Key West/Miami Suggestions

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So a cousin of mine and I were planning on going to Miami and Key West for Labor Day weekend. Kind of a last minute thing.

We're flying into Miami Thursday afternoon and spending the night in South Beach, and then spending the day in that area. Then driving to the Keys Friday night and basically staying there until we fly back Monday night.

We don't have anything planned on things to do so I figure I would ask you all if you have any suggestions on things to do/eat/drink in the South Beach area as well as Key West and the surrounding areas/cities in the Keys?

Thanks for any suggestions.

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Not exactly tons of time. Assuming you are planning to just bar hop or whatever South Beach and one day in Key west. There's a lot of stops along the way between Miami and Key West that you can find online, between that and the 3 hour drive that's about a day. South Beach a day, Walking around Key west for a day.

The drive to Key West has some amazing views once you cross Card Sound Road and head south out of Key Largo. Not sure I'd wait until the night to drive it.

If you care about touristy spots, either the road or the marker, or both, at the southernmost (publicly accessible) point were undergoing repair earlier this year so you may or may not be able to go there and get a picture.

In Key West check out the Hemingway House. Grab a drink at Captain Tony's (the original location of Sloppy Joe's) and try to throw a quarter in the mouth of the fish outside. Also be sure to check out the bar stools that pay tribute to famous patrons (Jimmy Buffett, Mike Leach, and others). The Mel Fisher Museum has a lot of the gold and silver from the Spanish galleon wreck he found back in the 80s. Mallory Square at sunset is a little carnival all on its own.

I think Old’s Havana is better than Versailles but Versailles has been ground zero for Cuban-American politics; it’s got some history.

I love love love Baires Grill (Argentine)—there’s one in South Beach, Brickell and Coral Gables. Website

Walking the Lincoln Road Mall is a good time as well. Tons of shops and restaurants.

There’s so much to do in Miami that you might feel like you’re short changing yourself by driving down to The Keys, especially if you’ve never been there.

In KW, Eaton Street Seafood for lobster rolls or fresh catch. The Banan Cafe for breakfast. Hop on hop off bus for getting to know everything about the island

On Labor Day afternoon that is gonna be about 5 hr drive from key west back to Miami. Was halfway to key west a couple of years ago and it took over 3.5 hours. Id try to leave early Monday and hangout in Wynwood before the flight out.

My advice, spend Thursday and Friday night in Miami on South Beach, party hard Thursday, Friday night eat a good dinner, but no late night. Leave at 5:30 am Saturday to drive to KW and catch an amazing sunrise driving to and no traffic.

Same on reverse, Saturday party night in the key, Sunday have a good dinner but not a late night. Leave at 6 am Monday to drive back to Miami and catch an amazing sunrise, then Little Havana in the morning, Wynnwood afternoon, head to airport to fly home.

I was in Key West over the 4th of July.

The best food i ate there was Sandy's Cafe. Their Cuban and breakfast burritos and coffee are amazing. In my opinion all of the touristy places like Conch Republic were ok. But nothing noteworthy.

The drive from Miami to KW has always been my favorite. Find a hole in the wall bar and stop in for a drink, talk with the locals and keep heading south. No Name Pub was a good one that comes to mind.
Take a side street and come across Key deer and find a random beach and relax for the afternoon.

Spending a night in South Beach before heading down to the Keys for a long weekend is a classic way to kick off a trip.

Hank's Hair of the Dog for live music

Irish Kevin's is always fun, and of course Sloppy Joe's, Hog's Breath, the sunset celebration at Mallory Square (though I think this has kinda died off from decades past). A booze cruise is always fun too...we liked the Fury catamaran sunset sail. Happy hour bar hop along the Key West Bight marina.