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Here are this week’s travel contests. You can win trips to Riviera Maya, Mexico; Italy; Europe; Sonoma, California; Jamaica; 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 Riviera Maya, Mexico

  • You could win a 4-night stay for two with breakfast daily to Fairmont Mayakoba in Riviera Maya, Mexico to pamper yourself in the sun. Other prizes include a $400 gift card towards travel compliments of 1440, a $250 gift card, a one month supply of bamboo toilet tissue by Honeycomb, a $250 gift card and a $400 gift card from The Gist.
  • 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 lives within the continental United States
  • Enter by June 5, 2021

Win a trip to Italy

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

  • Win a 10-day culinary tour through Turin, Bologna and Tuscany curated by America’s Test Kitchen (flights and hotels included)
  • Enjoy your choice of cooking classes, tastings and sightseeing activities
  • Score a $1,000 stipend and a 10-year All-Access membership to America’s Test Kitchen sites
  • Open worldwide
  • Enter by June 8, 2021

Win a trip to Italy

  • Be flown out to Italy and put up in a 4-star hotel
  • Meet Andrea Bocelli at his hometown in Tuscany, tour his vineyard and dine at his delicious restaurant
  • Score VIP access to Maestro Bocelli’s performance at the Teatro del Silenzio
  • Open worldwide
  • Enter by June 8, 2021

Win a trip to Europe

  • Spend a month in Europe on a curated trip to the city of your choice (get round trip tickets for two, if you’d like to bring a friend!)
  • Enjoy 24/7 access to Quintessentially’s luxury concierge service, and your very own Lifestyle Manager who will help plan your trip and make your every dream a reality
  • Get a $30,000 budget to cover all your travel, including high-end hotels and VIP treatment on any trips you plan while you’re away
  • Pocket $10,000 in spending money for anything you desire day-to-day
  • Travel in style with $4,500 to spend at Louis Vuitton® before you leave
  • Open worldwide
  • Enter by June 10, 2021

Win a trip to Italy

  • Be flown out to Modena, Italy and put up at Casa Maria Luigia, Massimo Bottura’s countryside hotel
  • Meet Massimo for a tour of his favorite art, visit his kitchen and learn to make the perfect tortellini
  • Enjoy lunch at Cavallino and a 9-course dinner at FRANCESCANA at MARIA LUIGIA
  • Explore Italy’s food capital in a rented Ferrari—including tours of the balsamic vinegar museum and the Ferrari museum
  • Open worldwide
  • Enter by June 10, 2021

Win a trip to Sonoma, California

  • 3-night stay in a suite at MacArthur Place & Spa, a Kind Traveler hotel
    $100 donation made to local charity, Sonoma Land Trust, in the name of the winner
    Dining & beverage credit to use on property during your stay ($200 value)
    50-minute spa treatment for two at The Spa at MacArthur
    Behind the Cellar Door tour with Bohemian Highway Travel Co. for two guests to three wineries, with transportation and a picnic lunch
    Kind Traveler gift box including travel accessories from conscious companies
    Earth Tu Face gift box: a plant-based 100% natural skincare line, free of toxins or synthetic compounds
    Gogh Jewelry Design gifting box of $500 travel inspired jewelry
    Eagle Creek luggage gift box
    Custom earrings from Closet Rehab
    Blendily gift box: natural, handmade, zero-waste skincare
    Freedom Deodorant gift card ($150 Value)
    $500 cash for travel expenses
  • open to anyone who is at twenty one (21) years of age and lives within the continental United States
  • Read about craft beer in Santa Rosa
  • Read about craft beer in Rohnert Park
  • Read about craft beer in Cotati
  • Enter by June 12, 2021

Win a trip to Jamaica

  • Win a 5-night/6-day vacation at GoldenEye, the Jamaican resort where James Bond was created (flights included)
  • Stay in the Fleming Villa, a private oasis designed by Ian Fleming, where he wrote all 14 Bond books
  • Enjoy a private beach, pool, chef, butler, watersports and more
  • Open worldwide
  • Enter by June 16, 2021

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 is not 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 enjoy traveling again, but for now we can dream. In the meantime, please practice social distancing & keep safe. Thanks!

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