St. Thomas by private jet is one of those trips that feels almost absurdly good the moment it starts. You land in Charlotte Amalie, step off the plane into the warm Caribbean breeze, and within an hour, you are watching your kids stare out a yacht window at water so clear it looks artificial. No commercial layovers in Miami, no connecting island-hoppers, no dragging heavy carry-ons through customs lines with a seven-year-old. Just the islands.

June is the sweet spot for this trip with a family. The Atlantic trade winds keep the air comfortable, the ocean is perfectly warm for swimming, and the winter crowds have cleared out, leaving the beaches beautifully open. Here is a 5-day plan that covers the highlights of the U.S. and British Virgin Islands without rushing.

GETTING THERE: CYRIL E. KING AIRPORT IS YOUR GATEWAY

Private aircraft arriving in St. Thomas fly into Cyril E. King Airport (STT/TIST). It features an excellent Fixed-Base Operator (FBO) setup capable of handling everything from light cabins to ultra-long-range heavy jets. By flying private, you bypass the main terminal hustle entirely, transitioning from the tarmac to a private chauffeured SUV in minutes.

St. Thomas is compact, but the island’s steep, winding spine can make ground travel slow. For an elevated arrival, you can arrange a seamless helicopter transfer from the airport FBO directly to select resort helipads or over to neighboring St. John.

Alternatively, if you are heading straight to a luxury villa or a charter yacht, a private luxury van can whisk you to the yachts at Yacht Haven Grande marina in under 20 minutes, bypassing the commercial taxi traffic completely.

WHERE TO STAY

For families who want space, privacy, and world-class service, The Ritz-Carlton, St. Thomas at Great Bay is exceptional. It sits on a quieter stretch of the island, offering a gorgeous infinity pool, dedicated kids’ activities, and its own private 65-foot luxury catamaran, Lady Lynsey II.

If you prefer ultimate seclusion, renting a private luxury estate cliffside in Peterborg offers sweeping views of Magens Bay and plenty of room for extended family.

Pro tip: If you plan to travel during the June sweet spot, book your villa or resort beachfront suites at least four to six months in advance.

DAY-BY-DAY ITINERARY

DAY 1: ARRIVE AND DECOMPRESS

Arrive in St. Thomas, clear customs quickly through the private terminal, and transfer to your resort or villa. Dedicate your first afternoon to doing nothing ambitious. Walk the beach, let the kids splash in the gentle surf, order a fresh tropical dinner on the water, and let everyone unwind from travel.

DAY 2: PRIVATE YACHT CHARTER TO ST. JOHN

This is often the best day of the trip. Charter a private luxury power catamaran for a full day exploring the pristine waters of the Virgin Islands National Park on neighboring St. John. Have your captain drop anchor at Honeymoon Beach or Maho Bay, where the kids can snorkel alongside wild sea turtles in calm, shallow water.

Enjoy a private lunch catered onboard or pull right up to a floating taco bar like Lime Out in Coral Bay. Arrive back at your resort just as the sun dips below the horizon.

DAY 3: MAGENS BAY AND HIGHER VIEWS

Spend the morning at Magens Bay, consistently ranked among the world’s most beautiful beaches. Because it’s a protected bay, the water is as calm as a swimming pool—ideal for younger kids and paddleboarding.

In the afternoon, head up to Drake’s Seat or Mountain Top for a breathtaking panoramic view of the entire British Virgin Islands chain. Grab a refreshing local drink, let the kids spot the distant islands, and head back down for a quiet dinner.

DAY 4: AN ISLAND-HOPPING DAY TRIP TO JOST VAN DYKE (BVI)

Because you have total flexibility on this trip, dedicate a day to crossing into British Virgin Islands territory. A private speedboat charter can clear customs for you smoothly at Cruz Bay before heading straight to Jost Van Dyke.

Spend the day at White Bay, wading through knee-deep turquoise water to the world-famous Soggy Dollar Bar while the kids build sandcastles on powder-white sand. It’s a quintessential Virgin Islands experience that feels worlds away from the everyday.

DAY 5: HISTORIC CHARLOTTE AMALIE, THEN DEPART

Before your afternoon flight, spend a couple of hours exploring historic Charlotte Amalie. Walk the famous 99 Steps (built from 18th-century Danish brick) up to Blackbeard’s Castle for a quick history lesson that easily holds short attention spans. Pick up some duty-free local treasures along the historic cobblestone alleyways of Main Street.

From downtown, it’s a quick 15-minute drive back to the FBO. Your aircraft will be prepped and waiting on the ramp, ready to fly you back to the mainland overnight or in time for a late dinner at home.

PRACTICAL NOTES FOR FAMILIES

• Terrain: St. Thomas is incredibly hilly with steep, winding roads. If anyone in the family is prone to motion sickness, booking a private SUV transfer rather than open-air island shuttles makes a massive difference.

• Passports: Even though St. Thomas is a U.S. territory, you will need passports if you choose to take advantage of the private boat charters into the British Virgin Islands (like Jost Van Dyke or Virgin Gorda).

• Timing: June offers excellent weather and quieter beaches. Try to plan your trip for early to mid-June before the brief late-summer tropical shower patterns become slightly more frequent.

READY TO PLAN YOUR TRIP?

The Caribbean rewards you immensely for doing it right. The right aircraft, a seamless FBO arrival, and a well-curated itinerary turn an island getaway into a smooth, unforgettable family tradition. If you are ready to map out your next island mission, the team at Holstein Aviation can help you source and secure the perfect aircraft for the journey.