Saint Martin, The Friendly Island

Cruising for Saints in the Caribbean Day 10: A day on the French and Dutch Island of Saint Martin with sailing on the prized Stars and Stripes Yacht then chilling on the beach!

Arriving in the Dutch port of we debarked and split up. The men of the group were going on a tour while the ladies went to the beach.

“America’s Cup” 12 Metre Regatta

We were joining a highly rated activity which involved manning a yacht and racing two other yachts.

A guy from the yacht club picked us up and walked us over to a neighboring port area. He gave us an introduction of America’s Cup and the yachts that we had a chance to run. The options were the two Canadian boats, True North and Canada II, and the prize winning American, Stars and Stripes.

He randomly picked team captains and with a coin toss, we won the Stars and Stripes! YES!

The Stars and Stripes 87 went to Fremantle, Australia to win the Regatta and bring the cup back to the USA. It was one of the last single hull yachts to compete as the cup soon evolved to multihull boats.

We were about to sail on a very fast piece of history.

The entire group boarded a slow transport ship that transferred the passengers between the yachts.

On board, the crew introduced themselves and gave us a rundown on how to sail the yacht. Each person was assigned a task, from time keeper to grinder. As we wanted to contribute, we were all assigned as grinders and our job was to man the winches to pull in or let out and haul up or bring down the sails. It’s the most active of the jobs. Our captain explained the terminology and how to respond to commands.

Soon enough we were off and raced around Great Bay. We developed a surprising camaraderie as soon as we left the port and maneuvered our yacht to the 1st place position. In the end, we were crowned the victors!

The whole challenge was exciting and intense, but relaxed enough that we had time (barely) to refresh with a beer.

After the race, we joined the transport boat then went to the club house were there were complementary drinks and souvenirs for sale.

Our group then joined the others at the beach. We drove across the border from the Dutch side to the French side. There was no border crossing, but there were signs to indicate the border.

Plage di Orient Bay

Our group was hanging out at Sun Beach Clubber. We joined them for drinks and lounging on the beach.

Of course a walk to the infamous nude section of the beach was a must. Though, once we got there, reality set in to replace our imagination of what a nude beach would look like… Let’s just say eye candy was not to be found.

Towards late afternoon, we packed up and headed back to the ship. What a great last island to explore!


About David

Founder and writer at, David is on a mission to travel to every country in the world and has less than 10 countries left! He loves new adventures, unique cultures, historic landmarks, and luxurious hotels. Follow along as David shares a journey of a lifetime!