Go confidently in the direction of your dreams. Live the life you have imagined.

Henry David Thoreau

Historic Key West Walking Tour

Wednesday December 16, 2015                                                           Most Recent Posts:
Long Key State Park                                                                            Moving to Long Key
Layton, Florida                                                                                    Indian Key Fiasco



Today is Wednesday and that means we’ll be heading to Key West to visit the Cancer Center.  But before that, David is filling up his vitamin and drug pill box for the week.  I don’t know how he keeps track of all this stuff.




I check on the sunrise and there are too many clouds, not a sign of the sun but the view out the window is still wonderful!




There seems to be a bulb out on the outside lights so David checks that out too before we leave.






It’s been 3 weeks since I’ve done the laundry and it’s time to do it again so he drops me off at M&M which has been in a previous post and goes on to 21st Century Oncology.

After he picks me up, we look for a parking place close to Old Town so we can have lunch at The Cafe. 

Most of the spots on the streets either say Pay to Park ($4 an hour) or  Resident Parking Only.   There are unrestricted spaces but you have to look closely.  We find one by chance right in front of the library. 

This is very fortuatous since I try to visit the library in every town we are in.  I read some blogs where people chalk up state capitols or other sights,  my collection is  libraries.  This one is a perfect pink for Key West.  Looks like it should be called Casa las bioblioteca.


It sure looks like Christmas inside.





In a library in Maine, you might find a real fireplace but here in Key West they have a great imitation.





I have found that librarians are the very nicest people there are and the Key West Librarians are no exception.



We use the wonderful library to access a computer and ask Yelp where we should go for lunch fairly nearby.  It’s nearly 2:00 and we are very hungry.  They say try try The Cafe so we walk over only to find that they are closed for the afternoon for a staff holiday party. 

On the way we walked by Margaritaville on the way over and I’m so hungry I let David persuade me that we should just go there.





I guess this is the official Mother Ship for the Parrot Heads in the Conch Republic.



Jimmy doesn’t look much like this now but David says he lives on Long Island and owns an business empire of stores including numerous Margaritavilles in this country and the Caribbean, over 39 Cheeseburger in Paradise restaurants,  Landshark Lager beer and a resort casino or two.   His business also contains Footwear, Frozen Foods, Tequila, Frozen Concoction Creators, and even naming rights to an NFL stadium!







It’s another big grin over a ridiculously sized sandwich.   I can hardly get my mouth around it.







Once the gluttony is finished we waddle out and use the map we picked up at the visitor Center early in our days here to check out the Historic Walking tour.

The bougainvillea in this town is beautiful and everywhere.  I am always amazed that there are two kinds of leaves on this plant, both green and flower like spring colored ones and that the little flowers are so delicate.

















Among other things that make  us smile are the roots of this banyon tree, a mobile bicycle tiki bar and the partner of this busking duo on Duval Street.









The Key West Historical Walking Tour contains 51 sites.  Don’t panic, I’m not going to show all of them or even all of the ones we had time to see.  We have already seen many of the historic sites like the 1879Wall & Company Warehouse on Mallory Square, the 1856 Coast Guard Building, the beautiful 1891 Customs House now the Art Museum among others.

These are a few that we liked from today’s walk.  The Martin Hellings House is an unusual brick home for this area built in 1892 by the manager of International Ocean Telegraph company.  Since 1941 it has been the home of the Key West Women’s Club. 




Captain John Geiger and his heirs occupied this home for 120 years. In 1958 this structure was scheduled for demolition to make room for a filling station. Saving this structure sparked the restoration movement in Key West.  The home opened in 1960 to commemorate the 1832 visit of John James Audubon and the 19 new species of birds he discovered here.  Next visit we’d like to see the one acre of tropical gardens in the rear, but not today.






