Vacation Advice - Key West

Mrs 138 and I are celebrating #20 this year and were thinking about places to go. We were thinking about doing Key West instead of spending $$$ on passport renewal and hitting an all-inclusive in the Caribbean. We’ve done that before.

Anyway, does anyone have opinions on KW? Unfortunately, our window is kind of limited to July because of work commitments for both of us. I know it’s gonna be hot and humid down there.

I was looking into the Southernmost Beach Resort but I’ll take any advice or suggestions!


I haven’t been to Key West since the 90s so my info may be terribly outdated, but my recollection is that there just isn’t a whole lot there. I remember checking out Hemingway’s house, having a drink at that one bar he always hung out in, and I think maybe there was a Margaritaville too. But probably not a bad place to take in some sunshine and sip some umbrella drinks.

I agree with dive, it isn’t an amusement park. but it can be nice to go down to the pier and bagpipe the sun down. I think there are fishing boat tours and things too, and if you have a car some of the other keys aren’t far and have nature preserves and such.

We went about 8 years ago…we had a blast because we love to snorkle and there is so much to see / do with this.

We stayed in a VRBO house near Pennekamp state park:

The park is amazing - very shallow and lots to see.

The good thing about the northern most keys in this area, is that you can take a 45 min drive north and see alligators, and do the big swamp boat air rides which are a hoot and then come back down for relaxing.

I wouldn’t go for more than a few days. I enjoyed a week or so driving and hanging out in the Keys last fall, but it’s all more or less the same - beach, snorkel, boat tour, sea food. Key West strikes me as the most expensive place to do all of those things. I was happy it was just a one day stop (end point) on the road trip, rather than the entire focus.

Thanks for the answers so far. We just want a place to enjoy the sites, hit the beach, maybe do some snorkeling and other things like that. Not looking for much more than that.

Also open to other vacation destination ideas.

US Virgin Islands. Similar climate to Key West, but a lot more to do. Really cool underwater portion of a National Park too.

The Casa Marina Key West (a Curio Collection resort hotel in the Hilton chain) is very nice and would make for a good anniversary trip stay. Full services, private beach, etc., though it is pricey. There is another similar resort not far away that is also in the Hilton lineup, The Reach I think it’s called. Same deal, super nice, but pricey as all get out. The 24 North is another hotel in Key West that’s very nice, but not quite as pricey as the resorts. It also has a cool bar called Republic that has a 1940’s look and feel. I’ve heard good things about Margaritaville Beach House as well, but never been there myself. There are also several bed and breakfast and AirBnB/VRBO rentals throughout Key West, and some of the “old school” motels have been remodeled to higher standards while retaining that old motel look and feel. The Blue Marlin is a good example, and it’s within walking distance to Duval Street and other attractions.

As for what to do, I agree with the posts above that unless you are there for a specific event you’ve got maybe 3 days worth of stuff to do and then you’ve seen it all. Duval Street is the obvious attraction, especially at night. Southernmost Point and Hemmingway’s House during the day. If you enjoy snorkeling you need to get on one of the snorkel charters, they are amazing and you can spend most of a day riding around on the charter getting in the water in multiple places and see some really cool stuff. If you’re a fisherman, same thing only with a fishing boat instead of a snorkeling tour.

Key West is a great trip to combine with a visit to Miami. It’s easy to fly into/out of Miami, then stay a couple of nights in South Beach. Take in the sights, especially at night, and maybe hit a Marlins game while you’re there. Then rent a car and make the 4 hour or so drive down to Key West. That drive is incredible…the map says 4.5 hours, but you’ll probably end up taking 6+ because you’ll want to stop often to explore a bit and take some amazing pictures. To this day that drive from Miami to Key West remains one of my all time favorite drives on any continent, it’s just beautiful.

The Keys don’t have much in the way of beaches. I think there’s one or two, but most of the shore is rocks.

Key West is cool, but it’s not big and you can see the highlights in a day or two. Kind of a party town.

Driving down on the bridges is pretty cool too.

But as was said beaches aren’t a thing in the Keys. All the sand has to be imported as the Keys are pretty much coral.

We’ve been several times. July and August can be muggy and sweaty times.

If you’re into history, the Keys was fascinating to me what with building the railroad down there, the hurricane of ‘35 etc.

There’s a travel book by Joy Williams in its 10th edition that goes though Mile Marker by Mile Marker things to do, places to dine and eat and gives a great background to Conch culture and the history of the Keys.

Visited the keys last year during our epic road trip. We stayed on Cudjoe Key, which is about a half an hour from the goodies on Key West–FYI there’s another resort about half an hour east on Marathon there is really nice (Isla Bella I think it is). But in July will be expensive, as are most places in the Keys.

My impressions on a couple of visits to Key West is that it can be a lot of fun–there are quite a few bars and eateries and a huge number of boat tours and assorted water sports that would take a couple of days to do. If you’re going to do Hemingway House, bring cash. Some well known local ghost tours you can do; one bar has a human skeleton built into it, another house served as the inspiration for Chucky (apparently). If you can get on a trip to Dry Tortugas, that will be well worth it–they sell out incredibly fast if you don’t do a private tour. If it’s also possible to do some kind of excursion into the Everglades by boat, that would be also great and such a fun experience. Key West also has all the typical amenities like grocery stores, theaters, etc.

There is a lot to see in the Keys as well, like a turtle rescue on Marathon (and a free bird sanctuary a bit further east). There are only a few really good beaches, including Bahia Honda and I think the good coral tours up are up at John Pennekamp Coral Reef State Park.

— Alan

Welp, the huge seaweed blob has us rethinking key west for July. Perhaps another time.

I’m sure it’s all overblown and it’ll be fine. Please find out for us, though!

— Alan

Bocas Del Toro, Panama. It’s been 12 years or so, but my thought was, “this is what Key West must have been like in the 60s.” Crystal waters, restaurants build half over water, all the watersports.