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 & prizes such as a trip to Scotland; a World Cup match in Mexico City; $25,000; New Jersey; Disneyland in California; the MLB All-Star Game in Philadelphia, Pennsylvania; an all-inclusive Sandals resort stay; Bozeman, Montana; Big Sur, California; outdoor gear; the 2026 World Cup Final and a stay at the stadium; a $10,000 custom trip; an RV; Chicago, Illinois; Switzerland; Barcelona, Spain; Costa Rica; the Kentucky Derby; the Dominican Republic; Boundary Waters, Minnesota; Las Vegas, Nevada; Scotland; a U.S. destination; California; Japan, Disney World or Disneyland; Aspen, Colorado; Missouri; an NHL game; and more. See all sweepstakes sites for specific terms and conditions.

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!

Do you find my weekly travel contest emails useful & have upcoming travel that you need to book? Use my travel resources page to make your bookings! There’s no cost to you, and you’ll be supporting my site. Thanks!

Win a trip to Scotland

  • round-trip coach-class air transportation for winner and 3 guest(s) to edinburgh airport
    three (3) nights hotel accommodations
    one (1) round of golf for winner and guest(s)
    one (1) $500 Callaway Golf e-gift card
    head-to-toe TravisMathew outfits
    Callaway Quantum Drivers
    premium OGIO luggage
  • Open to residents of the fifty (50) United States, DC, the United Kingdom, and Canada (excluding Quebec), 18+
  • Enter by May 17, 2026

Win a trip to a World Cup match in Mexico City

  • two (2) tickets to the FIFA World Cup 2026 match on June 11, 2026
    one (1) $1,000 gift card toward travel and hotel expenses
    one (1) $250 WorldSoccerShop.com gift card
  • Open to residents of the fifty (50) United States and DC, 18+
  • Enter by May 19, 2026

Win $25,000

  • $25,000 check for a garage makeover (but you can use it for anything)
  • Open to residents of the fifty (50) United States and DC, 18+
  • Enter by May 31, 2026

Win a trip to New Jersey

  • five (5) day, four (4) night trip for the winner and one (1) guest to Cape May, New Jersey from July 20–24, 2026, including:
  • round-trip coach (economy) air transportation from a major commercial airport near the winner’s residence to Philadelphia, Pennsylvania
    ground transportation to and from the airport and Cape May, New Jersey
    four (4) nights hotel accommodation at The Virginia Hotel in The Southern Suite (double occupancy, suite and tax only)
    daily $50 resort credit
    dinner for two (2) at The Ebbitt Room
    two (2) day beach tent rental
    one (1) historic Cape May trolley ride for two (2)
    beach access
    $1,000 spending money awarded as a check
    one (1) Lenox Spice Village Golden House
    Lenox Spice Village accessories including:
    a covered butter dish
    sugar & creamer
    teapot
    paper towel holder
    set of four (4) mugs
    hors d’oeuvres tray
    recipe box
    spoon rest
    Printfresh On-the-Go Tote in Pink Kitchen
    a set of two (2) can cooler glasses
  • Open to residents of the fifty (50) United States and DC
  • Enter by May 31, 2026

Win a trip to Disneyland in California

  • trip for winner and up to five (5) guests to Disneyland and Disneyland California Adventure Parks in Anaheim, California, including:
  • round-trip coach airfare for up to six (6) people
    three (3) nights hotel accommodations in Anaheim (two rooms, triple occupancy)
    2-Day Park Hopper® tickets for up to six (6) people
    one (1) VIP guided tour experience for up to six (6) people
    ABCmouse gift bag with assorted items
    $4,000 check for spending money
  • Open to residents of the fifty (50) United States and DC, 18+
  • Enter by May 31, 2026

Win a trip to the MLB All-Star Game in Philadelphia, Pennsylvania

  • two (2) tickets for winner and one (1) guest to the 2026 T-Mobile Home Run Derby in Philadelphia, PA
  • two (2) tickets for winner and one (1) guest to the 2026 MLB All-Star Game presented by Mastercard in Philadelphia, PA
  • $2,000 in the form of a check to be used toward transportation and lodging
  • Open to residents of the fifty (50) United States, DC, and Canada (excluding Quebec), 18+
  • Enter by June 30, 2026

Win a Sandals resort stay (new for Q2, previous entrants can enter again!)

