OT: Key West recs

[8893]

We have never been. We generally detest Florida and everything about it (sorry @Chin Diesel !) but many people have told us that we need to go to Key West because it is like New Orleans-meets-Martha’s Vineyard, and those are two of our favorite places.

Looking for recommendations for number of nights—thinking three or four. Flying from CT or NYC.

Best places to stay for a special anniversary.

Other thoughts and recs appreciated. Trip would be late September.

 

[husky8273]

sunset carnival at Mallory Square, Hemingway's house

 

[Deepster]

3 nights in Key West is perfect. You can also tack on a night or two in Key Largo or Islamorada.

Blue Heaven for brunch might be my favorite spot on the planet. You can do half day fishing charters for decent fish. Sandbar trips or a Dry Tortuga day trip ($$$). And every sunset at Mallory Sq. All the online advice is spot on. Just read up.

I'm actually there 9/30-10/4 and drinks are definitely on me if you're there the same time.

 

[8893]

3 nights in Key West is perfect. You can also tack on a night or two in Key Largo or Islamorada.

Blue Heaven for brunch might be my favorite spot on the planet. You can do half day fishing charters for decent fish. Sandbar trips or a Dry Tortuga day trip ($$$). And every sunset at Mallory Sq. All the online advice is spot on. Just read up.

I'm actually there 9/30-10/4 and drinks are definitely on me if you're there the same time.

Thanks. We may have some flexibility on dates; it all depends on Mrs. 8893’s work, which she’s trying to sort out this week.

We had originally planned on Italy but that’s out until 2022 due to Covid, and we’re already doing a week with the family in the Bahamas in November for Battle4Atlantis, so we’re just looking for enough of a getaway to commemorate and make it worth it, so we figure it’s a good time to check this one off the list and do it right. If we only have four nights max because of her work it sounds like we should maybe just stay put in Key West?

Will definitely let you know if we can push it another week and overlap. That would be hysterical. “How do you guys know each other again?”

 

[blackuc]

I will second Blue Heaven and also recommend the restaurant below AB's also owned by them More casual and still great food

 

[blackuc]

Cheeca Lodge in Islamorada is excellent if you want a night relaxing away from Key West

 

[Chin Diesel]

We have never been. We generally detest Florida and everything about it (sorry @Chin Diesel !) but many people have told us that we need to go to Key West because it is like New Orleans-meets-Martha’s Vineyard, and those are two of our favorite places.

Looking for recommendations for number of nights—thinking three or four. Flying from CT or NYC.

Best places to stay for a special anniversary.

Other thoughts and recs appreciated. Trip would be late September.

No hard feelings. Key West is about 16-18 hours drive from me.

Actual Key West island is small. Plenty of opportunities to visit other keys and have fun. Weather is great year round.
Mallory, Front and Duval have all the fun you want for drinks and people watching. The sunsets are especially fun. As for food, find whatever is the catch of the day and enjoy it grilled, jerked or fried.

If you get a chance to get out to Dry Tortugas Nat'l Park, do it.

And get your photo op at the southern most point in the US.

Tough not to have a good time in the keys.

 

[Chin Diesel]

3 nights in Key West is perfect. You can also tack on a night or two in Key Largo or Islamorada.

Blue Heaven for brunch might be my favorite spot on the planet. You can do half day fishing charters for decent fish. Sandbar trips or a Dry Tortuga day trip ($$$). And every sunset at Mallory Sq. All the online advice is spot on. Just read up.

I'm actually there 9/30-10/4 and drinks are definitely on me if you're there the same time.

Delay that trip for 3 weeks and go for Fantasy Fest. Words do not give it justice. It's a forever memory.

 

[Excalibur]

The massive amounts of Sargassum has made the Keys experience far less enjoyable. Last time I was there the stench was overwhelming.

 

[HooperScooper]

My wife and I went once and enjoyed it. We stayed at the Casa Marina (Key West Resorts, Casa Marina Key West Waldorf Astoria Hotel). It's a Waldorf Astoria flagged hotel. Liked it for a few reasons. It's easy walking distance to Duval Street but far enough away from the craziness so you can sleep at night. It's an old hotel with charm and character, the lobby is pretty cool, but with all the new amenities and it's well upkept. Supposedly it has one of the only beaches where you can walk right into the water and swim out. Most of the island is surrounded by coral reefs so to go into the water in most places you have to walk out on a jetty or pier past the coral reef. At least that is what we were told.

Lots of bars and restaurants down Duval Street. Can't remember what we did besides eat and drink.

I would suggest flying from Miami to Key West. The drive is pretty cool on that very long causeway between islands all the way down if you'd rather do that. But if you hit traffic going down there you're screwed. I was just talking to someone the other day who did the drive on a holiday weekend and it took them 8 hours from the Miami airport.

 

[MexicoHusky]

We have never been. We generally detest Florida and everything about it (sorry @Chin Diesel !) but many people have told us that we need to go to Key West because it is like New Orleans-meets-Martha’s Vineyard, and those are two of our favorite places.

Looking for recommendations for number of nights—thinking three or four. Flying from CT or NYC.

Best places to stay for a special anniversary.

