Latest Travel Contests and Sweepstakes

March 27, 2026

Win a Run or Cycling Trip in the CLIF Run the World Sweepstakes

Dreaming of an active getaway with big adventure energy? CLIF Run the World is giving away three amazing travel prizes, and each winner gets to choose a running or cycling trip for two to Australia, Argentina, or Japan, plus flights, hotel, and spending money to help make the journey even sweeter. Entries are accepted daily, which makes this a great one to keep in your rotation, and there’s also an optional extra entry if you opt in for marketing emails or use the mail-in method. Open to legal residents of the U.S., D.C., and Puerto Rico ages 18+. Ends July 31, 2026.

March 12, 2026

Win a Trip to Iceland in the Tiptoe Reykjavík Challenge Sweepstakes

Ready for waterfalls, geothermal spas, and stunning Nordic scenery? Tiptoe Reykjavík Challenge – Win a Trip to Reykjavík is giving one lucky traveler a getaway for two to Iceland, including roundtrip flights with Icelandair, a two-night hotel stay with breakfast, spa access, a three-course dinner, and admission to popular attractions like Sky Lagoon, Perlan Museum, and the Lava Show. This travel sweepstakes is a simple one-time online entry, making it easy to throw your name in the hat if Iceland has been on your bucket list. Open worldwide to entrants 18+. Ends August 31, 2026.

February 12, 2026

Win a Classical Greece Trip in the Road Scholar Campus of the Year Giveaway

Road Scholar’s Campus of the Year Giveaway is your chance to trade everyday routines for ancient ruins with a Grand Prize featuring the “Classical Greece: Islands of the Aegean” educational travel program for two, including airfare from a major gateway airport. If you’re 50 or better and dreaming of blue waters, historic temples and lifelong learning on the Mediterranean, this sweepstakes delivers a bucket list adventure in one unforgettable package. Single entry style, big reward energy. Open to U.S. residents 50+. Enter by June 30, 2026.

February 11, 2026

Win a Trip to Vegas to See Kenny Chesney at the Sphere

Blue Chair Bay Rum Kenny Chesney Sweepstakes is bringing full beach-to-Vegas energy, with prizes that range from fun instant wins to a full-on concert weekend. You can enter once, then come back daily to play the instant win scratch game for Blue Chair Bay Rum merch, and you’ll also be in the running for bigger prizes like Kenny Chesney autographed guitars and the grand prize trip for two to Las Vegas to catch Kenny Chesney at the Sphere. Open to U.S. and D.C. residents 21+, and yes, the daily play means more chances to win without doing anything complicated. Entries close June 28, 2026.

June 9, 2025

Win A Trip For Four To Universal Orlando Resort!

Enter The Fandango Trip to Universal Orlando Sweepstakes by July 4, 2025, for your chance to win a trip for four to Universal Orlando Resort in Orlando, Florida! The winner shall receive round trip airfare for four to Orlando, a four-night stay in a standard room at a Universal Orlando Resort hotel, transport to/from the airport/hotel whilst in Orlando, and 3-Park 3-Day Park-to-Park Plus 1-Day Universal Epic Universe Tickets for four! This prize is valued at $4,987.88! Enter today for your chance to win! Good luck!

Browse Ways to Win

More categories, instant wins, daily entries & big prizes

Tips for Better Odds

Safe entry habits, email organization, and scam red flags

Bee Travel Contests and Sweepstakes Smart

How to Enter Safely

Spot scams fast and protect your info.

Read ›

Are These Sweepstakes Legit?

Quick checks before you enter.

Read ›

Travel Contests and Sweepstakes FAQ

Are these sweepstakes legit? › How often can I enter? › Do prizes include taxes/fees? ›