Our first road trip of the summer – and it’s probably going to be the most romantic one
We’re off on our first ever trip alone. Since we had Logan we haven’t done much without him, actually, we haven’t done much at all. It’s been a long while since we took a vacation and oh baby, did we need this one. I’ve always lusted over the Florida Keys. The other day I was scrolling through Pinterest and I read this post on the perfect road trip through the Florida Keys. I figured we rent a convertible, drive through the keys and have a whole lot of kid-free fun! We spent this past week road tripping through the Florida Keys on a little honeymoon getaway. From snorkeling to eating a ton of Key Lime Pie, we did it all! Take a peek into our trip through my travel diary:
Day 1: Toronto to Fort Lauderdale to Islamorada
Probably the worst and most annoying day ever. We left late and barely made it to the airport on time. Luckily, I checked in the night before, so all we had to do was rush through customs and run onto the plane. JUST KIDDING! A few years ago, Brandon’s identity was stolen by some criminal who made all these crazy charges and got arrested a thousand times. It was cleared up by the police and they issued an apology, but that did nothing for us today. As we were making it through the US border inspection, the criminal record was flagged under Brandon and we were taken to an inspection room. We had an hour until our flight so I was hoping it wouldn’t take long. Boarding time rolls around and no one has come to speak to us yet. 20, 10, 5, 1 minute until our plane leaves and we’re still just sitting there. 2 minutes after our flight departs and the border guard comes in, explains the issue. It took about 10 minutes to get it resolved – GREAT! So now we have to get switched onto the next flight which of course is over 4 hours away.
We lunched at Wahlburger’s at the Toronto Pearson Airport. The food was pretty good, especially because we hadn’t eaten yet and it was already 1 pm. We then proceeded to wait for our flight to Fort Lauderdale.
Once we arrived in Fort Lauderdale, we stepped off the plane and went over to baggage claim. OF COURSE, only to find that Brandon’s luggage had arrived, but mine hadn’t. The airline had no idea where it was or when I could get it back. They offered an ambiguous stipend for me to purchase necessary items to tide me over until my suitcase came.
So, we picked up our car and headed first to Target. Luckily, this was my saving grace for the day. At our airline’s expense, I was going on a shopping spree and getting everything and anything, I wanted for this trip. Can I just say that a bloggers worst fear is losing their luggage? Between the sponsored post and overall experience, I had specific clothing picked for each day and products I was supposed to be featuring.
We then dined at Texas Roadhouse – which is Brandon’s favorite restaurant. They have a very carb, meat and deep-fried menu.
After dinner, we started our road trip to our first island stop, Islamorada. We were going to be staying at the Fisher Inn – a newly renovated hotel right beside the ocean. I was a bit disappointed – I planned this beautiful island driving road trip and our start is in the dark night, where we can’t see a thing. When we got to our hotel, the staff at the Fisher Inn were so sweet and understanding. They gave us some ice cream and helped us into our room.
I was so happy after Day 1 was done.
Day 2: Islamorada
Waking up in Paradise! Today was going to be a good day. We had a full day planned and I was so excited. We started first with a quick breakfast in our hotel, The Fisher Inn, then put the top down and started driving again.
Our first excursion was at John Pennekamp State Park, we were going snorkeling us off the islands. Brandon and I have never been snorkeling, so this was a first for us. We were a little nervous, especially since I’m not the best swimmer. Our first-time snorkeling was the best time snorkeling. The instructors were amazing and helpful – plus, they showed us the perfect spot to see so many beautiful fish! Here, we decided that we’re going snorkeling on every beach vacation we head out on in the future.
We lunched at Sundowners, a beautiful restaurant in the heart of Islamorada. The day we came, it had just been taken over by a new owner, literally the day before. So, they were starting to renovate and add on a bunch of new décor. The restaurant is already really pretty as you sit over the water, but I think the new owner is going to make some amazing changes! We were finally able to sample some of the seafood that the keys are all about. They prepared a Jamaican Jerk Fish Sandwich that was served with lime chili tater tots – so yummy!
After a delicious lunch, we headed back to our hotel for a little relaxing. Well, Brandon needed to relax, I didn’t. I went out on my own a little with a paddle board. The Fisher Inn has a bunch of fun equipment for their guests to use. I headed out on the water for a little before heading back to get ready for dinner.
