It’s ‘National Plan Your Vacation Day’ — Here’s how to make your dream trip a reality

Jan 28, 2020

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If you’re looking for a sign to use all your PTO this year, this is it.

It’s a well-known fact that Americans don’t take enough time off. In fact, a whopping 42% of people in the U.S. didn’t take a vacation in 2018, and many of those who did regretted how they used those hard-earned vacation days.

Don’t worry, we’re not going to let that happen to you this year. Whether you want to know the hottest places to travel or the most exciting places to stay, there’s a ton of inspiration out there to encourage you to finally book that dream trip.

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But just in case you need a little extra nudge, today is National Plan Your Vacation Day. In honor of this most auspicious “holiday,” we’re rounding up some of our favorite tips to help you, well, plan a vacation today.

So, get out your pen and paper and take notes, because vacation-planning class is in session.

Use transfer partners

Taking advantage of transfer partners is the best way to get the most value out of your points and miles. By that we mean, you’ll almost always get more value out of your credit card points by transferring them to airlines and hotel loyalty programs.

Take, for example, TPG reviews editor Nick Ellis. He’s going to Africa this summer and is planning on using 75,000 Aeroplan miles transferred from Amex Membership Rewards (transferred at a 1:1 ratio), plus $50, to fly from New York-JFK to Addis Ababa (ADD) in Ethiopia via Abidjan, Côte d’Ivoire (ABJ) in business class. He’ll then transfer 24,000 Chase Ultimate Rewards points to Hyatt (also at a 1:1 ratio) for two nights at the Hyatt Regency in Addis Ababa.

TPG’s managing editor, Alberto Riva, had a similar strategy. He says: “My wife and I wanted to fly to Milan (MXP) for my dad’s birthday party on April 1. When I read Nick Ewen’s story about a lot of award seats in the excellent Swiss Air Lines business class, I sprung into action. I easily found four [business-class] seats from New York-JFK to Zurich (ZRH) and back at the 70,000-mile saver award level on United, as United is a Swiss partner in Star Alliance. I didn’t have enough United miles, so I transferred 210,000 Chase points to my United Mileage Plus account to make up for the shortfall and booked. In total, I used 280,000 miles plus $116.90 in taxes and fees. From Zurich to Milan, it’s a quick connection on a high-speed train — and once we’re in Italy, we plan to spend a few days in Sicily, using a low-cost domestic flight.”

Be flexible and patient

Sometimes your vacation plan isn’t going to fall perfectly into place. You might have to boost some of your points and miles balances, or wait for award availability to open up.

That’s true for me right now. I’m planning on going to California with my family this summer. We’re using 95,000 Hilton Honors points per night to stay at the Waldorf Astoria Beverly Hills, and then transferring 60,000 Chase Ultimate Rewards points to Hyatt to stay at the Hyatt Regency in San Francisco for three nights … but we’re still waiting for award availability to open on American Airlines to book the business class flights I want. In fact, if it all works out the way I want it to, it will be my sister’s first time flying in business class, too!

The Waldorf Astoria Beverly Hills. (Photo courtesy of Jean George Restaurants)
The Waldorf Astoria Beverly Hills. (Photo courtesy of Jean George Restaurants)

Related: How I used a $330 business-class deal, free night certificate and points to vacation in Aruba

Take advantage of credit card perks

From travel credits to airport lounge access, your credit card is a tiny piece of plastic (or metal) that can open the door to some pretty incredible travel experiences.

Podcast producer Caroline Schagrin is taking advantage of the aforementioned transfer partners for an upcoming trip to London. But because she paid for the taxes and fees (about $180) with her American Express® Gold Card, she was credited back $100 from the card’s airline fee credit benefit.

Taxes and fees rarely trigger Amex’s airline incidental fee reimbursement, so this may be a stroke of good luck, but you can rely on this credit to offset other costs your dream vacation may incur, including seat selection and checked bag fees. If you have an “eraser” card like the Capital One® Venture® Rewards Credit Card, you can instead apply your miles at a 1 cent per point ratio to statement charges that code as travel. Because Capital One considers everything from airline and hotel purchases to train tickets, car rentals and cruises travel purchases, among others, you can more easily use a perk like this to offset the cost of your vacation.

Keep an eye out for deals

You don’t have to splurge to have the vacation of a lifetime. Following us on social is a great way to keep up with the latest deals, and if you see one you want, jump on it. Remember, you (almost) always have 24 hours to cancel or change a flight from, to or within the U.S., assuming the flight was booked at least seven days ahead of departure. So, book now — plan later.

