Unexpected Florida: A road trip stop in St. Augustine

If the thought of a Florida vacation conjures images of drunken spring breakers and white-haired snowbirds shuffling around golf courses brandishing nine-irons, it might be time to broaden your view. The penultimate stop on our recent Florida road trip found us smack in the middle of the oldest city in the United States: St. Augustine.

We left downtown Orlando and headed northeast to the coastal city of St. Augustine. The farthest north in Florida we’d ever been, we knew that despite the fact it was late February, the weather might not be beach-worthy. We were right. But we weren’t quite prepared for were the extraordinary historic landmarks that make up this little gem of a town.

Founded by the Spanish conquistadors in 1565, St. Augustine is sometimes described as the longest-established city in North America. However, St. John’s, Newfoundland here in Canada was established in 1497 and Mexico City in 1325. But it is the oldest “continuously-inhabited European-established settlement” in the US (at least according to Wikipedia). And that Spanish influence is evident throughout the little streets of the old town.

The town has a lengthy and storied history: invasions by pirates in the sixteenth and seventeenth centuries, a British loyalist haven after Florida was ceded to Great Britain in 1763, changing hands several times to one of the most interesting parts of its history: the “invasion” of tourists brought by the extension of the railroad in the late 1800s.

Henry Flagler, one of the owners of the Standard Oil Company (with J.D. Rockefeller) enjoyed winter in St. Augustine in 1883 after which he decided to form a new railway company to lure wealthy Americans from wintery places like New York and Boston south for the winter season. He built two hotels: The Hotel Ponce de Leon and the Alcazar. He then bought the already-established Cordova Hotel and the town flourished. That is until the railroad was extended farther south to Miami where visitors could count on warmer weather throughout the entire season. St. Augustine was no longer the winter darling of the northern visitors.

Even today, though, those old hotels are triumphs of Spanish colonial architecture and are still wonderful to see experience.

The Hotel Ponce de Leon is now the beautiful home of Flagler College as the two photos below show…

…and the Hotel Alcazar is a museum, both worth visiting. We did. Here are two shots that evoke what it must have been like “back in the day.”

And then there’s the old Cordova Hotel that Flagler renamed The Casa Monica. Well, that hotel is now part of the Marriott Autograph collection of quirky hotels and it’s where we stayed. We spent two nights in the two-story St. Francis suite, a nice upgrade for two very loyal Marriott guests!

Art (in a down jacket and hat) in front of the Casa Monica Resort and Spa. It was cold!

Here’s what the St. Francis suite looked like…

The view from our suite…

…and the Casa Monica lobby…

We had already experienced a lot of “quirky” places on this road trip (Orlando, Sarasota) but this one was different. Although those little streets in the old town suggest it storied past, they largely house tourist “traps” that you might enjoy.

We enjoyed walking around and seeing what was there but we’re not really the tourist-shop kind of visitors. Instead, we walked miles over to the island and explored as many of the quiet streets as we could.

Ah for the tourists who prefer not to walk. We did not partake!

When it was time to pull out of St. Augustine, we were headed to our last stop: Fort Lauderdale, that hotbed of drunken spring breakers. No kidding!

Sarasota, Florida: The road trip continues north

Three days in Naples, Florida was more than enough, so it was time to get back into the rented Jeep and head north. Next stop: Sarasota.

After the sprawling suburb that was Naples, we were looking forward to a bigger city – we do love a big city. We were going to have to wait some time, though, since Sarasota, although its downtown does sport a high-rise or two, isn’t really a city either. With a population just shy of 58,000, Sarasota was incorporated as a town in 1902. A few older buildings remain in the downtown area, including a mission church.

We checked into the Westin which is, in fact, located downtown, and walked the urban landscape. It didn’t take long!

The view from our room at the Westin
The Westin’s rooftop bar

The Westin itself is a very pretty, modern hotel. It did, however, have a few “issues.” The elevators were a nightmare – the waits were horrific. And the entire place seems to be understaffed. From the single person at the front desk to the fact that our room wasn’t cleaned until 5 pm the next day (after we called twice) to the wait staff running around the restaurant at breakfast like chickens with their head cut off. All in all, they do have a management problem.

The following morning, we headed across the bay to St. Armand’s Circle, a collection of restaurants, bars and shops.

We then carried on to see the beach through a residential area of laid-back, sometimes quirky little houses until we reached the beach.

A long stretch of white sand, the beach is located along an outer island that can only be reached, as we did, by crossing over a series of bridges that connect a series of keys. It was the weekend, the sun was shining, and the beach was busy.

Then it was time to stop for some rehydration (a beer) at ChaCha Coconuts, a funky little bar on St. Armand’s…

…before we headed back across the bridge toward our home-away-from-home. By the time we arrived back at the hotel, we had walked 15.5 kms. All in a day’s vacationing!

The map shows Sarasota’s downtown connected to the keys. We walked there and back!

Spending two nights in Sarasota was a good way to see the city. But more than that would have been too much. Next stop: downtown Orlando!

Naples (Florida): The road trip continues!