For a carefree evening, we used the complimentary bikes from the Fisher Inn. We biked over to the Ciao Hound, an Italian dining spot a few minutes away at the Postcard Inn. When I say this was my favorite restaurant of the trip, it was my favorite restaurant of the entire trip and any trip I’ve ever been on before.
Read more about Ciao Hound in Islamorada here.
From the delicious drinks and entrees and desserts to the amazingly friendly staff and welcoming toast, I don’t think I’ve been at a better restaurant and I don’t think I ever will.
Day 2 is finally the kind of vacation I was envisioning.
Day 3: Islamorada to Key West
I was so sad to leave, but it was time to head out from Islamorada. Our first stop was at Robbie’s Marina. Upon pulling up in the parking lot, I knew this was my kinda spot. There is a whole little outdoor market place that has the cutest and most photographable souvenirs. Robbie’s of Islamorada also has a whole watersport section where you can rent kayaks, stand up paddle boards, and more. But, our favorite thing was the Tarpon feeding. I’ve always wanted to try it and even though I was a little afraid of these giant fish, I did it. They dive out of the water to eat right from your hand!
We then had lunch at Robbie’s too. Their restaurant dining area is nice and shaded from the sun. My favorite thing is that it’s decorated in dollar bills. The belief is that you leave a dollar for a pirate to have a beer at the bar so they don’t rob you. We left our signed dollar on the side of the bar for any future pirates who are there 😉 We had a really delicious lunch there too. The menu is really fresh and is full of delicious options. It’s the first restaurant we visited so far that had lots of vegan/vegetarian options for me. I highly recommend the veggie tacos!
We then continued along our drive to Key West. Today, our drive was much better. There was so much of the beautiful islands to see – especially when we drove over the 7-mile bridge.
When made it to our hotel, the Southernmost Beach Resort, I was so excited to see the pool view from our room – and also the bar right beside the pool. We felt the luxury as soon as we stepped into the hotel. Their staff was so accommodating, they gave us a tour of the resort, let us know a little about Key West’s offerings and even toasted us with a little white wine. We checked into a pool view room and had a view that extended little ways to the ocean.
During this time (end of May/early June) the Keys are subject to sargassum – an overflow of seaweed that washes up onto their beaches. There isn’t much the islands can do since so much of it washes up every day. It does get pretty smelly, so we were told to avoid the beaches and definitely no beach view rooms.
Tonight we had a small snack at our hotel bar, the Pineapple Bar and a nice dip in the pool. Each pool is equipped with different toys, towels, and floaties. So, I spent the rest of our evening on a giant white swan bumping from side to side.
A little floating and snacking at our new home for the next few days.
Day 4: Key West
We woke up a little late, and it was so nice to sleep in our big comfy bed. We wanted to grab a quick breakfast to tide us over for a few hours so we drove over to McDonald’s – which ended up being the biggest mistake ever… Brandon learned that Nuggets are EXTREMELY cheap on Sunday’s in America, so he decided to get 60. Yup, 60, along with a bunch of other burgers and fries and drinks. Personally, I don’t like McDonald’s, as a vegetarian/vegan there aren’t any options for me to get there besides drinks and fries. We stopped at Taco Bell after for a nachos bell grande and a crunch wrap for me. Hey, don’t judge, at least I didn’t get 60 of them…
After our insanely massive breakfast/lunch, we headed straight for the pool beside the beach. Our hotel, the Southernmost Beach Resort has 2 pools, so for our second day, we headed over to pool #2. This pool is right beside a private beach area, also with a little bar, and it’s right beside the resort’s restaurant, the Southernmost Beach Café.
One thing I love about traveling with Brandon is that we’re comfortable enough with each other that sometimes, we can just do our own thing. While Brandon likes to stay on resort more, I like to go through the town and experience what the locals call home. So, I took to Duval Street. I stopped into a few boutiques and bought a few presents and souvenirs for Logan and my mom. I also had to stop and stare at just about every little house and dream about living in Key West. One of the most disappointing/best things that happened was when my phone died. Not only did I lose my map and all sense of direction whatsoever, but I also lost my ability to capture the moments.
