An Insider’s Guide to Key West

As a frequent visitor to Key West and someone who also travels there for business, I’m often asked: “What things do you suggest we do when we visit?”

First let me say that there is no shortage of things to do in Key West and I think I’ve seen and done most – but not all – of them.  I’ve listed only a few of my favorites here.  This is far from a complete list; just some of the many great things to do in Key West…  And things are constantly changing, with new great restaurants opening all the time.

Conch Tour Train – A good first thing to do when you visit any city is to take a city tour by bus, tram or trolly (“ducks” not so much).  The Conch Trains are ubiquitous on the streets of Key West.  The tour guides are friendly and give interesting information about the history and sights of the island.

Duval Street – This is the main street in Key West.  Running from the Gulf of Mexico to the Atlantic Ocean – just over a mile long (the width of the island).  Duval Street is lined with a cornucopia of bars and shops.  At night it’s “party central” for visitors to the island – so parents may want to leave the kids with a sitter.

Lloyd’s bike tour takes you to places in Key West that other visitors rarely see.

Lloyd’s Tropical Bike Tour – This is a fun way to spend a couple hours lazily touring Key West on bicycles.  You’ll get to see parts of Key West you can’t see any other way.  You’ll need to rent a bike but Lloyd can hook you up.  You must call ahead to book a spot on the tour because space is very limited and these tours sell-out quickly.

Key West Aquarium – This is not a huge “world class” aquarium… But I actually think that’s one of the most appealing things about it.  There is a small town intimacy and friendliness about the place that makes it a “must see” even if you’ve visited aquariums before.  Located in Mallory Square, there are lots of other things to do nearby – since your visit to the aquarium may only take an hour.  Kids can pet a baby nurse shark and there is a “Touch Tank” at the entrance where they can pick-up and examine many native sea critters including conchs.  Make sure you take the tour.

Whether five or six toes, the cats at Hemingway’s Home are all adorable!

Hemingway’s Home and Museum – How can you come to Key West and not visit the home of one of it’s most famous (or infamous) sons?  The house and lovely garden make for a leisurely tour but it’s the inhabitants that make your visit truly special; the six-toed cats.  Cats in general exhibit the laid-back island attitude that permeates Key West.  If you have children, just being around this many friendly cats will make the visit memorable.

Custom House – For a small community like Key West, this is actually a very nice art and history museum run by the Key West Art and Historical Society.  This restored 1891 building was the original home of Key West’s Custom’s Office and District Courts.  Located on the edge of Mallory Square, there are plenty of things to see and do in the surrounding area – including a mini-mall (with an ice cream parlor and ice cold air conditioning for hot summer days).

Lighthouse – The historic and quaint old Key West lighthouse feels like it’s just plopped down in the middle of a residential area.  You can walk up to the top and get a nice view of the island.  A bit pricey at $10, but a unique experience if you’ve never been in an old lighthouse and don’t mind the climb. One of, if not the, best views of the island.

The D’Vine Wine Gallery at The Gardens Hotel in Key West.

D’Vine Wine Gallery – My sister Kate’s wine bar located in her hotel, The Gardens Hotel, on Angela Street (just a block and a half off of Duval).  This state-of-the-art wine dispensing system needs to be seen and experienced to be understood and enjoyed.  Jazz artists perform on Sunday nights (in season).  D’Vine is open to the public 5-10pm Wednesday through Sunday and available only to hotel guests the rest of the time.

Fort Zachary Taylor Beach – The public beaches in Key West are not the typical picturesque tropical beaches you might expect.  Sand is not natural to Key West – I’m told all the sand has been shipped in (true)!  The one beach that is lovely is the one at Fort Zachary Taylor – a great place to spend the day relaxing.  There is a small fee to enter the beach area but it’s certainly worth it.

Art@830 in Key West for one-of-a-kind gifts.

Art@830 – This is a lovely little art gallery with a nice selection of original art and gifts at reasonable prices.  There are plenty of art shops on Duval Street that cater to tourists and are often wildly expensive.  Art@830 is located on Caroline Street, just a few doors down from Pepe’s restaurant – so put your name in for a late breakfast or lunch at Pepe’s and do a little shopping at this gallery while you wait.