These beautiful wrought iron are the Presidential Gates which close off the Truman Annex about which I’ve spoken in a previous post.  They were installed in 1906 as the ceremonial entrance to the Navy base and beyond.  To this day, these gates are only opened for dignitaries.  They were opened for Presidents Jimmy Carter, Bill Clinton and for Colin Powell in fairly recent years.  This guy tried to get in but no dice.




Within the Truman Annex is the 1890 home known as the Truman White House between 1946 and 1952.  Truman enacted a Civil Rights Executive Order which required federal contractors to hire minorities.  Later Dwight Eisenhower recovered here in 1956 from a heart attack and the house was used in 1961 for a summit between President Kennedy and British Prime Minister Harold MacMillan during the Bay of Pigs incident.






William Curry came to Key West from the Bahamas in 1834.  He established a lucrative ship’s chandlery, served as mayor and became Florida’s first millionaire in the late 1800s.  His son Milton built this exact replica of a 22 room Newport Rhode Island “cottage” in 1905.   The Curry Mansion is now a bed and breakfast.  It was over the top in holiday decorations.







Building your house of Cypress seems like a great idea.   Impervious to almost everything and never needs painting.




The Peter A Williams House on Eaton Street, now known as the Donkey Milk House, was built in 1866 and also remained in the same family for 120 years.  U.S. Marshall Williams saved his home from the 1859 fire by dynamiting along Eaton Street.  The large clay pot in front called a “tinajone” dates from the 1800’s, made in Cuba to collect rainwater.  Donkey Milk Alley, at the back of this home, was created for the 19th Century milkmen who delivered containers of cow’s milk in carts pulled by donkeys.


The Trev-Mor is an early 1900’s building used as the first Ford Dealership on the island, with two floors of a residential hotel above.  Ernest Hemingway and his second wife, Pauline, stayed here on their first visit to Key West in April 1928.  Hemingway fished and worked on the draft of A Farewell to Arms while awaiting delivery of his new new Model A.  The brochure tells us that the Mediterranean Revival building has been transformed into a private residence with an extraordinary atrium garden.  Tours are available but unfortunately not today the sign says.




Love this door and the “historic” sign next to it.










Our last stop for the day is the the most interesting.  It is Dane Alley.  The 2 story building on the street was a cigar factor in the late 19th century.  Behind it are the “ciar makers cottages” built by the factory owner for employee housing.  They are darling.  The factory is now The Inn at Simonton Court with rooms for rent from $459 to $185 a night.  Likewise, the Cottages at Simonton Court have been restored and are now for rent from $749 to $185 depending on the “season”.





We walk down the alley behind the “factory”.

Peeking in the door from the alley at the back of the factory we see French Doors and a pool.






The cottages are darling painted pink and with porches.  It must have been a wonderful neighborhood with all your friends and coworkers and their families living all around you.






Next week will be the last of our weekly trips to Key West.  If there is anything we haven’t done that is a don’t miss, let me know.


  1. You should check out the Blue Heaven Restaurant...even if you don't eat there, the atmosphere is fantastic! You could just walk around the grounds a little bit and visit the gift shop just to get your foot in the door....We had an amazing breakfast there, but won't say how much we spent for the three of us, when Kelly met us there.

  2. What a great tour of historic Key West! Love that pink cottage community built for the cigar factory workers. Things you haven't done that we've enjoyed in Key West include the Truman White House tour, Audubon house and gardens, West Martello gardens, and breakfast at Blue Heaven. You're the expert on Key West, though. :-)

  3. The bougain whatever plants are beautiful! XXXOOO

  4. Pre-internet, the library was the first place I'd find in every town I stayed in. I am reminded of the bougainvillea in Mexico, it's everywhere. Quite the tour and seems nicer walking than that bus thing. I've enjoyed seeing and learning about Key West through your stories.

  5. Lots of lovely stuff, but my favorite is the Pelican Poope Shop. I found some really cool metal fish there, blue tangs, that grace my bathroom wall. Never could find anything anywhere else for my tropical bathroom that didn't look tacky. Yeah...well...maybe a tropical bathroom is tacky anyway, but I love it. Nice day, Sherry.

