Fly Personal In The Caribbean

On demand, anywhere you need us.

First-class island hopping throughout the Caribbean. Seamless connections to St Barths, the BVI, USVI, Anguilla, St Kitts and Nevis, Antigua, Dominican Republic, and beyond!

Caribbean Private Charter Experience

Premium Aircraft

Our in-fleet Pilatus PC-12 aircraft are excellent options for short to medium-range flights. For larger groups and longer distances, we’ll secure the best medium and large cabin options from our trusted network of operators.

Convenient Transfer Hubs

Fly through San Juan, PR and easily connect with virtually all major airlines from the U.S. Direct flights from Canada, Europe and South America are also available. Fly to Antigua from London on British Airways or Virgin Atlantic for a convenient one-stop transfer to St Barths.

All Tradewind guests connecting through San Juan can relax and enjoy refreshments and complimentary WiFi in our private lounge. Once ready for boarding, guests are escorted through expedited security screening and directly out to the awaiting aircraft.

Complimentary VIP Experience

Our popular VIP Experience in San Juan is complimentary for private charter guests for a seamless transfer between flights. A Tradewind representative will meet you at the arriving airline gate and escort you to the Tradewind private lounge. Luggage is retrieved by a Tradewind representative and checked in while you relax in comfort and style.

Private Jet Connections

Connecting from another private jet? Our team will meet your aircraft arrival for a smooth transfer to your awaiting Tradewind connection.

Private Flights in the Caribbean

Discover the best way to travel throughout the Caribbean in the Tradewind-operated modern fleet of Pilatus PC-12 aircraft. Our San Juan hub features VIP transfers, an exclusive private lounge, and expedited security and boarding. Conveniently transfer from an airline or private jet and fly to your destination in comfort and style.

For frequent flyers, our Goodspeed Card Program offers block time discounts within our service regions in our Pilatus PC-12 fleet and other membership perks.

Book Your Next Trip

Close-up of a private charter aircraft on the tarmac, with the name 'TRADEWIND' visible on the fuselage.

Goodspeed Card Program

Fly with Freedom with a Goodspeed Charter Card. Take advantage of significant savings and simplified pricing on private charter in the Tradewind fleet of Pilatus PC-12 aircraft.

SIMPLE & TRANSPARENT

Pay only for the time you fly. No repositioning fees
No initiation or membership fees, peak day surcharges or blackout dates
Cancel up to 24 hours prior to departure with no penalty
No lead time requirement. Book a trip at your convenience
Access to smaller runways like Montauk, Fishers Island, and Provincetown
Three convenient service regions: Northeast U.S., Southeast U.S., and Caribbean

COMPETITIVE PRICING

20-30% less expensive than comparable programs
20% discount on day trips
Discounts on Tradewind Scheduled Service routes
Discounted charter rates starting at only 10 hours
Referral program available

Card Level	Hours	Rate
Goodspeed 10	10	$5,450
Goodspeed 25	25	$5,300
Goodspeed 40	40	$5,110

*Discounts based on retail rate of $5,700

Subject to fuel surcharge, FET and international fees where applicable.

Contact a Charter Specialist Today

Aircraft Options

Turbo Prop

A propeller aircraft labeled 'TRADEWIND' flying against a clear blue sky with wispy clouds.

Light Jet

Mid and Super Mid-Size Aircraft

Large Jet Aircraft

A private charter parked on the tarmac at sunset, with the sun casting a warm glow.

Turbo Prop

Light Jet

Mid and Super Mid-Size Aircraft

Large Jet Aircraft

Pilatus PC-12

A Proven Performer! The ultimate in comfort, reliability, and safety, the Pilatus PC-12 features a pressurized and air-conditioned cabin with equal and ample room for 8 passengers. On scheduled routes, the Pilatus is configured with 8 forward-facing seats, which allows for more room for luggage. Private service is operated in an executive-configured aircraft featuring a four-person club plus two rows of forward-facing seats and a fully enclosed lavatory.

View Gallery

View Range Maps

300 mph

Cruise speed

20,000 ft

Cruise level

1,700 mi

Range

6 - 8

Passengers

100 sqft

Luggage

NORTHEAST RANGE MAP

SOUTHEAST RANGE MAP

CARIBBEAN RANGE MAP

Light Jet Aircraft

Should your trip require a larger cabin or longer range than our in-fleet Pilatus PC-12s, we will happily assist you with securing the ideal aircraft for your journey. Each operator is vetted to ensure a strong safety record and high level of service. As an operator ourselves, we know just what to look for and the necessary questions to ask. We’ve booked trips for clients like flights from New York to Antigua on a Challenger 350, a Super-mid jet. Our reach includes all the latest models of Mid-size jets, including Falcon, Challenger 350, Hawker and Citation Xs, among others.

