How to Travel Like a Hollywood Star With an Oscars Swag Bag (But on the Cheap)

So you're not a Hollywood celeb with an Oscars gift bag. You can still travel in luxury and style without spending nearly a year's salary.
By Mia Taylor ,

NEW YORK (MainStreet) — At this year's Oscars, nominees were presented with swag bags that included three luxurious trips — one to Italy, another "glamping" in the United States and the third getting the royal treatment on a Rocky Mountaineer train ride in Canada.

The combined value of the vacations is nearly $40,000 — a price tag that includes $11,500 for the Italian jaunt, $12,500 for glamour camping and $14,600 for the rail trip through the Canadian Rockies.

If you're not a Hollywood celebrity lucky enough to be in possession of an Oscars gift bag, how can you travel in this sort of luxury and style without spending what amounts to nearly a year's salary for some?

Travel industry experts say it's actually not all that difficult. You just need to know how to work the system — and that's where credit card rewards, loyalty programs and key websites come into play.

"My wife and I have been using rewards points to travel like the 1 percent for about five years. On our own, we could afford to travel about once a year, on a coach flight, that would go from the East Coast to the Caribbean — to some all-inclusive type of place. Now our travel budget is in the $40,000-per-person, per-year range," says Ari Charlestein, co-founder of the Travel Education Network. "It's all about taking advantage of things you were going to do anyway, making sure you are always staying at same brand of hotel or same family chain and signing up for points programs."

Charlestein says his focus personally and professionally is on how to enable the everyday traveler to get out and travel like the 1 percent.

"Who needs thousands of dollars for a five-star trip to Italy?" Charlestein says. "My wife and I are leaving next week for a two-week trip to Rome, Scotland and Wales. The retail value of the two-person trip, including first-class flights on Emirates and business class on [British Airways] and Aer Lingus, would be $35,000. While we'll only be paying about $1,500 to $2,000."

The single quickest way to accumulate travel rewards points is by signing up for the right credit cards and getting the sign-up bonus rewards points, Charlestein says.

He has 20 such credit cards, all travel-rewards oriented, all of which he manages and tracks using a spreadsheet.

"I don't buy a pack of gum without putting it on a credit card," says the professional traveler.

One particularly useful card Charlestein recommends for earning luxury travel is the The InterContinental Hotels Group Rewards Club Select credit card from Chase

Not only does the card give you 70,000 bonus points after spending $1,000 on purchases within the first three months of signing up, but more importantly, the card gives you one free hotel night at any hotel in the world each year, Charlestein says.

"You can stay at any InterContinental Hotel Group property in the world," Charlestein says. "That could be a room in Bora Bora that costs $1,000 per night. My wife and I are using our two free nights — she has this credit card too — to stay two nights free next week at the InterContinental in Rome. That's $950 for free."

The Starwood Preferred Guest Credit Card from American Express is another that tops Charlestein's list.

"It is one of my personal favorites because their points are so valuable. You can transfer their points on a one-to-one ratio to 23 different airlines," he says. "And they treat me very well."

Members can redeem Starpoints for free nights at more than 1,100 hotels and resorts in nearly 100 countries and for free flights on more than 150 airlines.

What's more, the choice of hotels you can stay at for free as part of this card's rewards program includes the luxurious St. Regis hotels and the brand's other upscale offering, The Luxury Collection.

The annual fee for the Starwood card is $65.

Charlestein's company offers courses about how to maximize rewards travel opportunities. They take place around the country, typically on the weekends.

His first piece of advice is to start with just one credit card and set your travel goals.

"You can say 'I want to hit all seven continents' and then start by focusing on one. If your goal is to go to Italy, you should not be signing up for credit cards that will take you to South America," he says.

Charlestein also points out that there are five weighted factors that go into your credit score. The two largest factors are payment history, which is weighted 35%, and amounts owed, weighted 30%.

"As such, the most import thing to remember when playing this game is to pay your bills on time and pay your bills in full," he says.

Charlestein's second bit of advice when it comes to traveling like a celebrity: Sign up for loyalty programs at hotel chains or hotel groups, which also earns you upgrades, free rooms and more.

"A lot of people are traveling more and more for work, and you are typically allowed to choose the hotels you stay in. I used to be a road warrior as a sales rep. I would travel 40, 50, sometimes 60 or 70 nights a year. I would make sure to stay in the same hotel chain," Charlestein says. "Or I have friends or family who stay three or five nights a year in a hotel, and I would say 'I will check you in under my name.'"

