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My friend has big trip aspirations for this summer, but nothing booked.

• Approx July 12: Boston to France, Italy, or Spain
• July 13/14 to 24/25: work on a vineyard in France, Italy, or Spain
• July 25: vineyard location to Croatia
• July 26 to August 2: Yacht Week
• August 2: Croatia to Greece
• August 10/11: Greece to Boston
• August 22: Boston to Colombia
• August 31: Colombia to Costa Rica
• Sept ~7/8: Costa Rica to San Francisco

She emailed me for my suggestions. This is how I would book this trip.

Warning: this post combines a lot of my best material and ideas. It would be too much information to spell everything out, so in several spots I have linked to longer articles on the concepts I discuss. Click the links.

Approx July 12: Boston to France, Italy, or Spain

Some people have all the luck. She wants to fly from Boston to Europe during the two month window when such awards cost only 12,500 Flying Blue miles and $88.50 each way and award space is wide open.

See Fly from the United States to Europe this Summer for 25k Miles Roundtrip for full details.

Flying Blue miles are a 1:1 transfer partner of Membership Rewards, so she needs 13k Membership Rewards or a friend with 13,000 Membership Rewards. You can earn 40,000 Membership Rewards after spending $3,000 on The Platinum Card® from American Express. The card has a $450 annual fee that I think is more than made up for by having the best features of any card.

July 25: vineyard location to Split, Croatia

Traditional flight awards within Europe are generally a poor value. You pay miles plus high European air taxes, and you have to hunt for award space.

I usually fly around Europe on low-cost carriers. They are adequate for short flights, and as long as you follow their baggage and check in rules to the letter, you can usually fly around very cheaply.

EasyJet flies into Split, where Yacht Week starts, for several cities in France and Italy. I priced out a July 25 flight from Milan, and it came to 59.66 EUR ($82.85) if you fit everything into one cabin bag and about $20 more if you also need to check a bag.

By comparison, a United award would be 12,500 miles plus government taxes, and an Avios award from Madrid on Iberia is 7,500 Avios + $67.

The EasyJet flight is a far better deal than a traditional award. If she doesn’t want to pay $83 out of pocket, she can book the EasyJet flight with her Barclaycard Arrival Plus™ World Elite MasterCard® and then redeem Arrival miles to remove the charge.

The best part is that Arrival redemptions take just a few clicks, and you can redeem any time within 90 days of the purchase. She could actually get the Arrival card now, make the flight purchase with it, and then redeem Arrival miles to remove the charge in a few months when she has earned the Arrival card’s bonus.

August 2: Croatia to Greece

Transportation options from Split to Greece are awful. Croatia Airlines hasn’t released economy award space on the direct flight to Athens on August 2, which would cost 15k United miles. Instead there is only space in business class for 30k miles.

Thirty thousand United miles for an hour forty minutes in intra-European business class is a terrible use of miles because intra-European business class is just economy class with the center seat blocked off and a small meal.

It’s the same 30k United miles to continue on past Athens to anywhere in the country on connecting Aegean Airlines flights.

Cash tickets are extra-ordinarily expensive. The cheapest I found to Thessaloniki on August 2 is $436 and has two over night stops in Germany!

You can make the trip for 15k United miles if you’re willing to make two stops and travel 10 hours.

I’m really not sure the best option for this leg. Commenters?

August 10/11: Greece to Boston

Unfortunately this falls outside of the Flying Blue Promo Award period mentioned earlier. There are still good options though.

If you can find award space on Aer Lingus, you can book ATH-DUB-BOS for only 22,500 British Airways Avios and a small amount of dollars out of pocket.

Avios are a 1:1 transfer partner of Ultimate Rewards and Membership Rewards, so that same Platinum Card® from American Express I mentioned above to get Flying Blue miles could get you Avios. (By the way, since you’re coming into the U.S. twice on the trip, you’ll want Global Entry to skip the queue at immigration. The Platinum Card refunds the $100 application fee.)

If Aer Lingus has no award space, you can pay 30k miles for an award from Athens to Boston. The award I found wouldn’t be pleasant because it is four segments and has an overnight in Frankfurt (which is easy and lovely for an overnight), but it is a valid trip for 30k United miles plus taxes. (I found this by searching segment-by-segment.)

August 22: Boston to Colombia

August 31: Colombia to Costa Rica

Sept ~7/8: Costa Rica to San Francisco

All of these can be booked on one United award for 40k miles. You’ll fly TACA, LACSA, and Avianca, which are all Star Alliance partners of United.

Award space exists on all your days, but when I tried to put it together online, I got an error message, which happens frequently when constructing multi-city awards on united.com.

You can pick out the space you want and call in for a $25 fee. Even better you can avoid the fee like this.

You can get the United card with 55k bonus miles by signing up for a 50k offer and adding an authorized user.

Recap

Sorry for the information and link dump, but getting flights for free isn’t always so simple.

For 46k Membership Rewards, 55k United miles, and around 50k Arrival miles, you can get the flights completely for free. (Don’t forget to pay award taxes with Barclaycard Arrival Plus™ World Elite MasterCard® and then remove them from your statement.)

If it’s too complicated to continue on your own, you can hire the MileValue Award Booking Service.