You spend countless hours sitting on an airplane, use your co-branded credit card until the magnetic strip wears thin and do most of your shopping through the mileage malls. You read this magazine and take advantage of earning bonus miles through airline and hotel promotions. After building up a large stash of miles, what are you going to redeem them for? You could spend a few of your miles for a domestic award ticket to go to your niece’s wedding in Albuquerque. But if exotic destinations are more your style, those awards that take you to the far ends of the Earth, like an African safari or a whitewater rafting trip in Costa Rica, what are your options?

According to the Air Poll we posted last month, over half of respondents (55 percent) would choose to redeem miles for an around-the-world vacation and 22 percent would choose a luxury vacation if they had an unlimited number of miles and points to spend. While 40 percent of respondents consider upgrades to be the “ultimate” award, 27 percent of those polled would choose a vacation package with flights and an all-inclusive two-week stay at a private island and 22 percent would opt for a space shuttle to explore outer space. While space travel is currently beyond reach for most of us, we found some travelers who redeemed their miles for what we consider “extreme awards” and asked them what they did, how they did it and what tips they have for others who want to redeem miles and points for over-the-top awards.

Dream (Open Jaw and Stopover Award) Honeymoon
Gary Leff splurged when he got married a few years ago. The unofficial title of his wedding and honeymoon trip report was “How to Spend 670,000 Miles/Points on a Single Trip.” His first mileage redemption was 290,000 AAdvantage miles for two first class award tickets, Los Angeles to Tahiti for a stopover, and then on to Auckland. Using an open-jaw award (see more about open-jaw and stopover travel below), the return trip routing was Melbourne to Los Angeles. He purchased one-way tickets from Auckland to Sydney and Sydney to Melbourne in order to take advantage of American’s open-jaw option and get more bang for his miles. While he could have flown back from Sydney, he purchased tickets from Sydney to Melbourne because there weren’t any first class award seats available on the early morning Sydney to Los Angeles flight. So for an extra US$140, he was able to book later flights from Sydney to Melbourne and fly first class on the award routing from Melbourne to Los Angeles. American’s award tickets to the South Pacific have not changed since Leff’s honeymoon trip so AAdvantage members can redeem at the same award level today.

For his stopover stay in Tahiti, Leff redeemed 176,000 Starwood Preferred Guest (SPG) points for a fifth night free award for an over-water bungalow at Bora Bora Nui Resort & Spa. He describes the view as awe-inspiring and says, “Honestly, this is the most beautiful physical property I’ve ever seen.” The 120 luxury suites and villas at the resort are “located on 16 acres of lush and terraced land overlooking a private cove of crystalline waters.”

For the rest of his honeymoon, Leff redeemed a total of 204,600 hotel points: 60,000 Priority Club points for two nights at the InterContinental Tahiti; 24,000 Priority Club points for one night at the InterContinental Sydney (20 percent off award sale); 7,000 Starwood Preferred Guest (SPG) points for one night at the Sheraton Tahiti; 10,000 SPG points for one night at the Westin Sydney; 7,000 SPG points for one night at the Westin Melbourne. For the wedding, he spent 37,600 SPG points for 13 cash and points award nights for family at the W and Sheraton in Seattle; 14,000 SPG points for two nights at the Westin Seattle and 45,000 Marriott points for one night at the Ritz-Carlton Marina del Rey.

When asked how Leff’s wife felt about him using miles and points for their honeymoon, he responded that she “now loves miles and points just like I do. Mostly she knew it meant that we could take a dream trip without worrying about money during our travels. Spa appointments on Bora Bora are expensive, after all!”

Open Jaw and Stopover Basics
Using open-jaw and stopover award capabilities allows you to visit more places on a single award itinerary. With an open jaw, you can fly from your point of origin to one city and return from another city. Or, fly from one city but return to a different city. For Leff’s honeymoon, they flew from Los Angeles to Auckland with a stopover in Tahiti but flew back from Melbourne, all on one award itinerary for the same amount of miles as a roundtrip Los Angeles to Sydney flight. In general, a valid open-jaw routing requires both flight segments to be greater than the non-flight (open-jaw) segment. Northwest clearly states, “If the open-jaw portion exceeds the maximum permitted mileage, two roundtrip award levels are required.” So you couldn’t fly New York to London (3,450 miles) and return from Tokyo to New York because the distance from London to Tokyo is 5,940 miles.

