Empty Leg Flights to the Caribbean: Winter Escape Deals on Private Jets

The Caribbean: Winter's Premier Empty Leg Destination

When temperatures drop along the US East Coast, a predictable migration begins. Hundreds of private jets depart from Teterboro, Westchester, Palm Beach, and Fort Lauderdale bound for the turquoise waters of the Caribbean. St. Barths, Turks and Caicos, the Bahamas, Barbados, and the US Virgin Islands all see enormous surges in private aviation traffic from November through April.

This seasonal flow creates one of the most reliable sources of empty leg flights in global private aviation. Jets deliver passengers to island paradises and then need to fly back — often empty — to their US bases for the next charter. These repositioning flights are available at 50% to 75% off standard charter rates, making a private jet trip to the Caribbean far more accessible than most people realize. Browse current Caribbean deals on VOLO's empty leg marketplace.

Top Caribbean Empty Leg Routes & Corridors

The Caribbean empty leg market centers on a handful of well-established corridors from the US mainland:

• Teterboro (TEB) / White Plains (HPN) → St. Barths (SBH) — The crown jewel of Caribbean private aviation. St. Barths' short runway (2,100 feet) limits access to smaller aircraft, meaning light jets and turboprops dominate this route. Return legs from SBH are among the most sought-after empty legs during the holiday season, appearing at $12,000–$18,000 versus $28,000–$40,000 standard.
• Fort Lauderdale (FXE) / Miami (OPF) → Nassau (NAS) / Exuma (GGT) — The Bahamas are just a 45-minute hop from South Florida, creating extremely high turnover of short-haul charters. Empty legs on this route drop as low as $3,000–$6,000 on light jets, making private aviation to the islands genuinely competitive with premium commercial options.
• Teterboro → Providenciales (PLS), Turks & Caicos — A favorite destination for the New York finance crowd. This 3.5-hour route on midsize jets generates consistent northbound empty legs from December through March, typically priced at $14,000–$22,000 versus $35,000–$48,000 standard.
• Palm Beach (PBI) → Barbados (BGI) / St. Kitts (SKB) — The southern Caribbean attracts travelers seeking less crowded alternatives. Longer routes to Barbados produce particularly attractive empty leg deals on heavy jets.
• Various US → US Virgin Islands (STT/STX) — St. Thomas and St. Croix have larger airports that accommodate jets of all sizes. This corridor sees strong traffic from both the Northeast and Southeast US, with empty legs available in both directions throughout winter.

Seasonal Patterns & Best Timing

The Caribbean empty leg calendar follows a clear seasonal rhythm tied to US vacation patterns:

• Thanksgiving Week (late November) — The season opener. Private jet traffic to the Caribbean spikes dramatically as families fly south for the holiday. Return legs back to the US after Thanksgiving weekend are among the first high-quality empty legs of the winter season.
• Christmas and New Year (mid-December – early January) — Peak of peaks. St. Barths, in particular, becomes the epicenter of luxury travel during the holidays. Private jets queue up at Gustaf III Airport (SBH), and repositioning flights from the Caribbean back to the mainland are plentiful from December 26 through January 3. This is the period with the highest volume of deals but also the fastest booking pace.
• Presidents' Day / February Break (mid-February) — A second wave of demand from school holiday travelers. The Bahamas and Turks and Caicos are primary beneficiaries, with empty legs appearing most frequently on the return journey.
• Spring Break (March–April) — The final major wave of winter Caribbean travel. College-age and family travelers maintain demand through Easter. Empty legs become slightly easier to find as overall demand begins to soften toward the end of the winter season.
• Off-Season Opportunity (May–October) — While overall traffic drops, some operators keep aircraft in the Caribbean year-round. Repositioning flights at the start and end of hurricane season can produce exceptional deals for flexible travelers.

How Much Can You Save?

Caribbean empty legs offer compelling value, especially when shared among a group:

• Turboprops (King Air 350, Pilatus PC-12) to Bahamas/short hops: Standard charter $4,000–$8,000 → Empty leg $1,500–$3,500
• Light jets (Phenom 300, Citation CJ3) to Bahamas/Turks & Caicos: Standard charter $14,000–$28,000 → Empty leg $6,000–$12,000
• Midsize jets (Citation Latitude, Learjet 60) to St. Barths/Virgin Islands: Standard charter $25,000–$45,000 → Empty leg $10,000–$20,000
• Heavy jets (Challenger 604, Gulfstream G-IV) to Barbados/southern Caribbean: Standard charter $40,000–$70,000 → Empty leg $18,000–$32,000

For the Bahamas in particular, a group of four sharing a light jet empty leg from Fort Lauderdale to Nassau could pay as little as $800–$1,500 per person — less than a round-trip commercial ticket, yet with private terminal access, zero security lines, and a 45-minute flight time.

Tips for Booking Caribbean Empty Legs

The Caribbean market has unique characteristics that experienced empty leg seekers should understand:

1. Know the airport limitations — St. Barths (SBH) can only accommodate aircraft up to about 20 seats and requires specially certified pilots due to its steep approach. Turks and Caicos (PLS) handles all jet sizes. Some smaller islands have weight and wingspan restrictions. Check aircraft compatibility before booking.
2. Consider turnaround flights — Many operators offer discounted turnaround deals where you fly to the Caribbean on a standard charter and the return is priced as an empty leg (or vice versa). VOLO's team can help structure these arrangements for maximum savings.
3. Book the return, fly commercial one way — If no empty leg is available for your outbound journey, book commercial to the island and snag an empty leg for the return. Or book an empty leg southbound and fly commercial home. This hybrid strategy often captures significant savings on at least one direction.
4. Act fast during the holiday season — Between Christmas and New Year, Caribbean empty legs are claimed within hours of being posted. Set up real-time alerts on VOLO's empty leg page for your target island and be prepared to book immediately when a match appears.
5. Factor in customs and immigration — International Caribbean flights require customs clearance at both ends. Your FBO will handle this, but allow 30–60 minutes in your schedule for processing. This is still dramatically faster than a commercial airport experience.

Find Caribbean Empty Legs with VOLO

VOLO's Caribbean empty leg inventory peaks every winter, with new deals appearing daily from November through April. Our platform aggregates repositioning flights from operators across the US East Coast and Southeast, giving you real-time visibility into available flights to the Bahamas, Turks and Caicos, St. Barths, Barbados, and dozens of other Caribbean destinations.

A winter escape on a private jet does not have to carry a six-figure price tag. Empty legs make it possible to experience the convenience, comfort, and speed of private aviation at a fraction of the standard cost. Explore current availability on our empty legs page or reach out to our Caribbean empty leg specialists to set up alerts for your preferred island destinations. The earlier you start monitoring, the better your chances of catching the perfect winter deal.