Caribbean Sweepstakes
Found 13 total
CruiseOne Caribbean Cruise Giveaway - One Grand Prize: a 7‑night Celebrity Cruises Caribbean cruise for two people, booked through World Travel Holdings (Dream Vacations or CruiseOne), includes a Standard Veranda stateroom and has an approximate retail value of up to $4,500 USD. The prize does not cover air travel, insurance, airport transfers, extra nights, optional excursions, taxes, fees, passports, visas, gratuities, or personal items, all of which are the winner’s responsibility. Any costs exceeding the $4,500 value are also the winner’s responsibility. The winner must book the cruise by December 18, 2026 for travel no later than September 7, 2027; blackout dates and holiday sailing dates are excluded. The prize is non‑transferable, cannot be sold, and cannot be redeemed for cash. Booking will be made with the designated travel agent and is subject to availability. Additional terms and conditions may apply. The cruise sweepstakes entry period ends at 11:59 p.m. ET on October 12, 2026.
Win $4,500 in value – CruiseOne Celebrity Cruises Sweepstakes - Enter Now
2027 Holistic Holiday at Sea Cruise Giveaway. - One complimentary interior stateroom for the winner and one guest aboard MSC Poesia, with a choice of the Caribbean & Latin America voyage (March 7–18, 2027) or the Alaska voyage (August 2–9, 2027), plus participation in the Holistic Holiday at Sea onboard program. There will be one winner. The cruise sweepstakes entry period ends on 10-30-2026 at 11:59 PM ET.
Win $5,000 in value – 2027 Holistic Holiday at Sea Cruise Giveaway - Enter Now
Royal Caribbean’s September Travel Advisor Giveaway lets five lucky travel advisors win an oceanview stateroom for two on a short Caribbean cruise, valued at roughly $8 00 each (total $4 000). To enter, advisors must book eligible Caribbean sailings by September 22, 2026; bookings from Tampa or Port Canaveral earn double entries. Winners will be notified by November 13, 2026. Eligibility is limited to accredited travel agents in the United States (excluding Puerto Rico) and Canada (excluding Quebec). Enter now for a chance to enjoy a complimentary cruise experience!. This cruise sweepstakes ends on September 22, 2026. *Rules are not clear how to enter for free.
Win $4,000 in value – Royal Caribbean September Travel Advisor Giveaway - Enter Now
Enter the Legend Of The Seas VIP Cruise giveaway for a chance to send a deserving legend in your life on a once‑in‑a‑lifetime cruise. One winner will receive an invite for two on the inaugural Caribbean cruise aboard the all‑new Legend of the Seas, a $1,000 Royal Caribbean gift card, round‑trip flights for two to Fort Lauderdale, a pre‑cruise hotel stay for two, and a $100 rideshare voucher – a total prize value of approximately $3,900. To enter, follow Royal Caribbean and comment with your hometown legend’s story. Open to participants 18+ in the United States.
Win $3,900 in value – Royal Caribbean Legend Of The Seas VIP Cruise Giveaway - Enter Now
Enter the Royal Caribbean Giveaway for a chance to win a 7‑night Caribbean cruise, featuring a balcony stateroom for you and a guest. This sweepstakes ends September 20, 2026. One lucky winner will receive a cruise. To enter, follow Royal Caribbean Europe on Instagram and comment with your travel companion using #RoyalCaribbeanGiveaway. Open to participants 18+ in the United States. See terms for details.
Win $5,000 in value – Royal Caribbean Europe Giveaway - Enter Now
Enter the 7-Night Cruise on Star of the Seas Giveaway for a chance to win a luxurious stateroom for you and a guest on a 7‑night Royal Caribbean cruise celebrating 365 days at sea. Follow @royalcaribbean, comment and tag who you’d bring, and you could be the lucky winner. The giveaway ends on 09-27-2026. Prize value is estimated at $2,500. Open to U.S. residents 18 years and older. Enter now for your chance to set sail!. This sweepstakes ends on September 27, 2026.
Win $2,500 in value – Royal Caribbean 7-Night Cruise on Star of the Seas Giveaway - Enter Now
Enter the Delta Cruises Giveaway for a chance to win exciting prizes. The Grand Prize is a 7-night Caribbean sailing for two, valued up to $5,000, plus $2,000 in Delta Gift Cards, totaling up to $7,000. Other prizes include a 5-night Caribbean sailing valued up to $4,500 and a 3-night sailing valued up to $3,000. With a total prize value of $14,500, don't miss your free entry to win a amazing cruise sweepstakes experience courtesy of Delta Cruises.
Win $14,500 in value – Delta Cruises Sweepstakes - Win 1 of 3 Cruise Prizes - Enter Now
Enter the United Vacations Email Giveaway for a chance to win an unforgettable getaway. The Grand Prize includes a 3-night stay for two adults at a participating RIU Resort in Mexico or the Caribbean, with an Approximate Retail Value of $2,000.00. Don't miss your opportunity to win this amazing prize - submit your free entry before the vacation sweepstakes ends on September 30, 2026, at 11:59:59 pm EST.
Win $2,000 in value – United Vacations Email Giveaway - $2000 Value - Enter Now
Get ready to set sail with the Gluten Free & More Logo Celiac Cruise Oasis Bahamas Giveaway! Enter to win an unforgettable 4-night cruise to the Bahamas on Royal Caribbean's Wonder of the Seas, courtesy of Celiac Cruise. The prize includes an inside cabin for two people, valued at $1,773.26, and takes place from March 22 - 26, 2027. Don't miss your chance to win this amazing getaway - enter the cruise sweepstakes now and make your tropical dreams come true! Hurry, the giveaway ends on September 30, 2026.
Win $1,773 in value – Gluten Free & More Logo Celiac Cruise Oasis Bahamas Giveaway - Enter Now
Enter the Cruises.com Royal Caribbean Legend of the Seas Sweepstakes for a chance to win an unforgettable 6-night Caribbean cruise for two aboard Royal Caribbean's Legend of the Seas. This incredible prize, valued up to $4,500, includes an ocean-view stateroom and offers a wealth of onboard amenities. To enter, simply log in to your Cruises.com Rewards account or register for a new account, and submit your entry online. You can also earn up to 25 additional entries through optional methods. The sweepstakes is open to legal residents of the 50 United States and D.C., 21 years of age or older, with a valid email address. No purchase necessary, and each entry has an equal chance of winning. The sweepstakes period runs from July 13, 2026, to September 30, 2026. Enter now for your chance to win with Cruises.com Royal Caribbean Legend of the Seas Sweepstakes.
Win $4,500 in value – Cruises.com Royal Caribbean Legend of the Seas Sweepstakes - Enter Now
