Now the Croat is plotting a fifth Games appearance at Paris 2024, in sailing.
Kostelic, 39, spoke exclusively with Olympic Channel about his passion for yachting and admitted: "It's a possibility".
Last November, World Sailing's Annual General Meeting ratified the introduction of a mixed two-person offshore class for the 2024 Games.
And Kostelic admits, "It's definitely something a man should consider. I'm not saying I'm considering it but it's... it's interesting."
Ivica Kostelic toys with idea of becoming Olympic sailor
Ivica Kostelic toys with idea of becoming Olympic sailorCroatia's four-time alpine skiing silver medallist is considering a tilt at Paris 2024 in a new offshore sailing class.
Sailing is just one of many passions Kostelic has along with history, playing guitar, trekking in the Arctic, and, of course, skiing.
Olympic Channel: Can you tell us about your love for sailing?
Ivica Kostelic: Sailing is a different way of enjoying nature. It's a bit similar with skiing, you're inside the nature all the time and you're actually using the power of nature for your own propulsion. It's a constant dialogue with the wind and it inspires you in many different ways.
The sea, you know, nothing is comparable to the sea. The sea is freedom and because the sea is so big it will always be free. And we have lost a lot of this freedom, if we even have any in today's world.
The fact that you can sit on a floating object, raise a piece a cloth and sail around the world for zero dollars says a lot about sailing. It's freedom.
OC: What kind of boat are you sailing?
IK: I'm sailing a Class 40. It's an ocean class for single and double-handed sailing. There are three ocean classes at the moment - we have the Mini, the Class 40 and the Multis - all three classes are very popular and Class 40 is a boat that is capable of sailing around the world non-stop. So it's a very strong boat but very rewarding as well. It's a fast boat for fast downhill and reaching sailing. So a lot of fun but also physically quite demanding.
OC: There are 50-year-old sailors in the Olympics, like Argentinian Santiago Lange who was almost 55 in Rio. You're not even 40... How cool would it be to compete at the Olympics?
IK: I was actually thinking about it. They just introduced the offshore class at the Olympics. It's definitely something a man should consider. I'm not saying I'm considering it but it's... it's interesting.
OC: What are your chances of competing at Paris 2024? Give us a percentage...
IK: I don't know (laughs). When the decision is made then the chance is pretty big because... I don't want to brag but usually if I put myself into something, then I achieve the goal. But it's hard to make a decision.
My life is different now, I have a family and I don't have so much time as before so it's possible. I will see, this class is now new in sailing, this offshore class at the Olympics so probably we will have to see how it goes and then, yeah, it's a possibility.
OC: You are environmentally conscious and World Earth Day is coming on 22 April. We know climate change is affecting skiing. How do you see it and what can you do as a former skier to limit the effects of climate change?
IK: Well, certainly the knowledge of this change first should be spread among the people. They should be aware that things are going wrong and I believe that this personal education is the most important for all. Because we start from oneself - 'What can I do?' is the first question and then you do it. There's nothing not much more that you can actually do. You can spread the facts about this climate change and support the right steps to help the environment.
And the next thing is actually action, that's the most important thing, to act. That's in the power of all of us. You don't have to accept anyone else's support to fight against climate change although, for sure, the true change would start from those guys who make the most emissions, in industry the first place.
We can do only as much as we can do as private persons and put some pressure on the big guys to also start thinking the same way. Unfortunately today, it's a bad situation historically because the world today is interested about profit and that's a question for some other discussion. And as long as this is so, you cannot discuss strategies for preserving the nature as long as you're not willing to limit the profit for the better of the nature. It's not an easy task for industry because everything is based around earning money. But I don't know how long this can go on.
OC: What are you doing personally to take action?
IK: What can a man do? You can plant trees. You can put the pressure on the decision-makers, make as less garbage as you can. Re-use, think about water and that it's scarce. Walking is better than driving a car, ride a bike. And certainly there's a lot of things...
I am leading an expedition in March to Iceland to ski on some of the volcanoes, and we're not using any kind of motor transport. We are actually walking 150km to the volcano, we're climbing up by ourselves.
OC: Are you sailing there?
IK: That's also an idea. But what I'm saying, you can start from things like that. It's your own decision.
Making the switch
While several athletes, including the likes of Lolo Jones and Pita Taufatofua, have competed at Winter Olympic Games after being 'Summer' Olympians, the reverse is quite rare.
Laurine van Riessen of the Netherlands is the one of the last, having won bronze in speed skating at Vancouver 2010 before competing in the sprint and team sprint in track cycling at Rio 2016.
Also in Brazil, Eva Vrabcova-Nyvltova was 26th in the marathon after three consecutive Olympic appearances for the Czech Republic in cross-country skiing.
Connie Carpenter-Phinney is the most successful winter to summer 'switcher', winning individual road race gold at Los Angeles 1984 after representing the United States in speed skating at the 1972 Sapporo Games as a 14-year-old.
Her compatriot Connie Paraskevin took a similar path, competing in speed skating at the 1984 Sarajevo Games before taking track cycling sprint bronze at Seoul 1988.