One of the things we love about cruising is the virtually limitless options and complete freedom to choose. It’s also one of the hardest things to deal with. Unless you are decisive and have a clear picture of what you want, the questions “Where should we go? When should we leave? How long should we stay?” can circle round and round the chart table. As we travel, we learn our preferences, and as we discover what we love and don’t love, they become guidelines for future travel.

For instance, we have discovered that we don’t love crowded places. It’s one reason why we like to travel in the “off season.” If a cruise ship stops at your port, we will avoid you like the plague. If renting jet-skis is a highlight of your waterfront resort, we shall sail on by. If your beach is rated “#1 in the Caribbean” it is automatically not first in our book, because everyone will flock there to see if it really is the best. So, as we do in every other area of our lives, we choose the road less traveled, and have not regretted it for a moment.

Anguilla, British West Indie

Of the ten boats that left Gorda Sound the same day to travel south, ours is the only one that stopped in Anguilla. We had been told that Anguilla was expensive, that it had no support systems for boats (fuel, marinas, chandleries, etc.), and that “no one goes there.” Our ears perked up. We anchored in Road Bay at Sandy Ground, a little white sand beach lined with local boats and beach bars (Roy’s is our favorite). We made friends with a “belonger” who had moved to an Anguillian tax paradise, and had a lovely evening at the restaurant Veya and talked at length with Chef Carrie Bogar and her husband Jerry, who moved to Anguilla from Pennsylvania with their three kids ten years ago to start over. We found the locals to be exceedingly friendly and helpful, and the beaches rivaled those of the Exumas. It is true that Anguilla does not have support systems for boats, and that they have made their cruising fees prohibitively expensive so that the only way to explore the island is by rental car, and it does seem that people pass it up for more popular spots to the south. But it is also beautiful, the restaurants are top-notch (our favorite places were Ripples, Blanchard’s Beach Shack, and Veya), and rental cars and food stores are reasonably-priced. If one doesn’t mind staying overnight in Sandy Ground, Anguilla is not expensive or hard to enjoy.

Sint Eustatius (Statia), Caribbean Netherlands

Between St. Martin and St. Kitts, there are two little volcanic islands that poke their heads out of the sea: Saba and Statia. People often skip these two places because they are less accessible, have no beaches, and the anchorages are notoriously uncomfortable due to ocean swells. The wind blew us toward Statia, where we shared the mooring field with one other cruising boat, and had the entire volcano to ourselves the day we hiked. Statia is old-world, charming, and has beautiful natural areas to explore. One or two nights here is enough to get a feel for the place, go for a nice hike, and have a cold drink or an ice cream under an umbrella at Mazinga’s. The anchorage is very rolly, and there is an oil terminal on the northwestern side of the island, but all the same, Statia’s history and national parks make it a worthwhile stop.

Nevis, St. Kitts and Nevis

When we checked in at Bassterre, St. Kitts, we really weren’t sure where to go. Neither island had been on our “cruising itinerary,” but we needed a place to stop to wait for weather. I’m sure there are some interesting things to see in St. Kitts, but Basseterre is unattractive and uncomfortable, plus we had to dinghy past a cruise ship to check in, so we were already biased against it. A taxi driver in the crowded cruise ship shopping area attempted to sell us an island tour (right after a jeweler tried to sell us some duty-free diamonds), but we told her we were heading out as soon as possible, probably for Nevis. She said, “No—St. Kitts has more to offer! Nevis is too quiet!” That was all the encouragement we needed. And so we find ourselves in a beautiful place, with new boat friends, enjoying yet another great beach bar, and exploring the amazing history and beautiful natural scenery one finds off the beaten path.