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Here are this week’s travel contests!
You can win trips & prizes such as an all-inclusive Sandals resort stay; San Diego, California; Chicago, Illinois; Jamaica; Napa Valley, California; Bozeman, Montana; Big Sur, California; every MLB ballpark; Los Angeles, California; an RV; St. Thomas, Puerto Rico, Costa Rica, or Jamaica; New York City; a Caribbean cruise; the destination of your choice; the Cayman Islands; the U.S. Open Final; Austin, Texas; and more. See all sweepstakes sites for specific terms and conditions.
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Win a Sandals resort stay (new for Q3, 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 September 30, 2026
Win a trip to San Diego, California
- A three (3)-night stay at Kona Kai Resort & Spa
One (1) $200 Kona Kai Resort & Spa resort credit
Two (2) $700 flight vouchers
Over $300 worth of COOLA SPF products - Open to residents of the fifty (50) United States and DC, 18+
- Enter by August 10, 2026
Win a trip to Chicago, Illinois
- two (2) round-trip flights to Chicago, Illinois
three (3) night hotel stay in downtown Chicago, Illinois
dinner for two (2) at Ever or another Sponsor-selected fine dining experience
two (2) tickets to a Chicago experience (e.g., Cubs game or architectural tour)
$1,000 spending money (check)
$1,000 Crate & Barrel gift card
lunch for two (2) at Mr. Beef in Chicago, Illinois - Open to residents of the fifty (50) United States and DCs (excluding Rhode Island), 18+
- Enter by August 11, 2026
- One (1) Grand Prize Winner will receive:
- one (1) five (5)-night stay for winner and one (1) guest at The Tryall Club’s Point of View Villa in Jamaica
- daily breakfast for winner and one (1) guest
- one (1) romantic dinner for winner and one (1) guest at Ooshan
- one (1) welcome in-villa amenity
- one (1) signature couples massage
- complimentary resort club membership fees for two (2) adults
- one (1) $900 flight voucher
- one (1) $500 Rails gift card
- one (1) $300 Le Prunier gift card
- one (1) HigherDOSE Red Light Therapy Mask
- one (1) $1,000 Crate & Barrel gift card
- Open to residents of the fifty (50) United States and DC, 18+
- Enter by August 16, 2026
Win a Napa Valley camping trip (does not include transportation)
- one (1) four (4)-night campsite stay at Bothe-Napa Valley State Park in Napa Valley, California
- one (1) Stout Tent
- two (2) Cotopaxi Day Packs
- two (2) Rumpl Blankets
- two (2) High Camp Flasks
- one (1) S’mores Kit
- one (1) farm-to-table lunch for winner and one (1) guest
- one (1) guided tasting for winner and one (1) guest
- one (1) personalized Insider’s Guide to Napa Valley tourist spots
- Open to residents of the fifty (50) United States and DC, 21+
- Enter by August 31, 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 a trip to every MLB ballpark
- thirty (30) separate trips for winner and one (1) guest to attend MLB games at each of the 30 MLB ballparks (including Athletics’ 2028 Opening Day as one trip)
round-trip coach airfare for each trip (winner and guest)
up to two (2) nights hotel accommodations per trip (double occupancy)
two (2) tickets per game
all trips must be completed by September 30, 2029 - Open to residents of the fifty (50) United States, DC, and Canada (excluding Quebec), 18+
- Enter by September 7, 2026
Win a trip to Los Angeles, California (no donation required)
- Four tickets to the global premiere of “Avengers: Doomsday” with red carpet access
A 1-night stay in hotel accommodations near the premiere venue
Private glam squad services for up to four guests before the premiere
Private ground transportation to and from the premiere
Roundtrip airfare for up to four guests
Up to four 2-Day Disneyland Resort Park Hopper® Tickets
A 2-night stay in The Pirates of the Caribbean Suite at the Disneyland Hotel® for up to four guests
An official VIP tour of the Disneyland Resort® with a private tour guide, including a special visit to Walt’s Apartment for up to four guests
Dinner for four at Napa Rose at Disney’s Grand Californian Hotel & Spa®
$600 Disney Dining Card
