Why We Joined the St. Maarten Regatta: A Weekend of Sailing, Sun & Celebrations
From beach days to regatta parties, our last-minute decision to join the St. Maarten Regatta turned into an unforgettable weekend of racing, relaxation, and revelry.
Why We Decided to Join the St. Maarten Regatta
By early February, our friends kept asking the same question: “Why aren’t you going to St. Maarten for the regatta?”It made us wonder—why weren’t we going? After some discussion and a mad scramble to make last-minute travel arrangements, we were in! Our plan? Stay from Thursday morning through Monday evening to soak in every moment of the regatta experience.
Thursday: Arrival and Wine Tasting in Marigot
Our LIAT flight landed in St. Maarten around 10:00 a.m. We dropped our bags at our hotel and walked into the marina district of Marigot. After a bit of shopping, we enjoyed a leisurely lunch at a French restaurant on the boardwalk.
While exploring, our friends pointed out their favorite wine shop, where the proprietor invited us to a wine tasting that afternoon. Never ones to turn down free premium wine, we eagerly accepted. The selection was so good that we couldn’t resist buying a few bottles.
Tired from our day of shopping and sipping, we returned to the hotel for a quick dip in the pool and a nap before dinner. We knew we needed to rest up for the evening’s regatta festivities—partying was already proving to be more exhausting than expected!
By 10:00 p.m., we were ready to hit the first regatta party at Port de Plaisance. The only problem? We had no idea where it was! Undeterred, we followed a crowd of partygoers and soon found ourselves right in the heart of the celebration.
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Friday: Beach Day & Philipsburg Boardwalk Party
The day was bright and clear, but with almost no wind. While our racing friends scrambled out of bed early, we enjoyed a leisurely breakfast by the pool. By noon, we were lounging on the beach, watching the race fleet drift by in the light breeze.
Having wisely conserved our energy, we headed straight to the second night’s regatta bash in Philipsburg. Again, we had no idea where we were going, but a friendly security guard pointed us in the right direction.
The Philipsburg boardwalk was perfect for the event—lined with shops, restaurants, and small hotels, it provided the ideal backdrop for a massive waterfront party. We strolled along, greeting friends, enjoying the sunset, and soaking in the festival atmosphere.
By 7:30 p.m., the boardwalk was packed and buzzing. Instead of diving into the crowd, we decided to have a quiet dinner in Marigot with cruising friends from Bonaire. It had been another “exhausting” day of beach lounging and shopping, after all.
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Saturday: Exploring Marigot & Grand Case Beach
Once again, the racers were up early, while we slept in. We spent the morning browsing the open-air market in Marigot, where we ran into more friends from St. Thomas. The group decided to head to Grand Case Beach for an afternoon of sun, sea, and relaxation.
At Grand Case, we settled into a beachfront restaurant and spent the afternoon:
✔ Sunning & swimming
✔ Hunting for beach glass
✔ Playing dominoes (I won!)
✔ Watching the racing fleet struggle in light winds
After an early picnic dinner at our hotel, we walked into Marigot for the third big regatta bash. That morning’s marketplace had been transformed into a full-fledged party zone, complete with:
🎶 A live bandstand
🍻 Beer booths
🛍 Official Heineken Regatta gear
We collected Heineken hats, flags, and keychains before making our way to the front of the stage. We danced and sang along with Youth Wave until their set ended around 11:30 p.m. The crowd was massive—locals, racers, tourists, young, old—everyone was there.
After a late-night dinner, we danced our way back to the hotel well after midnight.
Sunday: Friar’s Beach & The Regatta Finale
Our group kicked off Sunday with crepes for breakfast—delicious! Then it was time to recover at Friar’s Beach before the grand finale at Kim Sha Beach in Simpson Bay.
Since we planned to dance late into the night, we decided to pace ourselves throughout the day. Our strategy?
✔ Relax at the beach
✔ Enjoy dinner with friends
✔ Arrive at the final party later in the night
Unfortunately, this turned out to be a mistake.
By 10:00 p.m., we set out for Kim Sha Beach—confident we’d just follow the crowd. What we didn’t anticipate was gridlock traffic. After 30 minutes of barely moving, we realized it would take another 45 minutes to get there.
Exhausted, we turned back and called it a night—missing out on Jimmy Cliff and the fireworks.
Conclusion: A Weekend to Remember
Despite missing the final regatta party, the weekend was a resounding success. As partiers instead of racers, we got to experience the best of both worlds—relaxing by day and celebrating by night.
The Heineken Regatta and the people of St. Maarten/St. Martin know how to throw an unforgettable event. Next year, we’ll be better prepared… and we won’t miss a thing!
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Key Takeaways from Our St. Maarten Regatta Experience
✔ Be spontaneous – Last-minute plans can lead to amazing adventures.
✔ Pace yourself – Regatta partying is not for the faint of heart!
✔ Know your locations – Don’t rely on just following the crowd.
✔ Arrive early for big events – Or risk missing out like we did.
📌 Would we do it again? Absolutely. But next time, we’ll plan better!
Have you attended the St. Maarten Regatta? Share your experience in the comments!
J. Summer Westman has written for ALL AT SEA since 2005.
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