When it comes to open jaws and stopovers, programs have adopted different policies. American AAdvantage has the most liberal policy and states in their terms and conditions that an award itinerary can contain one open jaw and one stopover: “Select flight awards may allow one stopover and one open jaw, with restrictions.” Northwest allows both only on international itineraries and United, US Airways and Delta allow either one stopover or one open jaw per award itinerary. Continental allows open jaws on award itineraries but stopovers require additional miles — stopover awards within or between the 48 contiguous U.S., Alaska and Canada are 35,000 miles.

Stopovers are planned breaks, generally of more than 24 hours on international trips and over four hours on domestic trips, which are usually restricted to the hub city of an airline or its partner. United and US Airways do not allow stopovers on awards wholly within a geographic region and Northwest only allows stopovers on domestic awards as part of a circle trip award, which allows for a total of two stopovers within a roundtrip award ticket itinerary for the mileage equivalent of three one-way awards.

When planning an award using a stopover or open jaw, do your homework before attempting to redeem your award. Search through the terms and conditions of the programs and ask questions of your fellow road warriors. In most cases, you will have to call the service center to redeem these types of awards and will usually incur a fee if they book the award flight for you — but this is well worth it if you get that extra vacation stop you want.

Round-the-World Award
While many people dream about using miles for an around-the-world ticket, unless you are retired, quit your job or take a leave of absence, how do you find the time to make it worth the cost in miles and travel time? We found one FlyerTalk member, Jaimito Cartero, who found a way. He booked a Northwest/SkyTeam around-the-world ticket in business class in 2006, spread out over 11 months, six continents, and five SkyTeam airline members for 220,000 WorldPerks miles and about $300 in taxes. He kept his job by returning to the U.S. twice during his trip on paid tickets to go back to work before continuing his journey.

SkyTeam allows six stopovers on the around-the-world ticket and Cartero’s itinerary was Los Angeles to Seoul to Sydney (stopover) to Bangkok (stopover) via Seoul. From Bangkok, he paid for a roundtrip ticket and flew to Los Angeles for a few months of work and then resumed his travel. From Bangkok, he flew to Johannesburg (stopover) via Paris and purchased an inexpensive ticket to Cape Town and spent a week there. Back in Johannesburg, he flew to Prague (stopover) and rented an apartment for two weeks. From Prague, he purchased a roundtrip ticket back to the U.S. for a 45-day work visit and once back in Prague, flew to Buenos Aires (stopover) via Naples. After a two-week visit, “Buenos Aires is my favorite city for food, so always good things to eat,” he continued on to Costa Rica (stopover) via Houston.

The entire trip spanned almost an entire year, from Jan. 25 to Dec. 20, and he flew about 52,000 miles. “This trip was the best value I’ve ever gotten out of an award. By buying inexpensive tickets back, I was able to really get full value out of the award, still keep my Platinum status, and keep my job!”

Round-the-World Award Basics
Continental, Northwest and Delta are members of the SkyTeam alliance and members of all three programs can book a SkyTeam around-the-world ticket. Tickets are 140,000, 220,000 or 280,000 miles for economy, business or first class tickets. Many of the international SkyTeam member airlines do not have a first class cabin so depending on your itinerary and the SkyTeam airlines involved, you may want to redeem a business class ticket since you could end up in business class anyway. Travel must take place in one continuous direction, east or west, and no backtracking is allowed. Six stopovers are allowed with a maximum of three stopovers per continent. A Delta representative said the average cost of taxes is $150-$200, depending on the countries visited, and the highest he has seen is around $350.

Around-the-world award tickets with the Star Alliance require significantly more miles and members of United and US Airways can purchase awards for 200,000, 300,000 or 400,000 miles for economy, business or first class tickets. The Star Alliance allows a maximum of five stopovers (10 segments), one open jaw is permitted and “you must use legal routings as defined in pricing rules and continue travel in the same direction.”

The around-the-world award for American Airlines and its oneworld partners is set up differently and the cost in miles is determined by the distance of your planned itinerary and class of service. Travel must include at least two oneworld partners other than American Airlines, American Eagle or AmericanConnection, and may not exceed 16 segments. There is no limit to the number of stopovers but only one stopover is allowed per valid city and only one open jaw is allowed anywhere in the itinerary. You can use all oneworld airlines and affiliates but you can only connect twice in each city, you cannot connect at the origination or destination city and travel is not valid on British Airways nonstop flights between the United Kingdom and the United States. American Airlines suggests you call the service center to determine the cost of an award ticket: “To determine the award for your travel plans, please call AAdvantage reservations with your complete itinerary, and one of our helpful service representatives will calculate the miles you are flying and advise you of the correct award to use.” Awards range from 30,000, 60,000 and 80,000 miles for itineraries that are up to 1,500 miles and 160,000, 220,000 and 330,000 miles for itineraries between 35,001 and 50,000 miles. If you aren’t planning on covering a lot of ground, an AAdvantage oneworld ticket may be your least expensive option for an around-the-world ticket.