One of my biggest regrets of this trip was relying on my GoPro which always was glitching when I needed it, and also not bringing a portable charger. Some of the things I got to see on my unplugged journey were Ernest Hemingway’s Home/Museum, The Key West Butterfly Museum (I took a few before the battery died!), and the popular Mallory Square. Every night they have a sort of street carnival at Mallory Square with different food trucks/carts, drinks, musicians and performers. I had much-needed fresh coconut water in an actual coconut and listened to some jazz before trying to find my way back to our hotel.
When I finally found Brandon he was somehow hungry again? Because we were in Key West, I said it was time that we had a slice of authentic Key Lime Pie, so we walked over to Café Sole. A bit like a hole in the wall, we weren’t expecting much. The restaurant is really small, but it is awfully romantic. The Key Lime pie is prepared with in house made marshmallow – HOLY BANANAS. Throw out what I said before, this is my favorite thing that we’ve eaten in the Florida Keys. I really wished that we didn’t share one slice because I probably could’ve eaten the entire pie. Café Sole has an entire lunch and dinner menu that we wished we had the energy to try.
Finally, a day to just relax.
Day 5: Key West
Probably the most exciting day. If I haven’t mentioned it before, we were really looking forward to going on an adventure through the Florida Keys. We really love being active and trying new things. After a relaxing day, we were ready for a fun packed day. I preplanned a watersport adventure with Sebago Watersports – so today we were going parasailing, jet skiing, paddle boarding, banana boating, snorkeling, kayaking, and another water sporting. The Sebago Watersport Power Adventure includes breakfast, lunch, drinks and even a wine and beer ‘happy hour’ after the day is done.
Our day started with a short tour and a small breakfast. Our first activity was parasailing. The staff was hilarious and amazing. They shot us up almost immediately to 300ft and then quickly dropped us into the water. We were flying so high, but it wasn’t scary at all! After parasailing, we had a kind of free time period – where we were able to use the jet skis, paddle boards, and kayaks. Brandon loves going really fast and I love screaming, so can you guess how our jet skiing went?
We then took a quick lunch break while the captain started to head out to the coral reef for the snorkeling. The captain took us to the Gulf of Mexico coral reef, which is thought to be the third largest in the world. We pretty much considered ourselves to be pros after our first snorkeling trip, so as soon as we got to the reef we dove off the boat. This was an experience like no other, compared to the last reef this one was so colorful and with so many different types of fish. It was a bit hard not to touch them since they were literally swimming with me. I will never forget feeling like the little mermaid. After about an hour, we headed to the boat for a beautiful sail back to the marina. We absolutely loved touring with Sebago Watersports and had the best day ever.
I was a bit surprised that we weren’t completely wiped out after our adventurous day. For dinner, we dined at the First Flight Island Restaurant and Brewery. It’s a really cute outdoor restaurant and micro-brewery. They have several of their own beers to serve and taste. It’s a really great spot if you’re planning to explore downtown Key West.
After today, we both crashed, but in a good way.
Day 6: Key West
Ready for the second day of watersport adventures? We had so much fun with Sebago Watersports, that we wanted to try it all again, but today with Fury Water Adventures. The tours are fairly similar and offer the same activities. With Fury Water Adventures, we took the Ultimate Adventure – a day filled with breakfast, parasailing, jet skiing, paddle boarding, snorkeling, kayaking, lunching and water obstacle course. Today started with snorkeling first, and we were happy that we were heading to a different reef. Since we are absolute masters at this point we’re in the waterway before anyone else. The visibility underwater was crystal clear and we were able to see for miles in front of us.
After snorkeling, we headed back to their docking station for the rest of our activities. We started first with parasailing. This round we spent more time in the water and less in the sky as per Brandon’s request. But still, so much fun! Plus, being so high in the sky were able to see all the way across Key West and even spot our hotel. After parasailing, we were able to jet ski and paddle board. But my favorite was the water obstacle course. They had huge towers, slides, and even a water trampoline. We spent the rest of our time climbing and jumping into the ocean.
