Dreaming of your next getaway? Let us help you narrow down your list! Head south to Havana, or fly a little farther afield to Cortona, located in Tuscany, Italy for an international adventure. Choose the destination that best fits your family-the cultural sites, enchanting landscapes, and delicious food of both locales will make either choice a winner!

Option 1: Explore the stunning architecture of Havana from your own two-bedroom apartment, featuring en-suite bathrooms and balconies overlooking the local square. The residential neighborhood is a quick walk to Havana's most popular attractions including the Capitol Building, Grand Theatre, and National Museum. Visit nearby Old Havana, or Habana Vieja, the historic center of Havana and a UNESCO World Heritage Site. With convenient airport pick-up and drop-off, you'll be set to soak up the sun on the beach, explore Cuban history and culture, or enjoy the local nightlife!

Option 2: Discover Southern Tuscany from your private apartment in downtown Cortona, a small city in the Arezzo province. Enclosed by stone walls dating back to Etruscan and Roman times, Cortona sits almost two thousand feet above sea level and boasts spectacular views of the surrounding Valdichiana, or Chiana Valley, and even Lake Trasimeno. Explore the Archaeological park of Sodo, just located at the bottom of the hill of Cortona, and set out on a day trip (or two) to visit a few of the many vineyards available for tastings, tours and dining.

Special Notes:

For Option 1: Accommodation in a private 2-bed, 2-bath apartment in Havana, Cuba for a 4-night stay for 4 guests. Winners have 2 years to travel from date of purchase.. Blackout dates include: Thanksgiving week, Christmas week, and New Years week.

For Option 2: Accommodation in a private 2-bed, 2-bath apartment in Cortona, Italy for a 4-night, mid-week stay for 4 guests. Winners have 2 years to travel from date of purchase. Blackout dates include: Thanksgiving week, Christmas week, and New Years week.