We are thinking of doing a Florida Keys vacation in 2022. Probably June when school gets out. Thinking of not staying in Key West since it's so crazy unless someone has a good recommendation for a hotel there that is kid friendly. My son will be 11 so doesn't have to be kiddie but just not a place known for partying college kids if you know what I mean! haha We want to take a couple day trips to do the Atocia Museum, shipwreck museum, the boat ride to the fort, etc so it would be convenient to stay there just have always heard it was a serious party town so wasn't sure about the hotels there. Also thinking of Hawks Cay Resort on Duck Key (I read the pool closes at sunset is that true?) and Cheeca Lodge in Islaorada. Anyone been to either of those? Or any other recommendations? Looking for a resort feel with pool and beach and restaurants. We would have a car since we will be driving. Anybody have any advice? Thanks!
We've been to all three (+ Fort Jeff twice), so I'll try to give you some feedback on all.
First of all, don't stay in Islamorada. It's the end of the Upper Keys and there is not much to do there outside of the resort. There are some very good restaurants there and nearby, but if you don't go further down you will miss the best part of the Keys. I stayed at Cheeca Lodge many years ago, so I can't really give much feedback on that specific resort -- other than it's pretty old. I'm sure it's been renovated several times since I was there, but still.
Beaches -- generally don't go to the Keys for beaches. There are no great beaches in the Keys, and only a very few even acceptable ones. Sombrero Beach in Marathon is probably the best. Smathers Beach in Key West has been covered in seaweed every time I've been there, and it's right next to the airport -- literally across the street. If you want a beach vacation, go anywhere except the Keys.
We (DW, DD 19 and I) stayed at Hawks Cay Resort for 3 nights for our 25th anniversary in October 2020. It is quite nice, but we were there during covid restrictions, so most of the restaurants were closed. We stayed in the main building (hotel room), but there are also lots of townhouses there and probably some are AirBnB's. One thing to understand about Hawks Cay is there actually is no beach there. There is a little sheltered sandy swim area, but you can't to any actual ocean beach.
I'm not sure of the pool hours, but it may close for swimming at sundown. However, they had nightly musical entertainment around the pool when we were there. The entertainment was actually pretty good; I think they were laid off Disney kids! We also did their Sunset Cruise one evening and had a good time.
We ate dinner two nights there. The first was Angler & Ale, which overlooks the marina. Everything there was excellent -- great food, great service, scenic view. Highly recommend.
The other night was Island Fish Company, located just on the outskirts of Marathon a couple of miles from Hawks Cay. I was unimpressed -- It struck me as the typical Keys low-rent "let's watch the sunset with cocktails" kind of place. The food was unremarkable and the service was mediocre at best. We will try somewhere else next time.
Most of the time when we visit Key West, we don't actually stay in Key West. We usually stay up the road somewhere between Big Pine Key (30 miles) and Ramrod Key (25 miles). Our favorite Keys activity of all time is a Looe Key snorkel trip from the Looe Key Dive Resort on Ramrod. And, a friend of ours used to own a house on Cudjoe...but unfortunately he's now sold it. You'll find some AirBnB's in both areas. On Ramrod, just across from Looe Key Dive Resort, is Boondock's (Boondock's Grill, Draft House and Miniature Golf -- seriously). They have good food, good service, and nightly live entertainment.
A lot of people in the Cudjoe area will talk about the Square Grouper restaurant, but I don't recommend it. Mediocre food, an incredible hour-plus wait even when they had open tables, very slow service, and inflated prices. We were there over 3 hours, but not because we wanted to be!
We have not stayed IN Key West in a number of years. In recent years, we've tried twice but had to cancel -- once because of a relative's illness and the other time due to covid. For both of those trips, we were going to stay on Stock Island -- which is immediately next to Key West. Once was at The Perry Hotel and the other was in an AirBnB. Sadly, we had to cancel both, but both look really nice.
There are a number of DIS posters who visit Key West often and can give you better hotel/BnB recommendations.
Oh, and I've spent two long weekends at Fort Jefferson several years ago -- but as a guest of the National Park Service. NPS boat, lodging, etc -- so I don't have any info on private tours.
