Key West, Florida

What To Do In Key West 

• Sunset In Mallory Square: Don't even think of visiting Key West and passing on this. Anyone on island will be able to tell you what time sunset is, head to Mallory Square about a half hour (or an hour even) before that so you can see the performers and stroll among the vendors. I will usually get there and perhaps purchase an adult beverage, then find a spot on the edge of the dock to sit or stand, and I just watch. The people all all around and the changing view as the sun is dropping. My friends know I;m not real chatty while I'm watching, it's rejuvenation time for me. And, when the sun is set, don't forget to applaud, it's only polite to show your appreciation.
• Sunset From The Top Of The LaConcha: The LaConcha Hotel (currently a Holiday Inn property) is, at six floors, the tallest building in Key West. They have a bar and observation area on their roof. It will cost you the price of a drink to go up there and it is very worth it. The hotel is right on Duval Street, and offers great views of the whole island and the sunset over the Gulf.
• Old Town Trolley Tours: Especially for your first visit to Key West, invest the time (and a bit of cash) into this tourist train. You will get a fully narrated ride through Key West to see the sights and have them explained to you. This train has the advantage that you can hop off of it to explore (you have ten opportunities to leave the train, then reboard).

Cool Places To Stay In Key West 

...a few of my favorite places.

Yes, there are a large number of the big chain hotels on Key West. I'm sure they are very nice. I can't say for sure since I haven't stayed in one and I won't. It's not that I don't like them, I have frequent stay programs with most of them and like earning points. But, not in Key West.

When I am in Key West, I want to be in Old Town. I want to stay in a place that has the charm of the town and in which I can lose all sense of the outside world. I want wood floors or tile floors, and I want ceiling fans, and wicker furniture. I want cats and chickens roaming the property. I may not get a television, or an alarm clock, or sometimes even a telephone. You know what? I'm good with that. Check out some of the places I've stayed if this sounds like something you might be interested in too:

• The Southern Cross Hotel: First, really - it's a cool name. That being said, it is a great location, right on Duval, right near everything. There are several buildings, and you may need to be able to negotiate stairs. There aren't elevators, there is no pool, and if you are on the Duval side of the establishment, your room could get some noise. It is a very clean hotel, the prices were very reasonable and the staff was some of the best in town.
• Eden House: This charming property is a bit of a walk, but worth every step. Their pool area is a tropical paradise you have to see to believe. The hammocks are just every where and they are waiting for you. The property is quiet, the staff is exemplary, and the morning coffee is really good. The rooms are small and some rooms share a bathroom with others (you will know this before you book the room!), and the ones that have a private bathroom are configured a little oddly, but that doesn't take away from this place at all at all.
• The Pilot House: This property is one street off of Duval, and easy walk to the nightlife scene. My room there was ever so spacious, with it's own kitchenette, and little private porch. The pool area was "clothing optional", but that wasn't a problem. I left my suit on and those that chose not to were very subtle about it.

A Few Quick Tips For Your Trip To Key West 

1. Please don't travel to Key West and expect it to be a beach paradise. It's not. It does have some very nice beaches (it usually will make someone's top ten list), but, really, there is so much more that is much better to do there.
2. Think about it before you take your kids to Key West. This is not to say that Key West, especially during the day, is not family friendly - it is, and you can find many activities that the kids will enjoy. But, when the sun goes down it is honestly more of an 'adults only' area.
3. Be smart with your health while you are on island. You're in the tropics - it's hot there. A steady diet of only alcohol, as tempting as that may be is only going to end you in the hospital.
4. Be smart with your safety while you are on island. I am not saying that Key West is a dangerous place, but it is known as a tourist destination. And, anyplace that is known to attract tourists also attracts predators. Just be smart.

Popular Key West Annual Events: 

...not an exhaustive or all inclusive list, by any means - but this gives you a rough idea.

• Acura International Boat Regatta ~ January
• Key West Literary Seminar ~ January
• Conch Republic Independence Celebration ~ April 23
• Red Ribbon Bed Race ~ April
• Survivors Party ~ May
• Queen Mother Pageant ~ May
• PrideFest ~ June
• Cuban-American Heritage Festival ~ June
• Hemingway Days Festival ~ July
• WomenFest ~ September
• Fantasy Fest ~ October
• Goombay Celebration ~ October
• Robert the Enchanted Doll Day ~ October 24th
• Parrot Heads in Paradise Convention (aka Meeting of the Minds) ~ November
• Boat and Holiday Parade ~ December