The Gift of guests: sailing for the first time (again)

in Life at Sea / Sailing the World
the gift of guests sailing for the first time sailing blog

I am sitting in the cockpit of Cheeky Monkey, enjoying an evening glass of wine with a view of several thousand gleaming boats in the Real Club Nautico Marina in Palma de Mallorca, when I get a message from my friend John saying, “I’m ready!” just as this picture comes through my phone:

sailing for the first time cheeky monkey turf to surf

I start laughing and immediately reply that Ryan and I are awaiting John and his partner Chris’ arrival to Palma with excitement – after all, it has been over 10 years since we lived just around the corner from them in Sevilla, Spain, where we taught English for a living.

I sip my wine, smiling, because this is the reason we chose such a large boat for ourselves – it wasn’t so much for us alone, but for the opportunity to bring friends on board for any leg of our journey around the world. And now it seems the dream we had of sharing our journey with loved ones is becoming a reality.


By the time we finally sold our businesses (teacher training schools and English as a Second Language schools in the U.S.) in February 2015, Ryan and I had been making our rounds to boat shows, shopping for what we dreamed would be the boat that would take us around the world one day.

Our first boat, Hideaway, had given us some of our best years in New York, teaching us to sail and to fix engines, tearing us away from the stress of building and running our own companies and inviting us to dream of what the future could hold if we ever decided to close the entrepreneurial chapter of our lives and do something completely different.

sailing for the first time again hideaway turf to surf
Our old Catalina 34, Hideaway, in the Bahamas.

And when that opportunity arose in the form of a signed Sales Purchase Agreement for both of our companies, we scrapped the boats on our what-we-can-afford-if-the-companies-don’t-sell list and we immediately plunged feet-first into the dream of sailing around the world on a Fountaine-Pajot Helia, a boat with more than enough room to have friends and crew comfortably on board as we sailed to countries that sparked our wanderlust and brought us back to the basic dreams that kick-started my and Ryan’s careers in teaching ESL: to travel and learn about the world through our travels.


When John and Chris hop out of their airport taxi in Palma, I’m surprised to see they’re not wearing their wetsuits and snorkels already. But soon after they arrive to the docks, they are jumping up and down like excited children, gasping at the boats surrounding them, as well as every detail of our new floating home.

No matter what lifestyle we choose, whether it’s living in an apartment in a big city, a house in the rice paddies of Bali, a log cabin in the woods or a boat that’s forever on the move, there’s always an initial thrill over the change in environment. But then that thrill eventually gives way to a daily routine that’s filled with menial tasks and friends who live the same lifestyle as us. Which means, at some point, the life we’re living slowly begins to feel completely normal. This is a good thing, of course, as it would be exhausting to wake up every morning with a distracting feeling of euphoria, causing me to fawn and delight over every detail of my mind-boggling and extraordinary day.

I mean, I’d never get anything done otherwise. “Honey, do you want breakfast…OH MY GOD! Have you seen this TREE?! It’s growing avocados! I’ve never seen an avocado on a tree before! Wait, what was I doing?”

It’s like falling in love – if we forever remained in that ecstatic love-sick state that we experience at the beginning of a relationship when we can think of nothing else but being near our lover, then we’d never be able to hold down a job.

Ecstasy gives way to a much more comfortable feeling of normal fondness, so we can all go about our day getting things done again. And that normal fondness is the feeling we have settled into regarding our new boat and our newfound freedom.

But then John and Chris arrive on a plane from Sevilla, wearing nautical-themed clothing and grinning from ear to ear.

“OH MY!” Exclaims Chris as we give her a tour of the galley. “Look, John! They even have storage in the floor! How amazing!”

John and Chris flit from one corner of the boat to another, amazed at the economy of size of everything on a boat, as well as the views from the deck, the steering wheel at the helm and the electronic instruments everywhere. They are excited by every little detail and their enthusiasm is wildly infectious. It has the effect of reminding us that, though our lifestyle has become normal to us, living on a boat is an extraordinary thing to experience for the first time.

the gift of guests sailing for the first time again sailing blog
Chris and I, making dinner in the galley of Cheeky Monkey.

Watching John and Chris on their first sailboat is like watching someone fall in love for the first time – I see the sparkle in their eyes and though I know the feeling will calm down eventually, I don’t want to spoil it for them. The joy they’re experiencing in the moment expands in the space around them and blocks the thoughts running through my head of the head that’s leaking and the sump pump that doesn’t work.

Within a day of John and Chris arriving to Palma, two more guests arrive who will be staying on board Cheeky Monkey through our Atlantic crossing. We met our friends Meg and Kristi when we were participating in the ’13-’14 Clipper Round the World Yacht Race, which Ryan and I did a few legs of while Meg and Kristi did the full round-the-world circumnavigation.

But even for experienced sailors like Meg and Kristi, who have lived on stripped-down 70-foot racing yachts for nearly a year, stepping on board a cruising boat like Cheeky Monkey is a new experience. For one, you won’t find an espresso machine, hot showers or an ice-maker on board a racing yacht.