  • There will be one (1) Grand Prize awarded following the conclusion of the Promotion Period. The Grand Prize Winner (“Winner”), upon confirmation of eligibility, will receive a 4-day/3-night “All-Inclusive” vacation package for two (2) adults (for travel a year from the printed prize certificate) to a Sandals Resort or Beaches Resort of Winner’s choice (excluding Sandals Royal Plantation, Sandals Barbados, Sandals LaSource and Sandals Emerald Bay) (“Prize” or “Grand Prize”). The Prize includes one room (double occupancy) Deluxe Suite and “All-Inclusive” amenities offered at the selected or designated resort, including local airport transfers, unlimited food and beverages (including premium brand drinks), an array of land and water sport activities (scuba diving for certified divers), daily and nightly entertainment, Wi-Fi in all rooms and public areas, resort gratuities and resort taxes. “All-Inclusive” amenities are subject to change and are to be determined by Sponsor in its sole discretion. The Grand Prize will be issued in the form of a prize certificate redeemable by filling in requested information and mailing back to the address indicated. The Grand Prize Winner must call the given telephone extension on the prize letter to arrange trip details. Note: Airfare is not included
  • open and offered only to legal residents of the USA and Canada, who are at least eighteen (18) years of age
  • Enter by June 30, 2026

Win a trip to Bozeman, Montana

  • a trip for one (1) to participate in the Field & Stream Yellowstone Fish Camp featuring Field & Stream Lodge in Bozeman, Montana, including:
  • three (3) nights’ single-occupancy accommodation at the Field & Stream Lodge in Bozeman, Montana (resort taxes and fees included)
    $800 prepaid Mastercard for airfare and/or transportation
    all food and beverages at the Lodge and during fishing excursions
    multi-day guided and self-guided fishing excursions (subject to weather conditions)
    $500 Sportsman’s Warehouse gift card for fishing gear and equipment
    one (1) year Field & Stream Premium Membership
  • Open to residents of the fifty (50) United States and DC (excludes RI), 21+
  • Enter by August 31, 2026

Win a trip to Big Sur, California

  • $4,000 gift card for Alila Ventana Big Sur
    $3,000 in spending funds
  • Open to residents of the fifty (50) United States and DC, 18+
  • Enter by August 31, 2026

Win outdoor gear

  • Don’t miss your chance to win this epic prize pack that includes:
  • ​Our packable Adventure Club Collection & $1,000 gift card
  • The Howl R1 Portable Fire Pit & R1 Haul Bag
  • A $1,000 gift card to Baja Designs
  • Open to residents of the fifty (50) United States and DC (excludes FL, NY, and RI)
  • Enter by May 17, 2026

Win a trip to the 2026 World Cup Final and a stay at the stadium

  • Grand Prize (1 Winner)
    A once-in-a-lifetime FIFA World Cup 2026™ Final experience. Wake up inside the stadium and be among the first fans on match day, thanks to Visa and Marriott Bonvoy.
  • Winner and a guest will head to the FIFA World Cup 2026™ Final Match on July 19, 2026, with an experience that goes far beyond the match.
    Experience includes:
  • One-night stay inside the New York New Jersey Stadium, transformed into a Marriott Hotels room.
    Two tickets to the FIFA World Cup 2026™ Final Match.
    Official FIFA World Cup 2026™ merchandise.
    Three nights’ accommodation in the New York/New Jersey area at a Marriott Bonvoy property
    Round-trip flights for two.
    Transportation throughout the weekend
  • Weekly First Prizes (4 Winners)
    Get closer to the action.
  • Win a trip for two to the FIFA World Cup 2026™ Quarterfinal in Miami, Florida.
    Experience includes:
    Round-trip flights for two.
    Three nights at a Marriott Bonvoy property in the Miami area.
    Two tickets to attend one quarter-final match.
  • open only to legal residents of the 50 U.S. & DC & Puerto Rico, Canada, Austria, France, Germany, Netherlands, Spain, Switzerland, United Kingdom, South Africa, India, Japan, South Korea, Argentina (excluding Mendoza, Neuquén, Salta, Rio Negro, & Tierra del Fuego), & Brazil (the “Eligibility Area”) who are Marriott Bonvoy members at least 18 years of age
  • Enter by June 16, 2026

