Southwest Airlines - Dare to Dive Sweepstakes (Expired)

Win a Trip to the Cayman Islands

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Note: This sweepstakes has expired, but you can find many sweepstakes with similar prizes on the US Vacation Sweepstakes List.



Would you like a chance to go diving in beautiful tropical waters? Enter Southwest Airlines' Dare to Dive Sweepstakes and you could win a free trip for yourself and three friends or family members to Grand Cayman, a prize worth $4,600. This sweepstakes has expired.

Sweepstakes Links:

  • Sweepstakes Entry Form:
  • Sweepstakes Rules:
  • Sweepstakes Homepage:


International Travel Sweepstakes, Medium Sweepstakes, One Entry Sweepstakes


Contiguous US (-HI, AK), 19+

Start Date:

June 01, 2017

End Date:

July 31, 2017 at 11:59 p.m. CT

Entry Frequency:

One time per person/email

Sweepstakes Prizes:

Grand Prize: A trip for four to Grand Cayman including airfare, a $2,000 gift card for a hotel stay from Ritz Carlton, and a $1,000 Visa gift card for spending cash. (ARV: $4,600)