I independently & honestly review all of my travel recommendations. If you click on links I provide, I may receive compensation

Here are this week’s travel contests. You can win trips to Napa Valley, California; Toronto, Canada; Boulder, Colorado; Greece; Bermuda; Cabo San Lucas, Mexico; Lake Tahoe, California; West Hollywood, California; Austin, Texas; the Hamptons, New York; Whistler, Canada; Jasper, Canada; and more.

Good luck! Be sure to subscribe to my 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 stay in Napa Valley, California (does not include airfare)

Win a trip to Toronto, Canada

  • Experience Toronto, a city that remixes business with leisure with Carl Friedrik x Cool Material. Enter for your chance to win a future trip to Toronto for you and a guest including:
  • 2-night stay at the St. Regis Toronto in a Superior Room, including daily breakfast at LOUIX LOUIS
    Air Canada gift certificate for travel to/from Toronto
    American Express $500 gift card
    Carl Friedrik $1,000 gift card
  • open only to legal residents of the United States residing in the fifty (50) United States and the District of Columbia (for greater certainty, this excludes Puerto Rico, the U.S. Virgin Islands and other U.S. territories and possessions) who are at least eighteen (18) years of age
  • Enter by July 26, 2024

Win a trip to Boulder, Colorado (no donation required)

  • What You Can Win
    2 VIP tickets with early venue access to see Tyler Childers in Boulder, Colorado at Folsom Field on August 17, 2024
    Exclusive backstage tour and soundcheck access
    Signed & personalized setlist
    Merchandise package
    Roundtrip airfare for you and a guest to Colorado
    Hotel accommodations for 2 nights
  • Open worldwide
  • Enter by July 28, 2024

Win a trip to Greece

  • A 9-day/ 8-night trip to Greece for the winner and one travel companion with Intrepid Travel (Premium Greece Cyclades Islands tour) to be taken at a time of the winner’s choosing. The winner must book the tour through Intrepid Travel by Dec 31st 2025. Visit https://www.intrepidtravel.com/us/greece/premium-greece-cyclades-islands-143479 to view the itinerary, available dates, accommodations, activities and meals provided by Intrepid Travel, and other information. The tour is not all-inclusive, and the winner will be required to pay for travel insurance, passports and/or other documentation and identification, activities, meals, beverages, accommodations, transportation, entertainment, taxes, gratuities, service charges, telephone calls, souvenirs, incidentals, and other goods and services not expressly provided by Intrepid Travel. Acceptance of the prize constitutes the winner’s acknowledgment of, and agreement with, the Intrepid Travel Standard Booking Conditions, currently available at https://www.intrepidtravel.com/us/standard-booking-conditions. As set forth in the Standard Booking Conditions, the winner and the winner’s travel companion must (a) have a valid passport and/or other documentation and identification for entry to, departure from, and travel through Greece, (b) meet Intrepid Travel’s minimum age requirement, and (c) maintain travel insurance in the amount specified by Intrepid Travel. Prize value depends on time chosen to travel. Approximate Retail Value (ARV) for 2 people is $13,000 (thirteen thousand dollars).
    2 (two) $1,500 flight vouchers for the American based airline of the winner’s choosing (ARV: $3,000). The winner will be required to pay for any flight or travel expenses that exceed the amount of the vouchers. The vouchers expire one year after purchase.
    One (1) Musco Olives gift pack (ARV: $60)
  • open only to natural persons who are legal residents of the contiguous United States (excluding residents of New York and Florida) and of the age of majority in their place of residence
  • Read about the best views in Athens
  • Read about loukoumades in Athens
  • Read about Panathenaic Stadium in Athens
  • Read about cocktail bars in Athens
  • Read about craft beer in Athens
  • Read about wine tasting in Santorini
  • Read about cocktail bars in Santorini
  • Read about craft beer in Santorini
  • Read about brunch restaurants in Santorini
  • Read about the best time of year to visit Santorini
  • Read about craft beer in Naxos
  • Read about cocktail bars in Naxos
  • Read about kitron in Naxos
  • Read about an Olive Oil Museum in Naxos
  • Read about craft beer in Kalamata
  • Read about cocktail bars in Kalamata
  • Read about Kalamata roast pork
  • Read about Greek pasta
  • Read about wine tasting in Arcadia, Greece
  • Read about an ouzo distillery in Greece
  • Read about Greek spriits
  • Enter by July 31, 2024

Win a trip to Bermuda

  • There will be one (1) prize (“Prize”) awarded. The prize winner (“Winner”) will receive a four (4) day, three (3) night trip for Winner and one (1) guest to Bermuda (“Trip”).
  • Trip will include: round trip economy class airfare for Winner and one (1) guest (“Guest”) from any Bermuda East Coast gateway city (as determined by Bermuda Tourism Authority in their sole discretion. List of the Bermuda East Coast gateway cities can be found here: https://www.gotobermuda.com/plan/getting-to-bermuda) to L.F. Wade International Airport in Bermuda; three (3) nights’/4 day standard hotel accommodation at Hamilton Princess & Beach Club; and a 3 hour island tour.
  • Open to legal residents of the 50 United States and D.C., 21 years and older
  • Enter by July 31, 2024

Win a stay in Cabo San Lucas, Mexico (does not include airfare)

  • Win a 6-night all-inclusive stay in Cabo San Lucas, Mexico in a Super Executive Suite with a hot tub and ocean view, with value of $10,397. The prize includes: 6-night stay for 2 adults and 2 children. All meals including breakfast, lunch, dinner and snacks – Sparkling wine in room – Couples massage – Private dinner for two – Private Guided Tequila Session – Dinners at specialty restaurants included (LaFrida, Quivira Steakhouse and Fellini’s) – Golf credit of $100 for Quivira Golf Club
  • open only to legal residents of the United States of America who are 18 years old or older excluding residents of Rhode Island, Florida, and all United States Territories
  • Enter by July 31, 2024

