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Here are this week’s travel contests. You can win trips to Brooklyn, New York; Chicago, Illinois; Los Angeles, California; Portland, Oregon; New York City; Rome, Italy; Cancun, Mexico; Punta Cana, Dominican Republic; California; Cabo San Lucas, Mexico; a Taylor Swift concert in Miami, Florida; Austin, Texas; the Bahamas, Jamaica, or St. Lucia; Boise, Idaho; New York City; Napa, California; London, England; Texas; New York City, Madrid, Spain; Nashville, Tennessee; 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 trip to Brooklyn, New York; Chicago, Illinois; Los Angeles, California; or Portland, Oregon

Win a trip to New York City

  • ONE (1) GRAND PRIZE: One (1) trip package for winner and one (1) guest to New York City. Trip package to include:
  • · Round trip, first-class air transportation for two (2) from a major airport near winner’s home (determined by Sponsor in its sole discretion) to New York, NY;
  • · Two (2) nights’ accommodations at a hotel determined by Sponsor in its sole discretion (single room, double occupancy), including breakfast the morning after each night of stay;
  • · Ground transportation to and from destination airport and hotel;
  • · Spa allowance of $800 at a spa determined by Sponsor in its sole discretion;
  • · Salon allowance of $800 at a spa determined by Sponsor in its sole discretion;
  • · $600 gift card for a meal at a French-inspired bistro;
  • · $1,000 gift card to major department store; and
  • · Two (2) tickets to be in the studio audience for a broadcast of Watch What Happens Live with Andy Cohen. (Subject to availability and additional guidelines).
  • open only to legal residents of the fifty (50) United States and the District of Columbia who are at least twenty-one (21) years old
  • Enter by February 28, 2024

Win a trip to Rome, Italy

  • Flight Cash from Dollar Flight Club
  • 4-5 night stay at citizenM Rome Isola Tiberina
  • Dates Subject to availability and blackout dates
  • Value: $4,000+
  • Open worldwide, 18+
  • Enter by February 29, 2024

Win a trip to Cancun, Mexico

  • Win a 3-night stay for two at RIU Palace Kukulkan including all meals, drinks, non-motorized water sports, roundtrip air seats on a Scheduled Air Flight and the services of a Funjet Vacations representative.
  • 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 February 29, 2024

Win a trip to Punta Cana, Dominican Republic

  • You could win a 5-night stay for two at Hard Rock Hotel & Casino Punta Cana including roundtrip air seats on a Scheduled Air Flight, all meals and drinks, non-motorized water sports, and the services of a CheapCaribbean representative.
  • 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 February 29, 2024

Win a Ford Bronco and a California road trip

  • 2023 Ford Bronco: Get ready to ride in style, cruising the California coast
  • 5 Day Roadtrip up the California Coast: Hit the road with your bud and soak up the sun
  • Roundtrip flights for you and a friend: Bring your buddy and catch some airtime
  • $4,000 Cash Card: Fuel up, grub out, or grab some rad gear
  • 4 nights accommodation at 4 of California’s top hotels: Sleep like a boss at epic spots
  • A surf lesson in Malibu: Hang loose and catch some waves
  • A boat ride in Santa Barbara: Cruise with the whales, ’nuff said
  • Yoga & meditation classes in Big Sur: Find your zen with killer views
  • Napa Valley winery tour: watch an epic sunset over beautiful grape vines.
  • open to legal residents of the USA who are at least eighteen (18) years of age
  • Enter by February 29, 2024

Win a trip to Cabo San Lucas, Mexico

  • Prize includes:
  • A 5-day/4-night Island inclusive stay at Breathless Cabo San Lucas Resort & Spa® located in Mexico.
    All-inclusive accommodations including meals, select drinks, access to gourmet restaurants, daily resort entertainment, a mix of fitness classes, watersports, and more!
    Roundtrip airfare credit capped at $500/per person
    Endless opportunities to unwind.
  • Open to residents of the 50 United States and D.C. who are 18 years of age or older and of the legal age of majority
  • Enter by March 1, 2024

Win a trip to see Taylor Swift in Miami, Florida

  • A pair of Taylor Swift Era Tour concert tickets for Miami, FL, plus a gift card in the amount of $2,000.00 to cover airfare and hotel stay for 2.
  • Total Prize Value $10,500.00
  • The sweepstakes is only open to legal residents of United States, 18+
  • Enter by March 2, 2024

Win a trip to SXSW in Austin, Texas (no donation required)

  • What You Can Win
  • Two SXSW Badges valid for the full festival
  • VIP access to Billboard The Stage @ SXSW concerts
  • Side-stage viewing opportunity during ILLENIUM’s performance
  • Signed merchandise from ILLENIUM
  • Round-trip airfare for you and a guest
  • Hotel accommodations for three nights
  • Open worldwide
  • Enter by March 3, 2024

