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Where are the easiest places to get with frequent flyer miles, especially if you’re just starting out?

I started thinking about it because I had a string of very tough requests through my Free Credit Card Consultation form. One in particular read:

Been following your site for about a year and haven’t been able to jump in. Shame on me. It’s all very overwhelming for a newbie even though you break it down well. [Scott: Agreed, but it doesn’t have to be. Start with the Free Credit Card Consultation and reading my beginners’ series.]

So here is my situation: my wife and I would love to get to one of three destinations over the holiday break (12/26-1/3 ish). The top destinations ( in order) are : Maldives, bora bora, or Bali. Right now I am essentially starting from square 1.

Unfortunately, it’s a nearly impossible request given the:

  • time horizon: he’d need to get the miles and book within 3.5 months
  • travel dates: everyone wants to travel over Christmas and New Year’s, so there is less award space
  • destinations: French Polynesia is tough to get to with miles and Maldives and Bali are just really expensive, requiring more credit cards than he has time to open

Don’t worry about this requester, though, I helped him come up with a plan to get to the Maldives next summer that I am confident he can accomplish.

The tough request got me thinking about all the people who come with a nearly impossible first idea for miles, fail to achieve it, and then give up on our hobby. The opposite, an early successful booking with miles, can hook someone for life. I started pondering: what is the easiest place for a beginner to get quickly with miles.

  • What four regions do I think are the easiest for beginners to focus on to jump start their miles success?
  • What time horizon and travel dates increase the chance of success?

I’ll focus on four areas that are well within reach quickly with miles.

  1. Europe
  2. Central America & Northern South America
  3. Hawaii
  4. Anywhere with cash flights under $460


You can get to Europe in economy by opening one credit card. Delta, United, American, and US Airways all charge 60,000 miles roundtrip in economy.

American Airlines, United, and Delta frequently offer 50,000 miles bonuses on their credit cards, so spending $10,000 on one card over time while collecting the 50,000 mile bonus gets you the 60,000 miles needed for a roundtrip award.

Award space is usually pretty open during the summer to Europe in economy if you plan ahead.

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A beginner could open one card, spend $10,000 on it over time, and book a roundtrip to Dubrovnik, Croatia for next summer.

If you don’t have to travel over the summer, you can book an award to Europe even more easily.

American only charges 40,000 miles roundtrip to Europe from October 15 to May 15 on its own flights or partners.

US Airways only charges 30,000 miles roundtrip to Europe from January 15 to February 28 on its own flights if you have The US Airways® Premier World MasterCard®, which comes with 40,000 bonus miles after first purchase.

Central America & Northern South America

These regions are super cheap at 30,000 to 45,000 miles roundtrip and have widely available award space year round. You might scoff at this part of the world, but it contains:

  • Machu Picchu (Peru)
  • the Galapagos Islands (Ecuador)
  • Costa Rica
  • Panama
  • Sofia Vergara (Colombia)

You can get anywhere in the region by opening one of several cards. I’d recommend the Sapphire Preferred, which comes with 40,000 bonus Ultimate Rewards after spending $3,000 in three months, because its Ultimate Rewards can transfer to United miles or British Airways Avios, giving you two great options to this part of Latin America.

United’s partners TACA, Avianca, LACSA, and Copa fly to the region from the United States to complement United’s own flights. American Airlines flights, bookable with Avios, have great award space and are cheap with Avios because of the short distances involved.

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Here’s my Top Ten Things to Do, See, and Eat in Peru.


Hawaii costs 25,000 to 45,000 miles roundtrip in economy. You can even go one way in a flat bed and one way in economy for only 47,500 Singapore Airlines miles, which you could get from opening one credit card.

Me asleep in my bed in United First Class between Washington DC and Honolulu

Which card to get for Hawaii depends a lot on where you live and what cabin you want to fly. I won’t go through all the permutations here–that’s what the Free Credit Card Consultation is for–but it’s super easy to get to Hawaii by opening one credit card per traveler.

Anywhere That Costs Less than $460 Roundtrip

Who says you have to start with airline miles? For a lot of trips, especially domestic and near international, you’re better off with bank points that can be used toward any flight on any airline with no blackouts.

If you open the Barclaycard Arrival PlusTM World Elite MasterCard® and spend $3,000 within 3 months, you’ll have 46,000 Arrival miles from the spending and sign up bonus.

You can use 46,000 Arrival miles for $460 in free flights or $450 off a more expensive flight. (Plus when you make the redemption you’ll instantly get back 4,600 Arrival miles worth another $46 in free flights.)

If you want inspiration on where to go with your Arrival miles, check out Explore harnesses the results of the thousands of daily searches on Kayak to show you the best deals others have found.

You can put in your home airport and your preferred dates (or not), and Explore tells you the lowest fare to each region of the world. You can then click on the fares to find more information and perform the search the previous searcher did to see if the fare is still available.

Looks like someone found Washington DC to Medellin, Colombia for $389 roundtrip, to Trinidad and Tobago for $433 roundtrip, and to Naples, Italy for $702 roundtrip.

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Kayak Explore is a great feature for the aimless wanderer just looking for a good deal. It’s the antithesis of the price alerts feature, which is for planners who know they need to go to a specific place at a specific time.

The Barclaycard Arrival PlusTM World Elite MasterCard® is a good place to get hooked with miles. You know you will get over $500 in free flights just by meeting the spending requirement, and that early success will hopefully propel you deeper into the game.

Bottom Line

Aim small to start. Get one free flight, and you’ll be hooked for good to the point that you can follow through on your loftier goals.

The easiest places to aim in the beginning are Europe, Hawaii, Latin America, and anywhere you can book a flight for under $460 roundtrip.

Let me assess how realistic your goal is and tell you what cards to get with a Free Credit Card Consultation.

Earn 60,000 bonus points after you spend $4,000 on purchases in the first 3 months from account opening.

Just getting started in the world of points and miles? The Chase Sapphire Preferred is the best card for you to start with.

With a bonus of 60,000 points after $4,000 spend in the first 3 months, 5x points on travel booked through the Chase Travel Portal and 3x points on restaurants, streaming services, and online groceries (excluding Target, Walmart, and wholesale clubs), this card truly cannot be beat for getting started!

Editorial Disclaimer: The editorial content is not provided or commissioned by the credit card issuers. Opinions expressed here are the author’s alone, not those of the credit card issuers, and have not been reviewed, approved or otherwise endorsed by the credit card issuers.

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