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Here are this week’s travel contests. You can win a cruise, plus trips to Portugal; Bora Bora; St. Lucia; Cancun, Mexico; Las Vegas, Nevada; San Diego, California; a cruise; Cairo, Egypt; Tuscany, Italy; and more.

Good luck & be sure to subscribe to the weekly newsletter so you don’t miss any sweepstakes, and please share this post with friends who might take you along if they win!

Win a trip to Portugal

Win a trip to Bora Bora

Book your hotel in Travel Contests - Win A Free Trip! now!

  • Win a 6-day getaway at the 5-Star Conrad Bora Bora Nui (flights included)
  • Relish in a breathtaking overwater villa with a private infinity pool and floor-to-ceiling windows.
  • Score $5,000 to treat yourself to rejuvenating massages, open-air dining, exciting excursions and more.
  • Open worldwide
  • Enter by June 3, 2022

Win a trip to St. Lucia

  • 4-night all-inclusive stay for two adults in Ti Kaye cottage with daily maid service at Ti Kaye Resort & Spa in Saint Lucia
    Complimentary welcome drink, coffee and tea
    All-inclusive meal plan (full breakfast, two-course lunch and three-course dinner) at on-site restaurants, select cocktails and specialty wines
    Complimentary snorkel gear and use of kayaks and paddleboards
    Complimentary Wi-Fi
    $250 Visa gift card compliments of Matt’s Flights
    $250 gift card compliments of Daniella Shevel
    $250 Visa gift card compliments of Woman’s World
    One month supply of dog supplements compliments of Bestfriend ($68 value)
  • Open to anyone who is at least eighteen (18) years of age and has reached the age of majority in their jurisdiction of residence at the time of opt-in (19 in Alabama and Nebraska; 21 in Mississippi) and a resident of the United States of America and the District of Columbia (excluding residents of Alaska, Hawaii, Rhode Island, overseas military installations, Puerto Rico, and other U.S. Territories)
  • Enter by June 3, 2022

Win a trip to Antigua

  • A 5-night all-inclusive stay for two adults to Pineapple Beach Club Antigua
    All meals including breakfast, lunch and dinner and beverages including non-alcoholic and alcoholic, round-trip airport transfers and included resort activities
  • Other prizes include a $250 Sivana gift card, $200 Visa gift card compliments of 1440, $250 Visa gift card compliments of Your Tango and a $200 Laya gift card.
  • open to anyone who is at least eighteen (18) years of age and has reached the age of majority in their jurisdiction of residence at the time of opt-in (19 in Alabama and Nebraska; 21 in Mississippi) and a resident of the United States of America and the District of Columbia (excluding residents of Alaska, Hawaii, Rhode Island, overseas military installations, Puerto Rico, and other U.S. Territories)
  • Enter by June 3, 2022

Win a trip to Cancun, Mexico

  • You could win a 4-night stay for two at Grand Fiesta Americana Coral Beach Cancun All Inclusive Spa Resort including all meals and beverages (room service not included)
  • – $250 Visa gift card compliments of The Gist
  • – $200 gift card compliments of Banda Bags
  • – $200 in product compliments of ICU Eyewear
  • – $200 gift card compliments of Tiny Rituals
  • – $200 Visa gift card compliments of Dunhill Travel Deals
  • open to anyone who is at least eighteen (18) years of age and has reached the age of majority in their jurisdiction of residence at the time of opt-in (19 in Alabama and Nebraska; 21 in Mississippi) and a resident of the United States of America and the District of Columbia (excluding residents of Alaska, Hawaii, Rhode Island, overseas military installations, Puerto Rico, and other U.S. Territories)
  • Read about my trip to Chichen Itza from Cancun
  • Read about my trip to Tulum from Cancun
  • Enter by June 3, 2022

Win a trip to Las Vegas, Nevada

  • Grand Prize:
    VIP Experience at International Fight Week: 2 Tickets to UFC 276, UFC Hall of Fame Ceremony, VIP access to 2-day fan experience, UFC HQ and Performance Institute tour, Airfare, Hotel Accommodations
  • open only to legal permanent residents of the United States (excluding Puerto Rico, and the U.S. Territories and Possessions) and of Canada (excluding Quebec), United Kingdom and Brazil, who are at least 18 years of age or the age of majority in their jurisdiction
  • Enter by June 5, 2022

