Flying to Oshkosh: A Pilot’s First Big Adventure

Author: Hawra Tustari,AGI,IGI |
Pilot Consultant | FAA Ground Instructor
May 19, 2025
Baron N994WY aircraft preparing for takeoff to EAA AirVenture Oshkosh mission at Van Nuys Airport
Baron N994WY Preparing for Takeoff Flying into Oshkosh
(Source Image: Documentation by 14DAYPILOT)

Flying into Oshkosh is a milestone many pilots aspire to. Each year, during EAA AirVenture, Wittman Regional Airport in Wisconsin transforms into the busiest airport in the world welcoming thousands of aircraft and aviation enthusiasts for one extraordinary week of flight, learning, and inspiration.

For Capt. Gema Goeyardi, this journey was more than a flight it was a defining achievement in his aviation career and a proud moment for the 14DAYPILOT Flight Academy.

Flying to Oshkosh AirVenture: Capt. Gema’s Journey from Van Nuys

14DAYPILOT Flight Academy crew assembled at Van Nuys Airport before departure to fly into Oshkosh AirVenture

14DAYPILOT Team & Student at Van Nuys Airport
(Source Image: Documentation by 14DAYPILOT)

Flying into Oshkosh is a milestone every aviator dreams of and for Capt. Gema, that dream took flight at Van Nuys Airport in California. At the controls of a Baron 994 Whiskey Yankee, he began his journey to one of aviation’s most iconic destinations: Oshkosh AirVenture, home to the busiest airport in the world during one extraordinary week each year.

But why is flying into Oshkosh such a revered experience for pilots? Because Oshkosh arrival isn't just a landing it's a rite of passage. For one week, Wittman Regional Airport transforms into a global aviation hub, drawing thousands of aircraft and enthusiasts to celebrate innovation, community, and the joy of flight. From VFR arrivals to the FISK arrival procedure, every approach into Oshkosh is a test of skill and preparation and a moment every pilot treasures.

Read More: The POES Oral Exam Coaching Program: Be the Key to Success?

Adapting Midair: Weather, Decisions, and Real Pilot Training

Capt. Gema piloting through sunset skies before diverting to Lubbock due to Midwest weather on route to Oshkosh

Capt. Gema Diverting to Lubbock Amid Sunset Skies
(Source Image: Documentation by 14DAYPILOT)

Flying into Oshkosh isn’t without its challenges weather, air traffic, and pilot fatigue all come into play. Midway through his journey, Capt. Gema faced thunderstorms sweeping across the Midwest, making it unsafe to continue under IFR. With sharp decision making, he switched to VFR and made a safe, unplanned stop in Lubbock, Texas.

This moment was a powerful reminder: good airmanship isn’t just about reaching your destination it’s about knowing when to adapt, pause, and prioritize safety. For many, flying into Oshkosh can feel daunting. But with the right training and mindset, it becomes a rewarding test of skill.

At 14DAYPILOT Flight Academy, students are trained to handle exactly these kinds of real world situations. Flexibility, precision, and smart judgment are core to the curriculum ensuring that every future pilot is ready not just to fly, but to lead confidently through any challenge.

Read More: How AATD Flight Simulators Cut Your Pilot Training Time

Final Preparation: Mastering the Fisk Arrival Before Flying into Oshkosh

Capt. Gema performing simulator training in Aurora, Illinois, to review FISK Arrival procedures before flying into Oshkosh

Capt. Gema Does Simulator Training for FISK in Aurora
(Source Image: Documentation by 14DAYPILOT)

Before entering the Oshkosh airspace, Capt. Gema made a crucial stop in Aurora, Illinois, to train on a flight simulator and review the unique Fisk Arrival procedure a special visual approach used exclusively during EAA AirVenture.

Flying into Oshkosh is unlike arriving at any other airport, pilots navigate by following colored dots painted on the runway, guiding them to their assigned landing spots. Aircraft arrive in tight sequences, requiring exceptional precision and coordination.

This complex system is what transforms Wittman Regional Airport into the busiest airport in the world during AirVenture, demanding intense focus from both pilots and air traffic controllers. The seamless orchestration of these arrivals showcases the skill and dedication behind the scenes of this legendary aviation event.

Flying to Oshkosh, More Than Just a Flight

Capt. Gema and family camping under the wing of their aircraft during EAA AirVenture Oshkosh experience

Capt. Gema and Family Camp at Oshkosh AirVenture
(Source Image: Documentation by 14DAYPILOT)

After safely flying into Oshkosh, Capt. Gema spent the week immersed in the unique atmosphere of AirVenture camping under the wing, meeting aviation legends, and sharing unforgettable moments with his wife and parents.

