How Sailing in the Caribbean Changed My Life

Melissa Alvarado Sierra
Melissa Alvarado Sierra

If I had to stay landlocked for the rest of my life, I'm not sure if I could be happy. I grew up in the Caribbean with a grandfather who adored the sea and who named his boat after me. Grandpa Javier would wake up my brother Omar and I at 4 a.m. to go walk on a sandy beach and then on a rocky coastline to fish, showing us his great passion for the ocean. As I grew up, I always longed for the sea, renting places by the sand and swimming almost every day. Then, in my early 20s, I met a handsome sailor named Alejandro (my now-husband) and I fell, inevitably, in love with him as I fell in love with sailing. Now I consider myself a woman of the sea, and I can only fathom a future filled with sailing adventures. I share this passion for the water through my writing because I want others to know of the life-changing power that lies in the ocean. There is something so utopian about sailing, so surreal, that it is difficult to put into words; you have to go out there to truly understand it. I always try to explain it anyway.

Maho Bay in St. John, USVI: a popular anchorage.
Melissa Alvarado Sierra

Maho Bay in St. John, USVI: a popular anchorage.

I have many powerful sea memories, but the one that best captures the simplicity and beauty of the ocean is also a very basic one. I always remember early morning walks. One in particular comes to mind: a time spent at an isolated beach in St. John in the United States Virgin Islands a couple of years ago. I remember walking on dry white sand, the kind that feels like baby powder because of its remarkable softness. I was the only person on the beach, walking toward the ocean, and when I reached it, a small wave brought the water close enough to touch my feet. I remember how it felt soothingly warm. The water was a very transparent, almost imperceptible, blue color, and it folded back rapidly, reuniting with the ocean and leaving my feet and the powdery sand behind.

Finding inspiration on an island off the coast of Nassau, Bahamas.
Melissa Alvarado Sierra

Finding inspiration on an island off the coast of Nassau, Bahamas.

You notice life's details when you are enveloped by a place that brings calm to your life, a place that helps you focus on the little things. For me, sailing in the Caribbean allows me to reach such places: where my days are spent being caressed by the ocean breeze and my nights are spent being serenaded by tropical lullabies. Life slows down here, and longtime worries are suddenly muted, sometimes even completely forgotten. Locals are evidently engaged in this easy-living vibe on many of these islands, and meeting them is yet another experience that feeds the dreamlike escapade. I go sailing here to rest, soothe my soul, and find inspiration for my work. It's what I call the island cure: a type of medicine I can only get in these islands; a medicine I need to truly heal. As a creative writer, I need a constant source of this mind-healing balm, and I always find it when sailing in the Caribbean.

Escaping to Anegada, British Virgin Islands.
Melissa Alvarado Sierra

Escaping to Anegada, British Virgin Islands.

Far from the brain fogs, the physical exhaustion, and the hurried lifestyles that are considered normal today, life in the Caribbean is simply easier. Lined palm trees, refreshing turquoise waters, and sultry music create, like I said before, an almost utopian atmosphere. The sheer uttering of the word "Caribbean" brings to mind images of escapism and paradise, and that is especially palpable when you sail here. We all have thought about escaping to an island and indulging in all its raw beauty, and while coming here by plane or cruise will definitely prove to be an unforgettable experience, I also think those ways of traveling are limiting, only allowing you to scratch the surface of a profound place. If you really want to delve into the lifestyle of this region and change the way you see the world and the way you see your own life, dare to take control of your vacation and sail the Caribbean on your very own sailboat.

The clear waters of Pirates Bight on Norman Island, BVI.
Melissa Alvarado Sierra

The clear waters of Pirates Bight on Norman Island, BVI.

Why a sailboat? Simply put: sailing is one of the most natural ways of traversing. All you need is the wind and the water to move along. And if traveling sustainably is not enough to convince you, think about the rare experience of moving with the wind and sliding over the water. Nothing quite compares to this, not even flying on a plane. There is a certain silence when you're moving on a sailboat — there are no artificial sounds, only the splashing of the waves and the flapping of the sails. You might hear the occasional creaking sound of a simple mechanical system that makes sailing possible, but that is it. You essentially glide through the ocean from one island to the next. And at every port, there's a different culture, cuisine, music, and sometimes even language awaiting your arrival. That's another reason why the Caribbean is an incredible playground for sailors. Islands are just a few hours away from each other.

Sailing to Icacos Island, off the coast of Puerto Rico.
Melissa Alvarado Sierra

Sailing to Icacos Island, off the coast of Puerto Rico.

Is sailing intimidating to you? Don't worry; I was scared when I first boarded a sailboat, mostly because of the uncertainty of life at sea. Granted, I was a little seasick and completely lost the first few times, but I was still strong enough to make eight-hour crossings without wanting to quit. I was hungry for the adventure. For my first real sailing trip with my husband and on our own boat — we had sailed before on other boats and in groups, but that is not the same experience — we sailed from San Juan in Puerto Rico to Anegada in the British Virgin Islands, making stops in Culebra, St. Thomas, St. John, Tortola, and Virgin Gorda.

There's a unique sense of abandon at sea.
Melissa Alvarado Sierra

There's a unique sense of abandon at sea.

That trip, which lasted a month, unearthed a side of me I had not seen in a very long time. Early mornings were especially enlightening, connecting me to the child my grandfather woke up at 4 a.m. to go fishing all those years ago. In the Caribbean I felt anew, as if I had been born again. Life's struggles had taken away some of the shine of the world, but when I was out there on the ocean, as the sun was rising and painting colors on all things, I felt anything was possible. I was able to design a lifestyle I adored, and slowly my dreams started to materialize, all thanks to an awakening I had while at sea. That sense of abandon is only possible when you are completely removed from the stressors of the world. I don't think you can have that when traveling on a cruise ship or staying in a hotel. It is not the same experience, not even remotely close.

Sailing to El Morro in San Juan, Puerto Rico.
Melissa Alvarado Sierra

Sailing to El Morro in San Juan, Puerto Rico.

Yes, sailing is not an easy hobby; it takes time to learn how to sail and time to go sailing. But if you want to experience nature and different countries, and if you want to reconnect with yourself in an authentic way, please give it a try. You don't even have to buy a boat. Just take classes at your nearest sailing club, charter a boat for a few days, and then come to the Caribbean and see it for yourself. There are also many chartering companies here with plenty of sailboat options.

A sailboat floating in Caribbean waters.
Melissa Alvarado Sierra

A sailboat floating in Caribbean waters.

Once you have made it here, don't forget to stop at great anchoring spots.

  • Dákity in Culebra, PR: for peaceful waters and fast access to the island’s downtown pier.
  • Maho Bay in St. John, USVI: where the water is serene for sleeping and the color of a swimming pool; it also has great access to a main road where public transportation is available.
  • Marina Cay in the BVI: a tiny island holding one of the most romantic stories in the entire Caribbean.
  • Nanny Cay in Tortola, BVI: for restocking on food, having a beer at the bar, and doing some shopping.
  • Anegada, also known as the “Drowned Island”: a flat isle with sand so white and bright it hurts your eyes . . . but in a good way.
An arch made of rocks in the town of Cabo Rojo.
Melissa Alvarado Sierra

An arch made of rocks in the town of Cabo Rojo.

In case you were wondering, yes . . . I still live in the Caribbean, although I had a five-year foggy stint in San Francisco. I came running back because I missed the sounds of the tropical jungles, the crashing of the turquoise waves, and the blustery days at sea. But most of all, I missed finding my inner child on those early morning walks.