French Polynesia, Thailand, Croatia, Fiji, Indonesia, Vanuatu, Papua New Guinea, the Seychelles, Greece, or the Caribbean? It turns out that’s a really, really tough question to answer.

Praslin and Cousin
My friend Travis (if you’ve followed this blog for a while, you’ll remember him from my time on the TMB) had planned to charter a boat this summer. Originally, I was just going to stop by for a week or two to visit, but when he realized that I was going to get my certifications, he invited me along to skipper for the length of the trip.

Lazio Beach
Travis initially planned to sail in French Polynesia but ultimately decided it would be worth investigating other options. With the early plan out the window, we spent several months talking about the trip, researching the world’s best sailing destinations, negotiating with charter companies, and having regular Skype calls, as we both bounced around different corners of the world.

La Digue Harbor
We have similar travel styles and both like to keep our travel options open as long as possible so, unsurprisingly, we found ourselves with time running short and no decision yet as to where we would sail. To nail things down, I popped over to Seoul, South Korea to meet Travis and spend several days ironing out the details.

Sunset on La Digue
We pored over all our options over three hectic days:
“French Polynesia would be amazing, but it’s challenging sailing, plus we’d be limited to the Societies and probably can’t handle the big reef breaks.”
“What about Croatia? It’s been hot for a few years, but it’s supposed to be great sailing and a ton of fun.”
“Vanuatu!!! Except they won’t let us bareboat.” [Translation: We’d need to hire a captain.]
“We could go to Indonesia, but … pirates.”
“Nobody goes to Papua New Guinea. It’s supposed to be stunning.”
“There’s always the Caribbean.”

Squall off Mahe
We could go anywhere in the world and suffered for it. We soldiered on, though, making the most of Seoul’s ridiculously fast wifi to sift through one dream destination after another, raising, rejecting, and resurrecting a dozen different possibilities.

Ready to Chow Down
Ultimately, we decided to split the planned 8-week trip in two; we’d spend the first month in the Seychelles and the second in another destination that we’d choose once we’d been in the Seychelles for a while and knew a little more about what we were looking for.

Grand Anse, La Digue
We booked flights for the small granite outcropping in the middle of the Indian Ocean and began negotiating for a boat. We landed on Mahe, by far the largest of islands and the country’s on “major” population center (in my book, 65,000 people warrants quotes around major). Mahe is home to the capital city Victoria and the major tourist center at Beau Vallon.
Negotiations with the international charter agencies were going slowly so we decided to cut out the middle man. We made our way to the Eden Island, the newest and largest private marina in the Seychelles and ultimately our headquarters for our time in the Seychelles, and began roaming the dockside offices of the local charter companies.

Hiking on Cousin Island
On our first stop, we ran into Stefanie, an interesting and knowledgeable French expat whom Travis had been exchanging emails with for several days. We had a great conversation with her laying out our needs and by late afternoon the next day we were booked on the Julienas, a 47-foot Jeanneau Sun Odyssey located on Praslin.
An hour after signing on the dotted line, we were airborne on our way to Praslin, the nation’s second largest island, so we could pick up the boat the next day.

Sunset on La Digue
We arrived at the marina in Baie St. Anne in the late morning, stopped by the local market to provision, and then headed aboard for the boat and navigation briefings. With all the details taken care of, we headed out of Baie St. Anne to begin exploring the tropical Indian Ocean paradise.