Choose Your Own Adventure: Italy or Barbados

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 to experience sun-kissed palms and powder-white shores on the breathtaking coral island of Barbados. Cradled between the Atlantic Ocean and Caribbean Sea, this tale of two coasts strikes the perfect balance between relaxation and adventure for sun-chasers, surfers, and anyone seeking irresistible island charm.

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 Airlines AAdvantage miles.

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 and Barbados
    • 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
    • Barbados
      • 8 guests, 5 nights
      • Five-Night Stay in a Private four (4) bedroom/ four (4) bathroom crescent-shaped villa with infinity edge swimming pool for eight (8)
      • One bedroom offers twin-size beds
      • Four (4) minute drive to the beach, 10-minute drive to Holetown’s unmissable restaurants
      • Housekeeping and cook service

Restrictions: 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.