Florida Keys Trip:  Part 1 – Islamorada

Florida Keys Trip:  Part 1 – Islamorada

I was out last week on a long awaited trip down to our country’s southeastern tip to spend some time in America’s tropical oasis, the Florida Keys.  Going along with another couple, we left the turning autumn leaves and plummeting temps of Western Maryland for the sunny skies, warm temperatures (make that extremely hot and humid temperatures), and the warm waters of both the Atlantic and Gulf of Mexico.

We started last Saturday out of BWI on a Southwest plane ride that I can only describe as the coldest in-flight experience I have ever encountered.  Seriously, I kept checking my toes for frostbite.  Not a seat was spared as other passengers were headed for cruise ports and exotic sailings out of Miami, while we rode the MIA rail train over to the rental car station, picked up our mini-van for the week, and headed south towards Route 1 and our island paradise.

I made a special Pandora (I know – I’m old) music station to commemorate our trip. We were soon jamming to island rhythms and Jimmy Buffet lyrics as we headed off of the Florida mainland and deep into the island chain of the Florida Keys.

Our first stop was our accommodations in Islamorada, one of the bigger islands of the upper keys.  We were staying at the La Siesta Resort, tucked right in on the oceanside, with a small marina, a few banks of hotel rooms, and our lodgings, small beachfront casitas nestled right along the water’s edge.  We were assigned a purple unit while our friends were given an orange colored one, and after settling in, we headed off to find some dinner.

Our tropical lodgings at the “La Siesta” Resort. A great way to get into the island spirit of the Florida Keys!

Our dining stop was Lorelei’s, just up the road and situated on the gulf side of the island.  This was true waterfront dining, and we sipped on our first tropical drinks in the humid air while sampling peel-and-eat shrimp, conch fritters, and blackened Mahi fish sandwiches.

The travel day had taken its toll on us, and we then retreated back to our casitas, sat out on the beach under the stars, and watched the distant thunderstorms light up the night on the ocean’s horizon.  It was a very good first day.

I arose before the sun on ‘Day Two’, grabbing a cup of coffee and heading out to the waterfront to enjoy my first sunrise.  The coconut laden palms were dropping fruit, and occasional crashes could be heard in the landscaping as heavy coconuts found their way to the ground from dozens of feet up.  The air was also thick with humidity, even in the pre-dawn darkness.  I registered a “real feel” of over 96 degrees on my phone, even in the black of the early morning.  It was a humidity we would battle all throughout the week, and it required us to drink plenty of fluids (non-alcoholic ones) to stay hydrated.

The water was calm as the sun changed the brightening skies from deep purple to orange, red, and pink as the sun made its way relentlessly towards the horizon.  The Keys actually don’t see much surf, as outlying reefs prevent the build-up of large waves from pummeling the shoreline.  All that could be heard was the gentle lapping of the water on the docks or the boats rubbing softly against their moorings.  The sun finally broke the horizon and the change in temperature was almost instantaneous.  It was going to be another hot day.

A sunrise like this is tough to beat – no matter where in the world you may be!

When all of our party got up and moving, we walked over for breakfast at the quaint Midway Café, situated halfway between Miami and Key West.  There, we dined on plates of eggs and brie cheese on ciabatta bread, fresh fruit, key lime muffins, biscuits and gravy, and crispy bacon.

Then it was off to do some exploring.  We stopped at Rain Barrel Village, a kitschy souvenir stand guarded by a giant plastic Key West spiny lobster named “Betsy”.  We strolled through the stands and bought a few gifts before heading back up the road, where we discovered a weekend farmer’s market.  Here we gathered supplies for the afternoon, including fresh lychee fruits, warm flat-breads, spices, yogurt balls, hummus, and olives.

With our lunch gathered, we headed off to the local marina to catch our afternoon charter on a pontoon boat out to an offshore sandbar to party the afternoon away in the water with Conch City Charters.  We were met by Captain Jack (yes, that was his real name) and first mate Sarah, who got us on board for our three-hour adventure out into the Atlantic.  Captain Jack first sailed us by some of the magnificent and over-the-top waterfront houses before we headed out about a mile or so to the sandbar, which was unmistakable.  Here, dozens of boats of all shapes and sizes were docked up in the shallow water, their occupants frolicking in the waist-high surf and listening to music.  There was even a floating food truck barge to provide snacks to those who didn’t pack any.  We spent the afternoon floating in the warm waters, chatting with strangers, talking about boats, and watching as large rays silently slid by our feet below.  Captain Jack and Sarah were wonderful hosts, and their personalities and hospitality made for a great afternoon on the water.

After our charter, we headed into Hog Heaven, another waterside eatery for some barbeque, wings, and more beers to round off the trip.  After sunset, we once again sat out in front of our casitas to have a few late night cocktails, this time under the protection of a thatched roof beach cabana (as a sudden rain storm brought some “liquid sunshine” to the close of our second night).

‘Day Three’ began with more coffee, another sunrise, and my first beer of the day (cracked at 7:30 AM – I’m on vacation for crying out loud) before we packed up our gear to head down towards our next destination, saying goodbye to the lovely casitas at “La Siesta”.

We then made a stop at Robbie’s, an Islamorada institution, where yes, we did indulge in feeding the massive tarpons that lounge around their waterfront docks.  For $5, you receive a small bucket of bait fish, which you must then carefully weave your way out onto the pier through persistent pelicans in order to dangle the bait out over the water.  Soon (and without warning), massive tarpons (some over five feet) come lunging out of the water to take your offering, resulting in frightened giggles and amusement to all those involved.  It really was worth the price of admission.

If you ever find yourself in the Keys, don’t pass up a chance to stop at “Robbie’s”. Sure it’s touristy, but it’s also a lot of fun!

Following a nice hand washing (to eliminate the fish smell), it was then time to continue our journey, which I’ll chronicle in next week’s post.  Hope you’ll come along for the ride!

NEXT WEEK:  Part 2 – Key West!

2 thoughts on “Florida Keys Trip:  Part 1 – Islamorada

  1. Sounds like a wonderful trip. The “Keys” have always been on my bucket list so very interesting to get your insights.

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