Key West holds a special place in my heart. Not only is the island tons of fun with scads of bars, restaurants, water sports and gorgeous sunsets, it’s also where Brad proposed to me in 2001. We were having dinner at Mangoes on Duval Street and it was his birthday as well as Mother’s Day. Getting engaged was not even on my radar, to say the least. Our server figured out what was going on when Brad got down on bended knee, and she brought us a couple of glasses of champagne as soon as she saw my thrilled and stunned reaction. Since then, I have enjoyed a glass of bubbly each time we visit (not to mention at a few other places on the island.)

Brad and I have returned to Key West a handful of times since that first trip, but it had been a while since our last visit. Since our 10-year wedding anniversary is this year, we decided to take a long weekend while the kids were on spring break (thanks for letting them stay with you, Mom!) As usual, we enjoyed some of our favorite places, but also tried some new things that included taking a wonderful sunset dinner cruise and renting some bikes to get around the island. Based mainly on this particular trip, here are some of my recommendations of places to try in Key West, both on land and on water.

Boats

We took two boat rides – one where we snorkeled, one where we dined. I can’t say enough good things about either!

Sebago Key West 

We took our first Key West snorkeling trip with Sebago and have booked all of our other excursions ever since. We’ve done both the morning and afternoon trips and recommend either. The morning snorkel is usually less crowded and more laid back, while the afternoon trip is definitely geared for those who want more of a party atmosphere. The crews on all of our cruises have been fantastic – professional yet fun, fun, fun!

Islescapes

I’ll be posting a separate blog about this experience – it was that awesome. I found this dinner cruise online and loved the reviews I saw about it. Great call – we had a blast! Limited to six people, you are in an intimate setting with delicious food and a one-of-a-kind view of the famous Key West sunset. Not only is Captain Alex laid back and entertaining, he offers a great meal to enjoy while watching the stunning sunset.

Bikes

What an awesome place to ride a bike, especially if you avoid Duval St., which is easy enough to do by taking Simonton or Whitehead as alternatives. Here are a few of the places we visited:

Key West Cemetery

This has nothing to do with food, but is quite a cool place to visit. But then I love cemeteries for some reason – they are peaceful and calming. At least most of them (the one in the movie Poltergeist would definitely not qualify!)

Southernmost Beach Café

We stopped here because we had never been, plus it was time for refreshments. Mine came in the form of a frozen mangorita, and Brad had a Corona. This is a great open place situated right on a sandy white beach, overlooking the beautiful turquoise waters. One of the bartenders was an N.C. State fan/grad to boot!

Peppers of Key West

We’ve bought hot sauces from this place before – it’s a cool little shop and I wish we had one like it in Raleigh. Since we weren’t checking luggage on this trip, we had them ship us a variety of hot sauces and some other stuff, which made it to our home on time and intact. The friendly staff will let you try any of the sauces, etc., so definitely take advantage of this.

Truman Annex, Old Town

This area is a neighborhood as well as a military installation off of Whitehead St, and President Harry S. Truman had his winter White House here. It is quiet, well kept and beautiful – even with its close proximity to crazy Duval St. Once you ride through it, stop off at Kelly’s Caribbean Bar Grill & Brewery, which is a great segue into my next section on bars.

Bars (a bit off Duval Street’s beaten path)

Duval Street has so many famous and cool places that I could blog about for years (hey- now there’s an idea!)  Same with the Key West Bight marina, with Schooner’s Wharf, Turtle Kraals, etc. – you definitely have to have a drink or two at many of the bars there. If you’re lucky you may get to see some manatees, which often come right up to the docks.

That said, I do have some other favorites that I can vouch for, believe it or not.

Kelly’s Caribbean Bar Grill & Brewery

This has been one of our favorite places for happy hour ever since our first Key West visit. From 4pm-7pm (only at the bar, which fills up quickly) you get great deals on microbrews ($2.00), well drinks ($2.50) margaritas on the rocks in pint glasses ($3.50) as well as a pound of tasty wings in a few different sauces for $4.00.

 Green Parrot Bar

This Key West icon has been a classic since it changed from a grocery store into a bar during World War II. According to its website, The Green Parrot “has seen all manners of human exploits, from poetry slams to divorce celebrations, from memorial services to hurricane parties and pet birthday bashes, from tattoo contests to fundraising benefits.”  All I know is that I have fun whenever I go, and have met people from many different walks of life.

Captain Tony’s Saloon

This is truly a dive bar if there ever was one, and every now and then, a good dive bar is just the ticket. This was the original home of the infamous Sloppy Joes, and a hangout of Ernest Hemingway from 1933 to 1937. The place is absolutely littered with business cards and brassieres. I left my business card years ago and found it on my visit before this one, but no luck this time. I did leave one of my old bras on this trip – a red one to honor NCSU’s trip to the sweet 16. Hopefully I’ll be able to find it on my next visit!

Alonzo’s Oyster Bar

Go to the bar (instead of the restaurant) for cocktails or wine and some of the best Oysters Rockefeller you’ve ever tasted. This place feels more like a traditional steakhouse bar with its dark wood, etc., and is a great alternative to some of the more “islandy” places.

Island Dogs Bar

This place is fairly new to Key West and was right next to where we stayed at the Pier House. Loved this bar – open air, great interior and friendly staff. I had a feeling that this is where locals go, which is always a good sign. I wish I had tried some the char-grilled oysters that have gotten great reviews – that’s top of the list for next time.

Beer Stands at Mallory Square

You can’t experience Key West to its fullest without going to Mallory Square to see the sunset and all of the craziness that goes with it. Luckily, there are a few of what I call “vendor bars” set up in the square that sell a limited selection of beer and wine to sip on while you revel in the awesome sunsets. Pricey? Of course – just like you’d find at any outdoor or sports venue. But worth it (if you didn’t bring your own!)

OK, I can recommend a number of other places in this fun loving town (such as the Hemingway Home and Museum by bike or Latitudes on Sunset Key by water taxi), so if you are going and need some suggestions, please ask. Or, better yet, take me as your tour guide. And, always, always, always – please savor the sunsets.

Eat, drink and be merry!