The Weekly Win Travel Sweepstakes Clearinghouse

Travel Sweepstakes

Travel Sweepstakes ~ How to Add a Sweepstakes ~ How to Bookmark This Page ~ How to Share the Winning

Because the only thing better than taking a trip, is winning one!

COVID-19 Update

When the global Coronavirus Pandemic brought travel to a virtual standstill, we made the decision to suspend updates to the Weekly Win. In light of domestic, and limited international travel opening slightly, we began restocking the Travel Sweepstakes Clearinghouse in September. We do not expect a rush of new opportunities to win travel, and we strongly encourage careful consideration before taking any trips, whether you win them or plan them on your own. Regardless, we wish you good luck because, even in the age of COVID-19, it’s always better to win a trip.

Clearinghouse
Noun [kleer-ing-hous]
A central institution or agency for the collection, maintenance, and distribution of materials or information.
Travel Sweepstakes
Noun Plural [trav-uhl sweep-stayks]
Giveaways featuring trips, tours, gear, etc., related to traveling. Something you should be winning!

Welcome to The Weekly Win!

No, we’re not giving away free trips, but lots of other people are. Since someone has to win these prizes, we figure it should be either you or us. Agreed?

That’s why we created this Travel Sweepstakes Clearinghouse! When we learn about opportunities to win a trip, travel-related gear, or good ol’ cash, we’ll tell you all about it here.

Naturally, you’ll want to bookmark this page and come back often!

The Travel Sweepstakes Clearinghouse!

The idea behind the Clearinghouse is simple: We wanted one page with a list of shortcuts to enter any/all of the sweepstakes we find. No searching for names you can’t remember, and no surfing all over the web trying to find your way back to that one web page. You’ll find basic info here, and links to enter and to the rules. (You do read the rules, right? Yeah, us too.)

We try to keep the travel sweepstakes arranged in order of entry deadline, soonest to latest. If you have seen a travel sweepstakes not listed here, please let us know! (Details below.) Best of luck!

Let’s win our way around the world!

Enter a Travel Sweepstakes

The Italian on Tour Travel Sweepstakes – Ends 11 March

Italian on Tour Travel Sweepstakes on TravelLatte

Oh to be Italian. And on tour. Or just to win the Italian on Tour travel sweepstakes and escape to “Italy’s Next Tuscany!”

This 7-Day Food & Wine Getaway for 2 to Italy’s Hidden Regions sponsored by the Italian on Tour has one fantastico Grand Prize:

  • The Italian On Tour 7-day Italy Undiscovered tour for 2 people
  • A total of $750 spending cash
  • One-Year Membership to Matt’s Flights
  • 2 Lifetime Subscriptions for Journo

There is some travel flexibility: Eligible tour dates are June 2021, October 2021, June 2022, October 2022, June 2023 and October 2023. However, the choice of travel dates must be booked by May 15, 2020.

How to Enter
Visit the travel sweepstakes site and complete the entry form for one entry. There is a limit of one entry per person/email address. However, you can complete additional tasks for bonus entries. Be aware that, by entering, you are opting in to receive marketing material from Travel Trivia, Acanela, Inside Hotels, Journo Travel Co., Bright Cellars, Matt’s Flights, and the Italian on Tour.
Who’s Eligible?
Open to legal residents of the continental United States who are at least 21 years of age at the time of entry.
Entry Type Deadline Links
One Time plus Bonus Entries 11 March 2021 Rules Entry Page
Sponsors: The Italian on Tour

VRBO Visit Florida Travel Sweepstakes – Ends 14 March

VRBO Visit Florida Travel Sweepstakes on TravelLatte

Do you hear that? It’s a beach in Florida. And it’s calling your name.

Okay, actually it’s a travel sweepstakes, and pretty much every beach in Florida is up for grabs in the VRBO Visit Florida Sweepstakes! One winner gets a $5,000 travel allowance to splurge on vacation rental accommodations anywhere in the Sunshine State, plus airfare. Sweet deal? Shyeah!

Just two gotchas, if you can call them that: Travel must take place in the 2021 calendar year, and you must have or create an Expedia Rewards account. Any funds not used may be converted into Expedia Rewards points.

