Hawaiian Beach/Pool Bar Golf Trail
by Fat Guy
Honolulu, HI:
The Course: Start off with a challenge at Ko'olau GC ($165). Carved out of a magnificent tropical rain forest, Koolau is considered by some to be the world's most challenging course. Multiple forced carries and tight fairways flanked by jungly vegetation make this highly stylized target golf. But aside from the 18th, an awkward par 4 that plays over a ravine, the course never feels tricked up. It eases artfully along a mountain backdrop, in a postcard setting. Not for the faint of heart or those with fragile egos, Ko'olau is the antiresort course, and a treat for anyone who relishes a fire-breathing test. Bring an extra sleeve of balls, don't bother keeping score and brace yourself for an exotic adventure on a layout that's like few others. [Golf Digest]
The Bars: Maxim's Great American Bar Search digs the Mai Tai Bar at the Royal Hawaiian. "This beachside hut was one of the first places to serve mai tais back in 1953. Down a few while telling bikini-clad surf girls about the 70-footer you tamed yesterday."
RumFire- If rum is your thing, RumFire is your kind of bar. This beach bar located at the Sheraton and just down the beach from Duke’s and the Mai Tai Bar comes fully stocked with 101 types of rum from around the world. Outside fire pits create a casual environment that is only enhanced by excellent drinks and company.
Harbor Pub- Where the now infamous “three-hour cruise” was set to cast off, the Harbor Pub is located at the edge of the marina (think Gilligan, Skipper, etc.). A great bar where many locals hang out, the Harbor Pub has $1.25 draft beers from 4-7 weekdays. You simply can’t beat that price! Add to that the old wooden bar and best pizza in town and you have yourself another beach hot spot at a very affordable price.
The Shorebird Beach Bar- Known for excellent food and a relaxed atmosphere, the Shorebird Beach Bar is relaxing with big open windows that look out onto the beach. You can choose to cook your own steaks or go for the pork sandwich and potato salad which (according to reviews) is quite impressive.
AOL Travel digs Beach Tree Bar @ 4 Seasons, Big Island.
Beach Tree Bar
Rush here for the sangria pitchers, choosing a seat at the north end of the polished tree trunk bar to enjoy its first class view of the setting sun (72-100 Ka`upulehu Drive, Kailua-Kona).
Per Travel Channel's Sexiest Beach Bars, "Located in the middle of the crescent-shaped beachfront, Duke's Waikiki is an institution enjoyed by tourists and locals. Visit the dining room for award-winning traditional Waikiki fare or grab a cocktail at the Barefoot Bar. There's no better end to a day in Waikiki than with salt in your hair, sand on your feet and a cocktail in your hand from Duke's."
The Course: There's very little on the Big Island that doesn't involve lava, from the festering red pools in Volcanoes National Park on the east side to the jagged rubble that cradles every golf course along the west coast. The game on this island is target golf, particularly on the South Course at the Mauna Lani Resort (808-885-6655; www.maunalani.com), where you're either on the grass or in the grit—soft, white imported sand if you're lucky, or black, scratch-inducing lava if you're not. The target on the 214-yard seventh is further compressed by raging ocean waves along the left and a rare Hawaiian sand dune along the right. It is a stunning golf hole, as is the 196-yard 15th, which requires you to hit over a caldron of swirling ocean currents. Such calendar-art holes are all part of Mauna Lani's sizzling black magic.
Maui, Hawaii
Fat Guy recommends: The poolside Midnight Lounge at the Westin Maui (Lahaina, www.westinmaui.com).
A great pool area features multiple pools, a canopy of swaying palm trees, water slides built into fake rock formations, a full grotto reminscient of the Playboy mansion, a secluded deck for couples massages, and it's only steps from a perfect beach.
After the sun goes down, hit the Westin's outdoor oceanside Tropica restaurant.
For something a little pricier and more intimate, the Serenity Pool at the Four Seasons Maui is for adults only, which makes the swim-up bar a place for quiet relaxation. 
The views of the Pacific and the West Maui mountain range over the edge of the infinity pool should help you find your happy place.
Or, the pools at the Hyatt Regency Maui Resort and Spa rock for the whole family. The Lahaina Pool is perfect for a relaxing swim.
Then hit the 150-foot lava tube slide, and settle in at the Grotto Bar nestled between two waterfalls.
The Hyatt Regency's Napili Pool has a swinging rope bridge and a whirlpool. Finally, the Keiki Lagoon children's pool has a 3,000 square foot sand play area, a 25 foot kiddie slide, and a sand island mid-pool with a spouting water fountain.
The Maui Hyatt's shaded Umalu poolside bar is a chic modern venue serving Hawaiian cuisine with ocean views and live tunes in the evening.
If that won't entertain your family for a weekend, I don't know what will.
Tee it up at the nearby Ka'anapali Golf Resort. The resort's newly renovated Royal Ka'anapali Course has wide fairways routed through rolling hills with beachfront views. The girls of Big Break Ka'anapali loved the Kai Course, which was also renovated in 2005 and is routed through the foothills of the West Maui Mountains, giving you great elevated views of the Pacific.
Tucked inside a man-made cave, the Grotto Bar at the Grand Wailea in Maui takes the prize for Hawaii’s most decadent swim-up bar. The tables for two carved into the walls of the cave are designed for discreet canoodling and sipping on “lava flows” or other fun drinks. This is probably as close to a Playboy Mansion party as you'll ever come.
Play the Wailea Emerald Course, a 1994 RTJ, Jr. track bursting with exotic blossoms and lush landscaping, with ocean views from every hole. Named a Top 10 New Resort Course by both Golf Digest and Golf Magazine. 3PM Super Twilight rates drop to $90.
For a great beach bar, head for Mala Ocean Tavern (Lahaina, www.malaoceantavern.com). Waves crashing at the base of the outdoor deck, and one of Hawaii's best Mai Tais.
Poipu Beach, Kauai, Hawaii:
The Courses: Poipu Bay RGC. A gorgeous tromp through lava-rock-lined fairways. Plush conditions, scenic oceanfront holes, and 86 white sand bunkers. The former home of the PGA Grand Slam of Golf.
If Poipu is a little rich for your blood, head over to nearby Kiahuna GC. An inland track semi-close to the beach, with a resort design typical of lack of real estate and hurried, cost-cutting construction. Short and not super-difficult (suffices to say I shot 88 here after a 5 Mai Tai lunch at Brennecke's), although not without imagination, and not in bad shape.
The Bar: Brennecke's has the feel of an old-time diver/surfer stop, serves up affordable lunches, and overlooks Poipu Beach, which was rated as the Best Beach in America by The Travel Channel. Split the Poo Poo platter, and definitely have a few of the house-specialty Mai Tais.
