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Here are your travel contests for this week. You can win trips to Riviera Maya, Mexico; Hong Kong; St. Lucia; Tuscany, Italy; New York City; Boston, Massachusetts; Punta Cana, Dominican Republic; Montreal, Quebec, Canada; Cancun, Mexico; Sonoma & Napa, California; Ashland, Oregon; Yosemite National Park; San Francisco, California; Florida; 140,000 Hawaiian Airlines miles; and more.

Good luck & be sure to subscribe to the weekly newsletter so you don’t miss any contests!

Win a trip to Riviera Maya, Mexico

  • Grand Prize package includes: (a) one (1) $1,500 VISA gift card to be used toward the purchase of round-trip airfare; (b) three (3) night, four (4) day, all-inclusive accommodations for two (2) in one (1) standard room at the UNICO 20° 87° Hotel Riviera Maya (presented in the form of a Travel Certificate); and (c) a $500 gift card for
  • Enter by May 28, 2017

Win round trip flights to Hong Kong on Cathay Pacific

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

  • Two (2) winners will receive [One (1) Round Trip Flight to Hong Kong on Cathay Pacific]
  • Enter by May 28, 2017

Win a trip to connect with your roots

  • One winner and one traveling companion (as chosen by winner but who is either at least 18 years of age or the age of majority in the relevant jurisdiction, whichever age is older, at the time of entry or alternatively has the consent of their legal guardian or parent to accompany the winner) will be awarded a prize that consists of memberships, travel vouchers, flight vouchers, luggage, insurance and other merchandise, excluding the genealogical research which shall be awarded to the winner only, with an approximate retail value of $10,198 (all monetary values in U.S. Dollars). These expenses will be incurred sending the competition winner and one traveling companion to the country nominated upon entry. The prizes consists of the following:
    Ancestry will provide two (2) complimentary and free 1-year membership to Ancestry (1 for each recipient) with the World Explorer membership (ARV of $420 USD). Though residents from any country are eligible to receive prize, specific products for Ancestry exist for only the following countries: United States, Canada, United Kingdom, Australia, New Zealand, Sweden, Germany and Mexico.
    AncestryProGenealogists, a division of Ancestry, will provide up to 20 hours of free genealogical research for the winner only. (ARV of $2,300 USD). There is no guarantee that said research and services can be conducted in any language other than English. Certain restrictions may apply
    TravelStore will provide up to $3,000 USD ($1,500 USD per person) in travel credit to be used for custom trip planning services provided by TravelStore. Travel credit is eligible to be used for any trip and services that can be arranged and booked by TravelStore. Some restrictions may apply.
    STA Travel will provide one (1) winner and their one (1) traveling companion with a flight voucher worth up to $3,000 USD ($1,500 USD for each person) for economy class travel, to be used for flights to get the winner and the companion to their destination. Voucher is valid until June 30, 2018. Booking must be confirmed at least four (4) weeks before planned departure. Cannot be combined with other offers. Not valid on ISIC/ITIC/IYTC cards or travel insurance. Non-transferable and cannot be redeemed for cash. Winner must redeem by calling STA Travel at 800.781.4040.
    Bluesmart will provide two (2) Bluesmart Ones (total worth $898). One per recipient. Not all countries are eligible for shipping. Some restrictions may apply.
    Lonely Planet will provide up to $100 USD ($50 USD per person) in credit to the Lonely Planet Shop.
    The Clymb will provide a $250 gift card (1 for each recipient) to shop at
    World Nomads will offer to provide a 2-week Standard plan travel insurance policy from World Pty Ltd. for two travelers traveling on the same itinerary departing/arriving from same departure city. Plan policy premium depends on country of residence. Sponsor will reimburse up to $300 USD.
  • Enter by May 29, 2017

Win a trip to St. Lucia

  • Includes Diamond Club luxury junior suite, plus a 50-minute couples massage ($3,995 value).
  • Buy a new vacation wardrobe or use the money towards your flight!
  • Honeymoon in style with gorgeous accessories from Kendra Scott’s newest resort collection.
  • Enter by May 30, 2017

Win a trip to Tuscany, Italy

  • Win a wine fueled trip to Tuscany.
  • Trip includes round trip flights for 2 from New York to Italy, full accommodations and meals, and plenty of Tuscany’s most famous wine, Nobile.
  • In addition you’ll go truffle hunting with your very own truffle dog and get to drive a Ferrari for 2 hours through the winding Tuscan roads.
  • Depart New York October 31 and return November 5th.
  • Enter by May 30, 2017

Win a trip to New York City & Boston

  • 2 round trip tickets to NYC, returning from Boston
    3 nights total at luxurious hotels in both cities
    A Spanish tapas cooking class, with wine (of course) in New York City
    Rueda verdejo flight with a meet + greet from Master Sommelier Alex LaPratt and dinner prepared by Executive Chef Laurent Kalkatour at Beasts & Bottles in Brooklyn Heights, New York
    Paired dinner by Grill23 Executive Chef Brian Kevorkian with an exclusive walkthrough of the wines by Master Sommelier Brahm Callahan in Boston’s Back Bay area
    Train transportation from NYC to Boston
  • Enter by May 30, 2017

Win a trip to Punta Cana, Dominican Republic

  • Round trip air travel for up to two (2) people via Southwest Airlines® to Punta Cana (PUJ) (Government-imposed travel taxes of up to $150 per person are not included and are payable by each of winner and guest prior to travel.)
    Four-night accommodations at CHIC Punta Cana.
    All-inclusive all meals, beverages, entertainment.
    Round trip airport/hotel transfers.
  • Enter by May 31, 2017

