Note: This is a mishmash of both the 2017 and 2019 races – Yes, it’s that good that we continue to go back every year possible!

With three half marathons behind me, and finding myself in the middle of training for my first marathon, I made the very last minute decision to sign up for the Wineglass Half Marathon with my friend Heather, aka Meatball, and her family. 

It was so last minute in fact, that the race was already sold out and I was put on a wait list.

Their family has been running various distances at this race weekend for years, and assured me most people end up clearing the wait list, so I would likely make it in. 

I knew absolutely nothing about this race other than “it was super fun, and you get glass medals at the end”. Um, okay. Sold!

I feel as though I should mention that I had already signed up for the Baltimore Half Marathon that was only 21 days later. Anyone who knows me now, knows I wouldn’t even bat an eye at this scenario currently, but back then, this might have been one of the dumbest things I have ever done.

Like all other days on this trip, day six started with being awake very, very, early in the morning. Today’s early morning wakeup was courtesy of not only the rooster, but also the insane wind. What was a minor light rain, turned into a massive storm overnight, and with it brought high winds and winter like temperatures. Okay, winter like temperatures by Cuba standards anyway. It was still in the high 60’s/low 70’s, and shorts weather, as far as I was concerned. 

It sounded like Kelly was awake in her room across the hall, so I went and asked if she wanted to go explore the Malecón, and watch the sun come up. I know, “watch the sun come up” words that rarely, if ever leave my mouth as a non-morning person.

If you read day three’s adventure, you will recall that the Malecón becomes amazing entertainment when storms roll in, thanks to large waves crashing up over the sea wall. Just short of a hurricane, today’s weather was about as good as it was going to get for witnessing this!

Health & Safety Note: This adventure occurred long before the current COVID-19 pandemic. Please be aware of, and follow, all local safety and health guidelines if you choose to travel during this time. 

Current regulations for American citizens traveling to Cuba can be found here.

Upon realizing our trip to Cuba was finally a reality, with flights and an apartment booked, I went into full research mode. I can’t help it, I like to plan. I like to know what there is to see, experience, eat, etc. in a new location.

I don’t necessarily need an to the hour planned out itinerary. In fact, that would actually drive me crazy. I do however like to go in with a list of things that are must do’s or a bit off the tourist beaten path, that you may not know about unless someone pointed them out to you ahead of time. 

When researching a new location, the first thing I do, is go on Pinterest and do a search for the location I am going to. This will usually bring up a wealth of blog articles ranging from top ten lists, must see or must do lists and off the beaten path lists. I look at everything, and old school style in a notebook, I start jotting down things that look interesting to me so I can look into them further. 

The other thing I do is go to the bookstore (yes, those still exist!) and go to the travel section. Being a visual person I much prefer a travel book with a lot of photos, versus a book that is all text. Descriptions are great, but I have saved myself great amounts of disappointment by searching for online photos of a location first. Many times what is talked about as this big fancy attraction, ends up being really small and run down, and not worth the hours trek out of the way to see it.

Health & Safety Note: This adventure occurred long before the current COVID-19 pandemic. Please be aware of, and follow, all local safety and health guidelines if you choose to travel during this time. 

Current regulations for American citizens traveling to Cuba can be found here.

Day four started out with another early wake up. Partially thanks to the Rooster again, and partially because we wanted to take a day trip out to Viñales Valley, where the tobacco is grown and cigars are made. The weather later in the week was looking a bit cold and rainy, so we were trying to cram in all outside activities while it was still warm and sunny.

From our many prior trips to the Hotel Nacional, we already knew they had day tours that left from there each morning to various other areas of Cuba. We stopped off at a local bakery we had found near our apartment, and grabbed some pastries to munch on for breakfast. 

We arrived at the hotel well before the listed tour time on the sign and found the desk to purchase our tickets. Only one problem, the tour was already sold out for that day. Womp womp!

They let us know tomorrow’s tour still had availability however, so we each purchased tickets for tomorrow, and came up with a plan B for the day.

Yep, this means you have to wait for one more blog post to learn about all things Viñales Valley, and trust me you will want to come back for that one! 

Philip, who had chosen not to go with us as he was still working through his photography assignment, had planned to be in Old Havana (La Habana Vieja in Spanish) that morning, so we decided to go try and track him down. As we learned from our lengthy walk on day two, Old Havana was a bit of a hike on foot from the Hotel Nacional. Since it was still quite warm outside, we decided to take a taxi there instead of walking. No need to be sweating to death immediately after showering.