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Here are this week’s travel contests. You can win trips to the Maldives; Costa Rica; Hilton Head, South Carolina; Chile; Cabo San Lucas, Mexico; Palm Springs, California; Florida; 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

  • YOU AND A FRIEND WILL:
  • Win a 6-day vacation at the 5-star Angsana Velavaru in the Maldives (with flights and all-inclusive meals on us!)
  • Stay in a stunning villa with a private deck and infinity pool overlooking the ocean
  • Score $3,000 to spend on spa treatments, dolphin tours, night fishing excursions, catamaran adventures and more
  • Open worldwide
  • Enter by November 4, 2021

Win a trip to Costa Rica

  • One (1) Grand Prize: 5-Night/6-Day Trip for Two (2) to Costa Rica. Prize includes the following:
  • · Roundtrip (coach class) air transportation to Costa Rica
  • · Five (5) nights (double occupancy) hotel accommodations at the Iguana Surf Hotel located in Tamarindo, Costa Rica. (@iguanasurf_tamarindo)
  • · Off Road Truck rental from Nomad America (@nomad_america)
  • Open to legal residents of the 50 United States and the District of Columbia, (“U.S.”) who are located in the U.S. and are at least eighteen (18) years of age or older
  • Enter by November 9, 2021

Win a trip to Hilton Head, South Carolina

  • 4 nights at the Sonesta Resort of Hilton Head in a Garden View Room!
  • – $1000 in cash towards travel!
  • – $500 food and beverage credit!
  • 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 November 14, 2021

Win a trip to Chile

  • Enter for a chance to win this incredible guided adventure to Chile with Ventisquero…
  • Getting there… $1,000 AMEX gift card towards round trip flights for two + $250 gift card to shop JANE to look great on the journey!
  • Day 1 – Complimentary transportation from the Santiago, Chile International Airport. The first day includes a city tour of the capital, Santiago.
  • Day 2 – Guided tour with wine tasting at the Estate Casablanca, home of Ventisquero’s world renowned Sauvignon Blanc, Chardonnay, and Pinot Noir vineyards. The day ends with dinner on the Pacific Ocean + deluxe beachfront accommodations
  • Day 3 – A quick drive to the La Trinidad Estate. Home to amazing Merlot, Cabernet Sauvignon, and Syrah vineyards. This day ends with a classic Chilean BBQ and night at the estate’s deluxe guest house!
  • Day 4 – Last stop is the Ventisquero Apalta-Colchagua vineyards, which produce the elegant Ventisquero Reserva Carménère! Catered lunch with valley views then back to the airport for your journey home!
  • 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 November 15, 2021

Win a trip to Cabo San Lucas, Mexico

  • P R I Z E I N C L U D E S
  • 4 nights accommodations in a 4-star or greater all-inclusive resort and $1000 toward 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 November 15, 2021

Win a trip to Palm Springs, California

  • Grand Prize Sweepstakes Prize (1): one (1) grand prize will be awarded in the Sweepstakes. The grand prize consists of a trip for two (2) people (winner and one guest age 21 or older) to Palm Springs, CA and includes: round trip coach airfare for two (2) people to Palm Springs, CA departing from the Sponsor designated nearest major airport to winner’s home, hotel accommodations for two (2) people—one room, double occupancy—for two (2) nights, and one (1) $200 gift card from the Sponsor designated gift card provider
  • open to all legal residents of the fifty (50) United States and the District of Columbia who are 21 years of age and older
  • Enter by November 15, 2021

Win a trip to Florida

  • A once-in-a-lifetime trip to Ponte Verde Beach, FL to attend THE PLAYERS Championship in March, 2022 as Rory McIlroy’s VIP
    Two (2) amazing seats to watch the best players in the world come together to compete on the world-renowned Stadium Course at TPC Sawgrass
    One (1) round of golf on the Stadium Course at TPC Sawgrass, after the event, for you and your guest
    Roundtrip airfare and hotel accommodations for two (2) nights for you and your guest
  • Only open to individuals who are at least thirteen (13) years of age, open worldwide
  • Enter by November 17, 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 may 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 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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