Travel Contests and Sweepstakes

If a San Juan getaway sounds good, Captain Morgan Sliced Puerto Rico Sweepstakes is giving one winner and a guest a 4-day, 3-night trip to Puerto Rico. The prize includes round-trip airfare, hotel accommodations in the San Juan area, a $1,000 e-gift card, and a $1,980 check that may be used to help cover taxes. This is a simple one-time online entry. Open to legal U.S. residents 21+. Ends June 30, 2026.

If a spring getaway to Washington, D.C. sounds appealing, Century of Celebration Sweepstakes is giving one winner a trip for up to four people to attend the 2027 National Cherry Blossom Festival Parade. The prize includes airfare reimbursement up to $4,500, two nights of hotel accommodations, ground transportation, up to four Telecast Grandstand parade tickets, and a festival swag bag. Open to U.S. citizens or legal residents 18+, excluding Tennessee residents. Ends June 30, 2026.

If a relaxing island getaway sounds like the perfect prize, Waiākea Wellness Retreat Sweepstakes is giving away two Hawaii travel packages. One mainland U.S. winner will receive a 4-day, 3-night trip for two to the OUTRIGGER Kona Resort & Spa, including airfare, ground transportation, an activities credit, a private helicopter tour, and spa and dining credit. A separate Hawaii winner will receive an inter-island wellness trip with similar resort perks and a helicopter tour. It’s a simple one-time online entry, making this a great travel giveaway to add if ocean views, resort time, and unforgettable experiences sound good to you. Open to legal U.S. residents who have reached the age of majority in their state. Ends August 31, 2026.