors, sleeper sofas, and teak captain’s chairs. Fluffy bathrobes, espresso machines, iHome clock radios, and luxurious designer toiletries make it feel like a boutique hotel.

If you prefer to stay among the fray, Ocean Key Resort & Spa sits squarely next to Mallory Square on the waterfront. You can request a room with a balcony overlooking the pier’s nightly sunset celebration and then repair for dinner to the restaurant upstairs named Hot Tin Roof, a reference not only to its roofing but also to Tennessee Williams’s Key West connection. This is a full-service resort, with excellent amenities such as a Thai-inspired spa. It’s small and without locker rooms, but each treatment room comes with a Japanese-style tub on the balcony.

Looking for something more intimate? The twenty-seven-room Marquesa Hotel fits the bill with marble baths, antique and reproduction furnishings, and the inimitable Café Marquesa next door.

The other place for dining—both lunch and dinner—is Louie’s Backyard, as creative as it is scenic with decks stepped toward the beach. Enjoy dishes such as shrimp with bacon and stone-ground grits, roasted king salmon and potato parmesan roulade, and chicken breast stuffed with Swiss chard and gruyere with spaetzle. With a gingersnap crust and raspberry puree, Louie’s key lime pie claims its own style in a town brimming with the dessert.

While in Key West, a seaplane hop to the Dry Tortugas makes for an interesting day trip. Spot sea turtles and shipwrecks, explore historic Fort Jefferson, go snorkeling and birding, or relax on the beach.

Any number of charters and tours can sail you out to sea for one of the world’s most famous sunsets, and getting out on the water is elemental to a Keys visit. Sunset Culinaire Tours also sets the table. It serves three-course meals with its daily tours, composed of savory selections such as wild mushrooms Napoleon with porcini and raclette-cheese cream sauce, roulade of chicken breast stuffed with prosciutto and asiago cheese, and Italian Arborio rice pudding.

Heading north, the scenery is its own luxury experience. Lunch on the road in the Lower Keys is bound to be a throwback experience to Old Florida. Some of the best and most locally colorful restaurants reside within a marina.

Geiger Key Marina & Smokehouse is one example. Hidden a mile east of Highway 1 in an RV park/marina complex, it’s an islanders’ secret where you can get a lobster BLT or the fresh catch of the day with a view of mangrove-clotted oceanfront. Or find your way to No Name Pub on the back roads of Big Pine Key. Watch for the undersized key deer as you drive through the national refuge that protects the endangered subspecies of white-tailed deer.

The Keys are not necessarily known for their plush beaches, but Bahia Honda State Park is the most notable exception. It makes a delicious midday stop for a fix of sand and sun, and even some recreation and a little history. Snorkeling and kayaking in the champagne-clear waters are the favorite pastimes, but you can also hike to the top of the Old Bahia Honda Bridge.

Next stop: Marathon. Not exactly an exciting town culturally or nightlife-wise, it does hold some interesting historic and eco-attractions, including Dolphin Research Center, where the top-of-the-line experience is Trainer for a Day ($650). You’ll learn all about the care, feeding, and training of dolphins; participate in a deepwater dolphin encounter; and receive a dolphin-painted T-shirt. At Crane Point, you can tour a museum, wander nature trails, and visit a wild-bird rehab center. The site’s Adderley House, the Keys’ oldest domicile outside of Key West, takes you back to the days when a Bahamian village cropped up here in the early 1900s.

For a look at a different village of Bahamian-style homes dating back to 1908, visit Pigeon Key. You can reach it by walking two and a half miles along an old railroad bridge. Or take the ferry that departs from a reception center located in an old railroad car on Knight’s Key, just north of the Seven-Mile Bridge at Marathon’s southern doorstep. The island, once a railroad builders’ community, pays homage to the near-miraculous feat of Henry Flagler’s railroad to Key West, often derided as Flagler’s Folly back in the day.

The most elegance this area has to offer in terms of accommodations is Hawks Cay Resort, a self-contained resort with a full marina and every manner of water sport available. Another dolphin interaction facility, Dolphin Connection, is right on property, and four restaurants mean you never really have to leave the beachfront resort. An on-site spa adds a touch of pampering. Indulge in a Caviar Facial or its version of the Javanese lulur wedding treatment, called Blissful Ritual.

Tranquility Bay Beach House Resort, by the same people who built Parrot Key in Key West, has a nicer beach than Hawks Cay and also lots of water-sports options. But the two- and three-bedroom townhouses tend to be noisier than at Parrot Key.

If you haven’t gotten out on the water by now, you’re overdue. So plan on a deep-sea, Hemingway-esque marlin-fishing expedition out of Islamorada, self-proclaimed Sportfishing Capital of the World. Charters aboard Fishabout provide four staterooms, private baths, a living room and kitchen, satellite TV, phone service, and separate crew quarters.

Land-side, if you’re looking for somewhere full-service, golf-coursed, and spa-equipped, station yourself at Cheeca Lodge & Spa, which reopens after a luxury remake on December 15. But for a delicious departure and one of the Keys’ most gorgeous resort beaches, find your way to the Moorings Village. With its eighteen new and historic cottages and houses spread wide over eighteen acres of old-growth trees, this feels like another world from neighboring Cheeca. It, too, has a spa, but if you’re looking for dinner, you’ll want to venture out to Pierre’s (owned by the same people as the Moorings). It’s known for the best French cuisine outside of Key West. The changing list of entrées might include shellfish risotto or pan-seared snapper with roasted corn and pepper hash.

Diving is divine throughout the Keys, but Key Largo boasts some of the best, so plan on a snorkeling or scuba trip with any one of the dozen or so operations. It’s a Dive runs out of Marriott’s Key Largo Bay Resort and offers resort dives for first-timers, a good way to gauge your enthusiasm for the expensive, time-consuming sport. The resort itself has its luxury qualities, but my pick for Key Largo would be an eleven-unit boutique property on Florida Bay named Kona Kai Resort. Here, attention is individualized and elements such as an art gallery and orchid house punch up the personality.

Key Largo’s restaurants tend to be as laid-back as its islanders, so opt for one of the classics such as the Fish House, where the seafood doesn’t get any fresher, or Sundowners, for a romantic front-row view of the day’s curtain call. It’s a fitting end to any Keys road trip, no matter what route you take.

Chelle Koster Walton is the author of Fodor’s Florida Keys InFocus.