Winter in Key West

What a wonderful winter this has been.  We’ve been docked at Stock Island Marina Village just five miles from downtown Key West since December 8th.  If weather agrees (which is 50/50 at this point), we will pull our lines tomorrow morning and head to our next port.  I’m sitting on our “back porch” leisurely drinking coffee as I have every morning for the last two months, and reflecting on the things we’ve done and the memories we’ve made here in Paradise. 🌴

Done Diggin’ sitting pretty….hopefully she’ll be moving again soon

After becoming Gold Loopers in Fort Myers, we traveled with our buddy boat Seas Today here to Key West.  We anchored out for three nights (that’s a lot for me!) and arrived here at Stock Island on the fourth day.  There were several other of our Looper buddies here and at the downtown marinas, so there was always something to do before we flew home for Christmas, and some of our Gold Looper friends came for New Years Eve.

Our friends and travel buddies Bruce and Grace.  We’ve spent a lot of time with them here in Key West and have loved getting to know them.
Sophie!!! She’s our buddy dog (lives on Seas Today with Bruce & Grace)


Being home this holiday was exactly what I needed, but unfortunately the germs on the plane got to Danny and he started feeling lousy on Christmas Eve and he’s been sick off and on since we got back to the boat.  He’s seen the doctor a few times and is now on his third round of antibiotic to treat the pneumonia they finally found on his second ER visit.  We are flying home for his 6 month oncology check in on February 18th, and he’s scheduled to get an immune system “booster” treatment, so hopefully he’ll soon be well.  He was generous enough to share his germs with me 😞 and I was sick for a bit too, but recovered much more quickly.  Apparently, this cough and cold has been going around the island and is referred to as “The Key West Crud”…..thanks Key West!!

Note all the meds on the table…..this is Round 3, but he’s still smiling ❤️

Despite Danny not feeling well, we did our best to see the island and make the most of our time here.  Since we’re about five miles away from downtown and don’t have a car, our bikes sometimes became our transportation to downtown, grocery shopping, errands and restaurants.  The marina is part of a resort that offers a free shuttle to downtown Key West, which has been super convenient as well.

Hogfish restaurant on Stock Island

This is a unique place and I feel fortunate to have spent so much time here.  Stock Island is much less developed than Key West but has a few good restaurants and we grew to love how much quieter it is than downtown.  Downtown is filled with old southern style homes and quaint shops and a thriving waterfront district with marinas, charter boats and restaurants and bars on the water.  Then there’s Duval Street!  I was told that there are over 90 bars on Duval, which is about a mile long; lots of them have live music and they’re usually pretty full any time of the day or night you pass by.  When there are cruise ships in port you can barely walk down the street.  We spent a little bit of time there (and NO, we did NOT visit all 90 bars!), but soon found that we preferred other places that were a bit off the beaten path.

The table in the middle is where the “vibrator races” take place. Yup, you read it right – every Thursday night at MaryEllen’s Bar in Key West…..we only went once!

Key West was originally populated by Native Americans and then people from Cuba and from The Bahamas, so the food and the way of life has been influenced by those cultures.  Locals proudly refer to the island as “The Conch Republic”, a nod to their effort to secede from the US in 1982.  Key West and Stock Island are heavily populated by roosters and chickens!  They are everywhere you go, and you get really used to seeing them and walking or biking around them!  They really do say “cock a doodle do”!

One of the many, many roosters that call Key West home


The site of the end of US Route 1! Very different topography from the Route 1 I traveled every day to Cambridge for work!
This buoy is at the southernmost point of the Continental US. People wait in a long line to take pictures of themselves in front of it. We did not, this was on a “drive by” from Danny’s bike. Very cool spot.

When we got here, we thought we’d be doing more kayaking and some boating out to a nearby reef for snorkeling.  Unfortunately the winds were too strong most days and we all pretty much stayed on the dock.  We did go out on The Lucky Me with Susan and Greg for sunset a couple of times, otherwise we were land lubbers. The weather has been in the 70’s and 80’s for the most part and the sun has been shining most days.  There were a handful of days that were in the 60’s and the wind was really strong – that’s when you can truly distinguish the locals from the tourists – the locals were wearing hoodies zipped up to their noses and even some down parkas!  The tourists didn’t give up their shorts and flip flops, they were here to experience tropical weather in the winter, and they were sticking to it dammit!  I have to say, having been in Florida for two winters now, my blood has thinned, and I pulled out the sweatshirts!!


The highlight of our time here was having my brother Jack and sister-in-law Linda, and my sister Brenda and brothers-in-law Mike come to visit.  The six of us stayed on the boat and we had SO much fun.  I was worried about them getting used to sleeping, showering and generally maneuvering around our space; we’ve gotten really used to living on a boat, but it is very different than being in a nice house!  Danny kept telling me it would be fine, and he was right, by the time they left they’d really gotten it all down pat!  We rented a minivan for the week they were here so we could play tour guides – I really wish I’d gotten some pictures of Linda and me getting in and out of the third row where we ended up most of the time – that was a sight!  We brought them to Duval Street and to the Seaport, to a couple of our favorite restaurants and to Sunset at Mallory Square, which is an iconic Key West event, and we toured the home of Ernest Hemingway.  We even hosted a Looper Docktails evening and we all got to meet some new Loopers. I think my favorite part was sitting on the back porch drinking coffee with everyone in the mornings. I just keep thinking how lucky we are to be able to spend time together, and I’m so happy that they wanted to share a part of our adventure.  Here we are senior citizens,  🤩 and we’re still making memories……we are blessed.


Brenda and Linda wanted to experience Looper “docktails” while they visited, so we did! They fit right in.


So…..what’s next?  When the weather allows we will venture out to the Gulf again and travel north with Bruce and Grace, taking 4 days and 3 nights (on anchor again!) to Fort Lauderdale.  We seriously considered a trip to the Bahamas, but for a few different reasons we’ve decided against it.  Maybe next year!  We have a reservation at the same marina where we spent time last winter and hope that the weather will allow us to spend some time on the beach – Danny wants to find more toys to add to his collection from last year.  We plan on being there for a month, then in mid March we will slowly start heading HOME!

One of the many beautiful sunsets in Key West

We have traveled  SO many miles and have many to go before this adventure is over.  Looper friends who are home now tell me that I will really miss this when it’s over…..I don’t know…..we’ll see.  I will blog from time to time on this last leg of the journey and know that someday it will be fun to read it and remember winters like these.

Thank you for traveling along with us.

Captain Dan and Cruise Director Jodi

PS – I hope we remember how to move this boat!!!  Oh My!

2 thoughts on “Winter in Key West”

  1. OMG – LOVED YOUR LATEST BLOG! 2 months in Key West – how fabulous! Now to continue the adventure. I believe we met you at the City Marina in Fort Lauderdale, right? Will continue to follow your blogs and hope that we can meet up when you get to the Chesapeake Bay, or if you do a side trip into DC. Fair Winds and Following Seas to our buddy boat……Kris & Rick (Eagle One)

    On Fri, Feb 7, 2020 at 9:20 AM The Done Diggin’ Diaries wrote:

    > donediggindiaries posted: “What a wonderful winter this has been. We’ve > been docked at Stock Island Marina Village just five miles from downtown > Key West since December 8th. If weather agrees (which is 50/50 at this > point), we will pull our lines tomorrow morning and head to our ” >


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