Win a $10,000 custom trip

  • We’ve based the value of this trip ($10,000) on trip expenses for a family of four, allowing for generous coverage. You will be able to adjust the details of your trip (number of attendees, length of trip etc), which may impact cost. If the cost exceeds $10,000, you’ll pay the difference. The Travel Specialist can help you plan your trip based on your needs.
  • The winner must be a U.S resident, 18 years or older.
  • Enter by September 30, 2026

Win an RV

  • There are four (4) Grand Prize RVs ($10,399 each), with one (1) Grand Prize will be awarded for each of the four (4) Entry Periods, as outlined in the chart below in Section 4. The Grand Prize is a 2026 Keystone Coleman 13B travel trailer (the “Grand Prize RV”), with an MSRP of $10,399.00. Total ARV of all prizes: $41,596.00
  • open to all legal residents of the 48 contiguous United States and the District of Columbia (excluding Alaska, Hawaii, and Puerto Rico), who are eighteen (18) years of age or older
  • Enter by December 31, 2026

Win a trip to Chicago, Illinois

  • one (1) trip for winner and one (1) guest to Chicago, Illinois to attend a Chicago Cubs home game on July 4, 2026 at Wrigley Field, including:
  • round-trip coach airfare for two (2) from nearest major airport to Chicago, Illinois
    two (2) nights hotel accommodations (single room, double occupancy)
    two (2) tickets to the Chicago Cubs game
    two (2) Chicago Cubs jerseys
    one (1) $100 Uber gift card
    one (1) $100 prepaid bank gift card
    Omaha Steaks For a Year package (four shipments of Omaha Steaks Triple Crown Combo including ribeye filets, filet mignons, top sirloin filets, classic burgers, and seasoning)
  • Open to residents of the forty-eight (48) contiguous United States and DC (excludes AK, HI), 18+
  • Enter by June 7, 2026

Win a trip to Switzerland

  • roundtrip airfare for two (2) to Switzerland
  • one (1) premium SWISSGEAR luggage set
  • one (1) $1,500 USD travel stipend
  • Open to residents of the fifty (50) United States, DC and Canada, 18+
  • Enter by June 15, 2026

Win a trip to Barcelona, Spain (no donation required)

Win a trip to Costa Rica (enter daily)

  • Trip for two (2) (winner and one (1) guest age 21 or older) to Costa Rica including:
  • Round-trip coach class airfare for two (winner and one guest age 21 or older) from the nearest major airport to the Sponsor-designated airport in Costa Rica (SJO – San Jose or LIR – Liberia)
    Three (3) nights standard hotel accommodations (one room, double occupancy) at Amor Arenal in La Fortuna, Costa Rica, or another Sponsor-designated hotel
  • Open to residents of the fifty (50) United States and DC, 21+
  • Enter by May 15, 2026

Win a trip to the 2027 Kentucky Derby

  • tickets for winner and one (1) verified guest to attend the 2027 Kentucky Derby horse race (up to two [2] General Admission Infield Tickets)
    $2,500 in the form of a check made payable to the winner for additional expenses such as travel, hotel accommodations, ground transportation, meals, gratuities, and souvenirs
  • Open to residents of the forty-eight (48) contiguous United States and DC (excludes AK, HI), 21+
  • Enter by May 15, 2026

Win a trip to the Dominican Republic

  • One (1) Grand Prize consisting of a four (4)-night all-inclusive stay for two (2) adults at Lopesan Costa Bávaro, Dominican Republic (Approximate Retail Value: $2,300). Travel must be booked and completed within twelve (12) months of the promotion end date.
  • One (1) $400 excursion voucher provided by TravelPirates
  • One (1) $600 flight voucher provided by Dollar Flight Club
  • One (1) $400 gift card provided by Cariloha, Inc.
  • One (1) $400 gift card provided by Aurate New York LLC
  • One (1) $300 gift card provided by Brooklyn Candle Studio LLC
  • One (1) $300 gift card provided by Spa Week Media Group, LLC
  • One (1) $300 Visa gift card provided by Matador Network, LLC
  • 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 May 17, 2026

Win a trip to Boundary Waters, Minnesota (enter daily)

Do you have upcoming travel that you need to book? Use my travel resources page to make your bookings! There's no cost to you, and you'll be supporting my site. Thanks!