Win a trip to San Diego, California

  • One (1) Grand Prize – A 3-day/2-night trip for the Winner and three (3) travel companions to San Diego, CA (“Trip”), including round trip economy air transportation from major airport nearest Winner’s home, hotel accommodations (1 room, quad occupancy), four (4) 1-Day Passes to the San Diego Zoo and one (1) Inside Look Tour for four (4) people as determined by SDZWA. (ARV: $4,026; actual value will vary depending upon point of departure and date of travel booking (see additional Trip Prize Details below); One (1) First Prize- Four (4) one-day passes to the San Diego Zoo (transportation and accommodations are not included) (ARV: $240); One (1) Second Prize – A Swag Bag comprised of San Diego Zoo merchandise and Lenny & Larry’s goodies (ARV: $100). The ARV of all Prizes (defined below) is $4,366
  • open only to persons ages 18 and older during the Sweepstakes Entry Period, and, who, as of the time of Entry, are legal residents of, and physically located within, the 48 contiguous United States or D.C.
  • Enter by June 6, 2022

Win a cruise

  • 7-night Caribbean cruise aboard award-winning Celebrity Cruises
  • Accommodations for 2 in a balcony cabin
  • Free drinks package, Wi-Fi and prepaid gratuities (courtesy of Cruise.com)
  • PLUS
  • A $250 Visa gift card (courtesy of @TravelDeals)
  • open solely to legal residents of the fifty (50) United States and the District of Columbia (excluding residents of Alaska, Hawaii, Rhode Island, overseas military installations, Puerto Rico, and other U.S. Territories) who are at least 21 years of age
  • Enter by June 9, 2022

Win a trip to Cairo, Egypt

  • 5 nights in Cairo in a superior hotel
    Daily breakfast
    Airport transfers on arrival and departure
    Transportation in an AC deluxe vehicle
    Sightseeing as per the itinerary
    Entrance fees as per the itinerary
    Services of English-speaking local guides
    Guided visit to the Grand Pyramids of Giza and the Great Sphinx
    All currently applicable local taxes
    Plus $1,100 travel cash
  • open to anyone who is at least eighteen (18) years of age and has reached the age of majority in their jurisdiction of residence at the time of opt-in (19 in Alabama and Nebraska; 21 in Mississippi) and a resident of the United States of America and the District of Columbia (excluding residents of Alaska, Hawaii, Rhode Island, overseas military installations, Puerto Rico, and other U.S. Territories)
  • Enter by June 12, 2022

Win a trip to Tuscany, Italy

  • Prizing package includes…
  • – $1,000 gift card towards round trip flights for two
  • – 4 nights at the deluxe Ottantotto Firenze, Tuscany
  • – $100 credit to visit Trattoria Da Burde Firenze
  • – 2 days touring Tuscan wineries including Antinori nel Chianti Classico & Castello Banfi – Il Borgo
    – $250 Wine Awesomeness gift card to explore Italian wines
  • open to anyone who is at least eighteen (18) years of age and has reached the age of majority in their jurisdiction of residence at the time of opt-in (19 in Alabama and Nebraska; 21 in Mississippi) and a resident of the United States of America and the District of Columbia (excluding residents of Alaska, Hawaii, Rhode Island, overseas military installations, Puerto Rico, and other U.S. Territories)
  • Enter by June 13, 2022

Go on an adventure at home or when you’re away with a tour or activity via Get Your Guide.

Which travel giveaway are you most excited about winning this week?

Why not share this post with your friends? If they win, maybe they’ll take you!

Want to see the newest travel contests? Go here!

Note: I realize that right now may not be a good time to be traveling. However, as long as there are still contests available, I will continue to share them.  Hopefully, once this all passes, we’ll be able to freely enjoy traveling again, but for now, we can dream, & most of these contests have redemption deadlines long in the future. In the meantime, please practice social distancing & keep safe. Thanks!

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