This post will be brief since we were actually traveling without kids, but we just got back from a 4 day, 3 night trip to Key West, also paid for with points and miles. This was to celebrate our 10 year anniversary so my mom and step-Dad graciously watched the kids for us.
We stayed at the Hyatt Centric which has a great location right in Old Town on the water between Mallory Square and the main docks. The hotel was awesome and had a pool, a tiny little beach that was great for snorkeling, and little turtle ponds! We told them it was our 10 year anniversary and they hooked us up with a bottle of champagne and chocolate covered strawberries.
Here’s how we got this trip for free:
2 round trip tickets from Syracuse to Key West on Delta = 70k skymiles (35 k each). I transferred American Express membership rewards to Delta (1:1 ratio). 35k a ticket is a little high for domestic travel but we needed specific dates and were flying small airport to small airport. We definitely could have gotten the tix for probably 25k each if we flew into Miami and drove (which would have been cool), but we really didn’t have a lot of time for this trip.
3 nights at the Hyatt Centric: My husband took out the Chase Hyatt credit card (I still haven’t been able to get this one because of Chase’s 5/24 rule). You get 2 free nights at any Hyatt after you spend 3,000. So we used those two nights and then added a 3rd night which I paid for with Chase Ultimate Rewards. Looking back at my receipt it seems I paid 40k UR, which seems like too much. You can also transfer UR to your Hyatt account and pay with Hyatt points (our room would have been 25,000 points), but I can’t remember why I didn’t do this. It may have been that they didn’t have award rooms available when I booked or it could have been a rookie mistake. But you should always compare transferring points to a travel partner (hotel or airline program) vs using points (e.g. Chase’s ultimate rewards or Amex’s Membership Rewards) via their travel portal to see which is the better deal.
Overall we had a great time in KW. I think you could take kids there but it wouldn’t be my first choice with kids. There aren’t a lot of things to do other than eating, drinking, and boating (which could be great for a older kids, minus the drinking of course). I think it would be a good trip for families as a tour of the keys. There also aren’t nice beaches like there are in other parts of the keys, although the state park had one and there’s another one closer to the airport (Dog beach).
Some things we did include, riding bikes around the Island and stopping at the Eco-Discovery center (free!) near Fort Zachary Taylor state park (2.50 each on bikes). The Eco-discovery center gives you some nice info about the ecology and conservation efforts of the Keys. The Hemingway house, of course, which I loved since EH was one of the only authors I liked reading in high school, despite his rampant mysogyny. Duval street is good for people watching, especially as the night goes on and people get drunker (although we saw a fair amount of daytime drunks too), and Mallory square has a cute little “sunset celebration” with street performers and a couple food trucks.
We also took the ferry out to Dry Tortugas national park, which is a full day excursion (8am – 5:30pm). It is a 2.5 hour boat ride there and back and they give you a simple breakfast and lunch. If it’s a rough day at sea you may feel it, so come prepared with Dramamine. I am usually ok on boats as long as I can stay on deck but at one point it was too rough so the captain made us go inside and that’s when I started to feel awful. The crew walks around with barf bags (which I didn’t need thankfully) and they will bring you ginger ale and water and ice. My husband was also pretty green but luckily he was able to hang tough. The national park itself is amazing. It’s the ruins of a fort which at one point was also a prison. There’s birding, fishing, And snorkeling around the fort. There is an awesome reef around the mote and you can snorkel along it. I saw a ton of great fish including huge parrot fish. I would highly recommend this trip if you can stomach the boat ride.
Otherwise we did lots of eating and drinking! Conch fritters and key lime pie are the “have to” treats, but we ate great meals throughout our trip. My favorite restaurants were The Flaming Buoy, Bien (amazing Cuban sandwiches), the Cuban Coffee Queen for coffee, and this great little tequila bar across from Mallory Square made an awesome basil Paloma.
All in all it was a great little “grown-up” trip and we had a great time. I would love to return one day.