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10 Tips for Traveling Like a Boss

The finer things in life-for less.

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A killer vacation doesn't have anything to do with your cash flow: It’s a state of mind. Living the ultra-luxe travel life is possible, even when your budget is modest.

We spoke to industry veteran Bob Diener, the co-founder of Getaroom.com and Hotels.com, about how to get the most bang out of your vacation buck. Diener's 25 years of travel expertise yields plenty of insight. Here are his tips for traveling like a boss.

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Time is your most valuable commodity.

"Remember that time is your most valuable commodity when on vacation. Splurge on entry to the airport lounge. Day passes can be had for $30 to $40. Would you rather spend four hours fighting over an outlet and sitting in a horrible chair, or have some peace and quiet, free snacks, and maybe meet a friend. The same rule applies to transportation. Is a $10 shared shuttle bus that takes two hours to arrive at your hotel better than a $50 limo ride that offers some booze and comfort?"

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Don't skimp on the rental car.

"Don’t skimp on the rental car. It’s hard to feel good about yourself while driving an econo-box. Luxury rentals don't cost much more than the standard-size cars and their comfort means you’ll arrive without a stiff back. In Las Vegas, you can even rent an exotic for the day. Trading the Taurus for a Lamborghini Gallardo or Ferrari 458 Italia is a great feeling, if only for a day."

Act as if.

"You can’t travel like a boss without the right attitude. Think of the “act as if” scene in Boiler Room. Haven’t seen the movie? Stream it on your iPad, then give some real thought to what it means. If you act as if money is not really a concern, (without being a prick), and you subtly own the room, then you give off a certain look and attitude which makes you and everyone your with feel more like VIPs."

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Look at vacation rentals, not hotels.

"Look at vacation rentals instead of hotel rooms. Particularly if you are traveling with a group of guys, renting a house can be both cheaper and much more exciting. A private house in Miami means you can bring the after-party with you, with your own drinks, music, and vibe. You can’t have 20 people in your standard hotel room without security shutting you down in ten minutes."

Ask for upgrades, but be nice about it.

"Ask for upgrades at all times, but be nice about it. You consider yourself to be charming, so use that charm to get first class upgrades or a better hotel room. If you need to tip 20 bucks to get a better deal, then consider it money well spent."

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Save on the upfront costs of the trip.

"Find ways to save money on the upfront costs of your trip. Traveling well doesn’t mean wasting cash or paying more than you have to for rooms. Consider sites such as Getaroom.com which offer spur of the moment flash sales that will help you get that boutique hotel in Chicago at up to sixty percent off. Every dollar you save on the front end is another dollar for drinks, a massage, or an old-school barbershop visit."

Travel where your dollar works hardest.

"Travel where your dollar goes farther. Look globally to fun cities such as Barcelona that are hurting in a bad economy. You can score great rates and have fun in one of the most energetic cities in the world. Use a site such as Getaroom.com to scour rates and find boutique hotels that offer five-star amenities at the four-star price."

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Dress sharp

"Dress sharp. Sweatpants are comfortable, but they need to stay at home, even if you’re taking the red eye flight. You don’t need to put on a suit, but a slick outfit that fits the scene of your destination is vital. Regardless of where you're heading, wearing clothes that are well-tailored and have an interesting mix of fabrics and textures to help you stand out as a VIP."

Be a generous tipper.

"Be a generous tipper. You don’t have to make it rain over the wait staff at a fine restaurant, but it shows real class to tip the concierge, housekeeping, valet attendants, and any other service employees you come in contact with. Vacations are supposed to be fun, and you will be surprised how good it feels to have someone give you a real “thank you” after receiving a bigger tip."

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Bring a friend who's loaded.

"Bring along a friend who does have some loot. While you don’t want to be a mooch, if you are a great wingman or have another talent, then at least you are a good traveling buddy for your deep-pocketed friend. Having a traveling companion with some cash is especially valuable in Las Vegas, where he can gain entry to clubs, get suite upgrades, and other benefits that allow you to be rich by association."

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