That night, we dined at Matt’s Stock Island Kitchen & Bar. A new restaurant right on the marina that serves coastal comfort foods. The atmosphere was really modern and hip and reminded me a bit of a Toronto eatery. There were so many things that we wanted to try and luckily, we got to try them all. My favorite thing, in particular, was the Green Fried Tomato’s – a dish I’ve always wanted to try. My favorite recommendation would have to be the Catch of the Day (which for us was Salmon), the Baked Yukon Potato (which was the biggest potato I’ve ever seen), the Hemingway Daiquiri, and the Triple Chocolate Pound Cake. Matt’s Stock Island Kitchen & Bar was a bit off the main Key West hotel cluster, but it was well worth the drive!
Day 6 with more good food and good fun!
Day 7: Key West to Marathon
I’m so sad to leave Key West! The island is literally a haven and I would love to live here. Every little street is filled with so much character, delicious food, and sweet people. Not to mention the beautiful weather too. After checking out of the Southernmost Beach Resort, we packed up and headed to the other side of the island.
This morning we would be having the dreamiest little breakfast on the Sunset Key. Just a short ferry ride from the Margaritaville Resort, we landed in front of our breakfast eatery, Latitudes on Sunset Key. The restaurant is part of a small cottage resort on the Sunset Key. It’s very upscale and well kept. This was our first seated breakfast and we were so excited for pancakes. We tried a little bit of everything, but the most delicious was the French Toast Croissant with Nutella and Strawberries. Not too sweet and not too dry, with a little warm syrup, it was my favorite breakfast of the trip. After breakfast, we walked around the Key, which only took about 10 minutes because that’s how small it really is! We waited for the ferry to take us back to land while watching a pelican eat fish right from the ocean.
After saying goodbye to Key West, we headed on our road trip back up the Florida Keys to Marathon. Before checking into our next hotel for the night, we stopped into the Turtle Hospital. Here we were able to see so many turtles that are currently being nursed back to good health. We were even able to feed a few of the resident turtles. On our tour, we learned a bit about different species, things we can do to save turtles and the history of the hospital.
Just a quick drive over to our last hotel in the Keys, the Hyatt Place at Faro Blanco Resort & Yacht Club. We checked into a spacious room and spent a few hours relaxing in front of the tv. After giving our suitcases a final pack, we headed down to the pool. In a perfectly shaded courtyard, we swam, we tanned, we relaxed.
After getting washed up we walked through the beautiful garden at the Hyatt Place at Faro Blanco to our dinner spot, the Lighthouse Grill at Faro Blanco Resort. For our last night, we decided to dine outside with a beautiful view of the Faro Blanco Lighthouse and marina. It was tonight, that we went a little overboard. Our server was amazing and convinced us to try just about their entire menu. Can I even pick a favorite thing that I ate here? The French Onion Soup of course because it was so so so cheesy, the side of Boursin Risotto was a close second, but the first was my Cheesecake. We actually packed up our desserts and brought them back to our hotel room to eat while watching the Raptors basketball game. It was the perfect end to a long day.
We saw so much on our last full day in the Keys.
Day 8: Marathon to Miami
We checked out of the Hyatt Place at Faro Blanco Resort & Yacht Club, packed up our little convertible Mustang and headed back down US highway 1. As we were driving I spotted a Starbucks with a sign that read ‘last Starbucks for 80 miles’ so of course, we had to stop for an iced coffee.
Our last stop was at Key Largo Chocolates and Ice Cream for that one last slice of Key Lime Pie, and ice cream… and some chocolates to bring home – for Logan of course.
On our drive back to the mainland we were finally able to have the beautiful scenic drive that I was hoping for all along. Driving along the islands is really a road trip like no other. On a few parts, it seemed like our car was wider than the entire island.
Between all of our excursions and my walking trips to explore the local areas, I really fell in love with the Florida Keys. The islands are perfect for a honeymoon vacation or even a couple’s getaway. One thing I loved about the Florida Keys is the laid back and comfortable atmosphere. In every island town we visited, we were greeted with open arms. Being such a friendly place to visit, I think we will be coming back with Logan next time. For anyone looking for the perfect scenic road trip, or even to escape with a loved one for the weekend, the Florida Keys and Key West are my top place to visit!
See all the pictures from our Road Trip through the Florida Keys!
