The Adventure of a Lifetime

Sailing the Bahamas aboard a 125-foot schooner.

Before my partner turned 30 a couple of years ago, I was on the lookout for something special we could do to celebrate—something we’d always remember.

Then my mind flashed back to the sailing trip he’d found online and shown me a few months earlier. For five days, you’d sail around the beautiful Bahamas, island-hopping and taking in the dreamy turquoise waters and light blue skies of a life at sea.

I was hooked. This was it.

I am by no means a sailor (and neither is he), but that didn’t stop us from jumping on board for a chance to sail on a real tall ship! He loves boats and being on the water, and I knew he would love this experience.

Our home for the week would be a 125-foot schooner called the Liberty Clipper.

Exploring Nassau

Before boarding the ship, we spent some time in the capital city and cruise ship port of Nassau.

As with other major cruise ship destinations in the Caribbean, the main strip near the docks was where 99% of the passengers seemed to congregate, making it a headachy combination of noise, locals trying to sell you anything and everything, endless taxi traffic and horns beeping, pumping beats pounding at the many bars and restaurants, and designer shops carrying your heart’s desire (for an arm and a leg).

Then, as you walked a few blocks further from this main area, everything got quiet and deserted.

Shops were vacant and boarded up, garbage littered the sidewalks and streets, and seemingly ancient hotels were abandoned and vandalized. Some looked like they’d been the scene of a raging party before everyone cleared out, never to set foot there again. It was fascinating and eerie all at the same time.

The Ship Awaits

Though I enjoyed exploring the town, visiting the museums to learn more about the history of the Bahamas, and trying some local food and beer, I was more than ready to get on that boat and have it take me far, far away from the “big city” when the time came.

Our departure from Nassau harbor was followed by five glorious days of total “going with the flow.” And I loved it!

With no phone service or wi-fi access, we were truly able to disconnect and reboot ourselves on this vacation.

Our days were spent relaxing, learning a little bit more about sailing (I still can’t say I know much), participating in the sailing process by helping raise the sails, floating in the clear Caribbean water, kayaking around the shores wherever the ship anchored, and snorkeling some of the reefs when the weather permitted.

I experienced some firsts on this trip as well: stand up paddleboarding (I didn’t fall!), cozying up in a hammock hung from the masts and lines on deck, jumping off the bowsprit of this impressive ship, and even snorkeling through hundreds of tiny jellyfish hanging out at one of our snorkel locations. That was a little scary at first, but they didn’t hurt…they just felt funny!

Going With the Flow

Each day was a blank slate, meaning nothing was decided in advance. When you’re on a giant sailboat, the weather (and especially the winds) determine your next destination. The captain would chart the course along the way, and we’d arrive somewhere new without expectations or preconceived notions about that place. I’d never heard of most of the places we visited, and even if I’d wanted to research them, I couldn’t!

The crew was friendly and welcoming and made sure you were having a great time, no matter what the weather was doing. They were also fascinating people—adventurers at heart, drawn to a job that consists of roaming the seas and discovering new places almost daily. When the guests would ask questions like, “So, where are we going?” they’d often respond with “Your guess is as good as mine” or something of that nature. And they usually meant it! Many of them were experiencing the Bahamas for the first time, too, and the route was liable to be changed last minute.

We learned quickly on this trip that it wasn’t the destination that mattered; what mattered most was being present and taking it all in.

The point of this unique getaway, after all, was to not know — not to plan, not to research, not to get caught up in distractions like the internet.

Here and Now

It took some time to adjust to this, but once I embraced it, I found that just going with the flow and being in the unknown was actually preferable, because I was really there.

I was along for the ride, experiencing this trip moment to moment. We were taking it one day at a time, focused only on what was happening here and now.

If we were swimming, we were swimming. There was no thought as to what was going to happen next or where we might be going or what we needed to do to prepare. Everything just unfolded naturally, at its own pace, without our intervention.

I also saw how much easier that way was, and preferred it so much more to my usual thinking/planning “busy” mode.

When we’re so caught up in our heads all the time, thinking our way through life as opposed to living it, we risk missing what’s right in front of us, moment to moment.

We miss the beauty that’s unfolding, and the opportunity within each moment. We can’t know what it is until it arises — but if we aren’t paying attention and aren’t fully present, it passes us by.

As much as this trip was an exciting adventure, it was also a lesson in stillness and presence.

Land, Ho!

It took me a while to get my “land legs” back, as they say.

I still felt the gentle rocking of the ship, as the waves lapped against the bow and the side where our little bunk bed was nestled. It was a weird sensation, sitting at my desk, and yet still feeling like I was gently rocking days later.

However, if this is the price I must pay for a truly memorable and meaningful adventure, I’ll gladly pay it!

Sailing in Boston

While the Liberty Clipper winters in the Bahamas, this magnificent ship lives in Boston from June to September, offering sailing outings, room rentals, and even private charters.

If you’d like to experience sailing on a real tall ship but aren’t up for a week-long adventure, you can also book several different day sailings around the Boston Harbor.

While sailing Boston on a tall ship harbor cruise, you’re welcome to help hoist the sails, take the helm, enjoy a drink from the ship’s bar, or just relax and take in the sights and sounds of Boston Harbor. — Liberty Fleet

If you’re interested in learning more about sailing, this is a great opportunity to get out on the water on one of Boston’s only tall ships!