  6. Because of all these great posts on Key West, we are now thinking we need to return to Blue Water Key RV Resort at least for a week. I really enjoyed biking around Key West. This is such a neat place. Glad you had time to explore the depths of the place:)

  7. You sure made the most of your weekly Key West visits. I want to thank you for taking to us to ALL the places we didn't get to see. I did see the Banyan Trees and they are amazing. After reading all you did, we may give Key West another visit when we return to the Keys. Especially appealing was bike riding and walking tour around the city. You certainly have become the KEY WEST EXPERT!!! Glad to see David got his early Christmas Present at Margaritaville.... his smile is wonderful:o)))

  8. looks like you have seen and done all that we ever found in the area...

  9. Rich and I spent a Christmas in the keys many years ago. I think I have every song Jimmy Buffet ever sang. I have to go back to read to see if you saw my "alma mater" - the Pan Am original HQ-house. I worked for them out of Idlewild/Kennedy out of New York.

    1. I've seen the Pam Am HQ and I believe I even have a picture of it somewhere. I'll think of you the next time I walk by. :)

  10. Those were huge sandwiches you got at Margaritaville. David sure looked happy with his.

    We like Carolines Restaurant, it's on Duval St, I think. It's an open air restaurant and very good food with reasonable prices, and a wide variety of choices, plus you can people watch, which is always fun in KW.

    You should probably try Blue Heaven though. Locals recommend it, as well as people that have been coming to the keys for years. We've yet to eat there, but I have heard they have a wonderful Sunday brunch.

    I've enjoyed seeing the Keys through your eyes, and I admit, it's making me miss it. Our experience with the Keys has never been wind, rain, and bugs like yours has been. We don't have a bug problem at Venture Out since it's not a wooded campground. I'm sorry you haven't had a good experience in the Keys, but hey, at least now you can say you've been there.

  11. Key West is growing on me with each visit. It is unique among tourist destinations and has so many interesting things to do and see. I'm glad we were able to make it work for us to be here!

  12. While a bit tacky, I really like Key West:) I cannot pass a banyan tree without taking a couple of pictures.

  13. Bill does a weekly pill sort on our table as well - a necessary step for combating diabetes. He has a great sorter with daily pocket size holders called "Two Elephants Weekly Pop-Up Pill Organizer with Time Compartments" that I think we got at Walmart. Doesn't Loreena have a "roots of the banyon tree" song? Great old tree! Love the Cypress House and the little pink cottages - what an interesting mix of wonderful history on that tour, thank you for sharing. Had no idea Jimmy is such an entrepreneur!

  14. We love Key West, it is so much fun and full of interesting things to see and do. In fact, when we win the lottery, we're going to buy a house there. (I understand that it helps to buy a lottery ticket to increase your chances of winning).

    I'm so impressed that you were able to walk at all after those sandwiches! I'd be lucky to have been able to stand up after eating one of them. ;c)

    Love your Christmas decorations!

  15. That banyan tree is truly remarkable! I agree that librarians and others who work at libraries are some of the world's nicest people.

  16. We went to Margaritaville in South Carolina when we were there for a rally. Fun place. Really enjoying your tour of Key West!

  17. Lovely shots of the place. I have vague memories of it from childhood.

  18. I loved your walking tour, as they are my very favorite tours of all. . .glad things will not be decorated for Christmas when we get there. . .

  19. Love the librarians - they look so happy! Great walking tour - so much more history in Key West than I imagined. Pretty houses, beautiful flowers and banyon tree roots!

  20. Ha! David is right, Jimmy Buffett has a house about 2 miles from where I used to live in Sag Harbor, Long Island NY. And in the summers we would do the dry cleaning for his wife and daughter. Too fun, love that burger and David looks quite pleased with it!


Your comments are the best part of this blog for me.
I LOVE hearing from you!