Mike Slone is another travel industry insider and expert traveler who has learned how to successfully work the system to earn luxury travel inexpensively.

He has traveled to all of the Italian destinations included in this year's Oscar gift bag — Tuscany, Lake Como and the Amalfi Coast.

He suggests using a handful of lesser known websites when looking for luxury hotels, and some key travel program memberships as well.

The websites he favors include TabletHotels.com and DesignHotels.com.

"They hand pick hotels that have to meet their criteria. Typically they are luxury or boutique hotels," Slone says of the two websites.

In particular, when it comes to the Tablet website, Slone highly recommends becoming a "Tablet Plus" member.  The program, which costs $195 a year, offers room upgrades, special perks and bonus amenities at hundreds of luxe hotels.

The third website Slone recommends is MrandMrsSmith.com — another insider's shortcut to the world's best luxury and boutique hotels, and he gives an example of its strengths.

Included in this year's Oscar's gift bag Italy trip was a luxurious stay at the Villa Armena in Tuscany. One look at the hotel's website and you can see why it is fit for a celebrity — elegant rooms, beautiful decor, stunning countryside. 

Now look on MrandMrsSmith.com and you can find a room listed at the hotel for just $199 per night.

"If you were in Boulder, Colo., and went down to Embassy Suites, it would cost $200 a night," Slone says. "You can definitely visit all of the places in the Oscars gift bag. You may not be able to stay in the suites, but you can still go to the same places."

Inspirato is Slone's last piece of advice when it comes to traveling like the rich and famous.

It's a luxury travel club of sorts from American Express that provides access to a collection of luxury vacation residences, custom experiences and VIP events. Anybody can sign up.

"You get access to exclusive properties throughout the world," Slone says. "Some of the most amazing places we've gotten to stay at have been through Inspirato. We stayed at a place in Tuscany quite close to the places mentioned in the Oscar grab bag through Inspirato. You can stay in places that in peak season that would be thousands of dollars per night, for just a few hundred dollars per night. When you're talking about being able to get access to places that celebrities and Oscar winners get access to, I don't know anyplace else that gives you access for such a little amount of money then Inspirato. The type of places you stay at are once in a lifetime sort of experiences."

Charlestein and Slone also stressed one other key way to save money on luxury travel, which should be obvious. But just in case it isn't — here it is: Travel in the offseason or shoulder season (that is, just before or just after high season).

"The difference in going to Tuscany in March, April or May versus June, July or August is probably double, triple or quadruple the price," Slone says. "And if you go in July and August you will be surrounded by a million other tourists. You want to pick a balance of it getting warmer and being before all the other tourists get there."

A visit to the Grand Hotel Excelsior Vittoria, in Sorrento on the Amalfi Coast (yet another opulent hotel included in the Oscar vacation offerings) can be had for around $278 per night in March. That price is for a Classic Garden room.

As for that Rocky Mountaineer vacation included in the Oscars gift bag — the above advice from Charlestein and Slone about credit card rewards and loyalty programs does not necessarily apply.

What's important to note here is that the train has various levels of travel you can choose from — including gold and silver levels. The $14,000 Oscar vacation includes gold service, naturally, an experience that involves a gourmet dining car staffed by chefs who have worked in Michelin-starred restaurants, deluxe hotel rooms and stops in Seattle, Vancouver, Kamloops, Jasper and Banff. 

Gold service also includes seats in an upstairs, glass-domed seating area that provides 360-degree views of the scenery.

But the Mountaineer's SilverLeaf service is also quite the experience and costs thousands less.

A Canadian Rockies Excursion in the SilverLeaf section of the train costs about $2,498 per person in April (again, think offseason for discounted fares). The trip starts in Vancouver and includes an overnight in Kamloops and ends in Banff.

"Silver Leaf cars are also beautiful, and include oversize picture windows," says Shannon Kidd, senior manager, communications for Rocky Mountaineer. "Our host team is also the same in silver and gold."

Celebrities who have traveled on the Mountaineer in the past, says Kidd, include Morgan Freeman, Bill Gates and Patrick Stewart. 

One thing they typically get, that you won't — no matter how many rewards programs you sign up for — is an entire railcar to themselves, so as not to be disturbed by adoring fans.

— Written by Mia Taylor for MainStreet

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