Florida Keys

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We decided to experience Southern Florida by way of a road trip through the Florida Keys this March. Having flown into Miami, our first stop was 90 minutes away in Islamorada. Known as the “village of islands,” it encompasses six of the Florida Keys. The Islands lie along the Florida Straits dividing the Atlantic Ocean to the east and the Gulf of Mexico to the northwest. Prior to 1900, they were hard to reach other than by boat, so American business magnate and the “brains behind Standard Oil, “Henry M. Flagler, began building a railroad to connect Jacksonville, Florida to Key West in 1903. He filled swamps, bridged waterways, conquered jungles, and rebuilt after hurricane destruction. Flagler first rode his train to Key West in 1912. Today there is one main road connecting all the Keys, the Overseas Highway, which is one of the longest overwater roads in the world, with 42 bridges, including one spanning 7-miles. Islamorada is known as the Sports Fishing capital of the world. Little did I know, that in March when we visited, it might have been the Spring Break capital of the world!

We joined our friends in the Keys, (both husbands went to Paintbranch high school with Scott.) One couple has a charming seaside vacation home in Islamorada, and the other couple drove their motorhome down from Virginia to stay at a local campground. We choose to stay at the Checca Lodge, in an oceanview room complete with a bathtub on the balcony. As we arrived at twilight, we spotted the beach BBQ, live music, and fireworks. The following day, after an eggs-benedict decadent brunch, we escaped the “Marco Polo” family pool party to spend time at our friend’s home playing pickleball, paddleboarding, kayaking, and taking their boat out to Alligator Reef for a swim by the old lighthouse. Of course, Scott swam, I was freezing in the boat while wearing a sweater and jacket.

Our room at Checca Lodge
Checca Lodge Beach BBQ
Scott getting his swim on
Me freezing

We had a delicious French Fusion dinner at Pierre’s, a two-story plantation house that resembles the old colonial-style residences found in West Africa. We dined amidst a glorious, palm-lined beach overlooking Florida Bay. We were given a choice of dining on the second floor, in an interior room, or on the veranda-accompanied by Islamorada’s spectacular sunsets and tropical views. We chose the second floor and caught the sunset while sipping martinis.

Our next stop was three hours further south towards Key West. We drove to Torch Key Shore Station, a welcoming lodge to “check-in, valet park our vehicle, get a complimentary rum drink while awaiting our Chris-Craft to take us to our private island. Our destination; Little Palm Island, ranked the #7 resort in the USA by Conde Nast. After our 15-minute boat ride, we were met dockside by our smiling concierge, Cat, who would be assigned to us for our stay. She showed us around the 4-acre island with its spa, gym, motor and sailboats, pool cabanas, and the most deluxe accommodations I’ve ever stayed in. Our bungalow came complete with an outdoor soaking tub, private beach, fire pit (which they lit for us every night when we left to go to dinner), living room, bedroom, ensuite bath, shower, and second outdoor shower, master with sitting area and West Indian curtained bed, and even our name on the entrance!. The resort had live entertainment nightly, indoor, outdoor, bungalow or beach dining, and basically anything you could dream of. To top it off, there are only 30 bungalows on the island, so it felt peaceful, quiet, uncrowded, and luxurious. As far as food goes, we dined like Kings and Queens. Scott had what he now declares as the best Cuban sandwich of his life.

The Cuban

Our last stop was a 4.5-hour drive north on the highway to Palm Beach. Luckily, we were headed against the traffic. We stopped in Miami for a BBQ lunch at the famous Shorty’s and then checked into The Breakers Hotel in the afternoon.

The Breakers was built in 1896 and is a grand dame. Room rates started at four dollars a night and included three meals a day. The guest register read like a “Who’s Who” of early twentieth-century America – Rockefellers, Vanderbilts, Astors, Andrew Carnegie, and J.P. Morgan vacationed alongside United States presidents and European nobility.

The Breakers Hotel

The lobby and ballrooms are gilded-age opulence with a magisterial presence! Our travel agent booked us in one of their remodeled rooms which was updated to chic Palm Beach pink and green decor. It’s a large hotel with four pools (the adult pool is a stone’s throw away from the kid’s pool, so it’s still loud) and a bit of a wait for the buffet breakfast, lunch, pool chairs, etc. The Spring Break mode was in full speed here too. Upon arrival, we stopped into the Seafood Bar for dinner and were hit by loud techno music, drunk flirting single Floridians, and an air-conditioned indoor crowded bar scene/restaurant, with nobody wearing masks. (I felt like I had gone from a private island to the third ring of Hell!) Eventually, I made my way a few days later to the Breaker’s Spa, however, which was soothing, top-notch, and rejuvenating.

The Breakers Hotel, Palm Beach, Florida
The Breakers Hotel, The Seafood Bar (in the morning…before the crowds arrive!)
Spa at The Breakers

We spent one afternoon touring the Flagler Museum, “Whitehall,” (home to Henry Flagler, the man who built the Keys railroad, The Breakers Hotel, and many other properties in Florida.) His Palm Beach mansion/museum features a plethora of antique-laden bedrooms, great rooms, music rooms, and even his personal train car. On August 24, 1901, Flagler married for the third time, to Mary Lily Kenan. Built as a wedding present to Mary Lily in 1902 and designed by architects John Carrère and Thomas Hastings, Whitehall became the Flagler’s winter home. With more than 100,000 square feet and 75-plus rooms, Whitehall was described in 1902 by the New York Herald as, “… more wonderful than any palace in Europe, grander and more magnificent than any other private dwelling in the world.”

Whitehall, The Flagler Museum

Worth Avenue is the shopping street for the Palm Beach elite, so we strolled up and down the beckoning blocks and had a blast meandering in and out of the little hidden courtyards behind the shops. (These nooks are called the “Vias”). We had a delicious lunch in one of those charming courtyards at Pizza Al Fresco. The courtyard was filled with blooming violet hydrangeas, lively conversation, and fashionable ladies who lunch. My lobster salad was scrumptious.

Worth Avenue

For dinner, we were able to secure a reservation at Lola 41, one of the latest hot spots serving Asian cuisine. It’s part of the White Elephant boutique hotel in the center of town. A local celebrity from Fox News was dining near us (I had no idea who she was) and many guests jumped out of their seats to take selfies with her.

My favorite lunch was at Swifty’s at the Colony Hotel. This place was a scene! The outdoor patio is covered with a ceiling made from artificial vines and flowers. The restaurant is adjacent to the hotel pool and hip diners chat away while watching the lively chic pool scene, complete with singer/guitar player. (See video below.)

Swifty’s at The Colony Hotel

Florida offers stunning beaches, lively nightlife, serene islands, and a shoppers paradise. When I return, I will avoid Spring Break, try a boutique hotel or two, and make sure to reserve outdoor dining at my new favorite hot spots. Until then, I’ll throw on my Lily Pulitzer pink and green, blend up a rum drink, and play some Cuban music when I want to stay in a Florida state of mind.

The Breakers Courtyard
Our Bungalow, Little Palm Island
Happy Hour Little Palm Island
Lunch at Swifty’s in Palm Beach




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