Cruising the Caribbean: Finding Artistic Inspiration on the Islands
Coming back from the beach in Tortola
Earlier this month, I embarked on an 11-night Caribbean cruise with my mom and brother. While I love the mountains and natural beauty of Colorado, I’ve always been drawn to destinations surrounded by water—oceans, rivers, or lakes—places that feel so different from our landlocked state. Traveling together has become a cherished family tradition, a chance to reconnect and catch up while exploring new cultures and landscapes. Winter is our favorite time to cruise, typically between Thanksgiving and Christmas. The off-season means fewer crowds, and escaping the cold in Wisconsin and Colorado makes the trip all the more rewarding.
This time, we went bigger than usual—an 11-night itinerary with eight ports of call. It gave us the perfect balance of adventure and relaxation. We even had a day to explore Miami Beach before boarding, a great warm-up for the trip ahead. Onboard the ship, I settled into a daily rhythm that balanced creativity, movement, and fun. Mornings started with my personal yoga and qi-gong routine, followed by days filled with swimming in the pool, navigating the ropes course, lifting weights in the gym, and walking the decks. Evenings brought live shows, comedians, and, of course, plenty of great meals at the buffets. I always travel with essentials like a sketchbook, a few art supplies, books, my tablet, and props like my kendama and juggling balls to keep my mind and hands active.
While the ship offered relaxation, it was the ports that truly inspired me, especially two stops: San Juan, Puerto Rico, and Antigua.
In San Juan, we explored the city’s historic district, filled with colorful architecture and cobblestone streets. It was there I met a local artist busking on the street, surrounded by his acrylic paintings. He shared his story of making a living entirely through his art—setting up his live painting station in the same spot every day. He explained how he’d earned this coveted location and was even able to store his supplies in a nearby shop overnight. As he painted, he showed me a cloud and smoke technique he often used in his work, a simple yet powerful skill I can’t wait to try in my own pieces.
His dedication was inspiring. Seeing how live painting allowed him to connect with passersby sparked my interest in trying something similar in Colorado Springs, where live painting is a big part of local festivals. While I’ve always admired the concept, I’ve hesitated to try it myself—partly because of the logistics of bringing art supplies, and partly because festivals are a time I usually share with friends and family. But after this experience, I’m determined to set up a small, simple live-painting station downtown once the weather warms. I want to connect with people through my art, just like this artist did in San Juan.
The second standout experience happened in Antigua, where my mom and I stumbled upon Quay Gallery, a hidden art gallery and collective. The gallery’s founder took the time to share his journey, explaining how he had started with a small space downstairs before expanding into a larger workshop and artist collective. His vision was to create a space where artists could collaborate, create, and showcase their work together. It was a modest yet vibrant space—art filled every wall, and a workshop area sat at the center, offering room for artists to work side by side.
I also had the chance to speak with one of the resident artists, who’s been part of the collective since its inception. He shared how the space had become an essential part of his routine, a place to paint consistently while connecting with fellow artists. This conversation opened my eyes to the potential of joining a collective myself.
Until now, I’ve primarily worked alone in my studio, creating art in a private space. But the idea of collaborating with other artists—sharing ideas, growing together, and building connections—feels like the natural next step. There’s a collective close to my home in downtown Colorado Springs that I’ve considered joining, and this experience has encouraged me to take that leap. I know it would help me expand my network, stay focused, and build momentum for my long-term goals of running a successful art business and, eventually, opening my own gallery or workshop space.
This trip reminded me of the value of stepping outside my comfort zone. Whether it’s live painting on the streets or joining an art collective, these moments of connection and inspiration abroad are shaping the next chapter of my creative journey. I returned home refreshed, motivated, and ready to take new steps toward growing Connors Designs—one brushstroke, conversation, and connection at a time.
Crazy mega yachts in St. Thomas
