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Here are this week’s travel contests. You can win trips to Jamaica; Maui, Hawaii; Miami Beach, Florida; Riviera Maya, Mexico; Playa Del Carmen, Mexico; Memphis, Tennessee; Cancun, Mexico; Anguilla; Iceland; Italy; Peru; Orlando, 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 Jamaica

  • YOU AND A FRIEND WILL:
  • 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

Win a trip to Maui, Hawaii

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

  • Prize includes:
  • • Four-night getaway for two people
  • • Stay in an oceanfront room
  • • $500 in gift cards to use toward flights to Hawaii
  • 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 18, 2021

Win a trip to Miami Beach, Florida

  • 4 nights for 2 people in either a standard king or queen room
  • $29/night resort fees are waived
  • $1,800 towards travel expenses
  • Subject to availability
  • 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 22, 2021

Win a trip to Riviera Maya, Mexico

  • PRIZE INCLUDES:
  • 5-Day/4-Night All-Inclusive Stay for Two Adults at UNICO 20° 87° Hotel Riviera Maya [$2,279 value] *Airfare not included.
  • $500 Free People Gift Card for a Travel Wardrobe Upgrade
  • $300 in Elizabeth Arden Beauty Products
  • $500 Cash Towards Travel from Inside Hotels and Elizabeth Arden
  • $1,000 Credit Towards LuxuryEscapes.com
  • 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 23, 2021

Win a trip to Playa del Carmen, Mexico

  • Prize includes:
  • – 4-Day/3-Night All-Inclusive Accommodations for a Family of 4 at Paradisus Playa del Carmen
  • – Food & Beverage is included as part of the Paradisus by Melià All-Inclusive vacation package
  • – $750 towards travel
  • -Complimentary wi-fi
  • 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 24, 2021

Win a trip to Memphis, Tennessee

  • Prize package includes:
  • Southwest Airlines: Two round-trip flight vouchers – $650
    Hyatt Centric Beale Street: 2-night stay in corner suites – $800
    Kayak Memphis: Mighty Lights private sunset tour from River Garden – $120
    Explore Bike Share: eBike passes – $50
    Go Ape at Shelby Farms Park: Treetop adventure passes $150
    Memphis Zoo: Free passes – $60
    Memphis Farmers Market: Tokens $20
    SUP901: Free group session at Hyde Lake at Shelby Farms Park – $80
    Gift certificate to the Memphis restaurant of your choice – $100
  • U.S. citizens 18 and older, except where prohibited by law, are eligible to win this giveaway
  • Enter by June 24, 2021

Win a trip to Cancun, Mexico

  • ● A 4-night stay for two at Planet Hollywood Cancun with all-inclusive meals and beverages.
  • ● A $250 gift card to Wine Awesomeness
  • ● A $250 gift card to WearPanda.com courtesy Panada Sunglasses
  • ● A $250 gift card courtesy of Choose Your Attitude
  • ● A $200 gift card compliments of Zatoru
  • open to anyone who is at least twenty-one (21) years of age and has reached the age of majority in their jurisdiction of residence at the time of opt-in 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 June 25, 2021

Win a trip to Anguilla

  • Set sail into the season with a much-needed escape to Anguilla, plus a load of fashion and beauty favorites specially chosen to make this the ultimate summer vacation. One lucky person will get a chance to win a trip for 2 to the best beach on the breathtaking island of Anguilla at Malliouhana, an Auberge Resort and over $2,000 in additional prizes:
  • 2-night stay for two people at Malliouhana, an Auberge Resort (valued at $2,500)
    $400 airfare credit
    $1,000 shopping credit to Tuckernuck
    $150 shopping credit to Bastide
    $250 shopping credit to Amorepacific skincare
    $500 shopping credit to Monos Luggage
    $200 shopping credit to The Laundress
    Complimentary 30-day Indagare Travel Tier 3 Membership
  • The Sweepstakes is open worldwide, 18+
  • Enter by June 28, 2021

Win a trip to Iceland

  • Economy class round-trip air on Icelandair for two (2) persons from these Icelandair gateways only: Anchorage (ANC), Baltimore (BWI), Boston (BOS), Chicago (ORD), Cleveland (CLE), Dallas (DFW), Denver (DEN), Kansas City (MCI), Minneapolis (MSP), New Jersey (EWR), New York (JFK), Orlando (SFB), Philadelphia (PHL), Portland (PDX), San Francisco (SFO), Seattle (SEA), Tampa (TPA), Washington D.C. (IAD), Edmonton (YEG), Halifax (YHZ), Montreal (YUL), Toronto (YYZ), Vancouver (YVR). Destination depends on availability at each time.
    Three (3) nights accommodations for two (2) in Reykjavik, Iceland at Hotel Nordica (or similar) based on double occupancy, with Scandinavian buffet breakfast daily, except on arrival date.
    Two (2) round-trip bus transfer from KEF airport to hotel in Reykjavik, Iceland
    Two (2) 72 “Hours Reykjavík Welcome Cards” providing free access to City of Reykjavík owned world famous thermal pools, museums and public transportation, plus various retail discounts.
  • open to residents the United States of America and Canada. All contest entrants must be 18 years of age or older to enter
  • Read about craft beer in Reykjavik
  • Enter by June 30, 2021

Win a trip to Italy

  • Enter to win a prize package that includes ALL of the following:
  • • A 3-night stay at Monteverdi Tuscany, including dinner with wine for two and two spa treatments
  • • A $1,000 gift certificate to Delbrenna Jewelry in Cortona
  • • A $500 gift certificate to ItalyAncestry.com
  • • A 16-Piece Lastra White Place Setting from VIETRI
  • • A one-year supply of pasta from DeCecco
  • • An assortment of heirloom seeds from Seeds From Italy
  • • A lifetime subscription to Rosetta Stone Italian Lessons
  • • A dinner for two with wine pairings, cookbook and gift bottle of wine from Toscana Brentwood
  • • A lifetime digital subscription to Dream of Italy Travel Magazine and Membership Site
  • • A $400 gift card to be used towards airfare compliments of 1440
  • • A $250 gift card compliments of Matt’s Flights
  • • A $250 gift card provided by Newser
  • 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 craft beer in Trento
  • Read about Castel Beseno near Trento
  • Enter by June 30, 2021

Win a trip to Peru

  • YOU AND A FRIEND WILL:
  • Win a 10-day fully guided adventure in Peru with flights and $1,000 included
  • Visit Cusco and cross Machu Picchu off your bucket list
  • Explore the Amazon from a one-of-a kind jungle lodge
  • Open worldwide
  • Enter by June 30, 2021

Win a trip to Orlando, Florida

  • You could win a 3-night trip for four people, including:
  • Round trip airfare to Orlando, Florida
  • Ground transportation between the airport and hotel in Orlando
  • Accommodations at Universal’s Cabana Bay Beach Resort
  • Admission to both Universal Studios Florida and Universal’s Islands of Adventure theme parks, plus Universal’s Volcano Bay water theme park
  • Open to legal U.S./D.C. residents, 18+
  • Enter by June 30, 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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