High season runs from mid-December to mid-April—simply because that’s when cold weather sends American travelers to the Caribbean. The rest of the year, prices are slashed by up to 40 percent, but the weather is much the same. And during this “value season,” the island is quieter and less crowded. Shoppers come for the annual sales, which run from May into early June, when there are bargains galore at the island’s boutiques. Everything re-opens in November after hurricane season, so things are fresh and new.

Over Christmas and New Year’s, villas triple in price, and most properties require a two-week minimum stay. It is the see-and-be-seen season for celebrities and pop stars, and the harbor is filled with millionaires’ yachts—but traffic, parking, and restaurant reservations are all difficult and can offset the glam factor. From early September to mid-October, the island goes on hiatus, with many shops and restaurants closing.

Depending on availability, rentals may begin on any day of the week and you can rent for any length of time, but there is a seven-night minimum in high season.

Many first-time visitors think that they need to rent a villa on the beach. Actually, most of St. Barth’s villas are located in its hills and leverage the views and trade winds—not to mention the greater privacy. Each beach has its own personality, so it’s fun to visit several over the course of a trip—and some of the most beautiful ones are undeveloped, so you couldn’t stay there anyway.

Not packing a bathing suit, cover-up, and change of clothes in your carry-on. If your luggage doesn’t make it onto the puddle-jumper in time (there are flights to St. Barth from St. Maarten and San Juan), you’ll still be ready for your first dip in the pool or ocean and dinner out that evening.

Since the island is so small—just nine square miles—visitors should focus on the villa itself and its amenities, as opposed to a specific location. Air-conditioning is a major consideration—especially if you’re prone to mosquito bites: All bedrooms have AC, but many of the living areas are open-air, which is fine when the trade winds are blowing. If you have small children, make sure the bedrooms are close together; in some villas, they are housed in separate pavilions.

You’ll need a rental car to explore the island and its beaches. If you opt for a Suzuki Jimney 4×4 (the best choice for the island), Peg can usually get a seventh-day-free discount, so weekly rentals come out to about 300 to 450 euros (though they are higher over the Christmas holidays). After a long day of travel, it’s also nice to arrive at a villa with a fully stocked fridge (she sends her travelers a grocery list before they travel). Have any other special requests? Birthday parties, in-villa massages, sunset cocktails with a mixologist, snorkeling trips, lunch and dinner reservations—just ask!

A member of Peg’s team meets each traveler at the airport, assists with luggage and rental car pick-up, then guides them to their villa and shows them around the property. Her island staff is on-call for emergencies 24/7, and the concierge is on duty during regular business hours.

Adapters and convertors for your electronic devices: St Barts has 220 voltage, and the outlets only accept plugs with two round prongs.

Unlike some other Caribbean islands, St. Barts is exceedingly welcoming to gay travelers. In fact, now that same-sex marriages are legal in France, the island is a popular wedding spot for gay couples.