We will be driving from Orlando to the Keys at the end of May (we are not from Orlando or we might know more about the Keys I'm sure). We will have the option of driving to Key West and staying there for 7 nights and then on the way back up, staying in one of the other Keys for 3 or 4 nights, or we might like to spend the first 2 nights at one Key, then Memorial Day weekend at another (we didn't plan to be down there for Memorial Day weekend, but the cruise we cancelled ran on these dates and we can't change our vacation time at work), then following Memorial Day weekend, spending 3 or 4 nights in another Key (or maybe Miami?).

We aren't sure which Key we'd like to be in for the holiday weekend, which one would be best to stay in for only 2 nights, etc. Any tips would be appreciated. Thanks!

Hi -

I am a die hard Key West fan, and have also stayed in Key Largo, but only for one night.

What will be important to you to do when you vacation? Good restaurants, shopping, sunset cruises, snorkeling, fishing, just hitting the bars for drinks and entertainment?

Key West has everything, but each key has great points.

Are you traveling with kids? Key West is very kid friendly with sunset activities and kid friendly restaurants.

You know the beaches in the Keys aren't like the rest of Florida right? The beaches in Key West are very, very, very narrow with rough coral in the sand as especially at the shoreline in Fort Zachary Taylor. Bring water shoes.
They aren't the most fashionable thing to wear, but you will be glad you did.

Try not to miss Bahia Honda State Park. This place has the closest thing to a regular beach that I have seen in the Keys - plus it is very beautiful. The water is gorgeous.

Sorry for the rambling - it is very late.

Feel free to ask more questions - I am sure some of my AOL Keys Travel Board buddies will be not far behind me here - and have tons of great information!!

Enjoy your trip!!!

Annie - Like Karen, I'm a die hard Key West fan. The first time we drove through the keys, we spent a night in Islamorada at the Cheeca Lodge and we've never stopped on our way down again.

I'm not a diver and have only a little snorkeling experience, but from everything I've heard the upper keys are much better for those two things than Key West is. Having said that, I can't think of another reason not to concentrate your time in Key West. If you stay in Old Town - and you really should - you'll be within close walking distance of fabulous restaurants, sunset celebrations and other tourist activities. You can be as busy (or as laid back) as you want. This board has tons of good information about Key West and the keys...you should do a search!

unlike the above, i am not a big key west fan. its OK for a day trip but i'm not into the bars, t-shirt shops, sightseeing trams and other goofy, tourist stuff. i want something a little more "natural".....someplace to go diving or rent a boat and head out to the reefs. so i try to avoid the big 3...largo, marathon & key west.

Thanks for the replies! We are not travelling with kids. This will actually be our first anniversary present to each other. We are mid to late 20's, but not that into nightlife. I would like some of the tourist things I know Key West has, but also some good beaches, definitely some natural sites, maybe a dolphin encounter or snorkel trip.

We are considering the Largo Lodge if we go to Key Largo, White Gate Court if we go to Islamorada (and a couple others too, but I don't know their names off-hand), and in Key West, the Jasmine House (although I'd like a pool on site), La Pensione, Key Lime Inn and the Merlinn Inn in Key West. I am torn about whether or not I'd like to spend the most time (7 nights) in Key West and just 3 or 4 nights on another Key on the way out. Unfortunately we can't split it more evenly because that runs us into the middle of Memorial Day weekend and the minimum stays involved. We couldn't just leave on a Saturday or even a Sunday in most cases. And we don't want to drive on Monday so that takes us to Tuesday.

Decisions, decisions. LOL!

PS - If it helps at all to determine whether or not we'll really enjoy Key West, we live in a city that reminds me of the northeast version of it. It's outside of NYC, tons of bars, and while we don't do the bar scene much, we like the atmosphere of all the shops and activity. Plus we're used to noise, if that makes any difference.

We stayed at Parmer's place on Little Torch Key, and found it to be a good location - its around MM 29, which makes day trips to KW possible, not too far from Bahia Honda (beach), and a short trip to Looe reef marine preserve for snorkeling. We used Strike Zone for our snorkel trip (on Big Pine Key) and had a great trip. Others go there for the fishing, we have friends who rented a small boat for 3 days and spent the entire time fishing and snorkeling from the boat. I found the keys most enjoyable when I was out on the water - snorkeling, beach, etc., and don't really care much for KW for the same reasons posted above. Just depends on what you like. It would be a quiet vacation there, that's for sure - not much nightlife, although its worth finding the No Name Pub on Big Pine for local flavor.

Unless I'm misreading your post, it sounds like you're going to have LOTS of time in the Keys. I'd split it between two Keys: Key West and the Islamorada area (Mindley Key through Long). I'd probably not stay at any other Keys just because I don't like to pack and re-pack too many times. Key West will give you a good selection of restaurants, shopping and lodging. Islamorada is a little lighter on the restaurant selection (although some of them are more "geniune") and a lot lighter on the shopping. There are, however, some good lodging choices in Isla. Such as Cheeca, Moorings, Chesapeake Resort, and several smaller mom-n-pop places. Islamorada is very laid back and the area really is more of an outdoor destination, ie, kayaing, deep sea fishing, snorkeling/diving, etc. Have fun in the Keys and watch for sunburns.

We just returned from Duck Key (MM60) and had an absolutely wonderful time. We stayed at Hawk's Cay resort where there are so many things to do, or nothing at all if you want to relax. We went parasailing, wakeboarding and snuba/snorkle (like scuba but without the tanks). There are about 4-5 pools including one just for adults. The food was ok but you are in easy driving distance from many other restaurant. We went to Key West for the day and evenning and it took about an hour. We ate at two places in Marathon (mm 48/50) that were surprisingly good. Marathon Pizza and pasta (we have kids) and Annettes where I had the very best snapper I have ever had. Key Largo is about45-60 minutes away but we found that everything that we wanted to do, we were close enough. We did eat there on ourway down from Miami airport. I DO second the need for sunscreen. Almost everyone there looked like lobsters within a day or two. The keys were beautiful and relaxing. Enjoy!