Itinerary Question

Question

Hi! We will be in Maui for spouse's conference, staying at the Hyatt Regency Maui Resort for most of the time. The conference ends on Thursday, March 5th at noon. Our flight leaves OGG at 7:45 PM on Sunday. Therefore, we have Thursday afternoon, all day Friday, all day Saturday, and 3/4 of a day on Sunday. Somehow, we want to fit in the Road to Hana. I have read numerous threads and websites, and am trying to figure out the best way to do this.

Right now, I am thinking that we could spend the night before we begin the RTH in Pa'ia. Then, take one full day to drive to Hana. Then overnight in Hana (if it's possible to secure lodging, which I assume is limited). Then drive back to the airport.

If this is feasible, how would you plan your days if you had Thursday afternoon, all day Friday, all day Saturday and 3/4 of Sunday available? I feel like it's too much time for the RTH, but not really enough to fit in something else. Also, maybe it wouldn't be a good idea to return from Hana the same day as our late flight, in case we have car trouble or something?

If it makes a difference, we are in our 50s, in average physical shape and enjoy mild-moderate hikes. I don't have a lot of interest in sitting on a beach once we check out of the resort, as I will have done plenty of that at the resort.

Please excuse any silly questions here. I appreciate any help you can provide.

Answer

Planning the Road to Hana (RTH) with the time frame you have can definitely work, but it requires careful consideration of driving distances, lodging availability, and timing. Since you have Thursday afternoon, all day Friday, all day Saturday, and most of Sunday, here’s a detailed way to approach your days while keeping it comfortable and enjoyable.

First, it’s a great idea to break up the RTH over two days rather than doing it as a long round-trip in one day. Doing so allows you to enjoy the waterfalls, hikes, and scenic stops without feeling rushed, and reduces the risk of stress if traffic or road conditions slow you down.

Suggested itinerary:

Thursday afternoon: After your conference ends, consider driving to Pa‘ia (about 45–50 minutes from the Hyatt). Check in to a small inn or vacation rental. This positions you well for an early start on Friday for the RTH. Depending on your arrival time, you could explore Pa‘ia town, grab dinner, and rest up.
Friday: Begin your Road to Hana adventure early in the morning. Drive the Hana Highway, making stops at key sites like Twin Falls, Garden of Eden, Wai‘anapanapa State Park (black sand beach), and Hamoa Beach. Plan for mild-to-moderate hikes such as Wailua Falls or Pipiwai Trail if time allows. Overnight in Hana is ideal—there are a few small inns and vacation rentals, but book as early as possible since options are limited.
Saturday: Explore Hana area in the morning, then start your drive back toward Pa‘ia or central Maui. Take your time to revisit spots you may have missed on the way in. Consider an alternate route back if weather and road conditions are safe. Return to your Hyatt or central lodging for the night.
Sunday: Use this partial day for a relaxed morning activity near your resort or a short hike nearby. Since your flight is in the evening, leave ample time to return the rental car and get through security (generally at least 2 hours for domestic flights). Avoid scheduling long drives on the same day as your flight to reduce stress.

Other considerations:

Book lodging in Hana as soon as possible. Options are limited and fill up fast, especially during peak travel months.
Start driving early each day to make the most of daylight, as the road is winding and slow-moving in parts.
Carry snacks, water, and a full tank of gas—services are limited once you’re past Pa‘ia.
Weather can affect your stops; check local forecasts for rain or road closures.
If you prefer a more relaxed option, consider doing a guided RTH tour with accommodations included, which can alleviate planning stress.

Overall, your plan to overnight in Hana makes perfect sense and allows you to fully enjoy the scenic drive, hikes, and sights without worrying about rushing back for your flight. Avoiding a same-day return to catch a late flight is wise and provides a stress-free experience.

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