This is the true magic of Oshkosh. It’s not just about airplanes or navigating the world’s busiest airport for a week. It’s about the deep connections forged among pilots and enthusiasts, the shared passion for flight, and living out the dream that unites the aviation community.

Read More: Accelerated CPL Training at 59: Nick’s Story with 14DAYPILOT

Looking Ahead: Preparing for Your Own Flying into Oshkosh Experience!

Iconic entrance gate at EAA AirVenture Oshkosh 2024, welcoming pilots and aviation enthusiasts from around the world

Iconic Scene at EAA AirVenture Oshkosh 2024
(Source Image: Documentation by 14DAYPILOT)

Flying into Oshkosh might feel like a distant goal for new pilots, but with the right training and mindset, it’s entirely achievable. At 14DAYPILOT Flight Academy, we emphasize building real skills quickly with our accelerated flight training program so students can confidently take on challenges like the Oshkosh arrival.

Your journey to Oshkosh doesn’t have to take years. With expert guidance, proven training methods, and a focus on practical experience, 14DAYPILOT helps pilots step into their dreams sooner than they expect. When you’re ready, we’ll equip you to fly into Oshkosh and beyond with confidence and purpose.

Beyond Oshkosh: The Pilot Lifestyle Awaits You!

Flying into world-class events like Oshkosh, exploring new cities, and traveling with your family, not as a passenger, but as the pilot in command, is the lifestyle awaiting you.

At 14DAYPILOT Flight Academy, we accelerate your path with proven flight training programs that turn your aviation dreams into real flights. Ready to take off? Start your journey today by connecting with our expert Pilot Consultant.

Flying to Oshkosh: A Pilot’s First Big Adventure

Baron N994WY aircraft preparing for takeoff to EAA AirVenture Oshkosh mission at Van Nuys Airport
Baron N994WY Preparing for Takeoff Flying into Oshkosh
(Source Image: Documentation by 14DAYPILOT)

Flying into Oshkosh is a milestone many pilots aspire to. Each year, during EAA AirVenture, Wittman Regional Airport in Wisconsin transforms into the busiest airport in the world welcoming thousands of aircraft and aviation enthusiasts for one extraordinary week of flight, learning, and inspiration.

For Capt. Gema Goeyardi, this journey was more than a flight it was a defining achievement in his aviation career and a proud moment for the 14DAYPILOT Flight Academy.

Flying to Oshkosh AirVenture: Capt. Gema’s Journey from Van Nuys

14DAYPILOT Flight Academy crew assembled at Van Nuys Airport before departure to fly into Oshkosh AirVenture

14DAYPILOT Team & Student at Van Nuys Airport
(Source Image: Documentation by 14DAYPILOT)

Flying into Oshkosh is a milestone every aviator dreams of and for Capt. Gema, that dream took flight at Van Nuys Airport in California. At the controls of a Baron 994 Whiskey Yankee, he began his journey to one of aviation’s most iconic destinations: Oshkosh AirVenture, home to the busiest airport in the world during one extraordinary week each year.

But why is flying into Oshkosh such a revered experience for pilots? Because Oshkosh arrival isn't just a landing it's a rite of passage. For one week, Wittman Regional Airport transforms into a global aviation hub, drawing thousands of aircraft and enthusiasts to celebrate innovation, community, and the joy of flight. From VFR arrivals to the FISK arrival procedure, every approach into Oshkosh is a test of skill and preparation and a moment every pilot treasures.

Read More: The POES Oral Exam Coaching Program: Be the Key to Success?

Adapting Midair: Weather, Decisions, and Real Pilot Training

Capt. Gema piloting through sunset skies before diverting to Lubbock due to Midwest weather on route to Oshkosh

Capt. Gema Diverting to Lubbock Amid Sunset Skies
(Source Image: Documentation by 14DAYPILOT)

Flying into Oshkosh isn’t without its challenges weather, air traffic, and pilot fatigue all come into play. Midway through his journey, Capt. Gema faced thunderstorms sweeping across the Midwest, making it unsafe to continue under IFR. With sharp decision making, he switched to VFR and made a safe, unplanned stop in Lubbock, Texas.

This moment was a powerful reminder: good airmanship isn’t just about reaching your destination it’s about knowing when to adapt, pause, and prioritize safety. For many, flying into Oshkosh can feel daunting. But with the right training and mindset, it becomes a rewarding test of skill.

At 14DAYPILOT Flight Academy, students are trained to handle exactly these kinds of real world situations. Flexibility, precision, and smart judgment are core to the curriculum ensuring that every future pilot is ready not just to fly, but to lead confidently through any challenge.

