The Florida Keys Girls Trip

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November 22, 2022

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Another successful girls trip for the Babes that Wander! I got together with my favorite travel blogging ladies for a visit to the Florida Keys and it did not disappoint! I was so happy to be in the sun and away from the screens for a few days. It was just the recharge I needed! We did so many activities, ate at so many restaurants, and visited breweries on our Miami to Key West road trip. I’ve already done a Key West travel guide, so this post will share more group activities, Islamorada restaurants, breweries, and general things to do in the Florida Keys.

Miami to Key West Road Trip vs Flying

Getting There
There are a few options for getting to the Florida Keys. If you want to fly, your best bet is going straight to Key West and using that as your base. Many people stay in Key West during their whole stay, but if you want to venture out to the other keys like Islamorada and Marathon, then you’ll have to rent a car. The other option is to do a Miami to Key West road trip, stopping at the other keys along the way. This is what our group did and it was so much fun! With this option, you get to explore Islamorada restaurants, breweries in the Florida Keys, Robbie’s Islamorada, and more! There are so many things to do in the Florida Keys, and driving through gives you an opportunity to experience much more than you would by skipping the Miami to Key West road trip and just flying straight to Key West.

Getting Around
If you’re planning to stay in Key West, then you can get around with Lyft and walking, but if you want to truly explore the Florida Keys, then driving is the only way! We rented two cars for the six of us and it was perfect. We got to explore on our own time and were not constrained by distance – one of the perks of opting for the Miami to Key West road trip vs flying. Parking was never an issue either, even in Key West!

What to Pack

No matter what time of year you’re heading to the Florida Keys, it will most likely be hot. However, it can get chilly at night. I needed a jacket every single night at dinner, so don’t skip packing one just because you’re going to Florida! Other than that, the Florida Keys are very laid back. I don’t think I saw anyone wearing heels except maybe one or two people in Key West. I actually packed some just in case, but never ended up wearing them. My fabulous Babes that Wander gals were all dressed to the 9’s with heels every night so if that’s your thing, go for it! It’s very Jimmy Buffet/Jack Johnson chill beach vibes in the keys so I soaked that up with casual dresses and matching sets. And of course, the more swimsuits, the better!

Where to Stay

Hawks Cay Resort
is located just south of Islamorada, and is a great place to stop if you’re doing a Miami to Key West road trip. This resort is on its own little key (Duck Key) and has everything you need on site. It seemed like an ideal place to stay for a relaxing family getaway, especially with small children. There isn’t too much action, the pools are nice, and there are a few different Islamorada restaurants within walking distance and right down the road. This is a great option for one of those off-the-grid vacations!

Southernmost Beach Resort
is located in a relatively quiet area of Key West. I’ve actually stayed in this area a few times and it is definitely my top choice in Key West! It’s far enough away from the daytime parties, but close enough to walk to the action if you want. There are 3 pools here and plenty of bars and restaurants. It’s lively, but not too over the top. It’s the perfect mix of tranquility and fun!

Where to Eat & Drink: Key West & Islamorada Restaurants

Going to the Florida Keys as a vegetarian is slightly limiting. Obviously, Key West & Islamorada restaurants are most well known for seafood like oysters and “dolphin,” which is actually Mahi Mahi as our group was relieved to discover. However, if I’m being honest, my favorite thing about going to restaurants is the experience and the atmosphere. I did find a vegetarian option at all restaurants, so here are my recommendations regardless of dietary restrictions!

Angler & Ale
Angler & Ale is on property at Hawk’s Cay Resort. It just takes a short golf cart ride or a nice walk to get there from your room or villa. The gorgeous views are unbeatable and the food is casual seafood fare. The coolest thing we witnessed here was their food delivery robot. It was very futuristic and entertaining to see! When you don’t want to venture out to the other Islamorada restaurants for dinner or drinks, this is the perfect choice. No driving necessary!

Robbie’s Islamorada
Robbie’s is a huge restaurant, shop, and activity center in Islamorada. This is where we went for all of our Sundance Watersports activities (more on that below), so we decided to grab food here before and after. It felt like a classic beach dive bar with food like chips and salsa, chicken fingers, and of course, margaritas! It definitely seems like one of the most popular Islamorada restaurants.

Islamorada Brewery & Distillery
We had so much fun at Islamorada Brewery! I believe they do serve food from a food truck during certain hours, but we just missed it during our time there. This is a great stop after a fun-filled day of activities. They offer flights not only of their beer, but also of their liquor! Featuring crafted cocktails on tap, outdoor games, and live music, this place is the perfect afternoon wind-down spot. More on this place below!

