{Trip Report} The FL Keys for Winter Break

Those who live in colder regions of the USA typically get a wonderful week off in February called ‘Winter Break.’ Throngs of people take advantage of the time off from school to get an actual break from the brutal winter weather. Most of us are plain SICK of snow and freezing temperatures by February. Last year I regretted not booking a warm weather vacation, but I did check for last minute deals: there were none left. Flights were booked solid with the exception of a few $1,000 seats left. Um, no thank you! I vowed not to make that mistake again. I budgeted our family of 3 approximately $2,500 (see expense report at the bottom) and began to research possible destinations that would fit my small (teacher) budget. In the end, the Florida Keys won.


Saturday: We are loyal Southwest Airline customers, especially after they integrated the A/B/C lineup concept; we despised the first-come, first-serve lineup gig they had years and years ago. Eight or so years ago we got rid of all our credit cards and signed up for the Visa Southwest Reward card. We get points for all our purchases, and we find that it helps fund our vacations. For instance, last year we cashed in our points and scored six free round trip flights to places like Florida and Puerto Rico. We currently have three free flights waiting to be used for our next trip. Since Southwest bought Airtrain, more and more international flights are coming available; soon we’ll be able to use our points easily to book flights on Southwest.com to Aruba, Mexico, Jamaica, the Bahamas, Bermuda, and the Dominican Republic. In a nutshell, we love Southwest, and we used points to help ease the cost of flying down to Florida during a prime time.

Our nonstop flight out of Buffalo was set to depart mid afternoon.  We were a little anxious about our flight being cancelled or delayed due to a storm that had wreaked havoc in many nearby cities. Just the day before we had received an additional 9″ of snow.

At 7:30 in the morning, Southwest text me to say that our 3:30 pm flight was already delayed. That didn’t sound promising! We hit the road just before noon and made it to Buffalo with plenty of time to spare. We were ushered to the prescreen TSA line where we didn’t have to remove our shoes or sweatshirts. They did test Nick’s hands, though. They also pulled his carry on because he had a big, big box cutter in it. Awesome.

We opted to try the famous Anchor Bar for some wings, we but found the food to be very average. If anyone thinks Buffalo Anchor Bar’s wings are the best, then they’ve never had awesome wings. The flavor was decent, but the wings were soggy and too large. As we walked to our gate, we saw that the plane had actually arrived, and the departure time was bumped up. However, the gate area was packed with strollers and kids. This was going to be a noisy flight. And it was. I was beginning to feel a bit claustrophobic by the end. I was ready to be rid of some of my fellow passengers.

The baggage area at Ft. Lauderdale was packed, too, so Nick went to get our rental car while I collected the suitcases. We used Budget for a mid size car as Southwest emailed me a good last minute deal. I promptly cancelled my Advantage reservation. The car we ended up with was very familiar to us: a red VW Jetta. Ha!

The sun had disappeared, but it was perfectly warm outside. So much so, that we drove with the windows down, savoring the warmth. We headed south for about 45 minutes to our hotel in Kendall. After checking in, Nick ran out to pick us up some pizza and beer. He came back just in time for the 9pm Gator basketball game.

Sunday: We woke up to blue skies and mild temperatures, ready for a fun-filled day in Florida. We started it by checking out of our hotel and driving toward the Everglades for a semi-private airboat tour through Airboat In Everglades.


Let me begin by saying that I grew up in Florida and have seen plenty of gators; additionally, I’ve been on an airboat tour before (St. John’s river in Central FL). Despite this, I LOVED this tour! We took the 1 hour semi-private tour and had a blast. Communication prior to the tour was top-notch, and I liked that this company uses Google Calendar. We were on the 11am tour on a clear and breezy February morning. We definitely needed our sweatshirts. Steve was our guide; he was thorough, friendly, and an excellent driver. We were able to get close to 2 gators and also saw 3 others in the wild (but they were very shy). We also saw a variety of birds including the colorful “swamp chicken.” Steve, our driver, received a lot of questions, and he knew all the answers. It was a very informative day out in the ‘glades.gator



Swamp chicken like cheesy puffs

We hopped into the Jetta and began our drive to the Keys, stopping first at Robbie is Here roadside stand to grab some produce and yummy shakes. Xander ended up choosing the best one: simple coconut! I picked up some mangoes, herbs, and a variety of unusual tropical fruits (which in the end I didn’t like). I also picked up a delicious tangerine infused honey.