Read More: How AATD Flight Simulators Cut Your Pilot Training Time

Final Preparation: Mastering the Fisk Arrival Before Flying into Oshkosh

Capt. Gema performing simulator training in Aurora, Illinois, to review FISK Arrival procedures before flying into Oshkosh

Capt. Gema Does Simulator Training for FISK in Aurora
(Source Image: Documentation by 14DAYPILOT)

Before entering the Oshkosh airspace, Capt. Gema made a crucial stop in Aurora, Illinois, to train on a flight simulator and review the unique Fisk Arrival procedure a special visual approach used exclusively during EAA AirVenture.

Flying into Oshkosh is unlike arriving at any other airport, pilots navigate by following colored dots painted on the runway, guiding them to their assigned landing spots. Aircraft arrive in tight sequences, requiring exceptional precision and coordination.

This complex system is what transforms Wittman Regional Airport into the busiest airport in the world during AirVenture, demanding intense focus from both pilots and air traffic controllers. The seamless orchestration of these arrivals showcases the skill and dedication behind the scenes of this legendary aviation event.

Flying to Oshkosh, More Than Just a Flight

Capt. Gema and family camping under the wing of their aircraft during EAA AirVenture Oshkosh experience

Capt. Gema and Family Camp at Oshkosh AirVenture
(Source Image: Documentation by 14DAYPILOT)

After safely flying into Oshkosh, Capt. Gema spent the week immersed in the unique atmosphere of AirVenture camping under the wing, meeting aviation legends, and sharing unforgettable moments with his wife and parents.

This is the true magic of Oshkosh. It’s not just about airplanes or navigating the world’s busiest airport for a week. It’s about the deep connections forged among pilots and enthusiasts, the shared passion for flight, and living out the dream that unites the aviation community.

Read More: Accelerated CPL Training at 59: Nick’s Story with 14DAYPILOT

Looking Ahead: Preparing for Your Own Flying into Oshkosh Experience!

Iconic entrance gate at EAA AirVenture Oshkosh 2024, welcoming pilots and aviation enthusiasts from around the world

Iconic Scene at EAA AirVenture Oshkosh 2024
(Source Image: Documentation by 14DAYPILOT)

Flying into Oshkosh might feel like a distant goal for new pilots, but with the right training and mindset, it’s entirely achievable. At 14DAYPILOT Flight Academy, we emphasize building real skills quickly with our accelerated flight training program so students can confidently take on challenges like the Oshkosh arrival.

Your journey to Oshkosh doesn’t have to take years. With expert guidance, proven training methods, and a focus on practical experience, 14DAYPILOT helps pilots step into their dreams sooner than they expect. When you’re ready, we’ll equip you to fly into Oshkosh and beyond with confidence and purpose.

Beyond Oshkosh: The Pilot Lifestyle Awaits You!

Flying into world-class events like Oshkosh, exploring new cities, and traveling with your family, not as a passenger, but as the pilot in command, is the lifestyle awaiting you.

At 14DAYPILOT Flight Academy, we accelerate your path with proven flight training programs that turn your aviation dreams into real flights. Ready to take off? Start your journey today by connecting with our expert Pilot Consultant.


Flying to Oshkosh: A Pilot’s First Big Adventure
Hawra Tustari,AGI,IGI
Pilot Consultant | FAA Ground Instructor
info@14daypilot.com

Hawra Tustari is an active aviation blogger who has high interest and expectations for the aviation industry. She is also an FAA Private Pilot who currently on a training to upgrade her licenses. Always up to date with the latest aviation news, Hawra aims to provide the best content on our website to help all pilots alike. We aim to provide flight training guidance and with information related to flying school materials and tips involved how to pass the check ride for all students.

Share article:

Flying to Oshkosh: A Pilot’s First Big Adventure
Hawra Tustari,AGI,IGI
Pilot Consultant | FAA Ground Instructor
info@14daypilot.com

Hawra Tustari is an active aviation blogger who has high interest and expectations for the aviation industry. She is also an FAA Private Pilot who currently on a training to upgrade her licenses. Always up to date with the latest aviation news, Hawra aims to provide the best content on our website to help all pilots alike. We aim to provide flight training guidance and with information related to flying school materials and tips involved how to pass the check ride for all students.

Share article:

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Flying to Oshkosh: A Pilot’s First Big Adventure
Hawra Tustari,AGI,IGI
Pilot Consultant | FAA Ground Instructor

Hawra Tustari is an active aviation blogger who has high interest and expectations for the aviation industry. She is also an FAA Private Pilot who currently on a training to upgrade her licenses. Always up to date with the latest aviation news, Hawra aims to provide the best content on our website to help all pilots alike. We aim to provide flight training guidance and with information related to flying school materials and tips involved how to pass the check ride for all students.

Share article: