Hi there, I am looking at Islamorada (Cheeca Lodge), Hawk's Cay (but reviews are spotty) and then someplace in Key West.I like KW but have been several times. I have four nights with a 12 and 13 year old. My husband and I are looking to relax but take a sunset sail, possibly snorkel and have some good food. So, my question is, should I stick to KW or are there other keys you'd suggest that might change it up but also be a good experience? I'd also split the time if Marathon or Islamorada were worth it. Any suggestions or opinions are welcome. If you prefer one place over another, I'd love to hear it. Thank you!

I like Islamorada and have been for the past four winters, for up to 5 days. There is very little nightlife but day activities include those you mention. But a good part of the attraction for me is my hotel, which is just south of Cheeca Lodge and far more low key. What kind of budget are you working with and how many rooms?

ekscrunchy,

Thank you for your reply, I appreciate it. We don't need night life but I'd like to be able to order a glass of wine in the evening. We are going in the heat of August so rates are better. If I can keep it under $350/night I'd be happy and one room. It seems like the beach is narrow but nice. If we can get out on the water, that would be great but not essential.

Ahh so rates are better in August?
We are going to the Olympics if things work out ( don't know yet if the boy has made the team but we've had to book of course)
We plan to stop in Miami on the way home after rio
I've booked dallas ...grapevine but hesitating about Miami...just too overwhelming ! I'm hoping to wing it? With 4 days to spend I'm all over the place with my itinerary but your comment re rates gives me hope that it won't be crowded
Maybe I'm dreaming ?
Have a fab time!

lanejohann, Miami isn't that bad. Driving might be a little nutty but it's not like NYC. You can handle it. I would think Rio would be a much bigger thing to deal with to be honest. So many places to go or see around Miami. If you pick one and stick to it for a couple days you're fine. If it's really overwhelming, stay at a resort and don't leave it. But it's fun to walk along S. beach or spent time in Key Largo. Hope your boy makes the team, very exciting stuff!