Key West sits 90 miles north of Cuba and roughly four hours by car from Miami — far enough that flying is the only practical option for most weekend trips, close enough to be one of the easier Caribbean-feeling destinations to reach by private jet from the Southeast. From The Jet Guys' home base in Upstate South Carolina, EYW is just under 2 hours by air. The airport's runway length is the single biggest planning consideration for any Key West charter, and it shapes which aircraft the Flight Desk recommends for each trip.
This page covers what you need to plan a private charter to or from Key West: the airport options and their runway constraints, route data for the city pairs The Jet Guys handle most often, what to expect by season, and answers to the questions clients ask before they book. The Jet Guys is a WYVERN Registered Broker and arranges every charter through vetted Part 135 operators.
Key West has one airport on the island and a second 50 miles north in Marathon. Both are runway-constrained for jet operations — the practical ceiling is light through mid-size jets at either airport, with some super-mid jets in cool conditions and weight-planned configurations. Heavy and ultra-long-range jets cannot operate to either airport reliably; for those aircraft the answer is to land at Miami-area airports and continue to Key West by short flight, helicopter, or car.
EYW is the only commercial airport in Key West, sitting 2 miles east of Old Town and the cruise terminal. The single 5,076-ft runway (extended in 2018 from its earlier 4,801-ft length) handles light through mid-size jets without issue and most super-mid jets in cool conditions with appropriate weight planning. Heavy jets cannot reliably operate to EYW. Signature Flight Support runs the only FBO on field.
Marathon sits about 50 miles northeast of Key West on Vaca Key, roughly an hour by car along the Overseas Highway. The 5,008-ft runway is functionally similar to EYW — same aircraft category limits apply. MTH is genuinely useful for clients with property in the middle Keys (Marathon, Duck Key, Islamorada area) or for charter trips that want to skip EYW's slightly busier ramp during peak winter weeks.
For clients arriving on heavy or ultra-long-range jets, neither EYW nor MTH is a viable option. The practical answer is to land at one of the Miami-area private aviation airports and continue to Key West by short flight on a smaller aircraft, helicopter charter, or car (4 hours via the Overseas Highway).
The Jet Guys' Flight Desk handles the connecting leg coordination for clients who need to start the trip on a heavy aircraft. A Miami-to-Key-West flight is roughly 35-40 minutes on a light or mid-size jet.
The Jet Guys don't publish fixed prices because every Key West trip is priced differently. Rates depend on departure city, aircraft category, dates, and operator availability. A summer Tuesday from Atlanta to EYW prices very differently from a Friday-night mid-size jet from New York during Fantasy Fest.
A few factors drive Key West pricing more than others.
Mid-December through April is peak season for Key West. Operators position aircraft into South Florida specifically to serve the broader Caribbean and Florida winter market, and Key West gets premium pricing — especially around Christmas/New Year's, Presidents' Day, spring break, and Easter. Three to six weeks of lead time is sensible for any travel during these windows.
Fantasy Fest is the year's largest single-event peak for Key West aviation outside the holiday weeks. The 10-day festival in late October (October 16-25 in 2026; October 22-31 in 2027) draws heavy weekend traffic on both bookend weekends and concentrated demand for the parade weekend specifically. EYW ramp space tightens, and pricing firms up. Three to four weeks of lead time recommended for Fantasy Fest weekends.
Because EYW and MTH are runway-constrained, light jets and mid-size jets are the most cost-efficient options for direct service. Clients who would otherwise prefer a super-mid or heavy jet often find the math works out better with a light or mid-size direct, vs. a larger jet to Miami plus a connecting flight. The Flight Desk works through this trade-off during planning.
The Northeast-to-Florida and Northeast-to-Caribbean corridors generate steady empty leg flights into South Florida. Empty legs occasionally extend down to EYW, particularly during peak winter months. They require date flexibility but can substantially reduce trip costs. The Jet Guys' Flight Desk tracks empty legs daily.
For a quote tailored to your specific trip, contact The Jet Guys Flight Desk.
Key West has the most pronounced winter peak / summer trough cycle of any U.S. destination outside Palm Beach. Knowing the calendar matters more here than at most domestic markets.
Key West sits at the southwestern end of the Florida Keys, with the rest of the chain stretching back toward Miami. Many private charter clients combine a Key West trip with stops elsewhere in the Keys or in South Florida.
The middle Keys sit about an hour northeast of Key West along the Overseas Highway. Marathon (MTH) is the gateway airport — light and mid-size jets only. Hawks Cay Resort on Duck Key, the Marathon hotel and dining corridor, and the bridges (including the Seven Mile Bridge) all sit in this area. A common alternative arrival point for clients with property or accommodation in the middle Keys.
