The Cruise Blog

If you keep up with Jamie at all, you probably already know he never stops painting. One look at his studio tells that story; his display of hard work is practically spilling over with paintings small and large, line-sketched and colored, on canvas and on paper. His giant body of work might suggest all work and no play, but even the master of bright, playful paintings has to play sometimes. And by play, I mean take a vacation. 

However, since Jamie’s passion became his job, I would argue his vacations don’t quite match most definitions of a vacation. Of course he does normal vacation things like relaxing and spending quality time with family and friends. But from what I’ve seen and heard of Jamie’s vacations, he always has his art satchel in tow. Inside his weathered and paint-stained satchel, he keeps a water bottle, Holbein paints, Bombay black ink, brushes, nibs, and various cuts of his favorite Fabriano water color paper. No matter where he travels, Jamie is always at-the-ready to sit down against a tree or a building and document whatever new scene strikes him as interesting. It’s my understanding that Jamie loves to paint “en plain air” (outdoors), so really, it makes sense that he spends his down time painting different locales. 

So picture the perfect Jamie Calkin vacation. Idyllic beaches? Fantastic mountains? A colorful new city? All scenes worthy of Jamie’s bouncy, loose style, for sure. But his most recent vacation wasn’t any of the usual scenes. This vacation promised more… challenge. 

The Jamie Calkin Cruise Blog 


Jamie and I had a lengthy conversation about how cruise ships are generally a weird experience for all of the obvious reasons. A bunch of strangers trapped on a boat together with nothing to do but eat, drink, swim, and get sunburned. The list goes on and on. Despite all of the weird-ness, Jamie found that the pool/ dance floor/ bar area was a great spot for people watching and painting.


Arguably the best part of cruises are the excursions. The big boat took a stop in Nassau in the Bahamas and gave Jamie these scenes to paint!

Despite all of the weird parts of cruises, Jamie said it was overall a great experience, mainly because he was able to spend time with his good friend, John, who was in desperate need of a vacation. Diagnosed with autism at a young age, John comes from a tough background and works extremely hard day-to-day. Needless to say, Jamie was overjoyed to share such a purely fun experience with a dear friend who deserved it! 

Another great part of the cruise was meeting some new friends, an incredible couple that joined Jamie and John for dinner one night. After some great conversation, they all spent a day together in Jacksonville.


As Jamie told me about his vacation, I got a real sense of what a genuinely lovely time he had in such an unexpected way. A cruise was not his ideal vacation, but the where is rarely what matters. Plus, Jamie can pretty much make any scene into a work of art ;)

If any of the above paintings tickle your fancy, take a look at some originals for sale below!