Cruise Sweepstakes & Vacation Giveaways
Win Free Cruises and Luxury Ocean Voyages
Found 28 total
Enter to win the Vagabond Cruise Gift Certificate Giveaway.
Prize: a $100 Vagabond Cruise gift certificate for a Hilton Head SC cruise (1 winner).
Eligibility not stated. Ends November 2, 2026; the winner is announced November 3.
To enter, follow Vagabond Cruise on Instagram, like the post and tag at least one person in the comments (each extra tag is an extra entry).
Win $100 in value – Vagabond Cruise Gift Certificate Giveaway - Enter Now
Enter to win the Seranova Beauty BFCM Cruise Sweepstakes - 2 Winners.
Two winners each get a $2000 Holland America electronic gift card (total ARV $4000).
Open to US and DC residents 18+ (or age of majority if higher). Ends December 31, 2026 at 11:59 PM EST. Winners drawn on or about January 7, 2027.
To enter, complete the free online entry form at tally.so/r/J11GYd or place an order through the seranova.com checkout (1 entry per person per day either way).
Win $4,000 in value – Seranova Beauty BFCM Cruise Sweepstakes - 2 Winners - Enter Now
Enter to win the New York Jets Your Ticket to Sail with Carnival Sweepstakes.
One Grand Prize winner gets a $2000 Carnival Cruise Line gift card and a $1000 American Express gift card (ARV $3000).
Open to legal permanent residents of the 50 US and DC who are 21 and older. Ends November 19, 2026 at 11:59 PM EST. Winner drawn on or about November 20, 2026.
To enter, visit nyjets.com/carnival during the promotion period and submit the official entry form (limit 1 entry per person, email and household).
Win $3,000 in value – New York Jets Your Ticket to Sail with Carnival Sweepstakes - Enter Now
Enter to win the TRAVEL + LEISURE World’s Best Awards 2027 Sweepstakes.
One winner and a companion get an 8-day Viking Châteaux Rivers & Wine river cruise from Bordeaux (Veranda Suite, tours, Silver Spirits package, business-class airfare); ARV $35772.
Open to US and DC residents 21+ with a valid US passport. Ends February 22, 2027 at 11:59 PM EST.
To enter, complete the World's Best Awards survey at tlwbavote.com OR email your full name and mailing address to [email protected] with subject "T+L World's Best Awards 2027 Survey Sweepstakes"; one entry per person/email. The drawing is on or about March 1, 2027.
Win $35,772 in value – TRAVEL + LEISURE World’s Best Awards 2027 Sweepstakes - Enter Now
Enter to win the Sip and Seek Adventure Road Trip Getaway Sweepstakes - 3 Winners. ( sponsor listing )
Three winners each receive one road trip package to a single destination (one winner per destination; total ARV $5775):
- The Palm Beaches Grand Prize: one winner receives a two?night, three?day stay at The Singer Oceanfront Resort for up to four guests (valued at $1,250), a Visit Palm Beach paddling excursion or catamaran cruise for four guests (valued at $575), a guided tour at Loggerhead Marinelife Center for four guests (valued at $100), a $200 BruMate gift card, and four pairs of Hobie Eyewear sunglasses, four mini?towels, and four hats (valued at $200). The Approximate Retail Value is $2,325.
- Twin Cities Gateway Grand Prize: one winner receives a two?night, three?day stay in the Twin Cities Gateway for up to four guests (valued at $1,000), curated local experiences for four guests (valued at $100), a $100 Jelly Bean & Julia’s BBQ gift card, a $250 Visa® gift card, a $200 BruMate gift card, and four pairs of Hobie Eyewear sunglasses, four mini?towels, and four hats (valued at $200). The Approximate Retail Value is $1,850.
- Visit Pinehurst Southern Pines Aberdeen Grand Prize: one winner receives a two?night, three?day stay at Courtyard by Marriott Aberdeen for up to four guests (valued at $400), a golf experience for four guests at Talamore Golf Resort, The Cradle, or World Golf Hall of Fame (valued at $200), four tickets to Sandhills Garden of Lights (runs November 27, 2026 through January 10, 2027 on select nights, valued at $100), a $250 Visa® gift card, a $200 BruMate gift card, and four pairs of Hobie Eyewear sunglasses, four mini?towels, and four hats (valued at $200). The Approximate Retail Value is $1,600.
