What do I want to do in Key West?

In My Humble Opinion
1

Never been there before. Going to be there Dec 27 to Jan 2 with a not-quite-21 year old and an 8 year old. Dad’s got a large boat we’ll be staying on; not sure what marina, but we’ll also have a rental car for day trips in the area.

What’s there to do in Key West after the sun soaking and the drinking of alcohol - neither of which will hold my interest for more than an hour or so? I don’t particularly care if I spend a week doing nothing but not-doing-paperwork, but Dad wants to know what we want to do while we’re there.

2

If it was me, I’d go to the Hemingway house and pet the cats.

3

Snorkeling to see the reef life springs to mind. [I know one of the state parks has a handicap equipped dive boat if you need one]

Walking around and window shopping - I collect refrigerator magnets for a couple friends when I travel someplace new.

Eat - conch is sort of important in the Conch Republic.

Get a Conch Republic passport

4

You could hang out at the sunny place for shady people, the Green Parrot Bar! Leaving the 2nd? dang you’ll miss DTB live in concert.

5

Walk up and down Devon street, it’s always interesting. The Hemingway house is a special place, I recommend going there. The “little White House” not so much unless you’re a history buff. I guess Sloppy Joe’s bar is a thing? Oh, and there’s a butterfly conservatory that is fun.

There’s lots of parasailing etc. if you’re feeling sporty.

One disappointing thing about Key West is that the beaches aren’t very good.

6

Definitely do not miss the Hemingway House and cats.
Stand up paddle boarding from Stock Island (just north of Key West) is fun.
Mallory Square at sunset has street performers walking tightropes, juggling fire, and such.
Renting bikes is a good way to see the island. I’d say bring your own if you can, but the salt is pretty rough on them, so maybe it’s best to rent.

7

Key Lime Pie.

I didn’t think I liked Key Lime Pie, but in Key West I tried some since I was there. It was really good. I think I was just eating bad Key Lime Pie before. The standards for Key Lime Pie in the Keys are probably high, so you might as well take advantage while there.

8

Thanks! Sounds like just what I need - a week of not a whole lot, and slowly.

Will definitely check out Mallory Square and the Hemingway House. I’m not much into sporty things, and seaweed scares me, but I’ll probably spend some time splashing is some water somewhere with the little one. Key Lime Pie is a must.

Are there any manatees around? Always wanted to see a manatee…

9

I enjoyed the Walking Ghost Tour. You know the “ghost stories” are embellished for tourists, but you learn a lot about the history of the area.

There’s also that museum with “Robert” the creepy possessed doll. We didn’t go there but it would be interesting.

10

Definitely the Hemingway House.

I thought it was worth the time to take a catamaran out to Dry Tortugas National Park. The trip out and back was fun and exploring Fort Jefferson and the area was really cool.

11

The Conch Train Tour is good cheesy fun. And of course you can visit the big red buoy marking the southernmost point in the US. I like sitting at the bar at the Ocean Key House (I think that’s the name of the hotel) at Zero Duval Street (not “Devon” Street), where you have the Atlantic Ocean on one side of the pier and the Gulf of Mexico on the other.

As well as Key Lime Pie, check out some conch fritters.

12

Ft. Zachary is worth checking out and has a nice little sandy beach. I’ve heard of manatee sightings in the area.
The Bight is another place you may spot one. They like fresh water and human activity, much to their detriment, so often hang around harbors and canals.

13

This is exactly what you’ll find in Key West.

I would rent a bicycle for everybody for the whole time you’re there. It’s by far the best way to get around the island, and I had a lot of fun just exploring on one. We waited until several days into our trip to get one last time and we really wished we had gotten them earlier.

The best beach around is Bahia Honda, about 40 minutes up the highway. While you’re up that way you can go to Big Pine Key and No Name Key and drive around looking for key deer. Drive very carefully, because the deer aren’t afraid of anything–hence being endangered–but that also means you’ll probably get a close-up look at a few, and they’re pretty adorable.

The best beach on the island is probably at Fort Zachary Taylor State Park. It costs a little to get into ($2/person or $6/carload, IIRC), and they don’t have a weekly pass or anything, and it’s still not much of a beach, but it’s worth it for one day.

Next time we go I’m planning to do the Dry Tortugas trip.

You couldn’t do it with the 8-year-old, but it’s definitely worth it to seek out the Chart Room. I won’t tell you exactly where it is, because finding it is half the fun. Go early in the evening when it isn’t busy and the bartender can tell you stories about Key West royalty, many of whom are still there at the bar (you’ll see what I mean).

14

Check out the Key West forum at Trip Advisor for more info than you know what to do with.