Win a trip to Montreal, Quebec, Canada

  • ONE (1) GRAND PRIZE: A trip for two (2) to Montreal, Canada. Trip
    package includes roundtrip coach-class air transportation from an airport near winner’s home
    (determined by Sponsor in its sole discretion) to Montreal, Canada; three (3) nights’
    accommodations at Queen Elizabeth Hotel; and $150 hotel credit
  • Enter by May 31, 2017

Win a trip to Cancun, Mexico

  • One (1) Grand Prize Winner will receive a seven (7)-day, six (6)-night trip to Grand Fiesta
    Americana Coral Beach Cancun in Cancun, Mexico for Winner and three (3) Guests, which
    includes round-trip airfare for four (4) people from any Aeromexico USA gateway nearest
    Winner’s residence to Cancun (ARV: $1,600), which may vary depending on location of
    Winner’s residence; six (6) nights hotel accommodations (ARV: $3,000), and two 80-minute
  • Enter by May 31, 2017

Win a wine trip to Sonoma, California

  • Three (3) Grand Prizes: A 4 day/3 night trip for two (Winner and one (1) guest; guest must be 21 years of age or older) to Sonoma County, California. Prize trip includes: 3 nights’ hotel accommodations (double occupancy), round trip economy air transportation for Winner and one (1) guest from a major airport near Winners’ residence to a major airport servicing the U.S. city closest to San Francisco, CA approved by Sponsor; transportation to/from airport/hotel, a total of seven (7) meals, two (2) spa treatments at hotel, a $200 gift card (for Winner only) for incidentals and a gift bag containing Rodney Strong Vineyard branded merchandise. An itinerary of scheduled events will be provided. Approximate Retail Value of each Grand Prize is: $3,500. Total ARV of all Grand Prizes offered is: $10,500. Actual value of prize may vary based on airfare fluctuations and distance between departure and destination. Trip must be taken July 6 – 9, 2017
  • Enter by May 31, 2017

Win a trip to Sonoma & Napa, California

  • A $1,000 gift card towards round trip flights for two
    3 nights’ luxurious accommodations in the heart of the Napa Valley at Yountville’s boutique North Block Hotel
    Explore Sonoma – a day dedicated to exploring the diversity of Sonoma County from its dramatic coast to the historic Sonoma Valley to the wetlands and enjoy complimentary exclusive wine tasting experiences at B.R. Cohn Winery, Viansa Sonoma and Sonoma Coast Vineyards
    Experience Napa – a day to savor the best Napa Valley has to offer. Enjoycomplimentary VIP wine tastings as you tour the iconic caves at Clos Pegase Winery, sip on wines and soak up the whimsy at Swanson Vineyards, and settle in for a taste of Napa Valley at the Girard Napa Valley tasting room in Yountville.
  • Enter by May 31, 2017

Win a trip to Ashland, Oregon

  • Round trip tickets on Alaska Airlines
    3 nights in Ashland at the Ashland Springs Hotel
    A wine pairing dinner at Larks Home Kitchen Cuisine
    Luxury Wine Hopper Tour in the Rogue & Applegate Valleys
    Private vineyard tour and tasting at Irvine & Roberts Family Vineyards
    Tickets to an Oregon Shakespeare Festival performance of your choice*
    VIP Rogue Creamery cheese tasting and tour
    A $100 gift card
  • Enter by May 31, 2017

Win a trip to Yosemite National Park

  • One Grand Prize Winner will receive: two (2) RT Flight Certificates valid from a JetBlue departure city, one (1) National Park Annual Pass, a 6-months supply of Field Trip Jerky (24 packages) and Field Trip swag, a $200 Western Rise Gift Card, a Rumpl Original Puffy Throw, 2 Shoes of the winner’s choice from OluKai, a Uinta Brewing 4-Pack of National Park Can Glasses, Hammock, Metal Uinta Tacker, and Golden Ale T-Shirt, 2 Arcteryx Atom LT Jackets, a Peak Design Everyday Pack & Field Pouch, an Oru Kayak Beach Kayak & Paddle, 5 Pairs of FITS Socks, a Mountainsmith Morrison EVO 2 & Halite 7075 Poles, 2 Kaenon Sunglasses of Your Choice, The Inertia Limited Edition Anniversary Book, and 4 Days of Avis Car Rental Free Day Coupons
  • Enter by May 31, 2017

Win a trip to San Francisco, California

  • Airfare to San Francisco
    Lodging (two nights)
    Timbuk2 Bags + Factory Tour
    Bikes from Pure Cycles
    Clothing from Kitsbow
    Helmets from Bell
    Lights and Locks from Kryptonite
    Water bottles and Socks from Ornot
    Sunglasses from Sunski
    Coffee Tour from Blue Bottle
  • Enter by May 31, 2017

Win a trip to Mexico

  • A three-night stay at Coqui Coqui Coba Residence & Spa
    A $500 travel credit
    A $500 gift certificate to The Line
    A $500 gift certificate to Outdoor Voices
    A pair of Khaite jeans
    A Flagpole swimsuit and cover-up
    A Clare V. Simple Tote
    A bottle of Vintner’s Daughter Active Botanical Serum
  • Enter by May 31, 2017

Win a trip to Florida

  • $800 for airfare to be booked by winner​​
    4-night stay for two in a one-bedroom condo at any North West Florida Wyndham Vacation Rental Property.
    $250 gift certificate, to be used at winner’s discretion.
  • Enter by May 31, 2017

Win 140,000 Hawaiian Airlines miles

  • ONE (1) GRAND PRIZE: 140,000 Hawaiian Airlines HawaiianMiles
  • Enter by May 31, 2017

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