Win a trip to Lake Tahoe, California

  • Grand Prize (4): four (4) grand prizes will be available to be randomly awarded. Each grand prize consists of a trip for four (4) people (winner and up to three (3) guests, each age 21 or older) for a Lake House rental during the Sponsor designated rental dates in Lake Tahoe, California. Each grand prize includes: round trip coach class airfare for four (4) people from Sponsor designated airport nearest winner’s home to the Sponsor designated airport servicing the Lake Tahoe, CA metro area (Reno–Tahoe International Airport – RNO); use of a Lake House rental for 5-nights during the Sponsor designated rental dates; $500 towards groceries and supplies; and a $1,000 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 July 31, 2024

Win a trip to West Hollywood, California (does not include airfare)

  • One winner will receive:
  • A free two-night stay at The London West Hollywood at Beverly Hills
    $1,000 gift card for meals and treatments in California
  • open only to legal residents of the United States who are 21 years of age or older
  • Enter by July 31, 2024

Win a trip to Austin, Texas

  • One (1) prize (“Prize”) will be awarded, which consists of: One (1) exclusive experience for the winner and guest with Aaron Franklin at Franklin Barbecue in Austin, Texas consisting of a 1:1 tour, lunch, 2 and 30min pit tutorial; tickets for two (2) to one of Austin’s iconic music venues; round-trip, coach class airfare for two (2) for two to Austin Bergstrom International Airport in Texas; $400 voucher towards a rental car or other mode of transportation; one (1) double occupancy standard hotel room for three (3) nights at a Hotel;
    and meals for two (2) consisting of one (1) breakfast, one (1) brunch, and three (3) dinners
  • open to all legal U.S. residents (except for residents of Maine and Texas) who are 21 years of age or older
  • Enter by July 31, 2024

Win a trip to the Hamptons

  • Grand Prize (1 total): Grand Prize winner will receive two (2) round trip tickets to
    the Hamptons, a three (3) night stay at Gurneys, a Seawater Spa experience at Gurney’s
    Montauk (including a 60-minute massage at the Seawater Spa, a 50-minute Bathhouse
    session, access to all fitness classes that day and all day access to the indoor seawater
    pool), a dinner at Scarpetta, VIP Gifting, and a one (1) year supply of Saint James Iced
    Tea (24 cases)
  • open only to legal residents of the US/DC who are eighteen (18) years of age or older
  • Enter by August 1, 2024

Win a stay in Whistler, Canada (does not include airfare)

  • Fairmont Chateau Whistler Gold Giveaway
  • Fairmont Chateau Whistler offers an exclusive chance to win a 4-night stay that promises luxury with every turn, with access to the coveted Fairmont Gold.
  • Fairmont Gold Experience & Dinner at The Wildflower includes:
  • Private Check-In and Concierge: Bypass the lines and enjoy personalized service from the moment you arrive.
    Exclusive Fairmont Gold Lounge Access: A sanctuary where you can unwind, enjoy complimentary breakfast and evening canapes and beverages, and relish serene mountain views.
    Priority Reservations: Be first in line for dining, tee times, and our premium hotel car service, ensuring every aspect of your stay is seamless.
    Customized Indulgences: Tailor your visit with luxurious amenities designed to make your stay unforgettable.
    Dinner for 2 at The Wildflower: Delight in an exquisite dining experience with a menu that promises to tantalize your taste buds.
    Valet Parking: Enjoy the convenience and luxury of valet parking, making your arrival and departure smooth and hassle-free.
  • 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 a resident of the United States of America and the District of Columbia (excluding residents of Alaska, Hawaii, Rhode Island, overseas military installations, Puerto Rico, and other U.S. Territories)
  • Enter by August 5, 2024

Win a stay in Jasper, Canada (does not include airfare)

  • Step into a wonderland of festive joy at Fairmont Jasper Park Lodge, where holiday dreams turn into reality. This isn’t just any celebration; it’s your golden ticket to mingle with the world of food star’s. This is Christmas in November.
  • Win a 3-night VIP stay at the luxurious Fairmont Jasper Park Lodge, where festivities meet glamour. Dine with celebrity chefs, enjoy private check-in, lounge access, and exclusive parties like the Signature Cabin Kitchen Party. Enter now for your chance to indulge in the holiday spirit like never before!
  • Here’s what awaits you and a lucky companion in this VIP once-in-a-lifetime food & wine festival, valued at over $3,700 USD:
  • 3-Night VIP Deluxe Accommodation for Two
    Arrival Gift & Private Check-in
    Christmas Sweater Reception
    Breakfasts, Lunches & Dinners Prepared by the Fairmont Culinary Team
    Signature Gala Dinner with Live Entertainment
    Reception & Dinner Beverages
    Interactive Classes, Seminars, Tasting Workshops
    Farewell Brunch
    Airport Transfers Included
    Complimentary Taxes and Fees
    & more!
  • 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 a resident of the United States of America and the District of Columbia (excluding residents of Alaska, Hawaii, Rhode Island, overseas military installations, Puerto Rico, and other U.S. Territories)
  • Enter by August 5, 2024

Go on an adventure at home or when you’re away with a tour or activity via Get Your Guide.

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!

Hi, I'm Jonathan, the traveler, writer, photographer, enthusiast, & terrible dancer of Everybody Hates A Tourist with decades of travel expertise. I've visited over 50 countries & territories so far. Join me as I share my personal experiences finding the best food, craft beer, cocktails & spirits, wine, culture, & history around the world!

What do you think? Add a comment!