How You Can Take a Baller, Obama-Style Vacation Using Points

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It's no secret that after eight years of possibly the most stressful job on the planet, the Obamas needed a little vacation time. After an immediate jaunt to Palm Springs, they headed to Sir Richard Branson's Necker Island Resort in the British Virgin Islands, followed next by a flight to Tahiti and a short hop 30 miles north to The Brando, a luxury eco-friendly resort that's entirely self-sustaining.

If you think these experiences are out of your reach, you may be surprised at how you can use points, miles, and a few nifty strategies to book a similar vacation for yourself.

Fly Private Jets

There are three ways I know of to make flying private jets free or affordable:

1. Redeem Delta SkyMiles for Delta Private Jets — Starting at 2.5 million SkyMiles, you can redeem miles for a $25,000 Delta Private Jet card, worth roughly 5 hours of private flying. Delta Jet Card holders normally receive Delta Diamond Medallion status, however Jet Card minimum loads require $100,000. Because you're only loading 25% of this, it's unlikely you'd receive top-tier status for redeeming miles this way, but it'd be a huge bonus if you did. Odds are, if you have have 2.5 million SkyMiles to redeem, you're probably already a Delta Diamond elite.

2. Merrill Points — Merrill + Visa Signature cardholders can redeem Merrill points towards flight hours on specific aircraft via private jet provider NetJets. You must redeem for a two-hour minimum, and 12 minutes per flight segment are added to the actual flight time to account for taxiing, takeoff and landing. While the cost isn't an insignificant amount of points, I imagine travelers looking to fly private put a lot of spend on a credit card. Here's a chart of the aircraft type and points required per hour:

3. FoundersCard Membership — Through June 30 of this year, FoundersCard is offering members a free three-month trial of JetSmarter's JetDeals access. This allows for one free seat on typically last-minute, open-leg private jet flights, which are first come, first serve.

Take Commercial Flights to Tahiti

If you can't redeem a few million miles or points to fly private to Tahiti, there are still a few options to use miles for commercial flights. Once you get to Papeete (PPT), in order to get to Bora Bora you'll have to pay cash as there are no intra-island flights bookable with airline miles. You can use a variety of programs that let you cancel out travel-related cash charges — such as miles from the Barclaycard Arrival Plus World Elite Mastercard or Capital One Venture Rewards Credit Card — to cover the inter-island flights.

And here are your options for booking a commercial award flight to Tahiti:

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1. LAX – PPT on Air France

These flights operate three times per week on a Boeing 777, which offers business and economy seating, but no first class. You have a few different options for redeeming miles on Air France.

Alaska Mileage Plan:

• Economy — 40,000 miles + $19
• Business — 60,000 miles + $19

Alaska doesn't let you mix and match partners, so you could get yourself to Los Angeles by paying for a cheap ticket. However, if you live in a city that's served by Alaska Airlines, you could tack on an Alaska award.

Delta SkyMiles:

• Economy — 50,000 miles + $5.60
• Business — 80,000 miles + $5.60

This is another situation where you might just want to pay for a ticket to Los Angeles and then get the saver award if you can find it for Tahiti.

Flying Blue:

• Economy — Starting at 30,000 miles + €168 (about $190)
• Business — 225,000 miles + €218 (about $250)

Economy space is not difficult to find on this route using Flying Blue if your dates a little flexible. Remember it's easy to get a large amount of Flying Blue miles rather quickly because you can transfer Amex, Chase, Citi and Starwood points to the program.

2. LAX – PPT on Air Tahiti Nui (AAdvantage partner)

Once again, there's no first class available on this aircraft — only business and economy.

American Airlines AAdvantage:

• Economy — 40,000 miles
• Business — 80,000 miles

Make sure you follow a few tips Live and Let Fly laid out last week when it comes to helping American phone agents find award space on Air Tahiti Nui (IATA code TN). Because the airline isn't part of Oneworld, it looks like you may need to coach them a little bit.

3. Honolulu (or Los Angeles through HNL) – PPT on Hawaiian (partner with JetBlue and Virgin America, and you can redeem AAdvantage miles only on flights from Honolulu)

Economy:

• 27,500 miles between Hawaii and Tahiti
• 47,500 miles between North America and Tahiti

First class:

• 47,500 miles between Hawaii and Tahiti
• 87,500 miles between North America and Tahiti

One-way AAdvantage rates (again, only on flights from HNL):

• Economy — 37,500
• Business — 65,000

Take a Tahiti Cruise on Points

If you want to see all French Polynesia has to offer, a one-week cruise visiting six different islands may be a great option. Contrary to the price tag you may expect, I found week-long cruises available for this September beginning at $1,735 per person on Windstar cruise line's Wind Spirit.