Tradewind is a Part 135 operator of Pilatus PC-12 aircraft. Any travel arranged by Tradewind using a different aircraft type is neither owned nor operated by Tradewind.

View Gallery

525 mph

Cruise speed

45,000 ft

Cruise level

1,875 mi

Range

4 - 7

Passengers

65 sqft

Luggage

Mid and Super Mid-Size Aircraft

Should your private chartered flight require a larger cabin or longer range than our in-fleet Pilatus PC-12s, we will happily assist you with securing the ideal aircraft for your journey. Each operator is vetted to ensure a strong safety record and high level of service. As an operator ourselves, we know just what to look for and the necessary questions to ask. We’ve booked trips for clients like a round trip from Zurich to Miami on a Global Express, a large cabin jet. Our reach includes all the latest models of Large cabin jets including Gulfstream and Global Express, among others.

Tradewind is a Part 135 operator of Pilatus PC-12 aircraft. Any travel arranged by Tradewind using a different aircraft type is neither owned nor operated by Tradewind.

View Gallery

650 mph

Cruise speed

45,000 ft

Cruise level

3,500 mi

Range

6 - 10

Passengers

1,000 sqft

Luggage

Large Jet Aircraft

Should your trip require a larger cabin or longer range than our in-fleet Pilatus PC-12s, we will happily assist you with securing the ideal aircraft for your journey. Each operator is vetted to ensure a strong safety record and high level of service. As an operator ourselves we know just what to look for and the necessary questions to ask. We’ve booked trips for clients like a round trip from Zurich to Miami on a Global Express, a large cabin jet. Our reach includes all the latest models of Large cabin jets including Gulfstream and Global Express, among others.

Tradewind is a Part 135 operator of Pilatus PC-12 aircraft. Any travel arranged by Tradewind using a different aircraft type is neither owned nor operated by Tradewind.

View Gallery

650 mph

Cruise speed

51,000 ft

Cruise level

8,000 mi

Range

10 - 16

Passengers

1,000 sqft

Luggage

Partner Experiences in the Caribbean

Rosewood Little Dix Bay

Guests who fly Tradewind scheduled service to Virgin Gorda and stay 3+ nights at Rosewood Little Dix Bay will receive complimentary VIP Experience for their transfer in San Juan ($300 value), while private charter guests receive a 5% discount. Once at Rosewood Little Dix Bay, guests receive between $150-$400 resort credit based on the booking room category.

Learn More

Casa de Campo

Exclusive for Goodspeed Card Members, fly to La Romana with Tradewind and stay at Casa de Campo Resort & Villas to receive a $500 resort credit per stay, 5% off any Exclusive or Ocean Front Villa category, complimentary airport pickup and return from the airport, private VIP services, and welcome amenities.

Learn More

Zemi Beach House

Guests who fly Tradewind scheduled service to Anguilla and stay 3+ nights at Zemi Beach House will receive complimentary VIP Experience for transfers in San Juan. Private charter guests receive a 5% discount on their air travel. Once at Zemi Beach House, receive between $150-600 daily hotel credit and a welcome amenity.

Learn More

Altamer Luxury Villas

Unwind on Anguilla’s Shoal Bay West with this offer from Tradewind and Altamer Luxury Villas. Receive a 5% discount on your round-trip private charter, as well as a choice of one complimentary add-on experience during your stay.

Learn More

Nevaeh Villa Anguilla

Guests who fly Tradewind scheduled service to Anguilla and stay at Nevaeh Villa Anguilla will enjoy complimentary VIP Experience for their transfer in San Juan ($300 value). Tradewind private charter guests will receive a 5% discount on their travel. Once at Nevaeh, Tradewind guests will enjoy a complimentary welcome barbecue dinner serenaded by a guitarist.

Learn More

Fairmont El San Juan Hotel

The Romance Package at Fairmont El San Juan Hotel includes everything couples need for a romantic weekend to set the stage for an unforgettable proposal.

Learn More

Hotel Le Toiny

Visitors who book this experience and check into a luxury one bedroom suite at Hotel Le Toiny will enjoy a private pool, VIP amenities including full daily breakfast, access to a full mini bar, and a special bottle of champagne.

Learn More

Discover all partner experiences