This article has partner links that I may receive compensation from at no cost to you. Thank you for supporting my site by using them!

sao jorge castle 700x700

Here are your travel contests for this week. You can win trips to Cabo San Lucas, Mexico; New York City; a Caribbean cruise; Punta Cana, Dominican Republic; St. Lucia; Lake Tahoe, California; Park City, Utah; Sydney, Australia; Patagonia; Hawaii; Ft. Lauderdale, Florida; France; Peru; Maui, Hawaii; Palm Springs, California; Lisbon, Portugal; and more.

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

Win a trip to Cabo San Lucas, Mexico

Win a trip to New York City

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

  • 3- Night Stay for two at Grand Hyatt New York in a Grand Club room
    Free daily breakfast and a sightseeing flexPass for 2 from Grand Hyatt New York
    Your own custom sterling silver three pendant necklace from Mathematics NYC ($365 Value)
    $700 in gift cards towards airfare from Swirled, MattsFlights and The Cut
  • Enter by October 19, 2018

Win a Caribbean cruise

  • 7-Night Caribbean Cruise aboard Royal Caribbean’s Allure of the Seas for two with balcony accommodations, drinks, tips and taxes included from CruCon Cruise Outlet (sailing out of Miami, FL on January 27th, 2019)
    $700 airfare voucher to get to Florida
    Pro-Collagen Ultimate Collection (Worth $299)
    $250 e-gift certificate to Elemis
    2 X-Bags from Bric’s Milano (worth $110)
    $200 gift card to Sole Society
  • Enter by October 20, 2018

Win a trip to Punta Cana, Dominican Republic

  • 01. $1000 airfare voucher to Punta Cana, DR.
  • 02. 5-day, 4-night stay at Hard Rock Hotel & Casino Punta Cana for a family of four.
  • 03. Learn to be a pop star at the all-new Kidz Bop Experience!
  • Enter by October 21, 2018

Win a trip to St. Lucia

  • 4-night stay at a Kiwi Collection luxury hotel in St Lucia
    $500 in effortless style from Habitual
    $500 in Airfare to St Lucia
    $250 shopping spree on HUM Nutrition
  • Enter by October 21, 2018

Win a trip to Lake Tahoe, California

  • Rest and rejuvenate with four nights at Hyatt Regency Lake Tahoe Resort, Spa and Casino
  • Enjoy the world-class Diamond Peak Ski Resort with three-day passes and ski equipment rentals for two.
  • Enjoy your mountain-side escape with $750 to spend
  • Suit up in style with $250 in luxury performance outerwear from NORTH & MARK
  • Pair of GREATS shoes, up to $250
  • Enter by October 21, 2018

Win a ski trip to Park City, Utah

  • One (1) Grand Prize is available. The Grand Prize Winner (“the Grand Prize Winner”) will receive a trip for two (2) to Park City, Utah. The Grand Prize consists of a five (5) day trip with round-trip coach airfare from the major commercial airport nearest the Grand Prize Winners primary residence; double occupancy standard lodging accommodations; lift tickets, transportation to and from the airport, and additional gear, apparel, and prizes
  • Enter by October 21, 2018

Win a trip to Sydney, Australia

Win a trip to Patagonia

Win a trip to Hawaii

  • – 4-night stay at the Hilton Hawaiian Village
  • – $750 for travel expenses from Box of Style, Jetsetter, and Kitchn
  • Enter by October 22, 2018

Win a trip to Fort Lauderdale, Florida

  • One (1) Winner will
    receive a two-night stay for Winner and up to three guests at Hilton Fort Lauderdale Beach
    Resort (standard accommodations, single room, quadruple occupancy) (ARV: $600), $100 food
    and beverage credit for Le Marche and/or Ilios; and in-room dining (ARV: $100), in-room
    family Fun Basket filled with movies, popcorn and other fun treats and items for everyone
    (ARV: $75), complimentary valet (ARV: $84), four (4) VIP cards for local attractions and
    activities, courtesy of the Greater Fort Lauderdale Convention & Visitors Bureau (ARV:
    $1,000), Beach Starter Kit (ARV: $25), one (1) restaurant certificate, provided by Greater Fort
    Lauderdale Convention & Visitors Bureau (ARV: $100), and $1,500 in the form of a check
    (which winner may use towards transportation costs) (ARV: $1,500)
  • Enter by October 22, 2018

Win a trip to France

  • 1-week stay at Le Relais du Vieux Beaune just minutes from some of the world’s most famous wine-making villages
    $300 shopping spree to Society6
    $450 to use however you choose from Society6 & Travel Curator
  • Enter by October 25, 2018

Win a trip to New York City

Win a trip to Peru

  • Win a spectacular 10-day culinary adventure for two, featuring the best Peru has to offer, including round-trip flights on LATAM Airlines and two nights on South America’s only luxury sleeper train.
  • Enter by October 26, 2018

Win a trip to Maui, Hawaii

  • Get roundtrip travel to Maui
    Stay at a breathtaking beachfront resort from November 28th – December 3rd
    Attend a historic reunion of Jack Kornfield, Sharon Salzberg and Joseph Goldstein, founders of the Insight Meditation Society
    Live “Imagine” listening session with Boreta
    Join guided meditations & contemplative practices with Mirabai Bush, Rameshwar Das & Trudy Goodman
    Insights, contemplations & words of wisdom with Ram Dass
    Nightly chants w/ Krishna Das
    Eat healthy award-winning meals and more
  • Enter by October 26, 2018

Win a trip to Palm Springs, California

  • Prize package includes:
  • A 2 night stay at The Saguaro Hotel Palm Springs ($500 value)
    $600 travel voucher from
    Matt’s Flights & Travel Curator
    (2) AWAY “The Carry-On” Luggage ($450 value)
    (2) Goby Electric Toothbrushes ($150 value)
    (2) $150 gift cards to ADAY Luxury Wardrobe Essentials
    (2) $150 gift cards to W&P Design “Cocktail Carry-On”
    (2) $50 gift cards to Bombas Socks
  • Read about the best craft beer in Palm Springs
  • Enter by October 26, 2018

Win a trip to Lisbon, Portugal

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!

What do you think? Add a comment!