Skyway Enterprises, Inc. is an established FAR Part 135/121 supplemental all-cargo airline headquartered in Kissimmee, Florida. Founded in 1982, Skyway specializes in providing reliable and efficient air cargo services across the Southeastern United States, the Caribbean, and parts of Central and South America. They operate a fleet primarily consisting of Shorts SD3-60 aircraft, well-suited for regional cargo operations. The company emphasizes safety, on-time performance, and customer-focused logistics solutions, serving as a critical link for freight in its operational regions.
Serves as the primary administrative, operational control, and maintenance coordination center for the airline's cargo network.
The facility includes office space for management and operations, and proximity to hangar and maintenance support for its Shorts SD3-60 aircraft fleet.
The work culture at Skyway Enterprises Inc. likely emphasizes safety, efficiency, and reliability, which are critical in the air cargo industry. It's a dynamic environment requiring strong teamwork and problem-solving skills.
The Kissimmee headquarters is central to Skyway's operations, managing flight scheduling, crew assignments, maintenance oversight, and customer logistics for its extensive Caribbean and Southeastern U.S. network.
Skyway Enterprises Inc. primarily focuses its cargo and logistics operations throughout the Southeastern United States, with extensive services to Puerto Rico, the U.S. Virgin Islands, the British Virgin Islands, and numerous other destinations across the Caribbean basin. Their network supports regional air freight, connecting key commercial points and islands, rather than a broad intercontinental global presence.
3900 Merlin Dr
Kissimmee
FL
USA
Address: Miami International Airport (MIA) Cargo Area (Specific office address not publicly detailed)
Serves as a key logistics point for South Florida, facilitating the movement of goods to and from international markets via its network.
Address: Luis Muñoz Marín International Airport (SJU) Cargo Area (Specific office address not publicly detailed)
Facilitates trade and essential goods transport for Puerto Rico and numerous surrounding Caribbean islands.
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As of April 2025, Skyways' leadership includes:
Skyways has been backed by several prominent investors over the years, including:
As a privately held company, Skyway Enterprises Inc. does not frequently publicize executive team changes. No major executive hires or exits have been identified in public records or news announcements in the last 12 months.
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While the exact email format for Skyway Enterprises Inc. is not publicly confirmed, companies of similar size and structure often use common patterns. The most likely domain would be @skywayent.com.
Common formats include [first_initial][last]@skywayent.com (e.g., jogilvie@skywayent.com) or [first].[last]@skywayent.com (e.g., charles.ogilvie@skywayent.com).
Format
cogilvie@skywayent.com
Example
60%
Success rate
JACDEC (Jet Airliner Crash Data Evaluation Centre) • December 7, 2023
A Skyway Enterprises Shorts SD-360 aircraft (registration N806SW, flight SKE303) experienced a nose landing gear collapse upon touchdown on runway 10 at St. Thomas-Cyril E. King Airport (TIST), US Virgin Islands. The aircraft was arriving from St. Croix. No injuries to the crew were reported....more
Aviation Safety Network • October 15, 2019
A Shorts SD3-60-200 cargo plane, registration N386MQ operated by Skyway Enterprises, sustained substantial damage in a landing accident at St. Croix-Henry E. Rohlsen Airport (STX), U.S. Virgin Islands. The nose landing gear collapsed during the landing rollout. Both crew members survived....more
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