Morada Bay Beach Cafe
Morada Bay Beach Cafe is absolutely gorgeous. With tables literally on the beach, the view is stunning. The service we received here was so great and the food was awesome. Go at sunset for a real treat! When it comes to Islamorada restaurants, I think Morada Bay was my favorite!

Half Shell Raw Bar
Half Shell Raw Bar just screams Key West beach life. The popular thing to order here is the oysters, which the group agreed were fabulous, but the real stand out to me was the service. Out server was so sweet and made us feel welcome, even though we were unwittingly 45 minutes late due to a communication error. They are also known for their house mojitos which were made with bourbon. So good!

The Docks Stock Island
This was a really cool and unique experience. Stock Island got its name from being the home to all the keys’ livestock back in the day. Due to this, it was always an undesirable place to live, leaving it to lower-income laborers. In fact, driving to the restaurant takes you through an actual neighborhood! Now Stock Island is being reclaimed and revitalized to bring more visitors and locals alike to the area.

The Docks was definitely the more high-end restaurant we visited in the keys. The restaurant has an intimate feel with a wide selection of seafood dishes. Unfortunately, this is where I had the most trouble ordering something I could actually eat. I ended up getting a “fig in a blanket” appetizer and ate around the fig like a barbarian. To be honest though, I’d go back even if just for the atmosphere and service!

Things to do in the Florida Keys

There are so many different things to do in the Florida keys! It’s so hard to narrow it down, but here are a few of my favorites.

Parasailing with Sundance Watersports
Parasailing was not originally on our itinerary, but due to strong winds, we couldn’t participate in our originally scheduled snorkeling, so Sundance offered to swap that out with parasailing, and it was an absolute blast! The strong winds worked in our favor for this activity, so we had no issues there. I’ve been parasailing before and enjoyed it, so I’m glad I had the opportunity to do it again. It’s so incredibly peaceful up in the air (even if I was clutching onto my safety harness for dear life!). It’s an interesting mix of adrenaline and stillness.

Tour & Tasting Islamorada Brewery & Distillery
I mentioned this above in the Islamorada restuarants section, but it can also be considered an activity when you do the tour & tasting! I love a good brewery, so when I saw this on our itinerary, I was so excited. Islamorada Brewery & Distillery has so much to offer. As you can tell by the name, they not only brew beer, but also distill liquor. We tried their vodka, rum, and gin and they were all very good! There was one rum in particular that had bourbon notes – definitely a favorite! The outdoor seating area is great for a casual afternoon drink and the staff is amazing. We met the manager, Kate, who was so friendly and fun. Highly recommend a stop here!

Sunset Boat Ride with Fury Key West
I’m definitely more of a private boat kind of gal, but unfortunately, weather issues caused a cancellation for that experience. Luckily we were able to join “Commotion in the Ocean” at the last minute and it was a lot of fun! The two-hour ride included snacks, drinks, live music, and gorgeous views. As time went on, the crowd became more and more lively. It was definitely entertaining!

Morning Yoga with Salute to Sol Yoga
After days in the sun sipping on cocktails, it felt so great to get a little stretch in! Our Salute to the Sol private morning yoga class with Rebecca took place in a park and it was exactly what I needed to feel revitalized! Since it was a private class, we could adjust the flow to whatever we wanted. We did a stretch-based flow and although it was a 45-minute class, the time flew by. I really loved it and definitely would recommend it for any group trip to Key West!

Jet Ski excursion with Barefoot Billy’s
This jet ski adventure was so much fun! As someone who has driven a jetski countless times, I wasn’t sure how exciting it would be, but I’m so glad we decided to do this. It was especially cool since we went snowmobiling on our last group trip to Bend, Oregon. Same same but different, you feel me? Jet skiing is the perfect mix of adventure and tranquility. There’s something so calming about being out on the water solo, yet also adventurous since you’re zipping around. A heads up though: the safety briefing before we went on the jet skis lasted about two hours. If you’re born after 1987, you have to take a graded test using a scantron. Then there are videos to watch and a speech from the tour guides. It was unlike anything I’ve ever experienced in all my travels! Barefoot Billy’s definitely takes safety seriously.

Drag Show at 801 Bourbon Bar
The drag show at 801 Bourbon Bar was absolutely the highlight of the trip and my top recommendation for Key West. I am a big fan of drag, so this was such a treat. Since I’d been before, I made sure we visited on our last night in the Florida Keys. It was perfect and everyone had an amazing time!

What are your top recommendations for things to do in the Florida Keys?

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Photos by various Babes that Wander.