Italy Sweepstakes 2026
Italy Giveaways
Found 8 total
Big Italy Production is hosting a sweepstakes where you can win a free Chromebook laptop. The contest ends on June 1, 2026. One winner will be selected to receive the prize. Enter to win this amazing giveaway and get a chance to take home a brand new Chromebook laptop. This is a free entry contest, so don't miss out on this opportunity to win a great prize.
Win $200 in value – Big Italy Production Chromebook Laptop Giveaway - Enter Now
Enter the Gateway Casinos & Entertainment Limited Ruffino Little Italy Giveaways sweepstakes for a chance to win an unforgettable trip to Italy. One lucky winner and their guest will embark on a 5-day adventure, complete with airfare, accommodations, and a winery tour, valued at approximately $7,750 CAD. Additional prizes include 32oz Aquifier Water Bottles, Guardian Coolers Soft Cooler Qubes, $25 Match Eatery & Public House gift cards, and 20% off bills at Match Eatery & Public House. With 72 prizes up for grabs, don't miss your chance to win. Enter to win free before the giveaway ends on 05/25/2026 at 3:00:00 AM ET.
Get ready for the ultimate Italian adventure with the Travel to Italy with Trevi Contest. Enter to win one of five incredible trips to Italy, each valued at $5,000, in this exciting sweepstakes giveaway. Trevi is offering a free entry for a chance to win a prize of a lifetime. Don't miss your chance to explore Italy - enter the Travel to Italy with Trevi Contest before the deadline on August 31, 2026, at 11:59 p.m. (EST) for your chance to win with Trevi.
Win $5,000 in value – Travel to Italy with Trevi Contest - Enter Now
Enter to win the AM 570 - The Answer Dream Vacation for Two to Italy Sweepstakes and take home an unforgettable Italy Unfiltered trip for two. One lucky Grand Prize winner will receive a 10-day getaway from September 29 to October 8, 2026, complete with 4-star accommodations, guided tours, and more. The prize package, valued at $9,990, includes centrally located hotels, entrance fees, daily breakfast, and four dinners with drinks. However, winners are responsible for their own air travel to and from Rome, Italy. Don't miss your chance to win this incredible prize - enter the AM 570 - The Answer Dream Vacation for Two to Italy Sweepstakes before 12:59 am EDT on September 1, 2026.
Win $9,990 in value – AM 570 - The Answer Dream Vacation for Two to Italy Sweepstakes - Enter Now
Ecco Domani Italian Getaway Sweepstakes is now open for entries. Enter to win a luxurious trip for two to Italy, valued at $10,000. The sweepstakes, presented by Ecco Domani, starts on March 1, 2026, and ends on December 31, 2026. One lucky grand prize winner will be selected by random drawing on or about January 2, 2027. The prize includes roundtrip airfare, ground transportation, and five nights of standard accommodations in a destination of choice, including Florence, Milan, Rome, or Venice. To be eligible, participants must be 21 years or older. The winner will be notified via email and must respond within two days to claim their prize. Ecco Domani's Ecco Domani Italian Getaway Sweepstakes offers a free entry for a chance to win this incredible Italian getaway, with all details and rules available for review.
Win $10,000 in value – Ecco Domani Italian Getaway Sweepstakes - Enter Now
The Word KFIA is sending one winner on an unforgettable journey, an Italy Unfiltered trip for two, running September 29 to October 8, 2026. The prize includes 4‑star accommodations, guided tours, entrance fees, daily breakfasts, four dinners with wine or beer, and all hotel taxes and service charges, valued at $9,990 USD. The Word KFIA The Italy Unfiltered Dream Vacation Sweepstakes entries close August 31, 2026, at 9:59 PM PDT.
Win $9,990 in value – The Word KFIA The Italy Unfiltered Dream Vacation Sweepstakes - Enter Now
The Word Miami is offering an unforgettable adventure. One grand prize winner will enjoy the Italy Unfiltered trip for two, running September 29 – October 8, 2026. The prize package includes 4‑star accommodations, expert local guides, daily breakfasts, select dinners with wine or beer, entrance fees, and all the extras that make travel seamless from baggage handling to hotel tips. The Word Miami The Italy Unfiltered Dream Vacation Sweepstakes entries close September 1, 2026, at 12:59 AM EDT.
Win $9,990 in value – The Word Miami The Italy Unfiltered Dream Vacation Sweepstakes - Enter Now
Philadelphia’s AM 990 The Answer is giving one lucky winner the Italy Unfiltered trip for two, set for September 29 – October 8, 2026. The prize features four‑star accommodations, expert‑led tours, daily breakfasts, four dinners with wine or soft drinks, and all the extras from entrance fees to hotel tips, a package valued at $9,990 USD. Airfare to Rome is not included, and entries close September 1, 2026, at 12:59 AM EDT.
