Notes

We love the Aqua Mania adventures dinner and booze cruises that leave from the docks behind the Simpson Bay Resort Marina and Spa. Pick a day where the cruise ships aren’t in for your best prices when shopping.

We like to do a little gambling while on island. From the Simpson bay area there are casinos in every direction. We often like to stroll around town and hop into one to try our luck.

Since we always stay on the Dutch side we don’t get to beaches like Orient often, but if you like wind sports that is the spot. A strong onshore wind is a notable feature of that beach. If you don’t like the breeze, you may not like sunbathing on this beach.

We love watching the planes take off and land while enjoying a drink at Driftwood Boat Bar right on the beach at the end of the runway.

If you want the cleanest beaches, and if possible even better food, a day trip to Anguilla might be right up your alley. You can leave from the terminal near the airport or catch a sailboat from a company like Aqua Mania adventures.

A great way to spend the very few poor weather days is a shopping trip to Philipsburg. A charming town with a huge variety of shopping experiences. ProTip: If you’re staying on island and want to save the maximum amount of money, choose a day without cruise ships in port.