Win a trip to a Sandals resort in the Bahamas, Jamaica, or St. Lucia

  • Grand Prize (total value of $4999)
  • (i) One (1) prize consisting of a five-day/four-night all-inclusive vacation for two (2) adults in a Luxury category room to any one of the Sandals Resorts Golf Destinations listed below (recipient’s choice) (“Sandals Resorts Accommodations”) plus roundtrip coach airfare tickets for two (recipient and travel companion) (“Airfare”) (Sandals accommodations and Airfare collectively, the “Sandals Prize Package”). Sandals Resorts Golf Destinations: Exuma, Bahamas, Ocho Rios Jamaica, and Gros-Islet, Saint Lucia. (ii) Sandals Resorts is an all-inclusive, adults-only destination. (iii) Prizewinner and travel companion must be at least 18 years of age or older. (iv) The Sandals Prize Package will include luxurious accommodations (one (1) room, double occupancy in a Luxury Category Room, all meals, unlimited Premium Liquors, daily & nightly entertainment, an array of land and water sports activities, including daily Scuba diving (for certified divers), snorkeling, Wi-Fi in all rooms and public areas, resort gratuities, resort taxes, and Sandals transfers to and from the selected or designated airport. (v) Flights: Round-trip coach airfare for two (2) recipient and travel companion valid to/from the nearest major U.S. gateway of the prize winner to the selected or designated resort’s airport.
  • 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 March 5, 2024

Win a trip to Boise, Idaho (no donation required)

  • Win a Trip to Treefort Music Fest & Watch Briston Maroney From Side Stage
    You and a friend will…
  • Fly to Boise, Idaho
    Attend Treefort Music Fest with Zipline Passes
    Catch sets from Channel Tres, Briston Maroney, Drama, Franc Moody, Ty Segall & many more
    Watch Briston Maroney from side stage + signed setlist
    Gain front of the line access at all music venues and Alefort (as capacity allows)
    Access to Lookout Lounge
    Plus: 5-night hotel stay at The Grove Hotel + rideshare credit
  • Open worldwide, 18+
    Enter by March 5, 2024

Win a trip to New York City (no donation required)

  • Win a Trip to NYC To See the First Preview of SUFFS on Broadway
    Package Includes:
  • Two (2) tickets to the first preview of SUFFS on Broadway
    Itinerary of Team Propeller’s favorite spots in NYC
    2-night hotel stay in Midtown, Manhattan
    Roundtrip travel to NYC + rideshare credit
  • Open worldwide, 18+
    Enter by March 6, 2024

Win a trip to Napa, California

Win a trip to London, England (no donation required)

Win a trip to Texas (no donation required)

  • An invitation to watch the 2024 total solar eclipse with Bill Nye! Prize includes:
  • Exclusive VIP access to all Eclipse-O-Rama activities
  • Honorary Planetary Society pinning by Bill Nye with photo op
  • Planetary Society Membership
  • $250 cash for ground transportation
  • Roundtrip flights for you and a guest
  • Accommodations for 3 nights at The Lodge in Fredericksburg, Texas
  • Open worldwide
  • Enter by March 10, 2024

Win a trip to New York City (no donation required)

Win a trip to Madrid, Spain

  • The Grand Prize winner will receive:
  • A trip for two to the 2024 Mutua Madrid Open
  • Roundtrip travel to Madrid
  • Three nights hotel accommodation
  • Tickets for two tournament sessions
  • OPEN ONLY TO LEGAL RESIDENTS OF THE 50 UNITED STATES AND THE DISTRICT OF COLUMBIA, CANADA AND THE UNITED KINGDOM WHO ARE (1) AT LEAST EIGHTEEN (18) YEARS OR THE AGE OF MAJORITY IN THEIR COUNTRY/PROVINCE/STATE OF RESIDENCE
  • Enter by March 13, 2024

Win a trip to Nashville, Tennessee (no donation required)

  • Win a Trip to Meet Chelsea Cutler on The Beauty is Everywhere Tour and Enjoy a Spa Package at 1 Hotel Nashville
    Package Includes:
  • Two (2) tickets to Chelsea’s show at the Ryman Auditorium on March 30th, 2024
    Meet & greet with Chelsea Cutler
    Luxurious 2-night stay at 1 Hotel Nashville w/ package at Bamford Wellness Spa
    $250 food & beverage voucher towards Harriet’s Rooftop / 1 Kitchen at 1 Hotel Nashville
    Roundtrip travel to Nashville
    Hotel stay, rideshare credit & more!
  • Open worldwide, 18+
    Enter by March 13, 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 40 countries so far. Join me as I share my personal experiences finding the best food, craft beer, cocktails & spirits, wine, culture, & history around the world!

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