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Key West things to do

Mark B

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Please find below the plans we have for our walking tour.....

  • We will take a walking tour of Key West.
    • We should arrive in the Mallory Square area when leaving the ship.  There are fun shops, artisans, food, and even an aquarium here.  We will grab some wonderful key lime pie at Kermit's Key Lime Pie Shoppe (431 Front Street # 2, Key West, FL, 33040).
    • We will leave Mallory square and walk SE down Duval Street (this street is supposed to have fun shops and eateries along the way) until we reach the end of the street and hook a left on South Street (SE direction-ally) to visit the Southernmost point in the continental US buoy (this walk should take about 1.30 miles).
    • Once we get pictures of a see the buoy, we will NE back on Whitehead Street basically heading back where we came.  The Hemingway House & Museum (907 Whitehead Street, Key West, FL 3040) will be along our way back on the right (east side of the street) right before Olivia street (about a 2,000 foot walk).  Admission is $15/adult and $6/child over 5 (cash only).  Across the street from it is also the Key West Lighthouse (938 Whitehead Street, Key West, FL 33040).   For the lighthouse, admission is $12/adult and $5/child over 6.
    • Then, we will walk up Whitehead Street (going NW), and turn right (going east) on Fleming Street, then turn right on Duval Street (next major street).  We should be able to walk right down to Margaritaville - Key West for a snack and drinks.  I know it is cheesy, but I love listening to Jimmy Buffet as I plan the trip and really want to go there and have a cheeseburger and margarita.
    • If we want more to do, we can take Duval Street up (going NW) back up to Greene Street, hook a right (going NE) and Papa's Pilar Rum Distillery (Hemingway Rum Company) will be on the right (south side) right after Simontim Street.  They give hourly tours for $10/person.
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We did KW almost 4 yrs ago on Enchantment (Nov 2016)

Here are my takes.

1. Be prepared to wait a long time for that photo at the buoy.  We walked from Hemingway's house to it and there were about 100 people in line waiting to take a pic.  My husband and I looked at it, looked at the line, looked back at each other and said....nope!  I do actually have a picture of us in front of it from across the street with the 100 tourists waiting in line!

2.  Best restaurant to this day that we ate at in any port was in KW. https://blueheavenkw.com/    key-lime-pie-ping-pong.jpg

It is such a cool place.  Order their Key Lime pie.  It is insane.  Basically as tall as your wrist to the top of your index finger.  The building has history.  

Through the years the property has hosted cock fighting, gambling and Friday night boxing matches refereed by Ernest Hemingway. 

The outdoor courtyard is paved with the slate pool table tops from the days the downstairs operated as a billiard hall and ice cream parlour.

A dance hall, a bordello and a playhouse have occupied the second floor. Today inside the Bordello Gallery above the restaurant, one can still peek through the sliding peep holes into the tiny rooms

3.  Beware it is an expensive place for buying any gifts.  It is an artisanal town, but expensive.

4. The roosters make that town so much fun!  They roam freely up and down the non-busy streets.  Our niece was our tour guide so she took us off the main streets for shortcuts.  

5.  KW is an open container city.  If you enjoy imbibing go to Fat Tuesday on Duval street.  You can get a drink in their re-fillable cup, walk the streets and it will make you feel more willing to spend that money on your souvenirs. 


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@monorailmedic did a really helpful podcast on Key West a couple of years ago. I found it EXTREMELY helpful.  Give it a listen (you can right from this page). It's about 20 minutes long.


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Check out the Duval Street Loop Bus, it's free and easy to get on.  Some good sites are Mallory Square, Truman Whitehouse, Hemingway House, The Butteryfly and Nature Conservancy.  Stop in Sloppy Joe's for a drink, the Southern most point had a long line when we were there last year and wasn't worth the wait to us.

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  • 1 month later...

My husband and I rode our bikes through the keys last summer for our 25th anniversary. We of course finished in Key West, where we stayed 3 days. We did a sunset sail (not sure what your arrival/departure times are) and visited the Hemingway Rum Distillery where "Pilar" rum is made. The tour was informative and engaging, and the bonus was the rum tasting at the end. Our favorite bar was "The Rum Bar" on Duval. The owner/bartender was very knowledgeable, and their stock was amazing!  https://www.speakeasyinn.com/
The Southern Most Point is a quintessential photo spot, and a very doable walk from the pier at Mallory Square.
We also did a haunted pub crawl, but again that's in the evening and could be subject to your departure time.