Sunset at Mallory Square/Sunset Pier - Beautiful scenes, street performers, and booze.

Key West Cemetery - Very beautiful and historic.

Happy Hour - Most places have really good happy hours on food and drink. Check out Alonzos and some of the other places in the area.

Southernmost Cafe - At the Southernmost hotel. Nice place on the beach to grab breakfast or a drink.

Dive bars - Key West has a multitude of them. Half Shell, Schooner Wharf, Chart Room, Green Parrot, some of the best in the country! Personally I find the Duval bars to be way too touristy. Take a walk by the bight and check out the scene there. Many of these places are fine for kids earlier in the day. The Porch is also a fun little place. Sloppy Joe’s is just a tourist trap and from what I understand, not the actual location where Hemingway hung out (that’s now called Capt Tony’s).

Nude Drinking - Look for the Bull and Whistle on Duval. Go to the Garden of Eden bar on the rooftop, order a drink and take your clothes off. Probably want to leave the kids at home for this one.

Food - Key West is one great restaurant after another. Blue Heaven, El Siboney (Cuban), Louie’s Back Porch, B.O.'s Fish Wagon, Garbo’s Grill (food truck), Latitudes (on an island, boat ride included). If anyone’s picky, there’s a Wendy’s, Denny’s and other fast food options on Duval. There are also plenty of dessert places. My favorite key lime pie was at Blue Heaven.

Fort Zachary State Park - Nice beach with rocks you can swim to. You can also just wander around the civil war fort. We had it to ourselves when we visited.

Dantes - Large pool with bar.

Cigars - Plenty of Cuban-style cigars. There are a few places where you can grab a good smoke and get a glass of wine. I don’t smoke and even I enjoy doing this (okay, technically I guess I do smoke then).

The beaches in Key West are very mediocre, but it’s a great town to just explore and chill. There are tons of unique shops, restaurants, and bars to explore. Have fun!

15

The snorkeling is fun. Most trips are an hour ride out, an hour in the water and an hour back. Very relaxing. The thing that surprised me was the difficulty of swimming down to get a closer look at things. The water is so salty/buoyant that it takes a real effort to “sink”. We intended to go on one of the eco-tours in the “back country” or whatever you call it, but ran out of time. Next time I will make it a point to do so.

There is a hotel at the west end of Duval that has a little beach area near the bar. I guess its supposed to be for guests only by our friend (who has a house there) just walks in like he owns the place. He has done it so often the staff knows him and his family and we went right along with him. Everyone is so laid back that I don’t think they really care as long as you are buying and tipping. There is a bad current towards the rope if you go swimming but its marked pretty well.

16

I don’t know how the food is these days, but I had an *excellent *dinner at Blue Heaven.

17

Hop a seaplane and fly out to Ft. Jefferson. Love that place!!

I also second the Garden of Eden visit.

The place with the butterflies is nice too. Watching the little kids react to this is even nicer than watching the butterflies.

18

I have to ask - is the Garden of Eden worth it if you’re not particularly interested in or titillated by clothing optionalness? I ask because we spend four to six weeks a year at clothing optional campgrounds, so that’s sort of old hat. But if it’s a really great bar, it might be worth checking out despite it being clothing optional. :smiley:

My dad mentioned, “lots of small shops, including some fetish shops.” I’m not sure I’m ready to go into a fetish shop with my dad. I’m not sure I’ll EVER be ready to go into a fetish shop with my dad. :eek:

Butterflies sound wonderful. The little one loves the butterfly garden here in Chicago, and I bet they’ve got different varieties in such a different climate. Definitely adding that to the list.

Fort Zachary sounds fun, and maybe manatees!

Poor WhyKidtheElder. Key West just 2 weeks *before *his 21st birthday! So unfair. What’s the Florida law on parents buying their kid a beer in a restaurant, anyone know? I know it’s legal in some states, although getting a bartender to serve is often not possible.

19

At the same level as Hemingway’s house is Harry Truman’s winter White House. The bar where Hemingway seems to have actually hung out is Captain Tony’s, rather than the usually-cited Sloppy Joe’s.
The tourism booth at Mallory Square has self-guided walking tour leaflets. I did my own, following the WPA guide walking tour of Key West in the '30s. The cemetery is historically interesting.
Part of the Overseas Highway is being turned into a historic trail:

If you want to do the full-tilt-boogie historical thing, include something Cuban-related and something Navy-related on your itinerary.

20

Beyond everything already mentioned, just wander in and out of the shops. You can even make a game of it by trying to count how many cats you see in the shops. For extra credit, try counting their toes.