Latest Online Travel Sweepstakes

April 8, 2026

Win a Free Viking Cruise in the Viking 2027 8-Day Journey Sweepstakes

If an eight-day cruise sounds like your kind of daydream, Viking Q2 2026 “2027 8-Day Journey” Sweepstakes is serving up one very big travel prize with an 8-day Viking cruise for two plus airfare included. This cruise sweepstakes covers river, ocean, Mississippi, and expedition options depending on availability, so it has that fun luxury-travel feel without making you chase a bunch of complicated hoops just to enter. It’s a simple one-time entry online, and the webinar option is free too, which keeps it pretty approachable for a prize this big. Open to legal U.S. and Canadian residents 21+, excluding Quebec. Ends June 30, 2026.

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 Travel Sweepstakes by Type

Explore common prize categories and trip styles.

🚢 Cruise Sweepstakes
Ocean cruises, river cruises, and sail-away getaways.
🇪🇺 Win a Trip to Europe
City breaks, guided tours, and bucket-list destinations.
⛷️ Win a Ski Trip
Resort stays, lift tickets, and winter adventure prizes.

How Travel Sweepstakes Work

Quick answers to common questions before you enter.

Are travel sweepstakes legit?
Many are legitimate promotions run by brands, media outlets, or travel companies. Always check the official rules, sponsor information, and eligibility requirements.
Do the trips usually include airfare?
Sometimes. Some prizes include airfare and hotel, while others only include accommodations or a travel voucher. The official rules explain exactly what’s included.
How often can I enter?
Entry frequency varies by promotion. Some allow one-time entry, while others allow daily or weekly entries. Always confirm in the rules.
Are there taxes or extra costs?
In many cases, prizes are taxable. Winners may also be responsible for optional upgrades, resort fees, or incidentals.

Sweepstakes Tips & Guides

Beginner’s Guide

How sweepstakes work, where to find them, and how to enter safely.

Read the Guide

Understanding the Odds

What “good odds” actually means — and how to spend your time smarter.

Read the Guide

Taxes on Sweepstakes Winnings

With great prizes come significant liabilities

Read the Guide