“Where was your favorite place?”

Anybody who has sailed to more than three or four countries is sure to get this question over and over and over and over again. And it seems that for most of us cruisers the answer is, “Well, that depends.”

And it’s true. It does depend. Are you talking favorite cruising grounds, favorite country overall, favorite experience, favorite people, favorite what? It’s like asking me what my favorite sandwich is. I mean, come on, I can’t answer that. There’s just too many variables.

But I’ve gone ahead and done it anyway. I can’t help myself. The masses want a freaking list I’ll give them a freaking list.

Now keep in mind here that I’m a milk-run cruiser. My destinations are pretty damn pedestrian compared to many world cruisers.

Looking at my list myself I find it kind of amusing that neither the South Pacific nor the Caribbean made our list. Everyone dreams of the Marquesas, but we didn’t find it to our liking at all. Maybe it was all the rain, maybe it was the incredibly overpriced food, water visibility of zero, petty thievery, or the terrible pizza (four really smelly cheeses have no place on a thin crust). I hardly remember any more, but know that a return trip isn’t in my plans.

As for the Caribbean, unfortunately for the long string of islands in that Sea we visited them on the tail end of our trip. By that point we had become so accustomed to lonely anchorages and a total lack of North American tourists, that to be suddenly inundated by both boats and sunburned feet wrapped in black Tevas was just too much for us. We hated the feeling of being just another tourist, and in cruising the Caribbean, let’s face it, that’s all you really are.

Here goes. My top five. And even at that small number I feel the need to add qualifications to each one. Even writing this I can’t make up my damn mind.

#5 Sri Lanka

All right, so there isn’t really any cruising to be done. All you can really do is get permission to tie up to a crappy floating dock a half mile walk from the road. So for cruising it sucks. But as a destination it rocks. It’s one of those places that you can be sure you’ll never visit in your lifetime unless you are sailing around the world. Because who, other than a few Australian surfers, goes to Sri Lanka on holiday? And really, it is all about the surf here.

This was also the first place Ali and I got to test out our “trust everyone” approach. While in Bangkok, Thailand, a month earlier we had told ourselves that it was time to stop thinking that people were always up to something when they approached us, and instead adopt the approach that they were all genuine and just being nice people. We’d believe that until they proved otherwise. It is a decision that to this day has completely changed the way we travel and interact with the people around us.

In Sri Lanka we wanted to buy a carrom board. A guy overheard us in a store asking about this and said, “You want a carrom board? I’ll just take you to where they make them.” Our initial thought was, “Why?” Then we smiled and said, “Great.” He then spent the entire afternoon with us going from place to place until we walked into a small shop and discovered them building the game boards by hand one at a time. At the end of the day we offered to pay our new friend only to be waved off. The people were that nice all the time. Great weather, great surf, great food, and great people. And this was in the midst of a civil war. Man, I would go back there again.

#4 Ashmore Reef

Pretty much the coolest place we ever moored our boat. A reef smack dab between Darwin, Australia and Bali, Indonesia. In the middle of the ocean all alone, tied to a mooring ball placed there by those ever efficient Aussies. When we arrived an Australian customs boat was there. They came over with a film crew doing one of those reality t.v. shows in which they deploy their speed boats to catch Vegemite smugglers. After they left we had the reef to ourselves for three days. Just us, the sea turtles, and the sea snakes. There was not a trace of wind, and just a faint ripple of white a couple hundred yards away where the little swell hit the reef. It was pretty much the perfect break in the middle of a thousand mile passage.

#3 Red Sea

Well, that’s a pretty general choice isn’t it? Sorry, we loved this section of our trip. The bash north up the Red Sea was really anything but a bash for us. We zipped through the Bab el Mandeb Strait with forty knots on our ass and after that did nothing much besides motor our way north in calm seas.

The Red Sea for us was more about the people and the land bound adventures. The cruising actually was pretty good, and in Egypt the water clarity made diving on reefs pretty exceptional, but in the end it was about more than the boat and the water. We had some amazing experiences in Eritrea, Sudan, and Egypt. It was the first time we felt like, “Hey, we’re really out there now. This is adventure.” In Africa we had experiences that were truly unique. We no longer felt like part of some cruising crowd just passing through.

#2 Greek Isles

These days when I think about cruising around the world again I often think about getting back to the Greek Isles. I could spend years there I think. There seems to be no end to the number of islands available to cruise, and they are all little more than a short daysail away from each other. I don’t actually have any strong favorites here, we just enjoyed them all for the protected anchorages, the swimming, and the cold beers sitting in waterfront taverns while watching the world go by.

#1 Bahamas

This was our very first sailing destination. Ever. Which means we greatly under-appreciated it. The Bahamas are awesome, and not just because they are a daysail away from Florida, or because a million cruisers congregate in George Town every season, but because the water is clear everywhere, the reefs are alive, the water is shallow and the bottom soft sand (perfect for beginner sailors like ourselves), and a safe anchorage is never more than a few miles away. Plus, spearing Grouper and Lobster for dinner will never be easier.

The Bahamas are where we cut our teeth. We had no idea how to sail a boat before our arrival, but by the time we left five months later, we felt completely comfortable on our boat, and we tackled the passage to Panama from there with no hesitation. It has to be the best place in the world to begin a circumnavigation from.