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!

tuscany italy 700x394

Here are your travel contests for this week. You can win trips to Sonoma, California; Italy; Portland, Oregon; Iceland; New York City; New Dehli, India; Scotland; Cancun, Mexico; Santa Barbara, California; and more. Good luck!

Win a trip to Sonoma, California

  • 3 Nights in the luxe boutique h2hotel in Healdsburg, CA
    the perfect leather wine bag from Ghurka
    $200 gift card to shop vintage denim with Re/Done
    the most amazing headphones from Master + Dynamic
    $500 travel voucher to get you to wine country!
  • Enter by June 10, 2016

Win a romantic getaway to Italy

  • One (1) potential Grand Prize Winner will receive the following: A $1200 gift certificate to be used toward airfare from Hitlist. Two (2) nights each at the following hotels: Relais Santa Croce, Florence (excluding blackout dates 6/13-6/16/16, 12/24/16-1/2/17, 1/9-1/13-17); Don Alfonso 1890 in Sant’ Agata sui Due Golfi, a junior suite and one dinner for two people of the La Degustazione menu and a selection of regional wines
  • Enter by June 12, 2016

Win a trip to Portland, Oregon

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

  • One (1) Travel stipend. Value up to $1,000. Two (2) night stay at the Ace Hotel in Portland, Oregon. Additional occupancy or room changes are subject to additional fees. Room cannot be combined with any other offer, promotion or sweepstakes. Value up to $1,500 USD. One (1) american express gift card or similar items to the sole sponsor’s choosing to be used for dining out and shopping. Value up to $1000 USD
  • Enter by June 13, 2016

Win a trip to Iceland

  • One complimentary trip on the Epic Iceland Yoga Retreat courtesy of Yogascapes
    $1,000 toward airfare courtesy of WellPath, Well+Good and CleanPlates
    $500 credit toward Premium Album courtesy of MyPublisher
  • Enter by June 14, 2016

Win hotel stays in New York, Berlin, or Paris (does not include airfare)

  • The competition’s prizes includes three 2-night hotel stays each including breakfast plus two vouchers each for a customized city tour with Touriocity. The participating hotels are Hôtel Americano in New York, Cosmo Hotel Berlin Mitte and Le Pigalle in Paris
  • Enter by June 14, 2016

Win a trip to New York City

  • A trip for winner and a guest to New York City, New York. Trip package includes round trip, coach-class air transportation for two (2) from a major airport near winner’s home (determined by Sponsor in its sole discretion) to New York City; two (2) nights’ accommodations at the Conrad Hotel (single room, double occupancy), breakfast at ATRIO Wine Bar & Restaurant and cocktails at Loopy Doopy Rooftop Bar; a one thousand dollar ($1,000) Henri Bendel gift card; a Red Door Spa pamper package and a $300 credit on Lyft
  • Enter by June 14, 2016

Win a trip to New Delhi, India

  • A 6 day/5 night trip for two (2) to New Dehli, India. Prize includes round trip coach class air transportation for winner and one guest from a major U.S. gateway airport nearest winner’s home to New Dehli, India, five (5) night’s standard double occupancy hotel accommodations and airport/hotel transfers
  • Enter by June 15, 2016

Win a trip to Scotland

  • Grand Prize consists of one (1) Insight Vacations 10-Day Country Roads of Scotland trip for Grand Prize Winner and one (1) guest including: (i) round-trip coach airfare and associated fees up to a maximum value of $1,500 for both Grand Prize Winner and guest between the major commercial airport nearest the prize winner’s residence and London or Edinburgh Airport, UK (each of which will be determined by the Sponsor in its sole discretion); (ii) eight (8) nights hotel accommodations (double occupancy standard room and tax only) at the Crowne Plaza Edinburgh – The Roxburghe/the Carlton, Edinburgh; Kingsmills Hotel, Iverness; the Station Hotel/St. Clair Hotel, Thurso; the Dunollie, Broadford; the Ballachulish/Isles of Glenco, Ballachulis; the Columba, Oban; and the Marriott, Glasgow; (iii) ground transportation between the airport and the hotel in Edinburgh and to Iverness, Thurso, Broadford, Glencoe, and Glasgow; (iv) daily breakfast for Grand Prize Winner and guest; (v) six (6) dinners for Grand Prize Winner and Guest; and (vi) use of a specified tour director
  • Enter by June 15, 2016

Win a trip to Cancun, Mexico

  • Four-night All-In Luxury stay at the Royalton Riviera Cancun
    Dinner for two at C/X Culinary Experience,
    the resort’s onsite exclusive chef’s table
    Plus, $700 towards flights!
  • Enter by June 15, 2016

Win a trip to Santa Barbara, California

  • Two nights’ accommodations in a Deluxe Bungalow at Belmond El Encanto
    Two 50-Minute Signature Massages at The Spa at El Encanto
    Access to The Spa Lounge and Yoga and Core Fitness Classes
    Daily Breakfast for two guests at The Dining Room and Terrace
  • Plus, $500 toward flights!
  • Enter by June 15, 2016

Win a trip to New York City

  • Start the trip by flying out to the Hamptons and enjoy a night at The Maidstone Hotel
    Continue the getaway in NYC with $500 hotel booking credit by Stayful
    Get a $1000 shopping spree to Tucker by Gaby Basora & a Diamond Noémie ring
    Relive the trip with a customized photo book by Tweed Wolf
    Enhance your life with one year of Mogul Courses while sipping on fresh smoothies by Daily Harvest.
  • Enter by June 15, 2016

Want to see previous weeks’ travel contests? Go here!

What do you think? Add a comment!