It is recommended to rent a car for this itinerary. Expect to pay around $50-$100 per day depending on the type of car you choose. The road to Hana requires a bit of skill and focus, so plan for a full day of driving with plenty of stops along the way. When driving to Haleakala National Park, dress warmly, and take your time when driving down as the winding roads can be challenging.
If you have more time, consider booking a snorkeling tour or visiting Lahaina town. If you have less time, skip the winery tour and stay at one resort for the day, like the Grand Wailea, which has a beautiful pool area and a lazy river. Be sure to pack comfortable shoes for the Road to Hana as there are plenty of opportunities to hike and explore.
The main airport serving Maui is Kahului Airport (OGG), which is located in the city of Kahului. It is about 30 minutes driving distance from the popular resort areas of Wailea and Kihei, and about an hour from the town of Lahaina. A smaller airport, Kapalua Airport (JHM) is also available for interisland connections and private flights.