Sweepstakes is closed
Enter to win: A one-of-a-kind Italian getaway
Step into a world of history, flavor and romance with a trip for two to Italy. Explore Rome’s iconic landmarks, enjoy rooftop cocktails after a sunset stroll through the Spanish Steps, and ride the rails to the hillside city of Orvieto—all on an unforgettable journey designed for indulgence and discovery. This prize package, valued at up to $8,000, includes round-trip airfare, rail travel, luxury accommodations and curated experiences.
You and a guest will spend two nights at the Liberty Boutique Hotel in Rome before heading to Locando Pallazone in Orvieto, a restored 13th-century retreat surrounded by vineyards. Each day brings something new: breakfast each morning, three elegant dinners, private skip-the-line tours of the Colosseum and Vatican, a garden evening at Le Jardin de Russie, vineyard e-bike excursions, wine tastings and more—crafted just for you.
Photo Credit: Agoda 
Photo Credit: Winalist 
Photo Credit: Primastoscana
ADDITIONAL DETAILS: This sweepstakes is sponsored by The Kevin and Kristen Leddy Charitable Fund and managed by Travel-Well. All accommodations are subject to availability. Only one entry per household, please. No gift is required to enter. If you win and change your mind, you can decline the prize when we contact you. Only entries between 5/9/25 6:00 a.m. and 5/15/25 6:30 p.m. will be eligible. Past sweepstakes winners . Sweepstakes Rules.
Your trip includes:
- Round trip airfare from Denver
- Rail travel within Italy
- Five nights accommodation at the Liberty Boutique Hotel in Rome (based on availability) and three nights accommodation at Locando Pallazone in Orvieto (based on availability)
- Dining and experiences will be planned between the winner and Travel-Well, working within the set budget, and includes:
- All breakfasts
- Three special dinner experiences
- Private ‘skip-the-line’ tour of the Coliseum and the Vatican
- Borghese Garden and dinner at Le Jardin de Russie
- Vineyard tours and tastings in Orvieto, located in the Umbrian region
- E-bike tour of Orvieto
- Other tours of Umbria and Tuscany
Total value: up to $8,000
Valued at up to $8,000, This is your chance to explore Italy’s “Green Heart”—Umbria—through truffle hunts, olive orchard picnics and hidden countryside tours. Toast with a welcome bottle of champagne and enjoy unexpected surprises along the way. Enter now for your chance to turn travel dreams into reality.
ADDITIONAL DETAILS: This sweepstakes is sponsored by The Kevin and Kristen Leddy Charitable Fund and managed by Travel-Well. All accommodations are subject to availability. Only one entry per household, please. No gift is required to enter. If you win and change your mind, you can decline the prize when we contact you. Only entries between 5/9/25 6:00 a.m. and 5/15/25 6:30 p.m. will be eligible. Past sweepstakes winners. Sweepstakes Rules.
