First off, many families with 2YO's visit Key West. And, of course, there are lots of families with 2YO's who live there.

Yes, there are homeless people in Key West just as there are homeless people in any city or town throughout the world but that shouldn't stop you. What is it about a homeless person that has you so worried? Chances are you won't encounter one and if you did, how would you know the person is homeless? Are you also worried about encountering homeless people while you are staying in downtown Miami (there are homeless people in that city, too)? Honestly, I think you are over reacting on that particular front.

We've visited Key west numerous times and always felt safe. Use the same common sense you do when you are out and about in your home town and you should be just fine.

Now, it's about 120 miles from Miami to Key West. The road is a single lane elevated "bridge" that links the various Keys. Think of it as a series of long bridges in between lots of small islets. The ride could take 2.5 to 3 hours each way, depending on traffic. Some people may find the "overwater" route a little intimidating at night.

Quite honestly, a day trip to Key West from Miami makes for a very long day, especially if you are doing it with a 2YO. Figure on a total of 5.5 to 6 hours of drive time (more if you are going on a weekend or holiday period) so you'll have to evaluate just how good a travelers your child is. In order to make it worth while you'd have to leave fairly early in the day and if you stay for more than a few hours you'll be getting back to Miami around dinner time or even later. So, ask yourself, is 6 hours of so of driving worth a 3 hour visit. You might be better off spending the night, that way you can have more time to really enjoy what Key West has to offer.

I don't think it's the homeless in Key West that you have to worry about. Key West is not my idea of a kid friendly destination.

Key West is all about drinking and partying. Not much to see or do with a two year old. Also too far for a day trip - you could easily spend six hours making the round trip drive.

There's a butterfly sanctuary, a conch train tour, catamaran rides and lots of fun shops ... it's a great town for a stroller ride... people from boulder usually only drink and party and miss the family stuff...

I agree that it's a long day trip from Miami to Key West, but I think it's a perfectly fine destination to go with a toddler. In fact, I'd rather take a toddler than a 10-year-old because a toddler can't read what's on all the suggestive T-shirts in the shops along Duval Street!

If I were taking my toddler to Key West, I'd stroll along the streets parallel to Duval Street that have such interesting houses and architecture. I'd go to the Hemingway House where the toddler could enjoy the gardens and the polydactyl cats. I'd go to the beach at Fort Zachary Taylor. I'd go to Mallory Square to see the neat statues. I'd go to the Key West Toy Factory. There's more to see in Key West, even with a toddler, than you can see in a day trip.

garyt22 - you got that right. I don't go to Key West to see butterflies. LOL. Still too far for a daytrip.

As much as I love Key West, I can't imagine taking a day trip from Miami there. You're looking at 8 hours in the car for probably 4 hours in Key West. Frankly, if I were you, I'd be inclined to split my time between Miami and Key West...maybe two days each place.

There are tons of things to do in Key West with children and toddlers.

It's a very long tiring ride to round-trip to Key West in a day, as others have suggested. You're talking 300 miles of driving in one day with a child, and the return is in the dark on a two lane road - you'll be tired and have a child with you - not a good idea. Homeless - chances are you won't see them or even know you are seeing them. Safety? It's a very safe place. I like the suggestion above of taking a child up Simonton or Whitehead rather than pushing a stroller thru drinking and smoking tourists near Mallory Square who are there to have a good time and are not necessarily be looking out for strollers. The island has a butterfly museum, a great aquarium, three beaches, and other child-friendly venues and restaurants, but I wonder about the long long drive for a child who will never remember the event. And quite frankly, I suspect you'll think "What a cool awesome place! But next time we get a babysitter!"