I didn't like this fruit

I didn’t like this fruit

We left and took a scenic route, driving by a variety of farms, groves, and palm tree nurseries. We spotted many u-pick opportunities and even a road stand selling orchids for $5! Before we knew it, we were entering the Florida Keys!


Ahhh, the Keys. The Keys are laid back Florida at its best; marina t-shirts and flip flops are mandatory attire. It’s where you can dine under towering palm trees, and tiki torches illuminate the evening sky.  The people are tanned and friendly and will most likely share a story or two with you. Fried fish baskets are on the menu everywhere as is lobster and alligator. It’s such a fun and beautiful place.

Enroute to Islamorada, we stopped for lunch in Key Largo at an obscure little canal restaurant called Shipwrecked. We found a table on the dock under a palm tree. It was time to order my first fried fish of the vacation. Oh, and to have a beer of course.

After a stop at Publix, we headed toward out hotel. I had received an email a week earlier stating that the Hampton Inn had been sold, but our reservations would still be honored. Strange…..


We nearly passed the hotel because it looked abandoned and closed. The Hampton Inn sign had been removed, the key cards we received were blank, and many things were broken (ice machines and one of the exterior entrance doors). Despite the strangeness…. I loved this hotel. Yes, it needs renovation. The living room furniture is dated, the pans in the kitchen are scratched and rusted, the pool bathroom is filled with mold.




On the plus side, the lobby is beautiful, the beach and dock is picturesque, the pool is warm (even in February), and the live music from the tiki bar is perfectly beachy. Our room was one of the few beachfront ones. We had an amazing Atlantic view. We spent time at the pool, marveling at the sunset. I cooked us up a batch of tacos in the hotel kitchen that night, and we sat out on the balcony  to watch the full moon rise up. It was an epic sight!

Moon rise

Moon rise

Monday: I woke up in time to view the sunrise while sitting on our balcony. The sky was perfectly clear which allowed unobstructed views of the sun as it emerged and tinted the sky orange and yellow. After a lackluster breakfast courtesy of the no-name hotel, we got dressed and went out to explore.

Good morning, Islamorada!

Good morning, Islamorada!

No photoshopping needed!

No photoshopping needed!

First we stopped at Robbie’s Marina so Xander could feed the huge tarpon that congregate in masses. We quickly saw that the pelicans also were congregating. Luckily, Robbie’s has a pelican security dude who whips a pole at any pelican that nears a visitor who is trying to feed the tarpon. Our $5 bucket of fish was quickly emptied, and Nick got a tarpon to jump out of the water. Though in turn. Nick jumped too. Ha! We explored around the marina and checked out the shops, kayak shack, and dock area. It’s a really neat little spot.



Watch your fingers!

Watch your fingers!


We then went down to the Rain Barrel to see the giant lobster, peek into some of the shops, and grab a “snack” to make up for the terrible breakfast.my ham and cheese was delicious and Nick had a lobster roll.


At 1pm we headed to the designated meeting point for our snorkel tour to Cheeca Rocks reef. Unfortunately, the water was terribly chopping, and Xander ingested a gallon of salt water as soon as he got in the ocean. The waves were quite rough, so he was immediately freaked out. Long story short, we had a very nice boat tour instead of a snorkel tour. Xander and I sat onboard and watched the brave souls bounce around the waves. Nick went out for a bit, but he tired quickly and joined us. One older man had to be rescued by the 1st mate, and one woman barfed off the back of the boat, so we had plenty of entertainment. The scenery was beautiful and the sun was warm; it wasn’t a total bust. When we arrived back at the marina, we watched all the fishermen filet their daily catch.