If you thought about getting in your car and heading west from the Florida Keys through the Everglades to the gulf coast, what would you expect to see? Crocodiles crossing the road? Panthers peeking out from behind mangrove swamp? Thick bush towering over the sides of the roadway? Well, that’s what we were expecting when we set out from Key Largo (first stop on the recent road trip) to Naples. Instead, what we saw were flat sawgrass marshes, mangrove marshes and lots of signs to beware of panther crossings. Oh, and then there was that line of traffic and no place to pass. But, then, that’s what road trips are all about.

We set out from Key Largo and the trip through Everglades National Park was actually quite a boring couple of hours. We arrived in Naples to find ourselves in automobile city. The traffic was unexpected and the fact that this is a city of cars not pedestrians really did surprise us. Since we are “walkers” (no, we do not have walkers), we found ourselves the only people out walking almost wherever we went except “downtown” where locals and tourists alike walked from the (many) parking lots to restaurants and the odd boutique. Surprising to us, that’s all there really is downtown.

Patty gets such a kick out of the “Florida style” ala Gretchen Scott (here) and the storied Lily Pulitzer. Not her style but quintessential Florida.

When we thought about Naples, and what we’d heard from people we know who winter there, we expected something more cosmopolitan than a town with a population of around 20,000 and miles upon miles of suburban sprawl. That explains the need for driving everywhere!

We, on the other hand, actually walked the kilometre-and-a-half from our hotel to the mall where there was – not kidding – no sidewalk or pedestrian access. Really! We had to tread in the roadway to even get near the place. But the parking lot was enormous! Clearly, they do not expect anyone to walk. And we walked much farther. It’s the only way to see a place. We did, however, join the locals by taking our car downtown so that we could walk in that area.

Downtown Naples

We drove down Gulfshore Boulevard to downtown (we walked the boulevard the next day) past incredible mansions.

We parked at 12th street then walked for two hours. The downtown is really just a few streets of small, upscale boutiques and some rather nice restaurants. We had lunch at the Ridgway Bar and Grill where the food was delicious and the outdoor, covered patio was a lovely way to sip a glass of wine with a leisurely lunch.

We walked to the Naples beach which is a very long public beach.

Naples beach

Unlike many tropical destinations, there are no hotels on the beach until you get much farther from the downtown area. Many lucky (and well-heeled) residents, though, do have beachfront houses and condos. There are lots of condos!

Three days in Naples was enough. On this road trip we have two and three-night stops. This one could have been two nights but we managed an extra 11 kilometers of walking on the extra day! Next stop: Sarasota.

Key Largo: First stop on a Florida road trip

What image comes immediately to mind for you when someone says “Key Largo”? Do you think of Bogie and Bacall in the eponymous 1948 film noir?

…or perhaps you’re more inclined toward the laid-back, beach-bum image created by the 1981 Bertie Higgins song?

Either way, Key Largo is something different. And it was our first stop in this winter’s Florida road trip.

We flew into Fort Lauderdale, rented a car and drove the almost two-hour drive toward the Florida Keys. The truth is that the drive is unbelievably boring and the traffic going into the Keys? Brutal. But at least Key Largo is at the top of the keys.

We pulled into the Key Largo Beach Marriott Hotel and got our bearings. Let’s start with location.

Great Florida vibe in the hotel lobby

Key Largo is less a “town” than it is a very long, four-lane highway running down the middle of a sandbar where, in places, there are a few streets between the road and the water on either side. Thus, if you’re trying to find a “downtown” hotel, close to everything, you’re out of luck. The Key Largo Bay Marriott Beach Resort, however, is walking distance to a number of bars and restaurants in addition to what’s on the property.

This is what runs down the Keys from one end to the other. Art is heading south.

One of the nearby bars is The Caribbean Club that bills itself as the filming location for Key Largo the movie back in the late ‘40s. Subsequent research, however, suggests that the movie was almost entirely filmed on the Warner lot with only the opening scenes filmed on location in Florida. We’d have to go back and watch the move again to see if this bar really figures in. If it doesn’t, it probably should.

We took a walk north from our hotel one evening and were lured into two spots by the music wafting through the air waves along with the rustling palm trees. At the first one, the band was just finishing a set, so we moved on and stumbled into The Caribbean Club. Filled with a wide variety of laid-back, T-shirt-clad music lovers, we took a seat at the bar and ordered two beers. Strictly cash only. No credit cards.

We sat back and enjoyed the band and our beers and when the set was finished, we moved on. The life-sized statue of Humphrey Bogart at the door was more Rick from Casablanca in his white dinner jacket, but no matter. Atmospheric it was!

The three days in Key Largo were laid-back and rum-filled. There is no reason whatsoever for anyone in Key Largo to wear anything other than a T-shirt, shorts and flip-flops. Since we don’t do downtime as well as many people do, one day we decided to drive to Key West.

Views from our hotel veranda

We’d been there twice before each for one day off a cruise ship and decided that we need to see the Keys in their entirety. Well, when people at the hotel heard we drove there and back in one day, they thought we were crazy. It took two-and-a-half hours to make it down the narrow highway to the end of the Keys and over three hours to drive back. Hideous traffic all the way.

Key West (images above of Papa Hemingway, his house and the southernmost-point-in-the-US marker after Hurricane Dorian) was mobbed by cruise ship travelers. We found a place to park, had lunch then headed back to Key Largo to mellow out a bit.

After three days of chilling it was time to get back in the car and head across the Everglades to our next stop: Naples, Florida.