When Steve and I went to Maui for our 25th anniversary, we did a couple of activities that are still available and very popular today. One day we took our rental car, cameras, and a picnic lunch and drove the “Road to Hana.” It’s a very curvy stretch of highway that clings to the coastline with spectacular scenery included for free. This would be a great place to have a convertible. Check out the info here for all of the how-to’s. You could easily return with a book full of waterfall photos.
We also took a sunrise trip to the top of the Haleakala Crater (elevation 10,000 ft.) and rode bikes all the way back down to the coast (about 26 miles). We were picked up at our hotel about 2:00 a.m. (yes, a.m.) and returned exhausted, exhilarated, and covered in mud about 4:00 p.m. that afternoon. We were MUCH younger then. If you are adventurous and not 60-something, then, yes, I’d recommend it. Read about it here. Bikes, helmets, and instructions are provided, of course.
Again, if this is your first trip, you simply MUST enjoy a luau. Pick one of these based on your location and your budget. They are all very similar. Don’t expect particularly delicious food but do plan to enjoy the setting and the entertainment. It’s possible to book all of these events through your concierge at the hotel once you arrive, but if you’re like me, you will want a Clipboard of Fun at least partially filled out and ready to implement when the sun rises for your first day on this incredible island.
On our most recent trip, we still drove around Maui in a convertible, stopped often to whale-watch and make pictures, and did some leisurely shopping in the town of Lahaina, but we also added a couple of new twists.
Steve wanted to go spear-fishing. My Silver Fox has done just about every OTHER kind of fishing in the world, but this was on his Bucket List. 
He contacted a company called Maui Spearfishing Academy located near Lahaina, and he highly recommends them to all of you. However, I doubt that he will repeat this particular adventure. As you know, he is 60-something. He was with a 30-something instructor and two 20-somethings. He DID manage to spear a fish, but the most frequent word he has used to describe the trip was “INTENSE.” You have to learn to hold your breath for a long time. An awesome surprise, though, was being under that water and hearing the whales singing in the distance.
Because of the wonders of Facebook, I had managed to stay in contact with a former student from Hartselle who now lives in Maui with her husband and beautiful daughter Gracie. We were able to drive to Kula and visit in their home. Not only do they have an amazing flower farm and sell protea, birds-of-paradise, and other flowers to hotels in the area, they also own a sailing charter.
We planned a sunset sail with them, but the weather/wind didn’t cooperate. I happily suggest that you check out Cinderella Sailing in Maui. Graham and Laura are highly skilled sailors, plus they are very safety conscious. It would be a memory for a lifetime.
Now you know where to stay, where to eat and what to do while you’re in Maui. Start saving, dreaming and planning. You’ll love it.
Benny and I toured the Hawaiian Islands in 2002, and Maui was my favorite island. We went to the Maui Tropical Plantation and Iao Valley. Included in this cruise was a trip to the south seas island, Fanning Island, Kiribati. Attending the Pearl Harbor Memorial was very sobering seeing the Arizona with the crew entombed in her hull, and oil still coming from the ship. It was this attack which prompted my father and two uncles to join the military and retiring as jet pilots and helicopter pilots.
I enjoy your posts.
Thalia
Thanks so much for commenting, Thalia. I love your suggestions. We took the kids with us to see the Arizona Memorial during Thanksgiving Week of 1989. They were probably a little young to understand everything, but we kept talking about how their Granddaddy Pearson had joined the Navy after that attack and spent time in the South Pacific. We looked and looked for pineapple fields in both Maui and Kauai on our recent trip but didn’t see a single one. I guess they are all on Oahu.