Back at the hotel, we relaxed and hit the pool. Later, we drove over to a local establishment called Lorelei’s where we dined on Mahi tacos.



 Tuesday: We decided today was a good day to explore, so we loaded up the Jetta and headed south. It was another beautiful day, so we kept the windows down for most of our ride. Our destination was Big Pine Key; we wanted to spend a day at one of the Key’s best beaches. We pulled into Bahia Honda State Beach Park shortly after it opened, and there was a line. We drove around the park before settling on the southwest side to set up our towels. We found a secluded spot under a towering palm tree. There was minimal sand due to ALL the seaweed that was on shore, and the water was FREEZING. But, hey, it was February. Oddly enough, the concession stand was excellent; we had a Jamaican patty, a turkey sub, and a corn dog.

Having fun on the seaweed beach

Back at the hotel Xander played in the pool with his new snorkel. He was actually really good with it! For dinner, we walked to Lazy Days restaurant for a beach side dinner. It was here that Xander discovered how much he loved fried alligator. Even though it was a tad bit breezy on the beach, we loved hearing the waves crash and having our toes in the sand as we ate.

X is proud of his beach-side drawing

Wednesday: Today is Key West day! Nick and I both love this key; it’s eclectic, colorful, and a ton of fun. Unfortunately though, Xander woke up with pink eye. Grrreat! A quick Google search told us that there was a highly rated walk-in clinic in KW: perfect! And the ratings were true; we were in and out in 20 minutes. The laid back doctor even gave us the eye drops free of charge! No need for a prescription.

We miraculously found street parking near our favorite breakfast place, Blue Heaven. We put our name in and found a seat at the outside bar. Time for a much needed mimosa and Bloody Mary- they are THE BEST! We didn’t have to wait too long since we opted to eat indoors. Our meal was delish; I had the pecan pancakes while X had regular pancakes and Nick feasted on a smorgasbord of items. We left full!

a little ping pong while we wait for a table

mimosa, tea, and a Bloody Mary



alittle ping pong while we wait for a table

For the rest of our day in KW, we stopped at the aquarium to check out their tanks and to feed the sting rays.


Jelly fish

Jelly fish


Then we got some ice cream and I did a little window shopping. We looked for some Hawaiian shirts, too, for our summer vacation. Nick came up empty handed, but we scored Xander a handsome little number. We ultimately ended our day trip with a stroll up Duval and a drink at Nick’s favorite dive bar, Captain Tony’s.


The drive back was uneventful, and we even saw some of the famous pine deer! We never got close enough, though, to get a decent picture. Once back in Islamorada, we decided on the Islamorada Fish Co for dinner, and thoroughly enjoyed our fish and alligator meals!

dusk enroute to Islamorada

dusk enroute to Islamorada

Thursday: All good things much come to an end. After a morning swim, we packed the car and headed north for the airport. For lunch we stopped at a Key Largo hot spot: Fisheries. It’s located in the back of a marina warehouse near a parking lot full of lobster cages. You order your meal at a window and then dine by the docks at a well kept and shaded picnic area. Time for more fresh fish!


We are now back to the ice, cold, greyness….aka reality. We day dream about the smell of sea water, the swaying of the palm trees in the breeze, the warm sun, and eating fresh fruit and fish alfresco. Til next time!

Budget Fun:

Flights: $404.70 (50% off thanks to Southwest FF miles)

Hotels for 5 nights: $1,476.74

—$1,291.95 (Hampton Inn Islamorada 1 bedroom beachfront suite, advanced purchase deal)

—$180.79 (Best Western in Miami, AAA rate)

Rental Car: $289 (Advantage, midsize)

Tours: $130

Food/Bar Tabs: who knows!

Basic Total: $2,300.44


3 thoughts on “{Trip Report} The FL Keys for Winter Break

  1. As always, I feel like I was with you! Looks like a fantastic trip and thank you for some of the ideas! The Dude doesn’t know it yet (birthday present in September), but I have signed him up for the Key West Half Marathon in January. Already booked our B&B (no kids this trip!) and have free airfare courtesy of our Southwest points!

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