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3 hours ago, krhardy said:

the Hemingway Rum Distillery where "Pilar" rum is made. The tour was informative and engaging, and the bonus was the rum tasting at the end. 

We went there while in Key West last Feb! We enjoyed it, thoroughly, especially the rum tasting at the end. lol

Key West, in my opinion, is best experienced best by having no strict schedule or plan.  Pick out one thing, go do it, then wander.  Drink, eat, drink some more....JUST MAKE SURE YOU GET BACK TO THE BOAT ON TIME. One of the funnest days of my life was spent in Key West.....and we did nothing more than sit outside by the water at Conch Republic Seafood, eat, drink, listen to music....then stagger over to Duval St. to Sloppy Joes, and then to Irish Kevins. 

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Definitely the Conch Republic for a drink and some fresh seafood!  We booked the on-and-off bus trip so we could stop where we wanted and stay on if we just wanted to sight-see that way.  DO NOT miss out on a Frozen Chocolate Covered Key Lime Pie on a stick!!!!  The absolute best and no one should visit Key West without getting one...great way to cool off!


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  • 4 weeks later...
On 6/10/2020 at 4:57 PM, Pooch said:

So just walking around is doable?  I don't really want an excursion. I just want to browse!

Yes, definitely! Key West is one of the only ports that I feel like I can just get off the ship with no specific plan in place. One trip we did the 'hop on, hop off' trolley and had the funniest driver - we stayed on the whole loop and didn't get off just because we loved him so much. When we went around the loop again, we were able to get off at Hemingway House, Southernmost Point, Duval St and Smathers Beach.  One thing I don't recommend is the 'Aquarium'. It was small, dark and very depressing.

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On 6/10/2020 at 2:13 PM, Mark B said:

Does anyone have recommendations regarding what to do in Key West? We're open to shore excursions, or wandering on our own. It will be our first time in Key West.


In October, we did a RCCL cruise that included a stop to Key West.

We did the train hop/on off (May also be called the conch hop on/off - I just remember it being more of a trolley). It was very affordable for our family of 3. Our son was 12 at the time.

It was great to have the guided tour and be able to hop on/off at any stop. So we hopped off at the stop by the “Southermost Point in the Continental US.” 

Was too crowded to really get a family pic, but we found a high ledge near it to snap a quick pic verses the 30 people deep line.

Anyway, we also had lunch at that stop at the Southernmost Beach Cafe. If you don’t mind sitting outside verses the covered patio, service is much quicker! There are umbrellas at the table. But it’s right on the beach. Very affordable, good food, and a great view! (It’s a block down from the trolley stop).

We then did a longer than realized walk to the Fort Zachary Taylor State Park Beach. Walking in was like $2-$3 per person. Very affordable. Reviews of the area said this was the nicest beach (and it was!) there was also restroom facilities. There are a ton of picnic tables too. We initially put our items at an empty table. But then shady characters (who weren’t swimming) sat at that table (verses the empty ones??) So we grabbed out items and moved down the beach. So be careful of theft!

In lieu of walking back (as the nearest trolley stop was a mile or so away), we did a cheap $5 uber back to the trolley stop. We then hopped back on and continued the rest of the guided tour! You could uber to the beach too, or enjoy a walk. It’s all residential walking to the beach from that particular trolley stop.

It was so nice to do what we wanted on our own time. You can even stop at the popular museums verses paying a higher fee through RCCL. Our family of three paid maybe $45-$50 for the guided tour, beach experience, and shopping experience (as the first/last trolley stop is in the middle of all the shopping action!) Saved a lot of money that way. And lunch was maybe $30 (but typically you have to pay for lunch separately anyway on excursions!)

It was an AWESOME experience! Highly recommend. Just be sure for any non-US ports that you do a RCCL excursions. The excursion places that RCCL uses internationally have to use US regulations to be included on their excursion list. Safety first!! ?








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