Other thoughts and recs appreciated. Trip would be late September.

I very much would like to drive the causeways all the way to Key West. Across the ocean. I think that would be kinda unique.

 

[Peacefrog]

I hadn't been to Key West in quite a while but went in May 2019. You like New Orleans so maybe you'll like Duval Street but I found it to be enormously cheesy. Probably pretty cool when you're 20-something but I found it to just be loud and raunchy in some places.

For a casual meal we enjoyed the Conch Republic Seafood Company. Good variety of beers on tap. Giant garage doors open to fresh breezes and views of the marina. Food was solid and a couple guys singing with acoustic guitars was a pleasant atmosphere and you could actually talk to each other.

I second Dry Tortugas if you have the time, it will swallow an entire day.

For a fancier romantic meal we went to a place called Latitudes. I think it is on Sunset Key and we had to take a little shuttle boat out to the restaurant. Our table was right out on the beach and the food was fantastic. Beautiful watching the sun set over the water. Inside they had a bar with a very large selection of bourbons.

 

[Chin Diesel]

And get some good key lime pie.

 

[Chin Diesel]

Not saying this is the best, but it was famous and about 15 years ago I went through a lot of time, money and energy (Okay, a bunch of us were drinking and I peeled off to buy one of these) to bring this back from Key West to Mrs. Diesel in Virginia Beach. That's when she kindly reminded me she doesn't like key lime pie, she likes key lime cheesecake.

You better believe the the anger and spite I felt towards her made every last bite of this taste even better.

HOME | KEY LIME PIE FACTORY (blondgiraffe.com)

 

[8893]

That looks awesome.

 

[Hans Sprungfeld]

I will second Blue Heaven and also recommend the restaurant below AB's also owned by them More casual and still great food

I'm trying to picture what's "more casual" than shorts, sandals, and print-splashed or t-shirts at a place that's pretty much outdoors with ping long tables and chickens sharing the floor space.

@8893 — On my visit, 3 nights staying in a beautiful home in The Meadows neighborhood a 5 minute walk from the Historic District (and beater biking everywhere else) was ideal. If driving to & from the Keys, I'd suggest a 4th night closer to Miami, rather than stressing about possible traffic-delays, which was part of our last day. We did get conch fritters at divey Alabama Jacks in Key Largo.

As to Freedom Fest, I had a men's group cohort who - after his wife died and his youngest went off to college - decided to be who he'd come to know he was during his decades as a Flushing pharmacist who raised a family in a split level home and n the Five Towns. One of his first adventures was a trip to Key West. During the Halloween Parade, he stuck his face into the local TV news camera and mouthed, "HI, MOM" with great gusto. Back on the mainland, he stopped in to see his dear, aging mother in Pompano Beach. Within minutes of his arrival, she calmly said, "You know, I saw you on television the other night." All of his wondering about how he'd come out to her with his big & scary secret news disappeared in an instant.

 

[ClifSpliffy]

3 nights in Key West is perfect. You can also tack on a night or two in Key Largo or Islamorada.

Blue Heaven for brunch might be my favorite spot on the planet. You can do half day fishing charters for decent fish. Sandbar trips or a Dry Tortuga day trip ($$$). And every sunset at Mallory Sq. All the online advice is spot on. Just read up.

I'm actually there 9/30-10/4 and drinks are definitely on me if you're there the same time.

thank you for mentioning fishing. that's the hook. lol. and, oh, unlike a previous post delicately dancing around another truth aboot kw, it is also a gay place. so what, nobody cares. it ain't eisenhower times no more. now, back to the fishing, that's the hook. come back ashore half wasted and sunburnt to a crisp, then try to go dancing.... good luck with that. lol. nice place, odd, but nice place. 1st thing there, throw your phone into the ocean.

 

[imno1]

Good scuba also. I got certified in KW

 

[ColchVEGAS]

I used to drive to Key West often when I was living in Miami my freshman year. Definitely a fun place and all the recs above are great. If going in October watch out for Fantasy Fest. All I can say is wow, that was an experience.

 

[Guapo]

As someone who also detests South Florida, the Keys are one of my favorite places.

My big suggestion is spend a day or two outside of Key West. We usually rent a house in Duck Key, just south of Islamorada - which is a cute, quaint town.

Highly recommend stopping and eating at Keys Fisheries in Marathon

 

[Guapo]

As someone who also detests South Florida, the Keys are one of my favorite places.

My big suggestion is spend a day or two outside of Key West. We usually rent a house Duck Key, just south of Islamorada - which is cute, quaint town.

Highly recommend stopping and eating at Keys Fisheries in Marathon

Also haven’t seen anyone suggest the Truman White House in Key West.

worth checking out if you’re a history nerd

 

[GG]

Love Key West. I like to go in the winter and generally spend a week. I would recommend renting a kayak and heading to the mangroves. https://lazydog.com
If you like Mexican, try https://amigostortillabar.com

 

[Deepster]

Highly recommend stopping and eating at Keys Fisheries in Marathon

Second this one. You're not getting fresher fish or a better view.

 

[Vancat]

always wanted to do the drive across the causeway.