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February 12, 2025
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February 19, 2026

Choose Your Own Adventure: Italy or Mexico

Guaranteed luxury and breathtaking views await as you pick your next getaway.  The difficult choice?  Where are you going and who is going with you?  This ultimate “choose your own adventure” package for eight (8) will leave your friends begging for an invite and while it might be challenging to choose the destination, whichever trip you pick, that is 100% the right choice! 

Option one is located near the historic town of Cortona, Tuscany.  This villa is the perfect place to spend a relaxing vacation immersed in nature.  The residence is set on the hillside amongst olive groves and woodland, with the most stunning view from the private pool.   

Option two will whisk you away with the gentle sound of birdsong and swaying palms as you step into the sanctuary of your Puerto Vallarta villa.  Perched in the hills of Conchas China and gazing out over the shimmering ocean, your home feels like a hidden oasis with whitewashed adobe and stained-glass windows blending seamlessly with the surrounding nature.  So, raise a glass and cheers to your next adventure, wherever it may take you.

Getting there will be a breeze with 175, 000 American Airline AAdvantage miles. 

  • 175,000 American Airline AAdvantage Miles
    • Vacation for eight (8) guests
    • Choose between Tuscany or Puerto Vallarta
      • Tuscany
        • 8 guests, 7 nights
        • Seven-night stay in a four (4) bedroom/ three (3) bathroom Tuscan Villa for eight (8)
        • Private Chef three-course prepared dinner
        • Guided Wine and Cheese Tour
          • First stop: Wine tasting in Poliziano, a famous “Nobile di Montepulciano”
          • Second stop: Monticchiello, a small medieval village hidden in the valley
          • Third stop: Pienza, known for their locally produced cheeses, especially Pecorino
          • Tour subject to change based upon season
      • Puerto Vallarta
        • 8 guests, 5 nights
        • Private four (4) bedroom/ four (4) bathroom villa with spacious terrace offering a heated infinity pool and outdoor bar
        • Explore the sands of Hidden Beach with a sailing tour of the Marietas Islands
        • Benefit from daily housekeeping and cook service for two consecutive meals per day

Restrictions: MEXICO: Cook service and housekeeping available Monday – Saturday, groceries and gratuities not included. Winners have 12 months from event date to confirm reservation and up to 24 months from event date to travel. Subject to availability and blackout dates, particularly between May 1 and October 31. TUSCANY: Ground transportation (other than wine and cheese tour) and 500-euro damage deposit not included. Wine and Cheese Tour subject to change based upon season. Please allow 15 business days to receive certificate. Subject to blackout dates and availability. Winners have 12 months from event date to confirm reservation and up to 24 months from event date to travel. Blackout dates are the weeks of Thanksgiving, Christmas and New Years. AMERICAN AIRLINES: AAdvantage miles must be downloaded into the winning bidders AAdvantage account prior to January 15, 2028. Certificates cannot be reissued once expired or lost! Travel does not need to be taken prior to the expiration date on the certificate but the miles absolutely must be deposited prior to that date. Once downloaded to the winning bidders account, AAdvantage miles do not expire as long as there is mileage earning or redeeming activity at least once every 18 months.

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Emily Hanna
Emily Hanna

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