Mel Fisher Maritime Museum – Mel Fisher is a legend in Key West and in the world of treasure hunting.  Over the course of 16 years of searching for maritime treasure, Mel started each day with his motto “Today’s the Day!”  Eventually, his motto became a reality when he found the priceless treasure of the Spanish galleon; the Atocha.  At his museum you’ll find some truly amazing and priceless treasures.

Croissants de France – Simply the best place for breakfast or lunch.  No trip to Key West is complete for me without eggs benedict at Croissants de France.

El Siboney – Really wonderful Cuban cuisine at an amazingly reasonable price.  This is another “must eat here” stop for any Key West visitor… Which sadly also means it’s usually packed – but the tables move quickly and the food is well worth the wait.

Latitudes Restaurant on Sunset Key – Very expensive (that’s why I suggest lunch) but a simply beautiful setting on a tiny island next to Mallory Square.  Part of the Westin resort, there is a boat that takes you over to the island for a wonderful and elegant tropical lunch or dinner with a beautiful view.  Make reservations – perhaps even for a romantic dinner for two right on the beach.  Don’t miss the boat… Literally!

Blue Heaven – Blue Heaven is the quintessential Key West outdoor restaurant – complete with live roosters and cats wondering around at your feet.  They make a great grilled cheese.  Leave room for “Banana Heaven” dessert or just go there for the dessert. Note: Blue Heaven has become so infamous among tourists – a “must see” – that it’s become increasingly difficult to get in without a long wait.  If you can’t get in and want another great place try Santiago’s Bodega.

Santiago’s Bodega – Tapas to die for.  Really great – not cheap but few things in Key West are.

Pepe’s Café – This is the place for locals and tourists to have breakfast.  There will most likely be a wait (see Art@830 above) but it’s another Key West place you must experience.

Roof Top Café – Second story restaurant located next to Mallory Square.  Nice view, nice food, reasonable prices – dine inside if you go for lunch, dine outside if you go for dinner.

The Half Shell Raw Bar’s walls are covered with license plates.

Half Shell Raw Bar – Eclectic bar and seafood on the Harborwalk area of Key West.

A&B Lobster House / Alonzo’s Oyster Bar – Great seafood.  Very swanky upstairs but I’m told the same kitchen supplies food to the casual Alonzo’s Oyster Bar on the first floor – for a lot less money.  There you can eat overlooking the water at the Key West Bight.  You’ll see plenty of fishing boats and a few yachts in the harbor.

Salute! On The Beach – Sometimes a tough restaurant to get into because it is right on the beach and has very good food.

Ghost Tours of Key West – A fun walking tour at night; interesting Key West history and, yes, a little spoky.  Bring your camera and see if you catch a ghost looking through a window.

A small cigar vendor on Duval Street in Key West.

Cigars – There are lots of places to smoke cigars in Key West and opportunities to buy locally hand-rolled cigars made by Cubans.  One of the nicest and newest lounges is the Southermost Cigar Club on the second floor of a little cigar shop on Front Street (next door to Roof Top Café).  The store is tiny but the lounge is big, comfortable and has a large balcony area as well.  Truly a relaxing place to get away from the bustling tourists below.

Key West is known for its breathtaking sunsets and Sunset Celebration.

Sunset Celebration at Mallory Square – You have to experience the Sunset Celebration at least once.  Just before sunset every evening local street performers, artists, and food vendors gather along the water at Mallory Square… Along with hundreds of tourists.  Jugglers, an escape artist, a tightrope walker, and “Dominique and his Flying Cats” are all mainstays at this celebration.  Be prepared to tip… But these amazing and often eccentric performers deserve it.  The acts are timed to end just before sunset when the crowd watches the sun sink into the ocean and everyone applauds Mother Nature’s beauty. Mallory Square is also a great place to visit during the day with its many tourist attractions, glass bottom boat trips, and Sunset cruises.  This is also where gigantic cruise ships moor during the day.

And this is only the beginning!  There are many more things to see and do in Key West and lots of amazing restaurants…  It seems like every great chef must share the common goal of moving to Key West.  ;^)  Enjoy!