Extreme Good Value Award
Not all “extreme awards” are about spending vast amounts of miles or points and traveling first class. Some are all about making the most of the miles you have. For example, AAdvantage members can redeem 25,000 miles for a simple coach award ticket from Chicago to any destination in the U.S. but for just an extra 10,000 miles, you can make it down to South America on partner airline LAN and with the magic of stopovers, make it a dream vacation of a lifetime. Maury Goodman says the best value he ever received for an award ticket was two coach tickets Chicago-Quito-Cuzco-Chicago on American Airlines for 35,000 miles each, with a stopover in Quito and paid side trips to the Galapagos and Machu Picchu. He and his wife “had always dreamed of visiting Machu Picchu, and when a chance to visit the Galapagos came up, starting in Quito, we were quite interested. I think we really just lucked out that we could arrange the trips to both Quito and Cuzco for what seemed to me a very small cost in AA miles.”

These awards are still available for 35,000 miles, and you can get to Peru for 5,000 fewer miles when you take advantage of an American Airlines flight to Lima for 30,000 miles during off-peak travel times (Jan. 16-Jun. 14; Sep.7-Nov. 14). And with the value of the dollar being so dismal in Europe, going to South America just might be the best bargain all around.

Another good value is Marriott Rewards travel package awards where members can redeem points for a week of hotel accommodations, airline miles and a 25 percent Hertz car rental discount. Packages start at 165,000 points for a seven-day stay at a category one through five hotel and 50,000 airline miles.

Luxury Flights
If you enjoy the on-board luxury and in-flight service of the flight itself as much as the destination, three U.S.-based airlines partner with Singapore Airlines, which has won numerous awards for its high standard of service and was recently voted the best airline in the world by Global Travel readers. You can fly first class from the U.S. on Singapore Airlines with partners US Airways (140,000 miles) United (120,000 miles) or Delta (140,000 miles). While you might not be able to test out the luxuries of the new “Class Beyond First” suites that Singapore Airlines introduced on its Airbus A380 that flies between Sydney and Singapore, first class travel on Singapore features world-class gourmet meals you can order in advance, Givenchy-designed pajamas and Ferragamo toiletry kits, and a flight attendant will switch your seat into a bed, complete with down-filled mattress, duvet and a large pillow when you want to sleep.

Luxury Hotels
Jeddah is home to the Qasr Al Sharq hotel “Palace of the Orient”, a member of the Waldorf=Astoria Collection. You can redeem 180,000 AAdvantage miles for first class tickets on Royal Jordanian to fly to Jeddah and stay at this seven star hotel originally built for the royal family. “Sheer opulence” describes the luxury hotel palace with pure gold details, handpicked crystal and porcelain china, intricate mosaics and fine art adorning the walls. The hotel provides guests with 24-hour butler service and Hilton HHonors members can redeem 120,000 points for a one-night stay in a Junior Suite or 160,000 points for an Executive Suite.

HHonors members can also redeem points for a luxurious getaway at the tropical Conrad Maldives Rangali Island (previously known as Hilton Maldives Resort & Spa). The resort is situated on two islands linked by a bridge over a beautiful lagoon and guests can enjoy gourmet meals at a glass-enclosed undersea restaurant 16 feet below sea level, viewing the reef and marine life while dining. Tranquility, white sand beaches and crystal clear waters can be yours for 40,000 points a night (rates start at $1,035 per night), although availability is limited.

Marriott Rewards members can stay at a centuries old authentic Irish castle turned luxury hotel. For 60,000 points per night off-peak and 90,000 points peak, you can stay at either the Ashford Castle or Dromoland Castle, both of which are located near Shannon, Ireland and enjoy the ambience of a medieval castle, minus the chamber pots.

Once-in-a-Lifetime Experiences
Throughout the years programs have scrambled to offer their most frequent customers more and more outstanding award options to keep them happy, and in recent years the “once-in-a-lifetime” type of awards have been very popular. You can do everything from fulfilling your “Easy Rider” dreams to being a backstage groupie or improving your golf stroke.

