- There are a few guided trolly tours where you pay once for the tour and then can hop and off at any trolley stop for the next 48 hours if you show your ticket. Good way to see the island and get some ‘free’ transportation.
- Blue Heaven is the famous spot for breakfast. In the backyard of an old house, good food with live acoustic music and a bar for bloody Mary’s etc. Usually has a wait, no reservations.
- If you want a nicer dinner, we usually try to go to Latitude’s. You take a 5 minute ferry to a private island that the restaurant is on, and can sit on the sand with a sunset view. Need to book far in advance for times around sunset.. https://www.sunsetkeycottages.com/key-west-restaurants/latitudes/
- Of the bars on the main Duval Street, we like Hog’s Breath Saloon and Smokin Tuna Saloon. Old outdoor/open air bars with lots of character. Sloppy Joe’s is the popular one with the biggest live music acts.
- We like to avoid the Duval crowds sometimes, so the area called The Bight is a more laid back area. There is a string of restaurants and bars along the harbor where all the boats dock. Conch Republic Seafood Company, Schooner Wharf, and Waterfront Brewery are good spots for food or a drink. There’s also a kind of hidden Galleon Sunset Tiki Bar that has great sunset views, much less crowded than the main sunset spots.
- Sunset Pier is a great spot to sit on the water for lunch or a drink.
- It’s a bizarre concept, but Better Than Sex is a dessert/drinks place that is really popular. Weirded me out a little since it’s setup to have a brothel type feel and the menu all has suggestive names, but it’s definitely a unique experience and the desserts were amazing. Absolutely not for kids though, ha.
- If you want an actual all day excursion, we’ve heard people rave about going to the Dry Tortugas. We’ve never done that though, just the water sport stuff. And if you want to drive up the keys one day (or make a stop on the way down), I’ve heard great things about Islamorada although I’ve never been myself. There are two breweries on that island as well.
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We'll be down there for a week. Put your things to do as well as eating and drinking recs here.