The Westin Key West Resort & Marina, Key West, Florida

10 Essential Experiences for Every Traveler’s Key West Bucketlist

Famed Key West historian and all-around awesome dude David Sloan noted, “One constant of Key West is change.” We couldn’t agree more. Even in the brief time since our visit in 2011, things have already changed. It’s amazing just how much there is to see on this tiny (barely 4-mile by 2-mile wide) island.

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Last month we checked out a handful of locals-only experiences and a few more “touristy but what the hell? They’re too awesome to pass up!” diversions. In no particular order, here are 10 things every traveler should add to their Key West bucketlist …

#1: Lunch @ Hogfish Bar and Grill

One of the best ways to get a taste (literally and figuratively) of Key West’s past is … to get out of Key West. Nearby Stock Island is Key West the way it used to be, before it had a Kmart and a Starbucks on Duval Street. It’s ultra laid back, rough around the edges, and not especially lush and beautiful in the idyllic tropical island sense. In other words: totally awesome.

Hogfish Bar and Grill, Stock Island, Florida Keys

The island’s Hogfish Bar and Grill is one of the best places to wile away a day in the Keys. On any day of the week, it’s rife with locals (and their dogs) fresh off their houseboats or a day of diving looking to relax with a cold beer, a bowl of conch chowder and a football-sized hogfish sandwich.

You’ll probably even run into the owner Bobby who’s called the area home for decades and is more than happy to share its history with you.

#2: Unwind with a Massage @ The Spa at Sunset Key

Sunset Key Near Key West, Florida
The Beach on Sunset Key © Mike Richard

Nearby Sunset Key is about as perfect as islands get in the Florida Keys. But if you’re not the sort of big shot who can afford to crash at the stunning, over-the-top hotel here, at least check out the Spa.

Aside from the requisite list of exceptional treatments one might expect of an uber-luxurious, five-star hotel, the spa takes amenities to whole new level. Each room is accompanied by a private garden area and en suite bathroom and shower, where guests are encouraged to relax with plenty of quiet time. The staff also encourages guests to request almost anything they’d like if it’ll help them unwind – chocolate dipped strawberries, a glass of bubbly, a puppy. (I didn’t actually ask for a puppy … but I highly recommend you do)

#3: Jet Like James Bond

Jetpack Adventures in Key West, Florida

You know what’s awesome about James Bond? Well … everything. But the most awesomest thing: his gadgets. If you’ve ever wanted to zip around the sky with a real life jetpack, the time is now, my friends.

The folks at Jetpack Adventures will hook you up with a Jetlev R200 Jet Pack:

… a water-powered system that allows you to levitate and fly at up to thirty feet above the water. You’ll feel sensations ranging from weightlessness as you levitate in the air, to feeling like a bird as you learn how to fly the Jet Pack in any direction, and at any speed that’s comfortable for you.

We strongly recommend the “fast” speed.

#4: Sunset @ The Westin Key West Resort & Marina

Key West celebrates every sunset like only a true tropical island can – like it’s the last sunset for all mankind. It’s as close as one can get to religion in the Keys. We previously recommended the Top of the Key as the go-to spot for excellent sunset views, but it’s since closed (ever-changing, right?).

These days, make your way to the Sunset Deck at The Westin Key West Resort & Marina where visitors are treated to completely unobstructed views of the western horizon. And the drink prices aren’t too shabby to boot (especially for a hotel bar).

Sunset silhouette of couple at Westin Key West hotel bar
© Mike Richard

I snapped this photo after about seven minutes in Key West … on my first try. It really is that easy because it happens here just like this every. single. day.

#5: Breakfast @ Blue Heaven

I’ve been coming to Blue Heaven “since before it was cool”. And with good reason: every last thing on the menu is fantastically — almost criminally — good. But there are two must-have (and I don’t say that lightly) dishes that make this an essential Key West destination.

Blue Heaven Restaurant, Key West, Florida
Blue Heaven Restaurant © Mike Richard

First, Blue Heaven is well known for their Eggs Benedict. But they take the tried-and-true breakfast staple to a whole new level. There are several options, but none more enticing than the rich BLT: fresh Florida lobster, bacon, avocado and lime hollandaise sauce (the last of which adds just the right amount of tang). Talk about “gilding the lily”.

