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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.
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
- 30% discount on day trips & 20% discount on overnight 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 | $5,190 |
Goodspeed 25 | 25 | $5,040 |
Goodspeed 40 | 40 | $4,890 |
*Discounts based on retail rate of $5,440
Subject to fuel surcharge, FET and international fees where applicable.
Private Jet Fleet
Turbo Prop
Light Jet
Mid and Super Mid-Size Aircraft
Large Jet Aircraft
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.
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. Light jets are ideal for trips up and down the coast, such as New York to Florida. Our reach includes all the latest models of light jets including Citation CJ3, Nextant 400XTI, Citation Bravo, Beechjet 400, 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.
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 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 one-way trip 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.
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.
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 ($250 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.
Necker Island
Fly Tradewind scheduled service from San Juan to the British Virgin Islands and receive complimentary VIP Experience at the San Juan Airport for a seamless transfer to your Tradewind flight. Or, book a private charter with Tradewind to the BVI to receive a 5% discount on your airfare.
Stay at Necker Island during an Exclusive Use booking to receive an additional night of complimentary entertainment. Or stay at Necker Island during an Individual Stay to receive $100 credit to be applied to the spa or gift shop.
Cap Juluca, a Belmond Hotel
Guests who fly a Tradewind private charter to Anguilla and stay at Cap Juluca will receive a 5% discount. Those who fly Tradewind scheduled service to Anguilla from San Juan will receive complimentary VIP Experience ($250 value) while scheduled service guests from Antigua or St Barths will receive 5% off. Once at Cap Juluca, Tradewind guests will enjoy an exclusive 10% discount on their hotel accommodation.
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.
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, or a 5% discount on scheduled flights from Antigua or St Barths. 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.
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 personalize your stay at Altamer by choosing amenities from either the Island Bliss Package or Island Explorer Package, or enjoy a discount off standard rates.
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 or a 5% discount for transfers from Antigua or St Barths. 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.
Exclusive Resorts
Experience the vacation of a lifetime, every time. Exclusive Resorts is a members-only club designed for families with a private portfolio of luxury residences and rare experiences. As an exclusive offer to Tradewind Goodspeed Card Members and Ticket Book Holders, become an Exclusive Resorts Member and receive $20,000 off your initiation fee.
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.
Quintessence Hotel
The Champagne, Caviar, and Chocolates package offers one of the most private and most exclusive experience in Anguilla.
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.
Favorite Destinations
Looking for your next adventure? Whether for business or pleasure, Tradewind can take you there.