How to Enter
Visit the travel sweepstakes entry page to complete and submit an entry form.
Who’s Eligible?
Open to legal residents of the fifty United States plus the District of Columbia and Puerto Rico, who are at least 18 years of age at the time of entry. Earn up to four additional entries for downloading the VRBO smartphone app, and referring friends and family members. Maximum of five entries per person.
Entry Type Deadline Links
One Time 14 March 2021 Rules Entry Page
Sponsors: Visit Florida and VRBO.

The Magic of Ohana Travel Sweepstakes – Ends 17 March

Magic of Ohana Travel Sweepstakes - The Weekly Win on TravelLatte

If you win this travel sweepstakes, you won’t be going to Disney World, but it might be even better!

Disney is famous for theme parks, but they have a wide range of resorts and Disney Vacation Clubs around the world. None are more magical than Aulani, the Disney Vacation Club and Resort on the Hawaiian island of Oahu. One lucky winner will be spending five nights in the Disney Vacation Club Villas at Aulani, with round-trip coach air fare for four, and a $500 Disney gift card!

Note: If you win, travel must be booked by 31 January 2022, and completed by 31 March 2022. Black-out dates apply.

How to Enter
Visit the entry page and select the link for either Disney Vacation Club members or non-members. There is no bearing on your odds if you are/are not a member, and you do not have to be a member to enter. After entering your information, watch a short video for one entry. There are three more videos you can watch for three bonus entries, but you can only enter one time.

Entrants must provide a valid email address, along with full name and address, phone number, and Disney Vacation Club Member ID, if they have one.

Who’s Eligible?
Open to legal residents of the 50 United States and the District of Columbia (cannot be living abroad), who are at least 18 years of age.
Entry Type Deadline Links
One Entry (plus bonus entries) per person. 17 March 2021 Rules Entry Page
Sponsor: Disney Vacation Club

Travel Channel Best of Travel Sweepstakes – Ends 24 March

Travel Channel Best of Travel Sweepstakes - The Weekly Win on TravelLatte

Another round of the grand-daddy of all travel sweepstakes is happening now! One lucky winner walks away from this one with $10,000 cold, hard cash to travel the world with! That is, once the Pandemic ebbs. Entry is simple, and you can enter twice a day, starting at the Travel Channel’s web site!

How to Enter
Visit the Travel Channel’s sweepstakes page every day. The first time there, you’ll need to complete an entry form. From then on, sign in with your email address. You do have to answer one travel-related trivia question each day. Hints are available, but it does not matter whether you get it right; you’ll be entered either way.
Who’s Eligible?
Open to legal residents of the 50 United States and the District of Columbia who are 21 years of age or older.
Entry Type Deadline Links
Twice Daily 24 March 2021 Rules Entry Page
Sponsor: The Travel Channel, LLC

Clean Plates’ New Year Revival Getaway Travel Sweepstakes – Ends 31 March

American Way 25k Aadvantage Miles Travel Sweepstakes - The Weekly Win on TravelLatte
Hoping to hop a jet plane to anywhere once this Pandemic is over? You could do it with 25,000 American Airlines AAdvantage Miles!

This travel sweepstakes by American Way magazine has just one prize: 25,000 Aadvantage Miles, redeemable for award flights on American Airlines and partner carriers. Not an Aadvantage member? Doesn’t matter, anyone can enter. However, you will need to enroll in the loyalty program to redeem your miles, should you win.

Who’s Eligible?
Open to legal residents of the 50 United States, the District of Columbia, and Puerto Rico who are 18 years of age or older at the time of entry.
Entry Type Deadline Links
Limit one entry per person. 31 March 2021 Rules Entry Page
Sponsor: Ink Global, publishers of American Way Magazine

Grand Breckenridge Giveaway Travel Sweepstakes – Ends 31 March

Grand Breckenridge Giveaway Travel Sweepstakes - The Weekly Win on TravelLatte

Calling all Ski Bums & Bunnies, this one’s for you! Although, with a week’s lodging on Peak 8, $5,000 cash, and a goodie bag, this is a great prize for anyone who loves a little winter fun.