You can redeem a variety of cash-based points for cruises at a flat 1 cent/point, meaning this cruise for two would require 347,000 Barclay Arrival Miles, Capital One Venture Miles, or Discover it Miles (not including taxes).

I would recommend using the Discover it Miles card which earns 1.5x miles on all purchases, and offers a miles match for the first year on all spend. That means for the first year you have the card, you'll earn 3% back on all purchases, which can then be redeemed for all or a portion of a French Polynesian cruise.

Stay at Necker Island

A week on Sir Richard Branson's island will currently cost you $30,730 for a party of two in addition to a 2.5% tax. The alternative is to redeem 1.2 million Virgin Atlantic miles for a week on the 74-acre resort and includes all food and drink including alcohol, activities on the island and return boat transfers to Necker Island from Virgin Gorda or Beef Island.

A new restriction added to the terms and conditions states that you must now hold Virgin Atlantic Flying Club Silver or Gold status to make the redemption. FoundersCard can come to the rescue again here because members can earn Flying Club Silver status after completing only one flight with Virgin Atlantic.

Because you can transfer Amex, Chase, Citi and Starwood Preferred Guest points to Virgin Atlantic in addition to earning miles directly with the Bank of America Virgin Atlantic World Elite MasterCard, a week at the private island may not be as far out of reach as you think. With a 30% transfer bonus now through May 22 for American Express Membership Rewards to Virgin Atlantic, a week on the island will only cost you 924,000 Amex points.

Visit Luxury Tahitian Hotels

The most common hotels people try to visit in French Polynesia using points are the two IHG Intercontinental properties in Bora Bora. Unfortunately, award space is extremely tight and requires daily searches in the hopes a night pops up. Using your annual free night certificate from the IHG Rewards Club Select Credit Card would be the easiest way to book a night if something becomes available.

The Hilton Moorea Lagoon Resort & Spa offers free nights beginning at 80,000 points for a standard room. At the time of writing this there are a few dates available in August for that price. More than likely you'll be asked to pay a premium room rate using points, which appear to start at 169,000 points per night. With the new Hilton program, you can decide to subsidize your room cost by selecting how many points you'd like to use to lower your room cost. For a King Lagoon Bungalow at the property, you can pay $690 per night, 199,000 Hilton points, or use 100,000 Hilton points to lower the room cost to $343 — which gives you an abysmal 0.3 cents/point in value.

The newly rebranded Conrad Bora Bora Nui has a few standard rooms available in the low season for 80,000 points, but most dates are asking an obscene 360,000 points per night for a premium room redemption.

With the cost of award nights sky-high and availability low, I'd suggest some alternative strategies to saving money on Bora Bora and Tahiti hotels. Using the Citi Prestige Card's 4th Night Free benefit could save you $3,400 if you booked The Brando resort for a total of four nights in the low season of August. You can also redeem Chase Ultimate Rewards earned from the Chase Sapphire Reserve for 1.5 cents each towards the cost of hotels when booked through the Chase Ultimate Rewards travel portal. The ability to earn Ultimate Rewards at 3x with the Sapphire Reserve means you're essentially earning 4.5% back toward free Bora Bora hotels whenever you use the card.

Bottom Line

If you're a frequent Delta flyer or FoundersCard member, you can book private jet flights for little or no money out of your pocket. If you hold a variety of transferable-point currencies, you can combine them into Virgin Atlantic for a week on Necker Island and hope you catch a glimpse of a few celebrities or Sir Branson himself. Meanwhile, if your dates are flexible and you start looking for award availability on a daily basis while saving your Hilton and IHG points, it's possible to score free nights in French Polynesia — though a cruise covered with cash-based points appears to be a much better deal.

The Obamas are certainly enjoying the fruits of their labor and there aren't too many exotic places we'd be surprised to see them appear. Our hope is that we can find an avenue to have our own baller Obama-style vacation wherever they decide to visit next.

How many points and miles would you be willing to redeem in order to travel in Obama style?