What to do during our 3rd trip to Key West
January 14, 2014 2:02 PM   Subscribe

My boyfriend and I are going to Key West for the 3rd year in a row. I'm psyched, but since we've already been there twice somewhat recently, I wondering just how we'll fill our time.

Yeah, yeah, I know it's vacation - just grab a spot on the beach or a barstool, get yourself a fruity drink and relax...but we do like to explore, people-watch and try new restaurants over laying at the beach all day, so I'm hoping you can help me out with some suggestions. I saw a couple of older threads on Key West, but was hoping for some up-to-date info, or off the beaten path suggestions (if such exists) of things to do that will be new to us.

Here's what we HAVE done in the past:

- Hemingway House
- Fort Zacharay Taylor State Park/Beach
- Aquarium
- Southernmost Point
- Sunset Key
- Dry Tortugas Day Trip
- Restaurants/bars I can remember trying already: Blue Heaven, La Te Da, Sarabeth's, Sloppy Joe's, Latitudes, Nine One Five, Banana Cafe
- Shops I liked: Besame Mucho, In One Era

What I'd be interested in trying but would love to hear about your experiences with any specifics:
- Drag Shows
- Yoga (especially on the beach)
- New restaurants or any must-trys
- Music
- Vintage / antique shops

Thanks so much!
posted by Shadow Boxer to Travel & Transportation around Key West, FL (10 answers total) 12 users marked this as a favorite
I see all of my Key West faves already in your list. The Mel Fisher Museum is pretty cool, as is the lighthouse tour.

You'd need a car, but you could drive up to Bahia Honda State Park.
posted by jquinby at 2:27 PM on January 14, 2014

I have done yoga on the beach several times in Key West and enjoyed it. It wasn't tremendously rigorous but it was lovely and relaxing and the instructors were good and attentive. Seven Fish was really nice for dinner -- yummy fresh fish -- and we liked the Flaming Bouy as well. The Truman Little White House is pretty cool if you're into that kind of thing; a time capsule of 50's beach decor. Some gorgeous but way expensive stuff at Duck & Dolphin antiques on Fleming.
posted by Cocodrillo at 2:41 PM on January 14, 2014

How about sailing? I can't recall any specific boats, but I noticed plenty of daysailers/sunset cruisers when I was there. It is a beautiful place to be on the water.

I saw the Hemingway House (so great) but regretted not also seeing the Audubon House and the Lighthouse & Keepers Quarters. If I went again I'd also check out the Key West Art and Historical Society. We walked by the lighthouse on a lovely wandering walk around that end of town, and stopped for an afternoon drink at the very fun Green Parrot bar, which was wide open to the street and had live chickens and roosters wandering around our feet. That one afternoon drink at that bar was, to me, the fondly remembered essence of tropical-langour.

When I was there, we stayed in a crappy hostel, but one afternoon we walked up to the gorgeous Southernmost House, and purchased a pass to use the outdoor pool all day for $5. We lounged on the chaises with books, got drinks at the poolside bar, swam in this awesome vanishing pool and wandered the lobby and parlors looking at the historic memorabilia. Felt like a million bucks, went back to twin beds in a concrete bunker. If you aren't staying somewhere lovely already, check it out, and even if you are - it's a nice place to hang for an afternoon.
posted by Miko at 2:50 PM on January 14, 2014 [1 favorite]

Learn to SCUBA dive and go check out the Vandenberg!
posted by matty at 3:42 PM on January 14, 2014

No details on how to do it. But I've had jetski'ing around key west recommended to me, I just didn't have time to do it when last there. Sounded like a fun thing to do.

Its silly, but if you haven't done the tourist trolley/train I enjoyed it. They pointed out a lot of details(gingerbread, etc) on the houses in the neighborhoods that I wouldn't have seen otherwise. Plus they have discount combo tickets to other things in town. +2, I wouldn't have realized no squirrels until they pointed it out.
posted by TheAdamist at 4:13 PM on January 14, 2014 [1 favorite]

What I'd be interested in trying but would love to hear about your experiences with any specifics:
- Drag Shows

Two main ones are Aqua and 801 Bourbon. Both are on Duval. There are recurring burlesque show as well, look for Key West Burlesque.

- Yoga (especially on the beach)
Yoga On The Beach at Ft. Zack and two other places.

- New restaurants or any must-trys
My info is a little out of date, but my two favorite bars were The Porch (Duval and Caroline, in the big Victorian) and The Rum Bar (under The Speakeasy Inn, 1117 Duval, NOT THE RUM BARREL). Save up your pennies and appetite and go to Better Than Sex, which almost lives up to the name. Best Cuban food is at El Siboney, good seafood at Seven Fish and Flaming Buoy, great French at Cafe Sole, Thai Life for, well, Thai.

- Music
Depends on the music. Irish Kevin's is always interesting.

- Vintage / antique shops
Can't help you there.

The Key West SuperMap is the best map, but kind of spotty to get.
You should rent kayaks from Hurricane Hole and kayak the salt ponds and canal. Try a sunset cruise on one of the schooners, or a snorkeling trip to the grass flats. I'd avoid Sebago, Fury, and Sunset, they are basically cattle cars. I liked Danger Charters and loved Eco Tours.
posted by the man of twists and turns at 8:45 PM on January 14, 2014 [2 favorites]

I lived in Florida for many years, and I've been to Key West a few times. I hate to say it, but every time I go (usually on an excursion from a cruise ship) I'm more and more disappointed.

You've seen pretty much what there is to see in Key West. If you like going to the pier and watching the performers, that's a thing to do. But the shops are the shops, the restaurants are the restaurants (with few exceptions) and it is what it is.

The reason people return to the keys is for the slow pace and warm weather. I've never thought of Key West as a "go, see, do" kind of vacation.

Here's the official site for the Florida Keys. Check them out and see what that's about. There's a calendar of events there, perhaps there's something going on during your vacation that piques your interest.
posted by Ruthless Bunny at 8:01 AM on January 15, 2014

I don't see anyone mentioning the Little White House. It's neat and the tours are interesting not just about the location but about how different the presidency is now vs 60 years ago.
posted by phearlez at 9:39 AM on January 15, 2014 [1 favorite]

Thanks so much everyone for your suggestions! I know this was a tough one, since there isn't THAT much to do or see in Key West that we haven't done yet. I really appreciate your help!
I'm definitely going to check out the Little White House, the trolley tour and getting a pool pass for the Southermost Hotel (didn't know you could do that!) Oh and I forgot to mention that I did book a sunset kayak tour so we've got that covered.
posted by Shadow Boxer at 10:12 AM on January 15, 2014

Best cuban sandwiches are at the White Street Laundromat. Yes, you read that correctly.
posted by matty at 11:41 AM on January 15, 2014 [1 favorite]

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