Islamorada

Square Grouper for dinner. Worth the wait.

Islamorada Brewing was a good time.

Grab some bikes from Postcard and explore the neighborhoods back behind Islamorada Brewing. Some incredible properties back there.

If you have kids with you, Theater of the Sea is a good time. We enjoyed it without kids, but it's a must do if kids are with you.

We stayed at Amara Cay (a sister property of Postcard) over Thanksgiving and had the best time.

Had a very nice dinner at Ziggy and Mad Dogs (you'll prob need a res)

Best sportsbar by far is Hog Heaven.

Had decent meals at Lazy Days in Isla and in Key Largo on our way down we hit Lazy Lobster. I had the whole snapper there and that was very good.

Islamorada Brewery has great beer and the beer garden out back is wonderful.

If you want to drive down to Marathon hit up Keys Fisheries. A no-frills spot with great stone crab, lobster ruebens, and plenty of other GREAT seafood options.

We drove down and spent the day at Bahia Honda: first half of day was a snorkel trip out to Looe Reef and spent the rest of the day with a picnic lunch and drinking on Sandspur beach. FYI this is pretty much the only "beach" you'll find in the Keys.

Take your boat just off of Postcard Inn for a sandbar excursion. You can actually see all the boats on the sandbar from Postcard Inn. Great spot for floating and drinking and listening to music and chatting with all the other boaters.

We also went down to Key West for the day and had a decent time. Very touristy as most will tell you but enough fun for a day trip.

ETA: Everything ODH said! lol. Loreleis I forgot about also. Go for the sunset but if not it's a great bar to sit and drink for a bit all times of the day. Good food too.

And yes do a convertible if you can. We rented one at MIA and never put the top up the whole trip!

My favorite things that I did when I went to Summerland Key for a week was fish, kayak, and snorkel. All of it was awesome. Love fishing in places where you never know what you are going to catch. Snorkeling at Looe Key was epic. Kayaking in that pristine blue water is incredible. Man, I want to go back so bad.