Travel Contests: September 15th, 2021 – Mexico, California, Orlando, & more

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tulum ruins beach 700x525 - Travel Contests: September 15th, 2021 - Mexico, California, Orlando, & more

Here are this week’s travel contests. You can win trips to Oregon; Orlando, Florida; Los Angeles, California; St. Barths; the Cayman Islands, Dominican Republic, or Mexico; Palm Springs, California; Sonoma, California; Morocco; Tulum, Mexico; Oahu, Hawaii; 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 Oregon

  • What’s Included:
    Willamette Valley
    Two Night Stay in a Winery Suite at Willamette Valley Vineyards
    +
    Private Winery Tour
  • Wine Credit not included. Subject to availability.
  • Portland
    One Night Stay at the Royal Sonesta Portland Downtown
  • Roundtrip Airfare for Two on Alaska Airlines
    Airfare for Two on Alaska Airlines
  • Columbia Gorge
    Dinner Cruise for Two on the Columbia Gorge Sternwheeler
    +
    Two Night Stay at the Hood River Hotel, Complimentary Parking and Breakfast for Two
  • Oregon Coast
    Two Night Stay at the Surfsand Resort in Cannon Beach
    +
    $150 at Wayfarer Restaurant and Lounge
    +
    $100 at Public Coast Brewing Company
  • Historic Tillamook Creamery
    Private Tour of the Tillamook Creamery for Two with Top Chef guest, Chef Josh Archibald
    +
    $100 gift certificate for Tillamook Creamery
    Must be scheduled in advance for a mutually agreed upon date.
  • Open to legal residents of the United States who are at least twenty one (21) years old
  • Enter by September 15, 2021

Win a trip to Orlando, Florida

  • -4-days/3-nights at the Hilton Orlando Buena Vista Palace – Disney Springs Area, a 4-star hotel.*
  • -$250 towards park tickets
  • -$450 towards travel
  • -$150 in cookies & merch from Goodie Girl Cookies
  • -$200 gift card to Bookshop to purchase must-read fall books perfect for a vacation from Bookfinity
  • 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 September 15, 2021

Win a trip to Los Angeles, California

  • A VIP trip to Los Angeles to see Maroon 5 at Banc of California Stadium on October 2, 2021. Prize includes:
    Two (2) premium concert tickets
    Roundtrip airfare and hotel accommodations for two (2) nights for you and a guest
  • open to individuals who are at least thirteen (13) years of age, open worldwide
  • Enter by September 19, 2021

Win a trip to St. Barths

  • YOU AND A FRIEND WILL:
  • Win a 5-night/6-day getaway at the iconic Eden Rock – St Barths hotel (flights included)
  • Treat yourself with $2,000, delicious daily breakfasts and an epic jet ski tour
  • Vacation like an A-lister—with uncrowded beaches, designer shops and gourmet dining
  • Open worldwide
  • Enter by September 22, 2021

Win a trip to the Cayman Islands, Dominican Republic, or Mexico

  • 4 nights for 2 in a 4-star or higher all-inclusive resort selected by Roomongo on an island of choice in Cayman, Dominican Republic or Mexico valued at up to $2,000
  • PLUS
  • $1,250 worth of cash gift cards for travel expenses
  • 1-year subscription to Experience Life magazine
  • 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 September 22, 2021

Win a trip to Palm Springs, California

  • Grand Prize: Two-night stay at the Parker Palm Springs and $1600 travel stipend
  • Open only to legal residents of 50 US/DC, 18+ years of age
  • Enter by September 22, 2021

Win a trip to Sonoma, California

  • The winning package includes:
  • – 2-nights at the newly renovated Flamingo Resort Santa Rosa
  • – 2-nights at The Sandman in Santa Rosa, with welcome amenity upon arrival
  • – Spa treatment for two at Flamingo Resort Santa Rosa
  • – Food and beverage credits at each hotel
  • – Kind Traveler gift box including travel accessories from conscious companies ($150 value)
  • – $100 donation in the name of the winner to Sonoma Land Trust, helping to protect the scenic, natural, agricultural and open landscapes of Sonoma County for the benefit of the community and future generations.
  • – Gracianna Winery, estate tour for two with the owners
    – The Worthy Company plant + protein + fiber bowls $300 gift box
    – Soko, a women-led and operated ethical jewelry brand, $200 gift card- Gracianna Winery, estate tour for two with the owners
    – 2 pairs of Panda sunglasses a sustainable sunglass company ($300 value)
  • – Earth Tu Face gift box 100% natural skincare line made with all-natural, organic ingredients ($150 value)
    – $700 in cash toward travel expenses
  • open to anyone who is at least 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 September 23, 2021

Win a trip to Morocco

  • 1 week/7 night stay for up to 2 people in a standard suite at Yon Essaouira
    Includes daily breakfast
    $750 towards airfare
  • 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 September 26, 2021

Win a trip to Tulum, Mexico

  • – A 3-night stay at the luxury, eco-boutique beachfront Sanará Tulum resort in Mexico
  • – A 6-month supply of grain-free tortillas and wraps from SANA Foods, plus some swag
  • – A prize pack from Genuine Health with over $500 worth of products to support your mood and energy, including a 3-month supply of Probiotics Mood, 3-month supply of Greens Extra Energy, 4 boxes of Fermented Organic Vegan Protein Bars, plus a coffee mug and shaker cup
  • – $700 towards airfare and travel expenses, courtesy of Newser, Matt’s Flights and Bright Cellars
  • – $450 credit to ROAM Luggage
  • – $125 credit to Honeycomb (sustainable toilet tissue)
  • 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
  • Read about my trip to Chichen Itza from Cancun
  • Read about my trip to Tulum from Cancun
  • Enter by September 27, 2021

Win a trip to Oahu, Hawai’i

  • You and a friend will:
    Receive an all expenses paid trip to the tropical island of Oahu, Hawai’i, for 5 nights and 6 days
    Take part in a beach cleanup on the shores of Oahu
    Snorkel with local marine life with a marine biologist as your guide
    Explore the fascinating world of plastic pollution research
    Receive a prize pack of 4ocean swag that includes our latest bracelets, t-shirts, and accessories
    Explore everything the island of Oahu has to offer with meals and transportation covered (up to $900)
  • Must be 18 and older and live in the United States to be eligible
  • Enter by September 29, 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!

Last updated on September 14, 2021


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