If it is your first time to Hawaii, I would do a couple of nights in Waikiki, perfect for retail therapy and glamorous cocktails by the water.
Waikiki:
Where to stay: We stayed at the Westin Moana Surfrider. A beautiful old hotel (the original on the beach) right on Waikiki beach it has the charm as well as the location. The hotel wraps around this beautiful giant banyan tree which is perfect to sit under and have a cocktail or two. If you want glamour and as well as being in the mix, this is the one for you.
http://www.moana-surfrider.com/
Cocktails: The beach bar at the Moana Surfrider is great for mid avo drink listening to live music as the waves crash in. Another hot spot is House Without A Key which is in the Halekulani Resort. Watch the former Miss Hawaii Luau as the sun sets behind her. Stunning cocktail list I recommend their signature Mai Tai.
http://www.halekulani.com/living/dining/house_without_a_key/
To eat: Not traditionally Hawaiian, but I had the best steak ever at Hys Steakhouse. The waiters are suited in tuxedos and the walls covered in Mahogany. Its a real treat to have a bit of a break from the flip flops and Hawaiian t-shirts. I would recommend sharing a t-bone steak with a range of sides, the meat is gorgeously tender, and you can watch the steak being cooked in the dining room. Chocolate lovers dessert (rated the best dessert in Honolulu) is worth splitting as well. Flambéed before your eyes, the making of it is an event in itself. http://www.hyshawaii.com/
Maui:
A beautiful island 30min flight from Honolulu, and well worth the visit. If you are looking for action but at a slightly slower pace to the main island this is the place for you. I found the culinary delights even more amazing here!
Where to stay: We stayed at the Westin Kaanapali. It is a nice hotel, but wouldn't be my choice when we return. I found it too big, with too many people, and a little too commercial. Great location though as the beach is lovely, and has a few close food gems, on the beach and at the nearby Lahiana.
Cocktails:
Hula Grill: A charming barefoot beach bar. A firm favourite, its a casual spot with the sand between your toes. Hang by the bar at happy hour where the cocktails are only US$5 and grab a pizza and some pupus (small plates) when you are feeling peckish. The crab and macadamia nut wontons are delicious, and the best pizza on the menu is the Thai chicken pizza believe it or not!
http://www.hulagrillkaanapali.com/.
Merrimans Kapalua: A stunning setting to watch a sunset, this stunning restaurant and bar looks over Kapalua bay. Make sure you have a Molokai Mule, with Bourbon, Pimm's, lime, ginger slices and orange bitters. After a cocktail or two head down to the beach and check to see if sea turtles are swimming around the rocks. Or why not make a night of it and stay for dinner?
To eat:
Laihaina is a neighbouring town to Kaanapali beach and has a New Orleans feel to it. Its great for dinner and drinks even Mic Fleetwood has a bar there (http://www.fleetwoodsonfrontst.com/). The outlet mall (http://theoutletsofmaui.com/) is really nice and worth a few trips!
Lahaina Grill: Fancy a fancy night out to dinner? The Lahaina Grill is the place to go. The food is sensational here, and the service is hard to beat.
Aloha Mixed Plate: Authentic Hawaiian cuisine served up at very reasonable prices. Very casual, but traditional big plates, with a great setting on the beach. Grab a cheeky cocktail while you wait for a table (you will have to, it's that popular) then treat yourself to an Aloha mixed plate - their most popular dish, with shoyu chicken, fresh fish and teriyaki
beef. The Mochiko chicken is also a great option. All come with Mac Slaw (local take on coleslaw) and rice. You must go here at least once!
Road Trip: Make sure that you hire a car for at least a day to do the Road to Hana. Ask the rental place to borrow a CD guide so you know where to stop. Beware its pretty windy and lots of one lane bridges so bagsnot driving if you can! There is a great ice cream place that uses coconut cream - Cononut Glens (http://coconutglens.com/) The chocolate and chilli is beyond amazing served with a coconut husk spoon!
Big night out: You can't leave Hawaii without heading to the Luau and what better one to go to than the absolute best Old Lahiana Luau (https://www.oldlahainaluau.com/). But beware this books out at least a month in advance. The food is great, traditional buffet, which allows you to try a bit of everything. Book a traditional seat right up the front for the best view of the stage. The dancing is world class, with a mythical storyline that goes with it makes it a cultural experience you won't forget. They send you home with a cute mini banana bread, perfect to munch on as you make your way back to your hotel.
Enjoy planning!