Howard,
We went to Maui in May. There is plenty to do. I who love the beach and but do not like sitting poolside was never bored and we went out 10 hours a day. We were so busy that we did not even have the time to really swim or go to Lanai or drive up to the Haleakala crater and cowboy country.
Do buy the Maui Revealed.
Dollar rent a car had the best rates for convertibles. We rented a Jeep Wrangler and had a ball.
We went to the Lahania Luau,Ziplined in Ka'anapali,visted IAO Needle State Park. Drove to Hana and also did the West Maui hwy past the Ritz(gorgeous views). Downtown Lahaina is charming. Spent a day in Kihei and Wailea. Flew with Blue Hawaiian helicopter close as one can get to the crater and the island. What a great experience. DH still talks about it.
Liked the Hula Grill for lunch in Whaler Village because of the view and the tables with sand floors and also Aloha Mixed Plate is inexpensive next to the Luau. If you eat there at night you can hear the music playing next door.
Safeway supermarket has the best prices for groceries per the resort and it was much better than Food Lion.
Highly recommend Mama's Fish House but go in daylight for the best view and and call ahead for a table with a view. It is about $50pp. Decor, service and food are wonderful but the view tops it all. It does not look like much from the exterior but it belongs on a poster.
I would also spend a few days in Wailea at the Marriott to enjoy that area and Kihei. In Kihei there are a couple of local stands where one can buy fruit or crafts and lots of casual places to eat. We ate at Alexanders Fish since a few tuggers recommended it.
Wailea is gorgeous and there is a beautiful cliff walkway near Grand Wailea and a super beach with the Four Seasons and Spagos looking out on the ocean. Central,West and South Maui areas are very different from each other and we enjoyed them all.
Hana- the idea of the Road to Hana is to stop and see the ocean, waterfalls and beaches. If you just drove straight through 2.5-3 hours each way does it but then why go as there are other Maui drives. It takes another 45-60 minutes to get to Paia and the start of the Hana Hwy from West Maui. At the little stops to see the waterfalls there are other cars and not always enough spaces. There are no gas stations and no restaurants. A couple of roadside stands. We ate a burger at Halfway to Hana which has no place to sit other than outside tables and is not really halfway. There is nothing much to do in Hana. There are 3-4 famous beaches Hamoa is one of them also down a side road. I would skip the Garden of Eden botanical garden nice but IMHO not worth the 45 minutes we spent there. It is rated as a must do in the Revealed book. I would have rather spent more time at the Black sand beach.
Most of the Hana Hwy is 15mph then it increases in the pasture areas of Hana to 35 mph and then reduces to 5 mph when 10 miles from the 7 Sacred pools and that is about as fast as you can go. We are not wimpy drivers as we drive in Boston commuter traffic.
We left West Maui at 8am got to milemarker zero on the Hana Hwy at 9am and to 7 Sacred pools at 4pm. It was 60 miles one way. There are about 70 stops but we did about 8-10. There is a fabulous black sand beach down a short paved road called Waianapanapa State Park that deserves more time then we allowed as does the Oheo Gulch /pools. You can and should swim at both locations. The ride back to Paia mile marker zero took 2.5 hours then another hour to West Maui. It gets dark at 7pm and this is not a road I want to be on at night. If you have never been before it takes longer and also are reading where to stop in the travel guide. We thought 4 hours tops and it was twice that so leave by 7am not 8 like we did.
http://www.hawaiiweb.com/maui/html/sites/waianapanapa_park.html
http://www.hawaiiweb.com/maui/beaches/hamoabeach.htm
We spoke to couples with kids that turned around and went back to the resort because of the time it took. You know when you visit mountain and coastal route roads how the winding curves and slow speeds make it take longer than you thought.
If you are going to stay in Wailea I would plan to drive the Hana Hwy when I stayed there as it is closer to start and to finish when you are tired and it is closer to the crater, cowboy country and the lavender fields on hwy 37. There is the general store mentioned which is a restaurant and there is the noted Komoda bakery in Makawao that we missed because we ran out of time. We did not tour the pineapple fields either but flew over them. We spent 7 days there and needed another 3-4.
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http://www.fourseasons.com/maui/dining.html
http://hawaiirama.com/2006/09/top-3-walking-beaches-on-maui
I must say that I am very glad we did not island hop every 3 days as we would have missed so much.
that ends up in Paia -- beautiful views, but some places two cars pass on one lane -- you go by a couple of very small Hawaiian towns not known to many tourists.