$10,000 cash - only open to legal residents of the fifty (50) United States and the District of Columbia, and U.S. territories, including Puerto Rico, the U.S. Virgin Islands, Guam, and American Samoa, who are at least eighteen (18) years of age
- Enter by November 15, 2026
- 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 St. Thomas, Puerto Rico, Costa Rica, or Jamaica
- One (1) five (5) day/four (4) night trip for the winner and three (3) travel companions to the winner’s choice of St. Thomas, Puerto Rico, Costa Rica, or Jamaica, including:
Round-trip economy airfare for the winner and three (3) travel companions
Five (5) days/four (4) nights hotel accommodations (based on double occupancy)
Sponsor-specified ground transportation between the airport and hotel (or Sponsor-specified rental car, depending on destination)
Resort credit of $750 (Costa Rica, St. Thomas, or Jamaica) or $1,000 (Puerto Rico) - Open to residents of the fifty (50) United States and DC, 21+
- Enter by August 9, 2026
Win a trip to New York City (enter daily)
- All-inclusive trip for two (2) to New York City during the 2026 Holiday Season (Nov. 26 – Dec. 26)
Three (3) nights hotel accommodations for two (2)
If travel occurs in November 2026: two (2) tickets to a MET Museum guided tour
If travel occurs in December 2026: two (2) tickets to a Private Holiday History Tour
Two (2) tickets to an event at Madison Square Garden, selected based on timing and availability - Open to residents of the forty-eight (48) contiguous United States and DC (excludes AK, HI), 21+
- Enter by August 11, 2026
- Grand Prize: One (1) grand prize (the “Grand Prize”) will be awarded. The Grand Prize consists of a seven (7) night Caribbean cruise for the winner and one (1) guest aboard the Silver Spirit, sailing roundtrip from Bridgetown, Barbados from December 12, 2026 through December 19, 2026.
- The Grand Prize does not include airfare or onboard credit. The winner and guest are responsible for all transportation to and from Bridgetown, Barbados, including airfare, ground transportation, pre- and post-cruise accommodations, travel insurance, and all other expenses not expressly included in the Grand Prize.
- open only to legal residents of the fifty (50) United States and the District of Columbia who are eighteen (18) years of age or older
- Enter by August 12, 2026
Win one of 102 trips to the U.S. destination of your choice (enter daily)
- three (3) day / two (2) night trip for winner and up to three (3) travel companions to a U.S. destination of winner’s choice (within the 48 contiguous U.S. / D.C.). including:
round-trip economy airfare for winner and travel companions from nearest major airport to destination
two (2) nights hotel accommodations (one (1) room, quad occupancy) - Open to residents of the fifty (50) United States and DC, 21+
- Enter by August 15, 2026
Win a trip to the Cayman Islands
- Roundtrip economy class airfare to Grand Cayman
3-nights at The Westin Grand Cayman Seven Mile Beach Resort & Spa, prime location, right on the sand. - 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 15, 2026
Win a trip to the U.S. Open Final
- Trip for the winner and one (1) guest to New York City, including:
- Two (2) nights double-occupancy hotel accommodations
Round-trip economy class air transportation for two (2) from the major airport nearest the winner’s home to New York, NY
One (1) $500 e-gift card for ground transportation and incidentals
Two (2) courtside tickets to attend the US Open Women’s Singles Final on September 12, 2026 - Open to residents of the fifty (50) United States and DC, 21+
- Read about when I won a sweepstakes and went to the U.S. Open Final!
- Enter by August 15, 2026
- three (3)-day/two (2)-night trip for winner and one (1) guest to Austin, Texas to attend the 2026 Lonestar Le Mans, including:
- round-trip standard economy airfare for winner and one (1) guest (or ground transportation if applicable)
two (2) nights hotel accommodations (one room, double occupancy)
two (2) tickets to the 2026 Lonestar Le Mans - Open to residents of the forty-eight (48) contiguous United States and DC (excludes AK, HI), 18+
- Enter by August 17, 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!
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!
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