For example, TPG’s social media lead, Caitlin Riddell, recently booked a round-trip economy flight on American Airlines for 35,000 miles from New York City to Madrid (MAD). Her advice? Take advantage of American Airlines Web Specials!

Famous Cibeles Fountain on a sunny day. (Photo by travel1116/Getty Images)
Famous Cibeles Fountain on a sunny day. (Photo by travel1116/Getty Images)

Reporter Liz Hund also took advantage of a recent American deal and was able to snag a round-trip economy ticket to Australia for 23,000 American Airlines miles total: 18,000 on the way back, but just 5,000 miles on the way there.

Related: How you plan and organize your trip says a lot more about you than you think

Buy miles when necessary

While it’s usually not a great idea to buy miles since you typically won’t get a ton of value out of this transaction, there’s a time and a place for everything. Namely: When you’re just a few miles short of your dream redemption.

In Liz’s case above, she was short about 3,000 American miles, and purchased 5,000 for about $150 through American since it was such a good deal overall.

Maximize your cash purchases

Of course, using points and miles can help you go places you never thought possible otherwise.

But it’s always worth checking cash prices to make sure you’re getting the best deal possible. TPG’s UX Designer, Mona Kim, is currently on vacation in Portugal. While she strategically used points for her flights, she ended up paying in cash for her hotels since it’s off-season and they’re a lot cheaper than usual.

Beach in Lagos, Algarve, Portugal. (Image by M Swiet Productions / Getty Images)
Beach in Lagos, Algarve, Portugal. (Image by M Swiet Productions / Getty Images)

Just be sure you’re putting your purchases on a credit card that will earn you bonus points for your trip, such as the Chase Sapphire Reserve (3x) or Chase Sapphire Preferred Card (2x).

Depending on what credit cards are in your wallet, you may also be able to get more value out of cash stays at hotels by booking through a program such as American Express Fine Hotels & Resorts or Chase’s Luxury Hotel & Resort Collection (LHRC). Both offer travelers elite-like perks such as daily breakfast for two, a property credit and an upgrade upon arrival, when available.

Consider creative itineraries

Flying in and out of different airports might give you more flexibility, and ultimately help you get where you want to go.

Just ask Carissa Rawson, a points and miles reporter at TPG. She took advantage of a Delta SkyMiles award redemption to book flights from Newark (EWR) to Bogotá (BOG). She’s then using Avianca LifeMiles to travel onward to the Galápagos; Chase Ultimate Rewards points for LATAM flights between Easter Island (IPC) and Santiago (SCL); and flying an open jaw itinerary again using Delta SkyMiles to get back to Newark from Santiago.

Ask your friends for help

Buckle up your seatbelts for this one.

Senior points and miles editor Nick Ewen said he’s heading to Vietnam, Cambodia and Thailand in May and June. He booked outbound flights in business class on Cathay Pacific through Alaska Airlines (50,000 miles per person, which he earned from the Alaska Airlines Visa Signature® credit card, plus various other flights over the last few years) and then is returning home in Japan Airlines business class to Seattle (SEA), also booked through Alaska at 65,000 per person.

He’s spending the first four nights at the Park Hyatt Saigon in a suite, which he booked by transferring Chase points to his Hyatt account and then transferring 96,000 points to a colleague’s Hyatt account to book on his behalf. Since this colleague has Globalist status, this qualifies as a Guest of Honor reservation, which means Nick will enjoy daily breakfast and a chance at an upgrade. Paid rates for the suite were over $500 per night, giving him a value of 2.15 cents per Hyatt point.

Nick then booked a four-night paid stay at the Six Senses Krabey Island (and hopes they’ll be participating in IHG Rewards Club by May!) and a four-night paid stay at the Park Hyatt Siem Reap ($230 per night booked through Hyatt Prive, so he will get breakfast, an on-property credit and a confirmed upgrade to a rooftop garden suite at the time of booking).

He’s ending the grand tour with a two-night stay in a suite at the Hilton Millennium Bangkok, where he’s planning on using his Diamond status perks courtesy of The Hilton Honors American Express Aspire Card. Finally, to get home from Seattle, he’ll use the companion fare benefit on his Alaska Visa, which will save over $200 off his daughter’s flight.

And that’s how you do it, people.

Featured image courtesy of © Images.

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More Things to Know
  • Earn 60,000 bonus points after you spend $4,000 on purchases in the first 3 months from account opening. That's $750 toward travel when you redeem through Chase Ultimate Rewards®
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Either $5 or 5% of the amount of each transfer, whichever is greater.
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