  • two (2) day fully outfitted and guided custom Boundary Waters canoe trip for two at Boundary Waters Ely, Minnesota, including:
  • cash travel stipend delivered via PayPal or Venmo ($2,500 if winner is more than 200 miles from guided experience check-in or $1,000 if winner is less than 200 miles from guided experience check-in)
    one (1) outdoor fire pit & stand
    two (2) paddle boards
    two (2) reclining camp chairs
    one (1) cooler
    fifty-two (52) coupons for any Kemps frozen product up to $8 each
  • Open to residents of the fifty (50) United States and DC, 18+
  • Enter by May 17, 2026

Win a trip to Las Vegas, Nevada

  • trip for two (2) to Las Vegas, Nevada, including:
  • round-trip domestic coach airfare for two (2)
    three (3) nights hotel accommodations (one (1) room, double occupancy)
    dinner for two at The Bedford by Martha Stewart
  • Open to residents of the fifty (50) United States and DC, 18+
  • Enter by May 17, 2026

Win a Scotland golf trip (airfare not included)

Win a trip to a U.S. destination

  • a trip for winner and up to three (3) guests to a domestic U.S. destination, including:
  • round-trip airfare for winner and up to three (3) guests
    hotel accommodations (standard quad occupancy, number of nights determined by Sponsor)
    travel expenses within a Sponsor-set budget
    7Brew for one (1) year
    7Brew swag kit for winner and guests
  • Open to residents of the forty-eight (48) contiguous United States and DC (excludes AK, HI), 18+
  • Enter by May 19, 2026

Win a trip to California

  • a 2-night, 3-day trip for winner and one (1) guest to Richvale, California, scheduled on mutually agreed dates in June, July, August, or September, including:
  • round-trip economy airfare (or ground transportation if within 100 miles of Lundberg Family Farms) to Sacramento International Airport (SMF)
    ground transportation between SMF, hotel, and Lundberg Family Farms
    three (3) days / two (2) nights hotel accommodations (standard room, double occupancy) within 25 miles of Richvale, California
    $600 total in meal vouchers ($300 per traveler)
    guided tour of Lundberg Family Farms
  • Open to residents of the fifty (50) United States and DC, 21+
  • Enter by May 21, 2026

Win a trip to Japan

Win a trip to Walt Disney World or Disneyland

  • Winners choice of a Magical Walt Disney World Vacation Package or a Magical Disneyland Resort Vacation Package for 4, including:
  • one (1) six (6)-night stay in a one-bedroom villa for the winner and up to three (3) guests at either Island Tower at Disney’s Polynesian Villas & Bungalows at Walt Disney World Resort or The Villas at Disneyland® Hotel at Disneyland Resort
    up to four (4) round-trip coach airfares between a major international commercial airport closest to the winner’s residence and a major commercial airport near the selected destination
    round-trip ground transportation between the arrival airport and the hotel
    four (4) seven (7)-day tickets with Park Hopper option for the group to Walt Disney World Theme Parks or Disneyland Theme Parks
    access for the group to member lounges while at the park
  • Open to residents of the fifty (50) United States and DC, 18+
  • Enter by May 25, 2026

Win a trip to Aspen, Colorado

  • trip for two (2) to Aspen, Colorado to attend the Aspen Food & Wine Classic, including:
  • round-trip coach airfare for two (2) between nearest major airport and Aspen, Colorado
    three (3) nights hotel accommodations (double occupancy) in or near Aspen
    two (2) tickets to the Aspen Food & Wine Classic
    dinner for two (2) at a Sponsor-selected restaurant
  • Open to residents of the fifty (50) United States and DC, 21+
  • Enter by May 25, 2026

Win a trip to Missouri

  • Two (2) reserved tickets to a 2026 Live Nation produced and promoted concert at Morton Amphitheater in Riverside, MO
    Round-trip, economy class air transportation for two (2) from the major airport nearest winner’s home within the U.S. to the major airport nearest the concert
    One (1) double occupancy standard hotel room for two (2) nights / three (3) days
    $200.00 pre-paid cash card for ground transportation
  • Open to residents of the fifty (50) United States and DC, 18+
  • Enter by May 25, 2026

Win a trip to a NHL game

  • One (1) NHL event package for winner and one (1) guest, including:
  • two (2) tickets to a 2026–2027 NHL event of winner’s choice
    round-trip coach airfare for two (2) from nearest eligible airport to event destination
    two (2)–three (3) nights hotel accommodations (one (1) standard room, double occupancy)
  • Open to residents of the fifty (50) United States, DC, and Canada, 18+
  • Enter by May 27, 2026

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!