Aerial view of Beach at Rosewood St Barth — Rosewood le Gounahani

By Kate Van Dell, Founder of Sebastian Luxe Travel

St. Barth is one of those rare Caribbean destinations that manages to be glamorous without trying too hard. The island is small but perfectly formed: a handful of luxury hotels, a constellation of beach clubs and restaurants, and just enough sparkle to feel indulgent without tipping into cliché. It is the kind of place where lunch casually turns into sunset, and every plan feels optional except the really good ones.

When to Go to St. Barth

One of the most common questions I get as a travel advisor is: When is the best time to go to St. Barth? The truth is, it depends on what kind of trip you want.

December – April (High Season): Peak glamour. Yachts in Gustavia harbor, designer caftans at the beach, and the type of crowd you have seen in Town & Country. The weather is perfect, but reservations are tough and prices are steep.
May – July (Shoulder Season): My favorite. Quieter beaches, easier to book, and friendlier on the budget. Still sunny, still chic, with more breathing room.
August – October (Hurricane Season): Many hotels and restaurants close, and the weather can be unpredictable. Not recommended.
October – November (Reopening Season): A sweet spot. The island stretches, wakes up, and reopens with lower prices before the winter rush.

The verdict: Visit St. Barth in fall if you want to feel like you have discovered a secret. Visit in May–July if you want sunshine and savings. Visit in winter if you want the ultimate people-watching scene.

Where to Stay in St. Barth

If you are planning a luxury vacation to St. Barth, your hotel matters. Two of the island’s best resorts, Rosewood Le Guanahani and Cheval Blanc St-Barth Isle de France, offer completely different takes on island glamour.

Rosewood Le Guanahani

Rosewood Le Guanahani is the hotel I recommend for travelers who want elegance with a side of calm. Tucked away on its own private peninsula, it feels like a hidden world: quiet, polished, and unbothered by the island’s louder scenes.

The Lagoon Suite is the star. Two bedrooms, generous space, and direct access to one of the few swimmable beaches on the island. Most St. Barth beaches are public, but here you can roll out of bed and into the turquoise water before breakfast.

Service is warm and intuitive, in that signature Rosewood way. The overall energy is understated luxury, the kind that whispers instead of shouts. And if you are looking for wellness, the spa is serene, restorative, and designed for deep relaxation.

Cheval Blanc St-Barth Isle de France

Cheval Blanc is the island’s high-gloss address. Interiors are sculptural beige, the air is softly perfumed with the brand’s signature scent, and the service is precise down to the millimeter.

It is glamorous in that very French way where lobster is a casual side dish and diamonds at breakfast do not raise an eyebrow. Guests look like they have stepped out of a Tom Ford campaign, and everything from the loungers to the sand feels styled.

The Cheval Blanc Spa by Guerlain is unmissable: cloudlike treatment rooms, indulgent facials, and post-massage tea service you will want to linger over. It is luxury polished to perfection.

Cheval Blanc is fabulous. But one of my most stylish friends stayed at both Cheval Blanc and Rosewood. She adored Cheval Blanc. Then she went back to Rosewood. That tells you everything.

Where to Eat & Lounge in St. Barth

Dining in St. Barth is part of the experience. Here are the best restaurants and beach clubs to add to your itinerary:

Bonito: Elevated but unpretentious, with views over Gustavia that make everyone look 20% more attractive. Best on a Saturday night.
Betula: Sleek, stylish, and one of the most insider-feeling dinner spots.
Nikki Beach: Sunday party chaos with DJs, Champagne showers, and rosé buckets.
Shellona: Barefoot chic on Shell Beach, with grilled seafood and cold rosé.
Tamarin: A lush garden dinner that feels like Nancy Meyers went tropical. The atmosphere is magical, with lanterns and tamarind trees, though the food can be a little uneven. You go for the setting more than the menu.
Eden Rock (Sand Bar, Drinks, or Dinner): Polished, comfortable, and ideal for people-watching. Do not miss the truffle pizza.
Gyp Sea: Boho, barefoot, and charming. Perfect for a lobster lunch that drifts into cocktails.
L’Isola: Classic Italian with dim lighting and excellent pasta. Entrées are not for sharing.
Le Ti: Dinner, costumes, dancing, glitter. Outrageous and unforgettable.

What to Do in St. Barth

Beyond dining and lounging, here are the best things to do in St. Barth:

The Spa at Cheval Blanc: Guerlain facials, world-class massages, and treatments that feel like a dream.
Rent a Boat: Explore turquoise coves, sip chilled rosé, and swim in perfect water.
Actually Use Your Beach: If your suite includes direct access, take advantage. It is rare in St. Barth.
Montaigne Market: A fashion-forward concept store in Gustavia where “souvenirs” look like Celine sandals.
Gouverneur Beach: Wide, wild, and stunning. Bring a picnic and stay all afternoon.
Make Lunch the Sport: The island’s most important ritual. Long, indulgent, and always two bottles deep.

A Weekly Flow in St. Barth

For the perfect St. Barth itinerary, here is how I would map out a week:

Saturday: Dinner at Bonito, 7:30 pm
Sunday: Nikki Beach, 3:30 pm
Monday: Dinner at Tamarin, 9:00 pm
Tuesday: Lunch at Eden Rock (Sand Bar), 2:30 pm
Wednesday: Lunch at Gyp Sea, 2:30 pm; Dinner at L’Isola, 7:30 pm
Thursday: Shellona for lunch, Betula for dinner
Friday: Drinks at Eden Rock, then Le Ti if you are still standing

Pack your linen and leave your stress.

The Sebastian Luxe Travel Guide to St. Barth