The Lost Girls “AMEX Pay-with-Points Trip” – Planning our Puerto Rican Getaway!

Adventure Travel, Planning, Puerto Rico — By on September 29, 2011 at 10:46 am

Planning our trip to Puerto Rico with AMEX rewards points

Recently, Amanda, Holly and I were presented with an incredible mission:  Plan a last minute, top secret getaway using only American Express rewards points, a compass and a Swiss Army knife.  Okay, so the compass and knife are an exaggeration.  But we were challenged with booking a soup-to-nuts trip for three—everything from airfare and lodging to transportation and fun extras—entirely with a bank of 300,000 AMEX points.

Now I know what some of you may be thinking:  Aren’t these so-called points programs complicated and confusing, fraught with restrictions, black-out dates and impossible-to-read fine print?  Surprisingly, no.  Not with AMEX, anyway.  Sitting down together with a laptop and only a vague idea of where we might want to go in the world (a three-way tie between dude ranch in Montana, a scuba destination in the Caribbean or vineyard in Sonoma), we logged onto the membership rewards site and started exploring the travel section.

Before long, we felt like we were in a personal Choose Your Own Adventure series (for those of you who are too young to know what I’m talking about, shame on you!).  Easily testing out different date and destination combos with just a few clicks of our mouse, we instantly received an array of affordable flights, hotels and vacation options.

If you were following us on Facebook and Twitter while we were away, you know that we eventually chose Puerto Rico as our mystery locale.  A huge congrats to Diane Nguyen, the winner of the $100 AMEX gift certificate, for correctly guessing our secret destination.

But how did we specifically divvy up our points to get the most bang for our travel buck?  To help inspire you to plan your own AMEX rewards journey, below is a detailed breakdown of exactly how we booked everything, what we spent point-by-point and helpful hints for navigating the Membership Rewards ( site.

And stay tuned over the next several weeks to find out more about our trip, all our adventures in Puerto Rico and a few unexpected twists and bumps in the road.

Happy travels!


The Lost Girls



 AMEX Pay-with-Points:  Our Trip Planning Overview



Enjoying a sunny day in Puerto Rico (after narrowly avoiding Hurricane Irene

  • What we scored:  3 round trip tickets from New York City to San Juan, Puerto Rico
  • Points spent:  106,497 (approximately $1,064 in value)
  • Do it Yourself:  Go to Travel → Personal Travel → Book a Trip → Book Travel with Points / Pay with Points Now → Flights and fill in all the required info.  Like other well-known travel search engines, you’ll get results back by airline, price, itinerary, etc.  After you’ve made your selection, simply opt to pay with points during check out.
  • Helpful hint:  Like with all points purchases, you can opt to pay for flights with all points or partial points, so even if you don’t have enough for a full flight, you can decrease your total.



  • What we scored:  5 nights in luxury hotels / resorts (2 nights in the El San Juan Resort and Casino, 2 nights in the W Hotel in Vieques and 1 night in the Wyndham Rio Mar Beach Resort in Rio Grande)
  • Points spent:  173,666 total (59,640 points, 85,181 points and 28,845 points respectively)
  • Do it Yourself:  Follow the exact same steps as you do for flights, except choose the Hotels tab in the search engine.
  • Helpful hint:  Be sure to check the hotel policy and certain rooms are non-refundable or require several days’ notice for cancellation.  The good news:  If something like, say, a hurricane makes it impossible to check into your hotel/your hotel issues refunds due to a natural disaster (teaser alert for our next blog post!), you can rely on AMEX to take care of you and help make alternate hotel arrangements.


Rental Car

  • What we scored:  Our own wheels for 1 week on the island
  • Points spent:  10,000 total ($100 Enterprise gift certificate)
  • Do it Yourself / Helpful Hint:  While you can search for and reserve cars by following the same steps/path as you do for flights and hotels, we recommend purchasing an e-certificate for Enterprise, Avis or National in the Rewards section (Rewards → Use Points → Car & Rail) and then reserving the car (filling in your e-certificate number when prompted).  Then you’ll simply need to print the certificate and bring it with you to the rental car counter.
  • Bonus:  You can also purchase a Express Rewards Gas Card in the same section of the site to help you fill up for less almost anywhere AMEX is accepted.


Travel Guide Book

  • What we scored:  A Lonely Planet Puerto Rico on
  • Points spent:  1,576 (Approximately a $12 value)
  • Do it Yourself:  From the Rewards home page, go to the Shop with Points on section, where you’ll be prompted to sign onto, link your AMEX to your Amazon account and then start shopping!


Fun Extras

  • What we scored:  $50 Hilton gift card, which we used to purchase a round of cocktails at the Hilton bar and next-day hangover coffees from the on-site Starbucks
  • Points spent:  6,000
  • Do it Yourself:  Go to Rewards → Use Points → Shopping → Gift cards and select Hilton Honors under the Brands box on the left (or scroll through the cards or enter Hilton in the search bar) and choose the certificate value that you want
  • Helpful Hint:  Be sure to allow several days to one week for shipping, depending which option you choose (a small fee is charged for rush delivery)



Lost Girls World is a proud sponsorship partner of American Express