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Where we’re at: I’m recapping my summer of 2018, which included this trip to Florida in July. In other news: we’ve added new Wander Women Retreats — don’t miss them!

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Somewhere between quirky Key West and cosmopolitan Miami lies a destination that’s just a little more laid back than the tourism superstars in either direction — The Upper Keys. For this segment of my scuba sojourn through Miami and The Florida Keys, my dive buddy Heather and I based ourselves in pretty and popular Islamorada, using it as a jump off point to explore Tavernier and Key Largo, too.

Around here, diving is the main event, along with other nature-based activities like fishing, paddleboarding, and beyond.


So yes, salt water is everywhere — but that doesn’t mean you need to hole up in a crusty motel (I mean, that’s definitely an option, for those that are into that, which I sometimes am, but I digress.) A chic and colorful boutique hotel is also re-open for business, for those that like their island relaxation with a side of style.

Lobby at Amara Cay Resort, Islamorada, Florida

Where to Stay in Islamorada: Amara Cay Resort

No one faced Hurricane Irma’s wrath quite as hard as Islamorada, and during my visit, a year later, much of the island’s accommodation was still under renovation. Amara Cay Resort had recently reopened for business, and I was honored to join their loyal fans eager to give a little boost back to the local economy.

Amara Cay Resort, Islamorada, Florida

Amara Cay Hotel, Islamorada, Florida

Amara Cay Hotel, Islamorada, Florida

Amara Cay Hotel, Islamorada, Florida

Like many local businesses, Amara Cay used the hurricane as an excuse to come back stronger than ever. There was a design detail worthy of a swoon around every corner, all while maintaining such a strong sense of place — there was no mistaking it, we were in Islamorada.

Amara Cay Hotel, Islamorada, Florida

Lobby at Amara Cay Resort, Islamorada, Florida

Amara Cay Hotel, Islamorada, Florida
Amara Cay Hotel, Islamorada, Florida

The low-profile Keys don’t have high rises the way much of Florida does — and cheers to that! — so we felt like we were on top of the world from our second story balcony perch. Like the rest of the hotel, our room was modern, tasteful, and full of nods to the natural wonders out the window.

Pool at Amara Cay Resort, Islamorada, Florida

Room at Amara Cay Resort, Islamorada, Florida

Bathroom at Amara Cay Resort, Islamorada, Florida

Room at Amara Cay Hotel, Islamorada, Florida
Beach at Amara Cay Hotel, Islamorada, Florida

Down on the private beach, we marveled at the number of amenities packed into a company punch — a spacious pool, a private dock, the use of complimentary kayaks and paddleboards, a fitness center, and plenty of fire pits that burst to life come sunset.

Pool at Amara Cay Resort, Islamorada, Florida

Pool at Amara Cay Resort, Islamorada, Florida

Pool at Amara Cay Resort, Islamorada, Florida
Travel blogger Alex in Wanderland

Pool at Amara Cay Resort, Islamorada, Florida

Travel blogger Alex in Wanderland
Beach at Amara Cay Resort, Islamorada, Florida

Beach at Amara Cay Resort, Islamorada, Florida

We had both a dinner and breakfast at Reelburger, the fantastic onsite bar and restaurant. At night, we dined out by tiki lights on creative and locally inspired burgers — Heather, a vegetarian, was thrilled to have no problem finding several options.

But let’s be honest — we’re breakfast girls! And dang if this wasn’t the best hotel breakfast we had in all of Florida. The complimentary options include everything from granola smoothies to make your own omelets to amaretto french toast. And, fellow tea nerds, rejoice — when I asked for the daily selections, they brought over a full sampler box of Tea Forte goodies. I settled on white ginger pear and loved it so much I had to order some of my own for home.

Restaurant at Amara Cay Resort, Islamorada, Florida

Restaurant at Amara Cay Resort, Islamorada, Florida

If you feel the need to leave the hotel — for some odd reason – there are complimentary push bikes and a free hotel shuttle to anywhere within a four mile radius of the hotel.

But honestly? Don’t be surprised if you don’t want to. I know my next trip, I’m building in way more time to do nothing but play musical hammocks and beach chairs around the Amara Cay property. This place is a gem.

Travel blogger in Alex in Wanderland

Where to Eat

Okay, there’s one reason you may need to occasionally leave Amara Cay — to eat! Here were a few of our favorite restaurants in the Upper Keys.

Ciao Hound

During my visit, Amara Cay’s sister hotel Postcard Inn was still under renovation. However, it’s onsite restaurant Ciao Hound was open for business — and knowing how much I loved the Postcard Inn in St. Pete, Florida, I knew that checking out whatever aspect of the place I could was a must! Heather and I had an incredible meal of Italian food here, and we weren’t alone — the place was absolutely packed, a sure sign of a good thing on an island with so many options.

(And now that it’s reopened, I can’t wait to stay at Postcard Inn Islamorada next time I’m back in the area!)

Ciao Hound Italian Kitchen & Bar, Islamorada, Florida

Robbie’s

Robbie’s is an institution is Islamorada — you pretty much have to go. We skipped the iconic activity of feeding the tarpon, but had a blast posted up on the driftwood dock bar, sipping key lime margaritas and toasting to a pretty sunset and another amazing diving adventure together.

Robbie's Marina, Islamorada

Robbie's Marina, Islamorada

Robbie's Marina, Islamorada
Robbie's Marina, Islamorada

Gratitude Watersports Cafe

Culinary gluttony is generally the order of the day in the Florida Keys — fresh, healthy eats, not quite so much. So we loved taking a brief break from the various forms of key lime indulgence for a lunch at Gratitude Watersports Cafe in Key Largo. Not only do they serve up smoothie bowls, salads, and fresh juices, but they also host events like ukulele jams and beach clean ups, and do paddleboard repairs.

