The Frugal Millionaire – Destination: Oahu

My friend Jack decided to take the plunge and propose to his girlfriend Stephanie who, amazingly, said yes. While the girlfriends of the bride threw themselves into “Bride-apolooza,” the groomsmen (me among them) decided that Jack deserved one last hedonistic weekend of freedom before the big day – and we of course would be with him every step of the way.

Because of our mutual love of golf, surfing, and fruity tropical drinks with tiny umbrellas, we decided to head to Oahu for our “Bachelor Party.” While Oahu, and Honolulu in particular, is traditionally geared toward families, honeymooners and rich Japanese tourists, we were convinced that with a little planning and imagination, we could pull off a memorable weekend.

After our five hour flight from LAX to Honolulu, we headed straight to our digs in trendy Kailua Beach. The area is home to many celebrities and visions of downing a brew with Justin or boogeying with Beyonce danced in our heads. After being tempted to rent Don Ho’s former estate (Don Ho!), we settled on an amazing 6 bedroom beachside home that went for a mere $900 per night. Between five guys, that worked out to be quite a bargain. We found ours through Home Away.com a website featuring homes for rent by owners. The house was a palace of tropical hardwoods and imported stone, with a full gourmet kitchen, huge indoor/outdoor living room with built-in BBQ and large outdoor teak dining table. Located within a stroll of the private beach, it was a perfect place to sip a morning cappuccino, or lounge in a hammock as you listen to the ocean and sip a Mai-Tai in the shade of the gazebo.

But we had a lot of plans for our brief three-day weekend, so no lazing around was permitted. After an amazing sushi dinner at Nobu in the famed Waikiki Parc hotel, we went in search of the perfect dive bar to share a few rounds with the locals. We found it at Creekside on Hamakua Drive. Creekside is the oldest lounge in Kailua, a popular hangout for everyone from college professors to construction workers to military personnel to the local biker club. It opens at 8 a.m. from Friday to Sunday, and the staff is all women. Yowzah! After several beers, including local microbrews, we headed home to get some decent zzzs before we hit the beach with our boards no later than 6 am – yeah, right. We did manage to get in at least an hour of surfing before heading out to the links.

Oahu is home to many top rated, championship level clubs, but we decided to challenge ourselves by playing Ko Olina Club Kapolei, a 18 hole par 72 course which promises you will “use every club in your bag.” And we did. Golf Digest named Ko Olina one of the “Top 75 Resort Courses in the U.S.” and the 16 water features on eight different holes, along with multi-tiered greens, gave us a great workout. Ko Olina is one of the courses that allow “fivesomes,” so we didn’t have to split the group. After playing a demanding nine holes before lunch, we were more than ready to head off for a relaxing afternoon aboard a private chartered yacht.

Tradewind Charters offers bachelor party tours on a select handful of boats. All cruises are on a private basis so you’re guaranteed to be partying exclusively with your own group of friends and acquaintances – like some of those cute hula girls we met at the bar last night who were only too happy to accompany us for some partying at sea. Buffet dinner can be provided for $30 a person, but we brought along our own goodies purchased at – surprise! – Alan Wong’s Pineapple Room located at Macy’s Third Floor in the Ala Moana Center. Wong has a more formal restaurant, but many locals prefer this more casual venue with affordable prix fixe meals.

After an amazing sunset viewed from the deck of our party ship, Kona Pale Ale in hand, we headed back for Honolulu and onto the night’s planned festivities. It just ain’t Hawaii without a hula lesson, so our “dates” invited us to attend their show at the Hawaiian Cultural Center. Did we look like idiots? Yes. Were we making a lasting memory? You betcha. Barely able to crawl home, we fell into our cushy beds and a deep sleep.

Our last full day there we had two objectives – watch the dudes challenge the wild surf at North Shore and do the latest sightseeing tour based upon our 44th president’s youthful upbringing in Hawaii. The Barack Obama tour takes you to all the meaningful places – it even schedules time to slurp down a shaved ice at the Obama’s favorite shop, the Waiola Shave Ice shop. As Jack put it: Coolest.Guy.Ever.

Stretching for more than 7 miles, the beaches of the North Shore host the world’s premier surfing competitions including the Super Bowl of wave-riding, the Vans Triple Crown of Surfing. We didn’t see any competition, but the guys out there were amazing. All this activity made us long for a nice spa treatment, so we headed for the Moana Lani Spa and Relaxation Room at the Moana Surfrider Hotel in Waikiki where we got in touch with our inner metrosexuals, enjoying relaxing lavender-orchid body wraps and hibiscus-infused scalp massages. Followed up by some cleansing green tea, we felt chastened enough to head for our final night on the town. The Royal Hawaiian Aha Aina Luau is one of the best luaus at one of Hawaii’s favorite hotels in Honolulu, the Sheraton’s Royal Hawaiian. For close to $200 a person, we spent our final night with Diamond Head and the shore as a backdrop to this mammoth feast. This time we were prepared when they called us up to do a little hip shaking.

The next morning, fortified by a hearty breakfast of macadamia nut pancakes with coconut syrup and Kona coffee, we headed for the airport and the five hour flight back to Los Angeles. Once back home, we honored our agreed upon guy’s code of silence, much to the dismay of Steph and her maids who wanted details, lots of details. We vowed to remain a band of brothers who will always share Honolulu memories. Be there. Aloha.

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