Epitaph in Southern Keys Cemetery, Key West: "I Told You I Was Sick"

48 Hours in Key West: Drinking, Diving and Diversions in Florida’s Southernmost Outpost (Day 1)

It’s been dubbed “Key Weird” and dismissed as little more than a “huge floating bar”. And by most all accounts, that’s exactly what it is. So much has been written about Key West, it’s a wonder that anything new and interesting can still be said of the continental United States’ southernmost outpost.

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As far as islands go, it’s a bit of an anomaly. There are virtually no waves, which means there’s little beachfront to speak of. Yet it’s an island that’s culture and community is heavily influenced – almost defined – by the ocean and the “beach bum” mentality.

Jimmy Buffet and amazing green pie aside, Key West is well known for a select few things: drinking, diving and general debauchery. I’m a fan of all good things in moderation (usually … OK, sometimes) and a full two days on the island requires it. There’s plenty of fun to be had and if you can’t find it on island, you’re probably dead.

Here, I present a small, well balanced sampling of all that Key West can offer in just 48 hours.

Day 1: Diving and Other (Non-Alcoholic) Diversions

The whole of Key West is extremely small – approximately two miles by four miles – making it a snap to get around. Many off-strip (meaning away from Duval St. and the “downtown” area) hotels offer shuttles and taxis and pedi-cabs are never more than a few minutes wait away. If you’re not fond of walking, there are also dozens of shops renting quick, affordable transportation including scooters and pint-sized electric cars.

But the best, for my money (around $10-15 daily) is Eaton Bikes. They specialize in bicycle rental, sales and maintenance … and that’s it. That’s all they do. It’s a low-key shop where you can pickup a rental and be in and out in less than five minutes. It’s a great, cheap way to explore the island from ground level.

Explore the Southern Keys Cemetery

Start your morning with a relaxed visit to the quintessentially Key West Southern Keys Cemetery. It’s a delightfully disorganized mix of overpriced granite crypts, dilapidated, hundred year old, wrought iron fences and hilarious epitaphs, including this which may be the best ever:

Epitaph in Southern Keys Cemetery, Key West: "I Told You I Was Sick"
Epitaph in Southern Keys Cemetery, Key West

It’s well worth a visit if only to garner a quick feel for the island’s quirky culture. Be sure to grab a free map at the entrance that details many of the history and interesting stops throughout the grounds.

Diving Wrecks & the World’s Third Largest Barrier Reef

Diver headed down to Vandenberg wreck near Key West
Diver headed down to Vandenberg wreck near Key West

Unless your a teetotaler (not that there’s anything wrong with that), there’s a serious bias towards alcohol-infused good times on the island. So, if you’re planning on diving, I recommend getting it done in the first day or so to ensure that you’re not trying to cope at depth with a nasty hangover.

Did You Know: The Florida Keys Reef Tract is the 3rd largest coral barrier reef in the world.

Which leads me to Dive Key West, where co-owners, Bob Holston and Cece Roycraft, have been running the same shop in the same location for more than forty years. And with good reason. Theirs is a phenomenal operation with a serious focus on safety and variety. Beginner divers will also appreciate that their instructors are happy to work at your pace and you’ll never feel rushed.

Both novice and expert divers will love their wide variety of dives, including many of the touchstone reefs and must-see wrecks in Key West: Joe’s Tug, Cayman Salvage Master and the Vandenberg. They of course offer all of the requisite rentals, sales, guides and what-have-you that you’d expect of any pro dive shop.

Lunch at Salute

Aerial view of Salute restaurant in Key West

After a morning of blowing bubbles, escape the hustle of Old Town with lunch at Salute. This sister restaurant of local favorite Blue Heaven offers the same funky, eclectic vibe and is one of the few truly beachfront restaurants on the island. They’ve an extensive menu of local favorites and the grilled snapper over mescal greens was fresh and plenty flavorful.

An Afternoon of Galleries Galore

If you’ve had your fill of diving in the morning, take a ride down Duval Street to while away the afternoon perusing the countless art galleries. Of particular note is Black Pearl Fine Art – a gallery which displays (and sells) many local Key West artists, as well as world-renowned painters such as Fabina Perez, Todd White, and Michael Godard. It’s a quirky, eclectic collection that even non-art lovers will enjoy.

Travel photographers absolutely shouldn’t miss Peter Lik’s stunning gallery as well. The man behind The Weather’s Channel’s hit show From the Edge has been known to wait as long as seven years to capture just the right shot. And it shows. His work is nothing short of jaw-dropping and seeing his larger-than-life prints first-hand is the best way to experience it.

Dinner at Cafe Marquesa

Interior of Cafe Marquesa restaurant in Key West
Inside the Cafe Marquesa, Key West

Whether you’re staying at The Marquesa Hotel or not, it’s worth a special trip to experience dinner at Cafe Marquesa. The decor is clean, Caribbean chic and is among the most romantic restaurant atmospheres on the island.

I was told by just about every local that I spoke with that everything on the menu is “out of this world” good. That said, I opted for the grilled Australian lamb shank encrusted with goat cheese – noted as the chef’s specialty. It’s perhaps one of the tastiest, most savory pieces of meat that I’ve ever put in my mouth. Sides included broccolini and the accompanying potatoes offered a delicate, yet perfectly complementary sweetness.