To enter, complete the registration form on the Road Trip Getaways website. Limit one entry per person per day.
Open to legal residents of the US and DC who are 18+. Starts September 21, 2026. Ends November 1, 2026 at 11:59 PM EDT.
Trips must be taken within 12 months of prize acceptance. Transportation is not included. Restrictions and blackout dates apply. *This was recently extended to November 1, 2026.
Win $5,775 in value – Sip and Seek Adventure Road Trip Getaway Sweepstakes - 3 Winners - Enter Now
Enter to win the MSC Cruises Holiday and Make it Grand Sweepstakes.
One winner gets a 7-night MSC World Atlantic cruise for up to eight people in the Grand Hamptons Villa, valid for one year starting January 2028 (ARV $30,000).
Open to legal US residents 21 and older (or the age of majority in their state). Ends January 21, 2027 at 11:59 PM EST.
To enter, comment on any designated MSC Cruise sweepstakes social post, tag up to seven people you'd bring and include #MSCWorldAtlantic and #Sweepstakes; each eligible comment is an entry.
Win $30,000 in value – MSC Cruises Holiday and Make it Grand Sweepstakes - Enter Now
Enter to win the Chris Young & Top Shelf Country Cruise Sweepstakes.
One winner gets the Chris Young and Top Shelf Country Cruise trip worth $14,500.
Open to legal residents of the US and DC 18 and older. Ends November 1, 2026 at 11:59 PM EST.
To enter, complete the entry form once per day; follow actions earn bonus entries. The cruise sweepstakes winner is drawn about two business days after the end.
Win $14,500 in value – Chris Young & Top Shelf Country Cruise Sweepstakes - Enter Now
Enter to win the World Travel Holdings Royal Caribbean Cruise Giveaway.
One winner gets a Royal Caribbean cruise voucher worth up to $5000 toward one balcony cabin.
Open to residents of the US, DC, Puerto Rico, US territories and Canada (excluding Quebec). Ends January 12, 2027 at 11:59 PM EST.
To enter, submit the entry form with your name, email and phone number on the Dream Vacations contest page. One entry per person.
Win $5,000 in value – World Travel Holdings Royal Caribbean Cruise Giveaway - Enter Now
Enter to win the Rise and Rhythm Cruise for Two with iHeartRadio Sweepstakes.
One winner and a guest get a 4-night Rise and Rhythm Cruise aboard the Norwegian Jewel from Miami, January 14-18, 2027, with round-trip airfare, a KEM toast and signed swag.
Open to legal residents of the 50 US and DC who are 21 or older. Ends November 1, 2026 at 11:59 PM EST.
To enter, sign in and enter once every 24 hours on the contest page at iheart.com or in the iHeartRadio app; click Listen on iHeartRadio for 20 bonus entries a day. The winner is drawn on or about November 2, 2026.
Win $10,000 in value – Rise and Rhythm Cruise for Two with iHeartRadio Sweepstakes - Enter Now
Enter to win the KitchenAid x Corkcicle MindFULLness Fridge Sweepstakes - 5 Winners.
Five Grand Prize winners each get a KitchenAid MindFULLness Fridge (a limited-run refrigerator with Intelligent Auto Fill and a guided mindfulness experience; a water line is required), a set of co-branded Corkcicle bottles (16 oz Mug, 20 oz Sport Canteen and 40 oz Cruiser) and $500 by ACH transfer. Each prize has an ARV of $4929 ($24645 in total).
Open to legal residents of the 48 contiguous US states and DC who are 18 or older; void in Alaska and Hawaii. No purchase necessary. Ends November 15, 2026 at 11:59 PM EST.
To enter, register with your name and email address on the KitchenAid x Corkcicle Sweeps website for one entry. You can earn up to 15 bonus entries (up to 5 each via Facebook, Pinterest and Copy & Share) when people register through your unique share link, for a maximum of 16 entries. Five winners are drawn at random on or about November 16, 2026 and notified by email.
