St. Barths Then & Now: The Island I Fell in Love With in 2005
- siennasinclaire
- May 8
- 6 min read
Updated: May 14
There are some places in the world that stay with you long after you leave them, not just because they’re beautiful, but because of how they made you feel the very first time you experienced them.
The first time I visited St. Barths was in 2005, long before social media transformed every luxury destination into a backdrop for content and performance. Back then, the island felt quieter, more intimate, and far more mysterious.
It still had glamour — beautiful people, yachts, incredible restaurants, nightlife — but it didn’t feel like it was trying so hard to be seen. There was something more effortless about it then, like you had discovered a hidden little world tucked away in the Caribbean that not everyone fully knew about yet, except the rich.
Today, St. Barths feels very different. The island is way busier now, harder to find parking, louder, more crowded, and much more social. Reservations are harder to get, the harbor is packed with even more yachts, and everywhere you look people are filming, posting, documenting, and trying to capture the perfect St. Barths moment.
Sometimes I miss the slower version of it — the quieter beaches, the calmer dinners, and the feeling that the island still belonged mostly to the people who truly loved it rather than the people trying to show they were there.
And yet somehow, despite all of that, I still love it. Even after all these years, it remains my second favorite island in the world behind the Maldives. Because no matter how much St. Barths changes, there is still nowhere else quite like it.
St. Barths February and November 2005
The Fashion of St. Barths
One of the biggest changes I’ve noticed in St. Barths over the years has been the fashion.
When I first visited back in 2005, and again in 2009, St. Barths was actually much more low key than people would probably imagine today.
The people there still had money, luxury still existed, and the island was absolutely beautiful, but fashion felt way more relaxed and understated. People wore flip flops, shorts, simple beachwear and casual sundresses during the day and even dinner. Nobody was trying that hard. It didn’t feel overly flashy or performative the way parts of the island can feel now.
Even the shopping scene was completely different back then. There were no giant luxury flagship stores lining the streets. No Louis Vuitton. No Hermès. The island was filled with beautiful little boutique stores, many of them French-owned, where the owners carefully handpicked unique pieces themselves. Maybe they carried a few designer shoes or handbags, but the focus wasn’t on massive luxury labels plastered everywhere. It felt more personal, curated and unique.
What I loved about the shopping back then was how curated everything felt. I’ve always loved boutique shopping because you find unique pieces that not everyone else is wearing, and back then St. Barths was full of those kinds of little discoveries.
Today, the island is very different. Luxury stores are everywhere now, and fashion itself has become much more elevated, glamorous, and intentionally styled. And honestly? I do love that part too. I love fashion. I love seeing people dress up. I love the sparkle, the drama, the confidence, and the creativity people bring to the island now.
When I visited in January 2026, I remember seeing a girl casually walking down the street during the day wearing a full-length sequin tank dress, sparkling in the sunlight, and I thought she looked absolutely incredible. It perfectly captured what St. Barths has become.
Places like Nikki Beach especially feel much more fashion-driven now. It’s no longer just about throwing on a bikini and a cover-up before lunch. People coordinate looks with their friends, dress to match the vibe, create full holiday aesthetics, and treat the island almost like part runway, part social scene.
And while I genuinely enjoy that evolution and participate in it myself, part of me still misses the simplicity St. Barths used to have. I miss when the island felt a little more effortless, when luxury whispered instead of shouted, and when style felt less about being seen and more about simply living.
My Naughty Girl Cabaret: Sparkle Collection goes perfectly in St Barths.
Nights in St. Barths
One thing that has never changed in St. Barths is how incredible the food is. No matter how much the island evolves, the restaurants always deliver. What has changed though is the atmosphere surrounding going out. Years ago, dinners felt more relaxed and intimate. People still went out, enjoyed amazing meals, and socialized, but it all felt much more understated and effortless.
Now, going out in St. Barths feels much more social and fashion-driven. The restaurants themselves have become more visually stunning, the crowds more glamorous, and the entire nightlife experience feels far more elevated and performative than it used to.
At times, it almost feels like some restaurants are competing to be the loudest or the most Instagramable, similar to places in Tulum. Years ago, St. Barths nightlife felt chic in a quieter, more natural way. The beauty was in the atmosphere itself, not necessarily in trying to create viral moments or over-the-top productions. Now there’s definitely more of a scene surrounding dinner and nightlife than there used to be.
And honestly, I do love parts of that energy too.
One of the things I’ve noticed most is how much more visually beautiful many of the restaurants have become. My favorite is still Bonito's because the atmosphere there at night is just magical. Between the lighting, the view, the people, and the energy, it perfectly captures modern St. Barths for me.
St Barths Nights Back in 2005 with my aunt Ellen + 2016 with my sister Jordan, Dad + Ellen
💋 Le Ti — My all-time favorite on the island and a place that’s been there since my very first trip back in 2005, and long before that. There’s nowhere else quite like it. If you want something over the top — dinner and a show — this is the place. They have sexy performances, encourage everyone to dress up, get people dancing on tables, and turn the entire restaurant into one big party. It’s the kind of place where everyone is laughing, dancing at their tables, and just having fun all night long.
Le Ti 2026: A lot more wild now
Le Ti 2005 + 2016
💋 Bonito — One of my favorite spots for the atmosphere and the stunning views overlooking Gustavia filled with yachts, especially around sunset. The vibe here is incredible with music, a DJ, beautiful people, and one of my favorite little stores in the front filled with sexy, unique pieces. Their drinks are honestly one of the reasons I love going so much because they’re so creative and delicious. The staff has always been amazing, the food is incredible, and the entire place perfectly captures the modern St. Barths scene for me.
Bonito 2016 + 2026
💋 Rosewood Le Guanahani — This was my first time visiting in 2026 and it almost doesn’t feel like the St. Barths I remember from years ago, which you probably wouldn’t fully understand unless you’ve spent a lot of time on the island. It feels newer, more updated, more polished, more Instagramable, and a little more Caribbean resort-style compared to the older St. Barths feeling I remember. But it’s still beautiful. We ended up going twice for lunch because we loved it so much and had amazing meals both times.
Rosewood 2026
💋 Sella — This used to be a very simple old fish restaurant before transforming into what it is now. The new design is still somewhat minimal, but much more stunning with amazing views and a completely different energy. It definitely has more of that modern Tulum-style atmosphere now with DJs, music, everyone randomly clapping and twirling white napkins in the air, and a much more social scene. And if you go, you absolutely have to order the “Sella Show” dessert at least once because it’s dramatic, hilarious, and part of the fun of the experience.
Sella 2026
💋 Black Ginger — Another newer restaurant on the island and one of my favorite places for Asian food. The staff there is so warm and friendly and they genuinely make you feel like a regular. One night I stopped in just to grab one of their espresso martinis because they made my favorite on the island and I wanted to take it upstairs to Bonito. The guy working remembered me from earlier in the week, made it for free, and told me to enjoy it there. Those little moments are part of what still makes St. Barths special to me. And beyond that, the food is just so good.
💋 Mamo Michelangelo — One of the newer restaurants on the island as of 2025 and probably my favorite restaurant design in St. Barths right now. It’s stunning in this sexy, rustic, intimate Italian way that still feels fresh and elevated. The crowd here also felt very different from many of the newer trendy places. It skewed older, wealthier, and much more what I think of as the classic St. Barths crowd — sophisticated people who probably came in from the yachts rather than influencers trying to create content. The entire atmosphere felt chic, elegant, and much more my style.
Mamo Michelangelo 2026