Mind you, you won’t find an ice-maker on board our yacht either, but that isn’t because it’s not supposed to be there. It’s just that ours still doesn’t work. I know, I know, #firstworldproblems

The joys of simple land-pleasures like comfortable seating, a queen-sized bed and a large dinner table are the things that excite Meg and Kristi when they step on board Cheeky Monkey for the first time, which makes me remember how bare and uncomfortable my boat Henri Lloyd was on the Clipper Race. Over the next few weeks, we will find ourselves saying, “This ain’t the Clipper Race!” often and with great delight.

With 6 crew on board, Cheeky Monkey, we pull out of Palma bound for Gibraltar, setting up a watch system where each of us is responsible for two hours on deck in daylight and two hours in the night, allowing for plenty of sleep and relaxation time for the crew.

Except John and Chris, who are only on board for three days, forgo most of their sleep to stay up and watch for possible marine life on the horizon.

gift of guests sailing for the first time again sailing blog
This is pretty much where Chris and John stood for 3 days straight.

One night, I groggily step into the galley in the pitch black of night to get a drink, when I hear John scream “Tasha! Come here! I think I see dolphins!”

I have only ever seen dolphins at sunrise and sunset and have never seen any sign of them in the dark, so I assume John is just seeing some flying fish jump out of the water.

John has a spotlight in his hand and is shining it on the water where, sure enough, a fin pops up above the smooth, black surface of the water.

“Oh wow!” we all squeal in unison.

“How long have you been out here looking?” I ask, rubbing my eyes.

“All night!” screams John as Chris bounces up and down next to him. “We’re too excited to sleep!”

Just then another dolphin pops up into the wake under the foredeck trampoline and all three of us rush to the bow to stare at the water beneath us.

“Look! There’s more!” screams John. “Should we wake Kristi?”

I look at my watch, which says 3 am, and laugh. “I think Kristi’s seen plenty of dolphins on the ocean before.”

“BUT HAS SHE SEEN THEM AT NIGHT?!” John shouts, running back to the cockpit. “I’m going to wake her!”

Shortly after, Kristi stumbles out to the foredeck, rubbing her eyes, as John and Chris are bouncing up and down on the trampoline screaming, “Look! There’s another one!”

To which Kristi laughs and says, “I’m going back to bed,” leaving me alone on deck with John and Chris, shrieking and pointing, filling the night air with the joyful noises of hysterical adults.

dolphins sailing again for the first time sailing blog
Chris, capturing a rare sight of pilot whales on the Mediterranean.

Normally, I like to spend my quiet night watches immersed in my introspective routine of reading and writing while the rest of the boat sleeps. But tonight is not a routine kind of night. It’s a night filled with the first experiences of jubilant friends who, for a few days, I get to share my extraordinary life with.

So, rather than retreat to my routine, I toss my book aside and I lay on the trampoline with John and Chris as we watch dolphins dive and swim beneath us, covered in a sheath of glowing green glitter as their bodies cut through the phosphorescent water, leaving a spray of fireworks in the air every time they jump out of the water.

Our faces are softly lit by the moon as we stare patiently at the water, waiting for the next astonishing thing to take us by surprise.

It’s true, I wouldn’t get much done on any of my night watches if I spent them all lying face down, staring at the water with big eyes full of wonder. But, in this moment, I’m grateful for the gift our guests have brought us – the gift of experiencing something extraordinary for the first time, again.


guests sailing for the first time again turf to surf
John, holding up his first catch. He smiled like this for 3 days nonstop.

Update from Tasha

Hey everyone! If you haven’t yet seen our video of John swimming with pilot whales on Chase the Story, our YouTube Channel, check it out here! I promise it will make you smile:

And if you like it, click the SUBSCRIBE button so you don’t miss our weekly updates! We’ve been working hard on editing videos so we’d love it if you could share it and give us feedback in the comments!

Thanks everyone for reading and watching – I really appreciate it!



0 Comments... Be the first to comment
  • Chris March 3, 2016, 12:10 pm

    Oh wow, Tash – thanks so much for such lovely words, and for recording one of our all-time best experiences!
    Sharing it all with you all was wonderful, and I hope we can do it again one day – though topping our dolphin-and-whale experience won’t be easy! Xxx

  • John March 11, 2016, 1:56 pm

    Thanks a lot Tasha, we had such a brilliant time and reading the post brought it all back to us!! As Chris says, we hope we can repeat the experience another time. Xxxx

    • Tasha March 12, 2016, 9:54 am

      You guys are welcome back on board ANY TIME! It was so wonderful to sail with you guys through the Med – let’s pick another destination and make it happen!

  • Paula October 29, 2016, 5:29 pm

    I loved this video, mostly because of John and Chris and their open enthusiasm and enjoy the moment – every bit of it – attitudes. Cant help but think that they wouldnt leave you in repairs while off at the bar drinking – John would be right in there trying to take part in another experience! Im smiling now just from second hand enjoyment of their enjoyment!

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