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11 minutes ago, DaveInTN said:

My favorite place to stay on Key West is about 400 miles north at Fort Wilderness. Key West is too far, too weird and too run down. IMHO of course. But I'm probably in the minority.

We went once it was a stop on a cruise and I wasn't too impressed 

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Does your mom know the southernmost point thingy isn't actually at the southernmost point?  The marker was moved several years ago.

That being said, I've been to Key West for a couple of day stops while cruising and really enjoyed the architecture there.  Walking up/down Duval Street is fun.  We always take a bicycle taxi to the "southernmost point" and then walk back toward the pier.  The Sloppy Joes and margaritas at Sloppy Joe's Bar are great.  IMHO the Hemingway house is a waste of time and money.  The Truman annex is okay, particularly if you're into history.  (I'm not.)

My initial feeling is that your parents will experience "culture shock" while visiting.  

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My 2 cents...

DW. And I have been there twice on a cruise ship and twice on a vacation.  We would like to go back there during the winter months but hotels are extremely expensive in the winter.  That being said we really like it.   Yes there are some cultural things that some people might be surprised by but if your not going during any of the special events it's not really that big of a deal. 

 

Duval street is the main street that has all the restaurants, shops, bars, etc.  

On the south end of Duvall street, is the ocean and the southern most cafe  it's has great food and a nice beach  it is also home to the southern most resort  beautiful hotel right on the water.

if they go one block north of the Southern most cafe, the first street they will hit is South street  turn left (west) and walk approx one block and they will hit the Southern most point buoy.  

on the north end of Duvall is Mallory Square. It's we're all the people go to watch the sunset. If you don't want to be around the masses of crazy people go next door, to the north, to sunset Pier.  It is part of the hotel next to Mallory square.  

 

And inbetween mallory square and the southern most beach are a ton of shops, restaurants, bars, etc.   just tell your parents to go to Sloppy Joe's and Margaritaville early in the day and they will avoid all the night time craziness.   And if they don't want to stay in key west because of cost or to avoid the night time craziness.  I would recommend stay in Marathon Key. It's about a 45 minute drive to key west.  But tell them not to miss seeing the sunset in key west. 

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I love the Keys!

If your parents are driving down, tell them to make a stop at Robbie's on Islamorada and feed the Tarpon.  Fun times: http://www.robbies.com/

We have rented houses through VRBO, and have also stayed in hotels.  I like the La Concha boutique hotel because it's right on Duval Street, and is a restored historic building. http://www.laconchakeywest.com/.  We've stayed there three times.  But, I'd also look at the ratings and recommendations on Trip Advisor, as there are a lot of options.

I enjoyed the tour that we took of Truman's Little White House.  I thought it was well done and very interesting. https://www.trumanlittlewhitehouse.com/

I did not care for Ernest Hemingway's house.  But, we were there in the summer, and a lot of that had to do with the fact that it was hot as heck and it wasn't air conditioned.

The touristy places are fun, too.  I like the Margaritaville there, and Sloppy Joes, and a bar named Irish Kevin's.

Although it is very touristy, I think the Conch Train might be good for your parents.  It's a guided tour around the island, with lots of information.

I have also enjoyed renting an electric car.  There are lots of stands around town offering these.  That's a fun way to get around and see all the sights, like the marker for the Southernmost point and Mile Marker Zero, which is a required photo op.

We were last there in 2014, and there are some photos and narrative starting with this post in one of my old trip reports:

TCD

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We visited Key West many years ago on a cruise. I remember very little of it- other than we did a trolley tour.

In 2014, we went for Christmas. We RV'd at Bluewater Key which is at mile marker 15. We loved it, but were overly disappointed in food. Some of the staples weren't great- B.O. Fish Shack and some others just didn't wow us. I did a trip report on that visit: 

In 2016, we went for Thanksgiving (not intentionally, availability happened). We again RV'd at Bluewater Key and loved it. Food this time was overall better- the little food trailer outside of the aquarium claims it has the best Conch Fritters and it really does. We ate there a couple of times. We also had dinner at Two Patios Friends Bar or something and that was good. The opposite- Stoned Crab was HORRID; 8 of us, 8 meals- all awful. We enjoyed the Butterfly House; the Conch Train Tour; the Shipwreck Museum; the aquarium; and walking around. We went over to the Eco Center and enjoyed out visit- very nicely done. We meandered up and down Duval St a few times- it's pretty "normal" during the day but gets a little nutty at night. No trip report, but here is a Flickr album of our stay:

https://www.flickr.com/photos/dougsetzer/albums/72157676660967705

 

 

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