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Here are this week’s travel contests. You can win trips to the Maldives; Cancun, Mexico; England & Scotland; Antigua; Legoland California, Florida, or New York; Colorado; St. Croix; Morocco; Kentucky; Mallorca, Spain; St. Andrew’s, Scotland; 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 the Maldives

  • Win a 5-day vacation at The St. Regis Vommuli Resort in the Dhaalu Atoll (flights included)
    Relax in a breathtaking overwater villa with a private deck and plunge pool overlooking coral atolls and sparkling turquoise lagoons
    Score $5000 to spend on tailored wellness experiences, a glass-bottom kayak tour, decadent dining, and more
  • Open worldwide
  • Enter by July 29, 2022

Win a trip to Cancun, Mexico

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

  • • 5-day/ 4-night all inclusive stay for a family of 4 at Dreams® Natura Resort & Spa
  • • $800 towards travel expenses
  • • $500 gift card to Free People
  • • $250 gift card to Tiny Rituals
  • 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 July 29, 2022

Win a trip to England & Scotland

Win a trip to Antigua

  • 5-night all-inclusive stay for two to Galley Bay Resort & Spa, Antigua
    All meals including breakfast, lunch and dinner daily
    Roundtrip airport transfers for two
    $250 Visa card compliments of The Gist
    $250 pre-paid card compliments of Winni
    $250 Jane.com gift card
    $150 Zaturo 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 July 31, 2022

Win a trip to Legoland California, Florida, or New York

  • Grand Prize: Each Grand Prize consists of a family trip for four (4) guests: each trip including (i) four (4) two-day LEGOLAND Resort tickets with admission to the LEGOLAND Park of the Grand Prize Winner’s choice (Grand Prize Winner must choose either LEGOLAND California Resort, LEGOLAND Florida Resort, or LEGOLAND New York Resort – the Grand Prize Winner’s selection is hereinafter referred to as “the Selected LEGOLAND Resort”); (ii) a gift card that will be substituted with LEGOLAND Dollars valid on retail or food beverage at the Selected LEGOLAND Resort with a value of two hundred and fifty dollars ($250); (iii) three (3) nights’ hotel accommodations for four (4) people (quad occupancy) at the Selected LEGOLAND Resort hotel; (iv) roundtrip airfare for four (4) people (not to exceed a value of $500 per person); and (v) a four day car rental (not exceed a value of $50 per day) (approximate total ARV $4,055).
  • open to all legal residents of the contiguous United States and the District of Columbia who are at least eighteen (18) years or older (nineteen (19) years or older for Alabama and Nebraska residents)
  • Enter by July 31, 2022

Win a trip to Colorado

  • -Roundtrip air travel on Southwest Airlines® for winner and one (1) guest
    -Two (2) tickets to a concert of the winner’s choice from a select group of mutually agreed upon ticketed events at Red Rocks shows between September 1, 2022 and November 13, 2022 (see Official Rules for complete details)
    -One (1) night hotel stay at Origin Hotel Red Rocks (single room, double occupancy)
    -Winners will be notified via email on August 2, 2022
  • Open to legal residents of the fifty (50) U.S. and D.C. (excluding Alaska, Florida, New York, and Rhode Island) age 21 or older
  • Enter by July 31, 2022

Win a trip to St. Croix

  • Win a 5-night stay for two at The Buccaneer Beach and Golf Resort, St. Croix with breakfast daily, one dinner for two and a Rub My Back Massage for two. Activities including kayaking, paddle boarding, and snorkeling are also included. Other prizes include:
  • $250 gift card from Tiny Rituals
    $250 gift card from Gogh Jewelry Design
    $250 Expedition membership
    $200 Amex gift card compliments of Dunhill Travel Deals
    $200 gift card from Daily Dig
  • 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 August 4, 2022

Win a trip to Morocco

  • • 7 nights for 2 on a twin sharing basis at a Superior hotel or similar
  • • Daily breakfast, 5 dinners at hotels, 2 lunches at hotels
  • • Transportation in deluxe A/C vehicle
  • • Service of a professional bilingual English/French speaking guide
  • • Entrance fees as per the itinerary
  • 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 August 5, 2022

Win a trip to Kentucky

  • Kind Traveler Winning Package Includes:
    – 3-night stay at Elwood Hotel, a Kind Traveler Partner, in Lexington, Kentucky, in a Signature King Suite
    – Horse & Barrel Bourbon Tour (for two), including transportation ($500 value)
    – Dinner for two at Fiddletree Kitchen & Bar to include an appetizer, two entrees, two desserts and two specialty cocktails ($150 value)
    – Breakfast for two each morning ($100 value)
    – Picnic lunch to include an appetizer, two entrees, two desserts, and two beverages ($100 Value)
    – Cultural adventure with two tickets to the Mary Todd Lincoln House (discover one of America’s most fascinating First Ladies) and historic Henry Clay Estate ($120 value)
    – VIP transportation to and from the airport ($200 value)
    – VIP Gift with choices of offerings to include a bottle of wine/spirit, travel toiletries from KY Soaps and Such, sweet and salty snacks, charcuterie plate, chocolates/bourbons balls ($150 value)
    – $200 donation in the name of the winner to support local charity Lexington Humane Society
    – Kind Traveler gift box to include eco-conscious travel products to inspire kind travel ($250 value)
    – Stranger’s Guide Premium Subscription to travel guides that deliver captivating stories that bring the world to you ($325 value)
    – $300 Visa cash card for travel expenses
  • open to anyone who is at least twenty one (21) years of age 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 August 6, 2022

Win a trip to Mallorca, Spain

  • -6-days/5-nights at the Hotel Samos, a 4-star hotel in Santa Ponsa.*
  • -$1,000 towards travel!
  • 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 the best things to do in Palma de Mallorca
  • Read about a day trip from Palma to Soller
  • Read about a day trip from Palma to Valldemossa
  • Enter by August 7, 2022

Win a trip to St. Andrew’s, Scotland

  • The Prize includes a trip to St Andrews, Scotland for winner and one (1) travel companion and one (1) in-store discount code for $1,000 US Dollars redeemable for eligible product only at the TravisMathew St Andrews Store. Discount code cannot be redeemed for products in the luggage and club covers categories on www.travismathew.com. Discount code expires 12/31/23. Prize package includes round trip, coach-class air transportation for two (2) from a major airport near winner’s home (determined by Sponsor in its sole discretion) to Edinburgh, Scotland (ground transportation to St Andrews not included); three (3) nights’ accommodations at a hotel determined by Sponsor in its sole discretion (one (1) room, double occupancy); and two (2) rounds of golf for two (2) people at St Andrews Links (to be played during the month of April 2023) (golf clubs not provided). All travel arrangements will be made through Sponsor’s agent. Trip must be taken in April of 2023. Trip must be booked at least twenty-one (21) days prior to departure.
  • must be a legal resident of the United States or Canada (excluding Quebec) and of age of majority (and at least 18) in your jurisdiction of residence. Void in Quebec and where prohibited. There is a separate contest for UK residents here.
  • Enter by August 7, 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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