About 90 minutes northeast of Key West, Islamorada is the sportfishing capital of the world and home to Cheeca Lodge, Islamorada Bay Club, and a concentration of high-end fishing charters. Most charter clients land at MTH (40 minutes' drive) or fly into Miami-area airports and continue by car.
70 miles west of Key West in the Gulf of Mexico, Dry Tortugas is one of the most remote U.S. national parks. Access is by seaplane or boat from Key West only — no private aviation lands at Garden Key. A common day-trip extension for Key West visitors. Seaplane charters depart from EYW.
Miami is roughly a 40-minute flight or 4-hour drive from Key West. For clients combining Miami business or hotel time with a Key West weekend, a Miami-to-EYW connecting flight on a light or mid-size jet is a common pattern. Fort Lauderdale offers the same convenience with FXE as the GA option. See our Miami destination page for more.
About 90 minutes east of Key West by air, the Bahamas (Nassau in particular) is a natural pairing for South Florida and Caribbean trips. EYW has on-field U.S. Customs for return clearance. See our Nassau destination page for more.
90 miles south of Key West and visible from the southernmost point on a clear day. Private charter to Cuba from the U.S. requires specific licensing under U.S. Treasury OFAC regulations and is not a routine charter destination. Worth knowing as context for Key West's geography rather than a typical trip option.
For most charters, Key West International (EYW) is the right choice — it's 10 minutes from Old Town and Duval Street, the 5,076-ft runway accommodates light through mid-size jets and most super-mid jets in cool conditions, and Signature Flight Support runs the on-field FBO with full services. Marathon (MTH) is the right choice for clients with property or accommodation in the middle Keys (Marathon, Duck Key, Islamorada area) — same aircraft category limits as EYW but less ramp congestion during peak winter weeks. For heavy and ultra-long-range jets, neither airport is viable; the answer is to land at Miami-area airports and continue by short flight, helicopter, or car.
No, not reliably. The 5,076-ft runway at EYW and the 5,008-ft runway at MTH both restrict heavy and ultra-long-range jets in nearly all operating conditions. The practical answer for clients arriving on a heavy jet is to land at one of the Miami-area private aviation airports — OPF, FXE, or FLL — and continue to Key West by light or mid-size jet (40 minutes flight time), helicopter charter, or car (4 hours via the Overseas Highway). The Flight Desk handles the connecting leg coordination.
Pricing depends on departure city, aircraft category, dates, and operator availability. Winter season (mid-December through April) firms up pricing significantly, especially around major holidays, Presidents' Day, and Easter. Fantasy Fest in late October creates a sharp event-specific spike. Summer is the year's most flexible pricing window. Because of EYW's runway constraints, light jets and mid-size jets are typically the most cost-efficient options for direct service. The Jet Guys' Flight Desk provides fixed-price quotes through vetted Part 135 operators — request a quote here.
Occasionally — the Northeast-to-Florida and Northeast-to-Caribbean repositioning corridors generate steady empty leg flights into South Florida, and some extend down to EYW during peak winter weeks. Empty legs require date flexibility but can substantially reduce trip costs. The Jet Guys' Flight Desk tracks empty legs daily.
Fantasy Fest 2026 runs October 16-25, 2026 — the 10-day costume and street festival that's the year's largest single non-holiday demand event for Key West aviation. The 2026 theme is "Musical Icons & Iconic Musicals." The grand parade on Saturday October 24 typically draws the heaviest aviation traffic. Three to four weeks of lead time recommended for the bookend weekends; longer for the parade weekend specifically. (Looking ahead: Fantasy Fest 2027 is October 22-31; 2028 is October 20-29.)
Hurricane season runs June 1 through November 30, with peak risk from August through mid-October. Key West has been affected by significant storms historically (most recently Hurricane Ian in 2022), and trip insurance is worth considering for any travel during this window. Operators monitor named-storm activity closely and rebook trips when systems threaten the Keys — typically with 24-48 hours of flexibility. For September and early October travel especially, the Flight Desk discusses contingency planning during booking.
Roughly 2 hours 20 minutes from Greenville-Spartanburg International (GSP) or Greenville Downtown (GMU) to EYW. This is well within the range of any light jet for a 6-passenger trip; a mid-size jet handles 7-8 passengers with full luggage comfortably and is often the right choice for the runway considerations at EYW.
Yes — Key West pairs naturally with Miami (40-minute flight, see our Miami page), Nassau in the Bahamas (90-minute flight, see our Nassau page), and Palm Beach (1 hour 15 minute flight) for multi-stop Florida and Caribbean itineraries. A common pattern: Miami business Tuesday, Key West weekend, Nassau Monday, then home Tuesday. The Jet Guys' Flight Desk regularly builds multi-stop routes through one aircraft and crew. Contact us to discuss your routing.
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