Tall Ships, Sea Travel, and Life

Sandy Island

I’ll begin this little piece by saying that I’m an unabashed fan of tall ship sailing and travel. It’s something everyone should do, everyone should experience, and something that must be done over at least a week of your life. For me, it’s a personal experience because my first sail occurred at a time when I was reassessing my future and the experience helped me decide on my direction. My experience on the Caribbean Sea on a tall ship played a very direct role in why I’m writing this today and why I’m working to develop the first truly nautical travel company around.


Tall ship sailing is the best way to travel on the seas and oceans of the world because you are closer to nature, you can unplug from the rest of the world as much as you’d like, you can visit many more ports and communities as compared to bigger ships, and you can truly make new friends because you’ll get to know everyone onboard your ship.

The Ships

When it comes to tall ships, one often thinks of the Age of Sail when sailing ships ruled the sea prior to steam ships and the modern cargo-carrying behemoths of today. Today’s tall ships are mostly geared toward leisure sailing, while some are still used for training and other functions. My experience was on Vela with Island Windjammers in 2016 and 2018. Vela is a lovely ship that is 156 feet long, has a crew of 10, and can carry up to 26 passengers. Similar ships are available through Liberty Ships of Boston, such as the Liberty Clipper, as well as Arabella, which is chartered by the American Sailing Association.

If you have a worry about motion sickness on small ships (which you really shouldn’t worry about), then you can opt for a larger tall ship, such as one of the ships of Star Clippers. You can choose from Star Clipper, Star Flyer, and Royal Clipper, which are much larger and range in length from ~379 to 439 feet and can accommodate up to 227 passengers.

Regardless of the size of the tall ship, you will enjoy a truly unique experience by being pushed along by the wind. You’ll also likely have the chance to learn a bit about crew operations, and you might even be able to help hoist a sail or drop an anchor. It’s a much more … personal … way to travel.

Life Onboard

Fortunately, tall ship travel today is much more comfortable than back in the day before the arrival of modern amenities such as air conditioning, good food, and rugged ship construction. Cabins on tall ships are a bit smaller than on cruise ships, but the important thing to remember is that you really will only be in your cabin to sleep. When there, you’ll have air conditioning, a comfortable bed (bunk bed or single), a modern (if small) bathroom, and you can rock yourself to sleep at night by the gentle actions of the waves.

On deck, you can typically do whatever you want on these types of sails. Some people live for going ashore and some people simply want to stay on the ship as that’s why they are there in the first place. Water sports is a common activity – and my favorite activity was the rope swing where you catapult yourself off the bow railing and into the water below! Yea, lots of fun there, I tell you!

One typical routine is to sail overnight, stop for a port visit in the morning, have breakfast, go ashore, and come back in the evening for dinner and relaxation. Of course, most of us love port visits as we want to meet people where we travel, try the food, and become a part of the destination. You simply hop from island to island for the duration of your sail.

The food is also very, very good. You won’t be underfed, that’s for sure, and you may want to pace yourself as there is not only breakfast, lunch, and dinner, but oftentimes snacks as well as having the drinks flow all day long!

I also have to mention the crew. For Caribbean sails, you may very well get to meet people originating from a variety of Caribbean islands. It’s always fun to learn about the people who run the ship, why they are doing it, and to learn their perspectives on life, sailing, and the world.

Island Hopping

During shore visits, you can enjoy guided tours, self-guided tours, or you can simply go wandering around on your own. The only typical stipulation is you have to return to the dinghy by a certain time, lest you get left behind and that would likely put a damper on your travels. As each island is a culture and experience of its own, you should try to get to each one as every place has much to offer. There are also abundant opportunities for hiking, swimming, and snorkeling at the various islands. The crew know the best places to visit for different activities and they will do their best to show you the very best of each island.

Closer to Nature

Have you ever been on a ship and watched the dolphins swim with the ship at the bow? Witnessed a huge school of spinner dolphins? Been (almost) up close and personal with a whale? Been snorkeling and gone head-to-head with a puffer fish? Well, all of this and more is possible when sailing on a tall ship.

The smaller sizes of the ships, the use of the wind to travel, the fewer people around – all of this will begin to detach you from the workings of the modern world and you can return to nature in its purest form. It always reminds me that we humans are a part of nature, not separate from it. That means we have a special responsibility to take care of the places that we visit, to travel sustainably, and to work every day to stop climate change from forever changing our home in a very negative way.

Our Ambitions

So, our focus at Naked Pirate Travels is to truly embrace tall ship sailing and to introduce this mode of travel to more and more people. It’s about connecting and reconnecting with the oceans. As our vision is to help people explore and protect the planet, the most visible way that we will do that is – ultimately – to operate a fleet of tall ships. It may not be an understatement to say that the Second Age of Sail may soon be upon as we think of ways to travel the ocean in a more responsible manner. Our ships will help people explore the islands of the world, sail the oceans, and to contribute to protecting the oceans for future generations. We even plan to contribute to real, meaningful, and impactful scientific research and ocean conservation while on these sailing expeditions. Much has yet to be done to get ready for all of this, but that is our vision.

It’s not just about travel; it’s also about education, learning, experiencing, and contributing to the betterment of the oceans and our world.

Our inaugural sail, chartering the Liberty Clipper in February 2023, is also different from the average tall ship sail. While we will be island-hopping across the Bahamas, we will help people relive the Golden Age of Piracy, get a grasp of what it was actually like to be a pirate of the Caribbean in the 17th and 18th Centuries, and to dive into history as well as the natural beauty of our destinations.

It’s these kinds of unique, immersive, and interactive travel experiences that we think is different, is better, and is what people want. Interested? Check out our Sailing Sojourns page at https://seadogtravels.com/sailing-sojourns.

I hope you’ll join us on one of our future sails, or at least get on a tall ship somewhere, sometime. Maybe that experience will change the course of your life, and for the better.

Published by Paul Hardersen

I am the CEO of a startup nautically-focused travel company, former associate professor and research scientist, traveler, lobster lover, and now doing what I can to help preserve the planet for future generations. The ocean is the key.

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