Prize includes seven nights in a one-bedroom condo at the Grand Colorado on Peak 8, plus $5,000 spending money, and gift bag full of Breckenridge gear and treats. The prize is good for travel through the 2023 ski season, so it’s there when you’re ready. However, several black-out dates apply.

How to Enter
Enter this travel sweepstakes at any of the home pages that have been published. (Such as the link below!) You will have to answer a brief questionnaire. Be aware that by entering this travel sweepstakes you opt in to receive marketing emails from Breckenridge Grand Vacations, a timeshare resort development company, and related companies.
Who’s Eligible?
Entrants must be 21 years of age or older at the time of entry.
Entry Type Deadline Links
One Entry per Person 31 March 2021 Rules Entry Page
Sponsor: Breckenridge Grand Vacations

See Tampa Bay Your Way Travel Sweepstakes

See Tampa Bay Your Way Travel Sweepstakes - The Weekly Win on TravelLatte

A note from the sponsor: “In light of developing concerns surrounding the coronavirus (COVID‑19), Thrifty has decided to temporarily suspend the Tampa Bay Your Way Sweepstakes. We will reinstate this promotion and begin taking entries and selecting remaining weekly winners and a Grand Prize winner in the future.”

We’ll admit: we had no idea how much there is to see and do in Tampa Bay! This travel sweepstakes lets you pick what interests you, so you can See Tampa Bay Your Way! There will be six weekly winners; each will receive the use of a Thrifty loaned vehicle for seven days. One Grand Prize winner will receive a trip for four, including:

  • Coach-class air transportation to Tampa Bay
  • Seven nights hotel accommodations (one room/quad occupancy)
  • Seven day Thrifty car rental
  • $2,500 cash
  • Winner’s choice of three excursions (see entry page for options)
Who’s Eligible?
Open to legal United States residents residing in the 48 contiguous United States and the District of Columbia who are licensed and insured drivers and at least 20 years of age at the time of entry.
Entry Type Deadline Links
One Time plus Bonus Entries for each weekly entry period 27 March 2020 Rules Entry Page
Sponsor: Thrifty Car Rental




How to Add a Travel Sweepstakes

Have you entered a travel-related sweepstakes that we haven’t included? Found a travel sweepstakes you want to share? Let us know and we’ll share it with the world! Just Tweet us (@TravelLatte), stop by our Facebook page, or leave a comment here to let us know about it. You don’t need to include all of the details – we’ll find that stuff. Just let us know what it’s called, and the web page URL to enter, or get more information. Thanks in advance for sharing!

How to Bookmark This Page

  • On Android: More > Star
  • On iPhone: More > Add Bookmark
  • In Chrome, Firefox, Internet Explorer: Ctrl-D
  • In Safari: Cmd-D

How to Share the Winning

It’s super simple to share the good news: Just use the social sharing buttons on this page to share on Twitter, Facebook, Pinterest, email, or whatever app you choose!

FYI: Some travel sweepstakes invite you to share the sweepstakes to earn additional entries. Sharing this page won’t work – you need to share from their pages in order to earn those entries.

Caveat Emptor: Why You Should Always Read the Rules

For one thing, they could change between the time we find the sweepstakes and the time you enter. The chances are slim, but it could happen. There may be black-out dates or other limitations to the prize that may affect you. Be sure you’re aware of “gateway airport” requirements for international travel sweepstakes, too.

More importantly, many companies use travel sweepstakes to entice us to give them our contact information for marketing purposes. It’s not uncommon for your entry to be an opt-in for emails, snail-mails, and even phone solicitation from sponsoring companies and their partners. If you don’t like that stuff, don’t enter that sweepstakes.

Note: Sweepstakes featured in The Weekly Win are not affiliated with, administered by, or endorsed by TravelLatte. The Weekly Win is neither solicited nor compensated*. In the belief that it’s better to win a trip than to scrimp and save for one, we just thought you’d appreciate hearing about some of the travel sweepstakes we find.

Remember: Prize, entry, and drawing information in the official rules always supersedes information found here.

*Some entry links may give TravelLatte additional sweepstakes entries.