Perhaps more importantly, grab a slice of key lime pie. For breakfast?! Sure, why not? You’re on vacation after all; treat yourself! Plus, Blue Heaven definitely takes the award for tallest key lime pie.

Key Lime Pie at Blue Heaven, Key West, Florida
World’s *Tallest* Key Lime Pie © Mike Richard

If you’re looking for the best, most authentic and only true key lime pie, I’ll let you in on a little secret: there isn’t one. Or at least no one knows for sure. Countless stories abound and every eatery on the island claims to have THE BEST AND ONLY KEY LIME PIE YOU NEED TO TRY!

No one really knows where key lime pie originated because there are many, many different stories and even more variations. Must it include graham cracker crust or pie crust? Whipped cream or meringue? Must it contain egg (as Guinness Book of World Records folks claim)? There’s no right answer. The aforementioned David Sloan asserts that travelers should simply find one they like and roll with it.

#6: Grab a Drink @ The Green Parrot

Skip the margaritas. Thanks to Jimmy Buffet, everyone thinks of the giant frozen margarita as the iconic Key West drink. That couldn’t be less true.

Root Beer Barrel shots lined up at the Green Parrot, Key West, Florida
Root Beer Barrel Shots at Green Parrot, Key West © Mike Richard

Here, it’s all about the root beer barrel – essentially a boilermaker with root beer schnapps and cheap beer (honestly the cheaper the better). It tastes exactly like an old school root beer barrel candy. The taste is so smooth, it’s way too easy to drink enough to be tipsy by lunchtime.

#7: Stop at Key West’s Only Bookstore

Key West Island Books

For such a tiny island, there’s a fantastic book store right in the heart of Key West. Key West Island Books is a haphazard affair with an eclectic mix of used, rare and new books … whatever your poison.

The selection of Key West-centric books — both by the island’s authors or simply about the island in general — is exceptional. Aside from the expected Hemingway titles, you’ll find plenty to read on the subject of “how to abscond from corporate life and retire early to the Florida Keys”. It’s a great place to stop for a souvenir with plenty of local flavor.

#8: Visit Key West’s First Legal Rum Distillery

Key West has had a long, sordid history with alcohol (and other illicit substances). But, believe it or not, the island’s first legal rum distillery just opened. A visit to the appropriately named First Legal Rum Distillery is a trip down Key West’s memory lane. As it’s built on the site of an old Coca Cola bottling plant, this place is dripping with history with tons of artifacts found during construction of the distillery and on display in the tasting room.

Key West First Legal Rum Distillery, Florida
Key West First Legal Rum Distillery © Mike Richard

Owner and distiller Paul Menta is happy to take you on a tour of the small, but fascinating location. And don’t leave without sampling their unique Green Flash cocktail — a light, refreshing and lightly carbonated blend of ginger, lime, demara sugar, and vanilla brûlée rum.

#9: Jet Ski Around the Island with Barefoot Billy’s

Whether you’ve jetskiied or not, I highly recommend a tour with Barefoot Billy’s. It’s an insanely awesome way to check out the island! They offer hotel pickup and the staff couldn’t be more friendly, professional and fun.

Jet Ski
© Aristocrats-hat

Be forewarned: this one isn’t for nana. It’s a full throttle, hour-and-a-half, 28-mile blast around the entire island. Afterward you’ll feel like you just spent ninety minutes inside an industrial washing machine set to “vigorous”. (Tip: Bring goggles or sunglasses because you will get sprayed in the face a lot)

#10: Explore the Mel Fisher Museum

To fully understand and appreciate the history of Key West, the Mel Fisher Maritime Museum is a must-visit. The museum offers a variety of exhibits showcasing one-of-a-kind, near-priceless historical finds — including treasure from a 1622 fleet of Spanish galleons — by Mel and his crew.

Their latest exhibits include Spanish Coins in the New World, the Real Pirates of the Caribbean, and the Science of Shipwrecks. Visitors are also welcome to take a lab tour to see how history is revealed through excavation and conservation of shipwrecks.

For boatloads of other great things to see and do, check out the official website for the Florida Keys & Key West!

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