Starwood Preferred Guest member Rich Spear redeemed 200,000 points for a Super Bowl XL package. The offer was extended to all Platinum members with 200,000+ points and the first four to accept were awarded the package. In addition to two tickets at the 47-yard line, Steelers sideline, 20 rows from the field, the package included two nights at the Four Points Ann Arbor as “VIP” guests, invitations to the official NFL Super Bowl night-before party with the Four Tops, Joan Jett, the Bangles and Smashmouth and the official pre-game party in a heated tent across from the stadium. About the experience, Spear said, “Yes, I could have stayed 25 nights in a Category 4 hotel, but it was worth it.”

Many hotel and airline programs have online auctions where you can bid on once-in-a-lifetime experiences. Elite members of Frontier’s EarlyReturns can bid on packages such as an ultimate Denver sports getaway which includes tickets to an Avalanche hockey game, Nuggets basketball game, $75 dinner certificate and two deluxe room nights (including breakfast) at Denver’s new downtown Ritz Carlton.

InterContinental Hotel Group Priority Club offers some exciting experiences such as swimming with sharks off the coast of Mexico for 100,000 points, being a fighter pilot for a day or spending a day driving a car such as a Ferrari 360 Spider or Lamborghini Gallardo for 475,000 points.

Hilton HHonors members can try out a dream job for one to three days through VocationVacations. For 450,000 points, you can spend two days learning the fine art of winemaking with a master vintner or discuss color, design and floor plans with a successful interior designer.

Where Do You Go from Here?
Now that we’ve mentioned a few of the extreme options out there (and started dreaming about our own extreme vacations), how do you book the awards? We’ve heard many stories from people about the difficulties they’ve encountered in obtaining award tickets. But with some effort and know how, an extreme award is always within your grasp. Gary Leff says he’s “never been denied an award that I wanted after a) doing my homework and b) having just a little bit of flexibility.” Here are five tips that will help you.

Top Five Tips for Extreme Award Travel
Be Flexible
When permitted, open jaws and stopovers not only extend your trip, but allow you to be more flexible when you can’t find an award seat. Maybe you can find an award ticket to Bangkok, but you can’t find one for the return trip. If you’re flexible, you can use an open-jaw ticket and return from Hong Kong and take a train, bus or flight from Bangkok to Hong Kong, and check out China while you’re at it. It may take a bit longer to get to your destination, but looking for award tickets to cities near to where you ultimately want to go can open up your options and help you land an award ticket. And you’ll get to see some interesting places you might have otherwise not considered visiting. Also, be flexible with your dates whenever possible.

FlyerTalk
Read FlyerTalk — http://www.flyertalk.com — and ask questions in the forums. We frequently use FlyerTalk as a resource and the members of the online community have a lot of experience and know the program rules, sometimes better than the airline and hotel employees. Relying on telephone agents isn’t always effective. How many times have you called to book an award reservation and been told it was unavailable, only to call back and speak to another representative who gave you an entirely different answer? If you know exactly what you want and whether it’s available and within the rules of the program before you call, you can improve your chances of a successful award booking. Leff says, “Usually when booking a difficult-to-get and especially valuable award, I’m told by the customer service rep that it isn’t possible. I show them how it is, and boy are they surprised!”

Know the Partnerships
If you know you want to go to Amsterdam on SkyMiles, looking on the Delta Web site for award availability isn’t going to work. Many airlines do not include the award inventory of partner airlines so you’re best bet is to check the Web sites of partners who fly to where you want to go — in this instance, Northwest or Air France/KLM.

Book Awards Early
Renee Moss managed to book 12 roundtrip tickets from east coast cities to Seattle in August 2008. She says she and her husband were on the phone at midnight exactly 331 days before the flight date and by using different airlines and classes of service, 12 of her family members will be meeting her in Seattle during the busy summer travel season — all on award tickets.

With many airlines, awards do not become available until 331 days in advance. In some cases, an airline will open up more seats for award ticketing two days before a flight to fill up seats, but to be safe, book as early as possible.

The Phone is Your Friend
Not all award flights can be booked online and you can increase your chances of finding an award ticket just by picking up the phone and calling reservations. And if you happen to get an unhelpful agent, call back later. If you know the time zone of the call center, call during the regular work hours of the place you’re calling. Agents working during the day might be more knowledgeable and alert than someone stuck working the night shift who is tired and inexperienced. Do your homework before you call and be pleasant, but persistent.