There's so much more to this charming string of Islands in South Florida than Jimmy Buffett could ever sing about.

Pulling in to Key West at dusk, we immediately wished we could ditch our car for one of the pastel colored cruiser bicycles ridden by the carefree crowd we passed. They were tan, flip flopped and downright happy looking as they pedaled along the two-by-four-mile island. The daiquiris were already flowing on Duval Street (but I think that might always be the case no matter the time of day), as we pulled into town.

From Victorian bed and breakfasts to hotels right in the middle of the action, the accommodation options are endless. The 100-room Ocean Key Resort & Spa (0 Duval Street) sits at the end of Duval with views of the Gulf. Everything feels classic Key West — the beachy décor in the spacious rooms with balconies and the Sunset Pier (one of the best spots for waterfront dining in town). You can walk right out your door to get in on all the action on Duval (a drag show is a must and Randy Roberts at La Te Da (1125 Duval Street) does it best as Cher and Lady Gaga). After a breakfast of divine crepes from La Creperie Key West (300 Petronia Street) and a tour of Ernest Hemingway’s House (907 Whitehead Street), which is carefully presided over by the late writer’s six-toed cats, we headed to Fort Zachary Taylor Historic State Park, the best place for a beach picnic or lingering in the sand. One night out on the town in Key West was enough for us, but we still weren’t quite ready to move on to the next Key as we planned to work our way back up north.

It was a quick boat ride to Sunset Key Guest Cottages, A Westin Resort (catch the ferry at Mallory Square just outside the Westin Hotel on the main island). I had heard that Oprah Winfrey rented the entire island to celebrate her 44th birthday, so I was excited to see where the woman herself had chosen to spend a birthday above anywhere else in the world. Pulling up to the dock, the crisp, white cottages with Victorian-style tin roofs along the waterfront looked inviting and cozy. They are perfect for a couple or a family, with one, two, three or four bedroom floor plans, each equipped with a kitchen and living room. The 27-acre island felt serene, but hopping over to bumping Key West only took a few minutes. We chose to soak up the island with tennis, reading on the spacious private beach (a rarity for many of the Key West area hotels) and swimming in the pool. The highlight had to be a dinner on the beach at the more formal restaurant Latitudes, a destination many travelers not staying at the hotel make the special trip to. After so much time in the sun (and starting the day with a delicious breakfast delivered to our room in a picnic basket), the Rose Hydrating Facial in the modern Spa at Sunset Key was just what I needed. Sadly, it was time to make our way back to the next Key, but we couldn’t leave Key West without trying another must for a trip there — Cuban food! El Siboney (900 Catherine Street), just off the beaten path, was just the spot for delicious roasted pork and a Cuban Mix sandwich.

After a drag show, a slice of Key Lime Pie, a stroll through the Hemingway House, some authentic Cuban food and a beautiful sunset dinner on the beach, we felt like we saw the quintessential Key West, so it was off to Little Torch Key for a stay at Little Palm Island. We pulled up to a discreet building on Little Torch Key ( just off Pirates Road…yes, that’s the real name) to leave our car, where a cheery bellman greeted us with a summery cocktail to lead us to the motor yacht that would take us on a breezy 20-minute boat ride to Little Palm. I have always longingly looked at photos of the thatch-roofed hotels in Bora Bora and Fiji, wishing I had time for a longer vacation to enjoy one. As we arrived at the dock, I realized I might never have to go that far for a true private island experience — the sand was white, the water, blue and there were those bungalows I had dreamed of. A shaded path lined with palm trees led us to our suite which was marked with our last name spelled out in wood blocks — a sign of the personalization and amazing attention detail that comes along with staying on a private island with only 30 suites. Everything felt secluded and peaceful. There’s really no need to ever leave the island, especially when the award-winning Dining Room at Little Palm is a short walk away. Led by Chef Luis Pous, dishes on the inspired menu (that changes nightly) use Pan-Latin ingredients with clever French cooking techniques. Meals can be enjoyed on the beach, in your room or in an assortment of adventurous ways through extra experiences like the “Private Island Picnic” where guests are flown on a seaplane to a private island for three luxurious hours to enjoy a five-star picnic, complete with caviar and champagne before takeoff (starts at $2,700 per couple).

It seemed that whatever the request, the Little Palm staff would make it happen. After breakfast on the porch of our bungalow, we started our days with a chat with the warm and friendly Rolondo Barrera who manages all the recreational activities like kayaking, paddle boarding, fishing and the motorboats that guests can take anytime. Barrera has worked on the Island for almost a decade, and he, like every other employee we met, seemed thrilled to be at work every day. “It’s paradise,” he says. “How can you not be happy here?” If merely stepping onto the Island doesn’t trigger enough relaxation, the tree house-like spa offers an array of heavenly treatments. The television in the property’s library is the only one on the island, making not disconnecting from the mainland near impossible. We savored our last moments on the island before bidding farewell to the highlight of our trip. We stopped for lunch at the wonderfully dive-y No Name Pub (30813 North Watson Boulevard). It was built in 1936 and is covered in dollar bills from floor to ceiling from the many travelers who have passed through its doors. We tried the famous pizza and were not disappointed.

Our final stop of the trip before flying back to Austin out of Fort Lauderdale (Jet Blue offers a direct flight and the smaller Fort Lauderdale airport is easier to travel through than neighboring Miami) was to one of the northern most keys, Islamorada, for a stay at the Cheeca Lodge (81801 Overseas Highway). Known for being a favorite vacation spot of the Bush family, it’s not just the prepsters who frequent this resort, a long-time favorite of regional, national and international travelers alike. This was the first room we had, where you literally walked out the door and onto the beach. Something about the art deco buildings and nine-hole pitch and putt golf course felt nostalgic, but at the same time fully equipped with all the best modern amenities. Our last Floridian supper was at the perfect spot — Lorelei’s Restaurant and Cabana Bar (81924 Overseas Highway), just a short drive down the highway from Cheeca. A Jimmy Buffett look alike provided the musical entertainment that night and a few locals danced their hearts out as the packed house of diners on the waterfront noshed on coconut shrimp and cracked conch sandwiches. It was a picturesque end to the trip. As we pulled out of the Keys, we vowed to take the laid back approach to life that seems infectious there back with us…unfortunately, it didn’t last long, so a return trip is already in the works.