Throwing the aforementioned moderation out the window, I opted for two desserts (or perhaps one and a half). First the Neige Quebec apple ice cider. After trying this for the first time in Quebec City earlier this year, I was over-joyed to discover it on a menu this far south. I also ordered the Key Lime Napoleon with fresh berries – a dish that provides a perfect balance between tart and sweet.

The relatively small restaurant is extremely popular, particularly among locals, so reservations are highly recommended.

Witness the Sunset from The Top

Watching the sunset from The Top at La Concha, Key West
Sunset from The Top at La Concha, Key West

There’s no better way to cap a long day of diving and window shopping than sitting down with a frosty beverage and watching the sun go down. Key West sunsets are legendary and with good reason – the unobstructed views into the Gulf of Mexico provide a truly stunning vantage point.

Take a trip to The Top at La Concha hotel. It’s the tallest building and best vantage point on the entire island, by far. Arrive plenty early – at least an hour or two before the sun begins to set – so you can reserve a chair and grab a drink from the rooftop bar before the crowds rush in. Depending on the time of year and day of the week, you could find yourself amongst plenty of other sun worshipers.

Retire to Your Hotel for the Evening

There’s no shortage of great accommodations in Key West. I’m committed to only staying at small, locally-owned hotels and B&Bs and have never been disappointed. Several hotels – all with their own charms and within various budgets – were kind enough to host us during our stay and I would recommend any one of them without reservation.

Front of The Marquesa Hotel, Key West
The Marquesa Hotel, Key West

The first – The Marquesa Hotel (a member of the gorgeous Select Registry Distinguished Inns of North America / nightly rates from around $150 + tax) – is a luxurious retreat comprised of several, restored “Conch houses”, all surrounding a quiet garden area and two pools. The focus is on privacy, luxury and an overall sense of rest and relaxation.

It’s been named to Conde Nast Traveler‘s “2011 Gold List of World’s Best Places to Stay,” and among the Top 40 Small Hotels in the United States and rated #1 in Key West and Florida by Travel & Leisure magazine’s “T&L 500, The World’s Best Hotels” in January 2010.

Our suite included an ample sitting area, king-sized poster bed, work desk, private patio, in-room refrigerator (with mini bar) and large bathroom with plenty of room to spread out. Amenities for all guests include “marble baths, central air conditioning, telephone, cable television, irons, hair dryer, makeup mirror, bathrobes and a security safe”, as well as free WiFi and continental breakfast brought to your room each morning.

The staff couldn’t have been more helpful. From local attractions to dining recommendations, they were among the most friendly and accommodating of any hotel that I’ve ever experienced.

Night by the pool at Eden House, Key West
Poolside at Eden House, Key West

For our second night’s stay, we found ourselves at Key West’s oldest hotel – Eden House (off-season nightly rates start around $115 + tax). For unabashed, “toes in the sand” adult fun, there’s a lot to love about this iconic island hotel. It’s not for everyone and owner, Mike Eden, doesn’t want it to be. Of all of the hotels on the island, it’s perhaps the most laid back of them all.

If you appreciate that a beer tastes better with sand between your toes, you’ll love the Eden House. It’s a perfect balance between the hard partying side of Key West and the laid back chill vibe that Jimmy Buffet commoditized so well.

Key points include: free beer at check-in, daily happy hour (open bar to boot!) around the pool, $1 cans of Budweiser and Bud Lite (cheapest on the island according to reception and I’ve no doubt that’s true), a large sun deck where it’s also easy to find a chair, and a “sundry” shop with nearly everything you could possibly need for a weeklong stay on the island.

The Gardens Hotel, Key West
The Gardens Hotel, Key West

Our final stay took us to The Gardens Hotel. It’s been featured in 1,000 Places to See Before You Die; Travel & Leisure rated it among their top 21 favorite beachside hotels; and has received countless reader’s choice and similar awards from just about every glossy travel magazine you can name. In short: it’s gorgeous, charming and incredibly luxurious.

Once the most expansive and, I believe, expensive properties on the whole of the island, it comprises more than an acre of lush, tropical landscaping. In the past few years, the entire property was purchased and renovated into seventeen unique, luxury suites and guestrooms. The decor is quintessential Key West with a serene atmosphere that feels far more like a home than a hotel. If you’re tired of staying at huge resorts with no sense of place or character (and there are plenty of those on the island), The Gardens Hotel is definitely for you.

If you’re splashing out on the very best digs that Key West has to offer, don’t miss room #714 – the Eyebrow Cottage. It’s the former caretaker’s quarters inside a detached guesthouse with a large, private porch, a gated parking space and direct, private entrance to the street. Inside, you’ll find a large, jacuzzi tub, dedicated sitting area, work desk, king bed and all the trappings of home. I was assured it’s not the “honeymoon suite” per se, but it may as well be.

Furthermore, the hotel’s location is fantastic – just a few blocks from just about everything, including Duval Street, nearby CVS any vacation sundries, Key West’s cemetery, and more.

Also, don’t miss their onsite, a la carte wine bar called d’vine. I believe it’s the only one of it’s kind on the island!


Rest up because tomorrow we trade non-alcoholic diversions for plenty of drinking and Duval Street debauchery.

Founding Editor
  1. Great choices, though there are so many on that little island and so much to experience. We live about 30 miles north (for the past 8 years) and there’s always something new and unique happening. Looking forward to Day 2!

  2. Actually, Florida State road 60 goes from Clearwater beach, gulf of Mexico, to Vero beach Atlantic Ocean. :-)

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