Gratitude Watersports Cafe, Key Largo

Key Largo Chocolates

Back to the sweet stuff! We couldn’t leave the Keys without swinging by Key Largo Chocolates, where we lovingly selected a few treats for ourselves, and went wild stocking up on gifts for our luckily families back home.

Key Largo Chocolates
Key Largo Chocolates

Mrs. Mac’s Kitchen

Eating at Mrs. Mac’s Kitchen was another Keys tradition we just had to experience for ourselves. Unassuming with a menu bursting with local fare, it was the perfect lunch stop on our way to a big day of diving.

Mrs. Mac's Kitchen, Key Largo

Mrs. Mac's Kitchen, Key Largo

Mrs. Mac's Kitchen, Key Largo

Mrs. Mac's Kitchen, Key Largo

Mrs. Mac's Kitchen, Key Largo

What To Do

We used Amara Cay as a leaping pad for so many incredible local adventures. And because it’s me and Heather, they mostly involved blowing bubbles underwater or getting boozy at the surface — though fear not, friends: always in that order!

Scuba Diving

We had a few different diving adventures in the Upper Keys. First, one afternoon we set off for a two tank dive with The Florida Keys Dive Center from Tavernier, one of the smaller Keys between Islamorada and Key Largo.

Scuba Diving in Islamorada

Scuba Diving in Islamorada

From one dive I was hooked on the Key’s iconic aquarium-like waters, and I’m already itching to go back and dive top sites like Spiegel Grove and Molasses Reef in Key Largo and Conch Wall and Davis Reef in Islamorada.

Scuba Diving in Islamorada

Scuba Diving in Islamorada

Scuba Diving in Islamorada
Scuba Diving in Islamorada

And of course, I can’t wait to finally visit John Pennekamp Coral Reef State Park, home of the famous “Christ of the Deep” statue and a landmark as America’s very first underwater park.

Scuba Diving in Islamorada

Scuba Diving in Islamorada

Scuba Diving in Islamorada
Scuba Diving in Islamorada

Scuba Diving in Islamorada

This trip, however, we decided to dedicate most of our diving time to quirky, “only-in-the-Keys” experiences. First up, working with The Coral Restoration Foundation, an incredible group dedicated to preserving and restoring the magic of South Florida’s reefs. The work they do is so special I’m dedicating a post to it — so stay tuned!

Scuba Diving in Islamorada

Scuba Diving in Islamorada

History of Diving Museum

We didn’t let the scuba fun stop at the surface interval: we headed straight to the History of Diving Museum. From the outside, it looks unassuming, but  enter the exhibit halls and you’ll find not just a kitschy roadside attraction but a true, education and passion filled museum, created with love by Women Divers’ Hall of Fame member Sally Baur and her late husband Joe.

The History of Diving Museum is dedicated to preserving and sharing the history of mankind’s quest to explore, understand, and venture under the sea. While it tells a full global history – in fact the museum’s collection represents contributions of more than thirty countries — the museum also celebrates the special role that South Florida and the Florida Keys plays in this story.

Read next: The Wanderland Dive Guide to the Florida Keys

This is a place worth planning a trip around — perhaps check the calendar for upcoming editions of the Immerse Yourself series, free lectures offered the third Wednesday of every month, covering topics like underwater art, conservation, and more.

History of Diving Museum, Islamorada, Florida

Stand Up Paddleboarding

When it came time to decompress from diving, Heather and I signed up for a Sip and SUP tour with Aquaholic Adventures, though we also agonized over their SUPing with manatees, kayaking with dolphins, and LED-lit board night paddles. (I’ll tackle one for each future return trip, I hope!)

We paddled along Key Largo’s bayside bars, as at the time, many of the oceanfront watering holes were still recovering from the hurricane. We paddled,  knocked back a few more key lime coladas, watched a stunner of a sunset, listened to a live band play under the arch of a rainbow, and concluded that it was the perfect evening activity for Key Largo. The same tour is also offered in Islamorada and heck, I might just have to check that one out — for research — as well.

Stand Up Paddleboarding tour of Key Largo

Stand Up Paddleboarding tour of Key Largo

Sip and SUP Tour with Aquaholics Adventures, Key Largo, Florida

Sunset in Key Largo, Florida

Till Next Time

Perhaps it’s because the islands just look so tiny on a map (ha!) but I somehow thought I’d planned a sufficient amount of time in the Upper Keys. Not even close! I loved my road trip all the way from Key West to Miami for giving me an overview of the Keys and filling me with ideas for future trips, but I definitely can’t wait to linger longer here in particular, someday.

Travel Blog Guide to Islamorada

Travel Blog Guide to Islamorada

Travel Blog Guide to Islamorada

Up Next: Our stay at the Jules Undersea Lodge! Stay tuned!

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Many thanks to PADI and to The Florida Keys for their hospitality. Read more about the top scuba sites in the Florida Keys, and dive and travel tips for the Florida Keys on their sites and follow their social media accounts for daily doses of scuba and sunshine. Want to book a dive trip to Florida? Check PADI Travel for more information!

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2 Comments...
  • Lurlene
    July 1 2019

    I love these cute, boutique hotels! They are so much more original than the well-known hotels like Hilton and Marriott. I will consider staying in boutique hotels instead! Thanks for sharing this gem!

    • Alex
      July 1 2019

      Agreed, I love staying boutique whenever I can! It’s always amazing to get some local flavor <3

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