Cruise Sweepstakes & Vacation Giveaways
Win Free Cruises and Luxury Ocean Voyages
Found 32 total
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
Little Steven’s Underground Garage Cruise 2027 SiriusXM Sweepstakes. - One Grand Prize will be awarded to one winner who meets the eligibility requirements. The Grand Prize consists of round‑trip coach air transportation for two to Miami, FL, from the major commercial airport nearest the winner’s primary residence in the United States, the District of Columbia, or Puerto Rico, with the sponsor reserving the right to substitute ground transportation if the winner lives within 150 miles of the destination. The prize also includes one night of hotel accommodation in a standard double‑occupancy room with room tax only in Miami, FL, checking in on April 23, 2027, and checking out on April 24, 2027. The winner will receive two Balcony Cabin tickets for the Little Steven’s Underground Garage Cruise scheduled for April 24‑28, 2027. Additionally, the prize includes a $500.00 credit to use during the event. The approximate retail value of the prize is $6,350.00. The sweepstakes ends at 11:59 PM ET on October 5, 2026.
Krysta Alanna The Endless Summer Giveaway offers a collection of prizes valued at approximately $520. Entries close on Sunday, September 13 at 11:59 p.m. ET. - Retrospec Chatham Step-Through 7‑Speed Beach Cruiser in ivory - Wicker bike basket - Meet Me There sweatshirt - Meet Me There hat.
Win $520 in value – Krysta Alanna The Endless Summer Giveaway - Enter Now
Raymour & Flanigan Aloha Sweepstakes provides the following prizes.
- Grand Prize: One five‑night trip for two to Honolulu, HI, with transportation to and from the airport and hotel, and the winner’s choice of two of the following experiences: Pearl Harbor, a VIP Hawaiian luau, a sunset dinner cruise, or the Polynesian Cultural Center (ARV $8,000).
- First Prize: One winner’s choice of a three‑night or four‑night Bahamas or Caribbean cruise, plus round‑trip airfare to either Miami, Port Canaveral, or Fort Lauderdale (ARV $3,500).
- Second Prize: One two‑night trip for two to Miami, FL (ARV $2,000).
The sweepstakes expires on September 14, 2026, at 11:59 PM EDT.
Win $13,500 in value – Raymour & Flanigan Aloha Sweepstakes - $13500 Value - Enter Now
Marriott Bonvoy Cruise With Points Sweepstakes offers a Grand Prize and First Prizes with a total approximate retail value of $6,600. The Grand Prize includes a cruise voucher valued up to $5,000 that can be redeemed toward any available Celebrity Cruise Line sailing sold through the Marriott Bonvoy Cruise With Points program, subject to availability and applicable terms and conditions. The cruise voucher must be redeemed by December 31, 2026 for travel completed by December 31, 2027 or the prize may be forfeited. The Grand Prize winner also receives one hundred thousand (100,000) Marriott Bonvoy Points deposited into the winner’s valid Marriott Bonvoy account, subject to program terms and conditions. The approximate retail value of the cruise voucher portion is $5,000 and the points portion is $800 for a total ARV of $5,800.
- Grand Prize (1): One cruise voucher up to $5,000 redeemable through the Marriott Bonvoy Cruise With Points program, must be redeemed by December 31, 2026 for travel by December 31, 2027, plus 100,000 Marriott Bonvoy Points deposited into the winner’s valid Marriott Bonvoy account. Total ARV $5,800.
- First Prizes (2): Two awards each of 50,000 Marriott Bonvoy Points, sufficient for redemption of up to a one‑night stay at certain participating Category 5 hotels, subject to availability and Marriott Bonvoy program terms and conditions. ARV of each First Prize $400.
Total ARV of all prizes available in the Cruise Sweepstakes is $6,600.
Win $6,600 in value – Marriott Bonvoy Cruise With Points Sweepstakes - Enter Now
Jackpot Beauties Halloween Cruise Giveaway 2026 is offering an elevated large balcony cabin for two on a Virgin Voyages Halloween sailing, departing from Miami on October 25, 2026, and returning on October 31, 2026. - 1 winner will receive the cabin with an approximate retail value of $4,500 USD. The cruise sweepstakes entry period ends on October 3, 202,6 at 8:00 PM ET.
Win $4,500 in value – Jackpot Beauties Halloween Cruise Giveaway 2026 - 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
Announcing the Jamrock Reggae Cruise SiriusXM Sweepstakes.
- Grand Prize includes:
One round‑trip coach air transportation for two to Miami, FL from the nearest major commercial airport in the United States, the District of Columbia, or Puerto Rico (Sponsor may substitute ground transportation if the winner resides within 150 miles of Miami).
One hotel accommodation for one night in Miami, FL (standard double occupancy room, room tax only), checking in on November 10, 2026, and checking out on November 11, 2026.
Two Balcony Cabin tickets (standard double occupancy room, room tax only) aboard the Jamrock Reggae Cruise scheduled for November 11‑16, 2026.
Approximate Retail Value of the prize: $7,500.
Entries must be received by 11:59 PM ET on September 30, 2026.
Win $7,500 in value – Jamrock Reggae Cruise SiriusXM Sweepstakes - $7500 Value - Enter Now
Lake Country Family Fun Gift Card Giveaway includes a fall‑tastic prize package. - $100 off a cruise from Magic Mom Travel LLC (Emily Schultz: Agency Owner) - $75 gift card to The Corners of Brookfield - $30 gift card to Peck & Bushel Fruit Company (apple picking and cider donuts) - 1 month membership at Mathnasium of Hartland (new students only, locations: Hartland, Oconomowoc, Brookfield & Waukesha) - 1 Pass to Pleasure Valley Pumpkins - Delafield Brewhaus BBQ Box (pair of glasses, sauces, hot sauces and a $20 gift certificate) - $100 off a Myofascial Release session from Balance Within: Integrative Physical Therapy Delafield - 1 Ticket to Lapham Peak Fright Hike 2026 - 4 Tickets to The Hollows at Phantom Lake YMCA 2026 - 50% off an evaluation at Bloom Physical Therapy & Wellness Giveaway ends September 30, 2026 at 11:59 pm
Win $1,000 in value – Lake Country Family Fun Gift Card Giveaway - Enter Now
