After a full day of racing, there’s nothing I want to do more than put the boat away and hit the rum tent. I need some separation between my body and the boat. When asked if I want to spend the night on a boat, what I actually hear is, “Do you want to sleep in a pile of recycling that we keep down in a wet cellar? There’s a bathroom right by your head.”

So no, I am not a cruiser. But when my husband, Trevor, and I were given the chance to enjoy a sailing honeymoon in St. Martin aboard a 40-foot monohull with more square footage than our apartment, we couldn’t resist.

Really, what could go wrong?

We wanted to make sure we made the most of our time in the Caribbean, so we sat down with friends Bill and Renee, one-time St. Martin expats. Their views conflicted on several fronts (mainly which bars were either total dives or totally awesome dives), but both agreed that Saba, an active volcano with less than 2,000 inhabitants, should not be missed. Looking for an adventure, we decided to sail first from St. Martin to Anguilla, then to St. Barts, and finally to Saba.

We touched down in St. Martin on a Friday and were on the boat within 45 minutes. The staff at Horizon Yacht Charters was fantastic and soon briefed us on our Bavaria 40, Brown Eyed Girl. I started to wonder why I had been sailing J/24s all my life.

Our first stop was to meet Kim at The Scuba Shop in Simpson Bay. She outfitted us with scuba gear and gave us an excellent guide to area dive spots. As certified divers, we can set up our own dive spots if we drop a dive flag from the stern or dinghy. Kim provided us with a list of “not to miss” places around St. Barts, where we anticipated doing the most diving.

As quickly as we’d entered St. Martin, we departed, and started our sail around the west coast to Anguilla.

With its expensive cruising permits and high-end lodging, Anguilla is known to be tough on sailors cruising on a budget. Pulling into Road Bay at sunset after the customs office had closed, we decided to keep a low profile until we could clear in the next morning. We grilled steaks on the stern of Brown Eyed Girl, drank Red Stripe and enjoyed our first night on our own. I tried out a recipe for grilled cookies, but these got filed alongside other disappointments in my life, such as “Dance Moves” and “Things I’ve Knitted.”

Anticipating a long haul ahead of us, we set a course for St. Barts early the next morning, but not before stopping at Sandy Caye, an oversized sandbar in Road Bay Harbour. With its lean-to beach bar and pristine beach, Sandy Caye is a tourist hot spot during the high season. In October, the moorings were all empty, and the only sign of an alcoholic beverage was a faded, wind-beaten Heineken sign.

An hour later we were back on the boat rounding Scrub Island, happy to be on our way. Now, more seasoned cruisers might have noticed the darkening skies, the frequent rain showers, the gathering chop. But when you’re on your honeymoon, you live in the moment, relishing the present. So I was fully focused on a perfect rainbow touching down on the cliffs of Tintamarre. Within 30 minutes the rainbow had collapsed into a wicked horizontal rain squall. We abandoned our sprint to St. Barts and instead tried to tuck into Orient Bay on the west coast of St. Martin.

As we approached Orient Bay, Trevor said he was uncomfortable with the water depth. The high seas and encroaching shoal inspired me to pull out Chris Doyle’s Cruising Guide to the Leeward Islands in which the first words on Orient Bay read: “It is unwise to enter this bay in rough conditions.” On average, six charter boats a year run aground here, falling victim to the big seas coming off Ilet Pinel. Our depth sounder indicated we had over 10 feet of water, but with waves and wind both building, we opted instead to head for Oyster Pond just a mile and a half down the coast. Here we found the reefs of the well protected inlet are clearly marked with red buoys. I was soaking wet when we pulled up to the marina’s fuel dock and requested a berth from the harbormaster. With a heavy French accent he replied, “Eh, stay where you are. No one will need the gas tonight.”

Well, isn’t that a good thing.