$4,999 Sydney Trip or Cash for 1 Winner in the Naked Sundays Sweepstakes

Choose a Sydney vacation for two or $4,999 cash

The single winner can choose between two prize options. The first is a Sydney, Australia, trip for two valued at up to $4,999. The second is a $4,999 cash payment.

That choice gives the winner flexibility. Someone ready to visit Sydney with a best friend, partner, or another companion can select the travel prize. Someone who cannot travel—or simply prefers money—can select the cash payment instead.

Only one person wins, and the promotion does not split the value among multiple recipients. If the winner chooses travel, the prize accommodates the winner and one companion. The companion is part of the trip, not a second sweepstakes winner.

The travel option is described as being valued up to $4,999. It should not be treated as an extra $4,999 cash allowance alongside the vacation. Before accepting either option, the selected winner should review the official prize details and any fulfillment instructions supplied by the sponsor.

Complete your one allowed entry carefully

Start on the official Naked Sundays promotion page during the entry period. Follow the page instructions and provide the requested entry information accurately. Email marketing signup is required, so entering involves agreeing to receive marketing emails rather than submitting a stand-alone drawing form with no subscription requirement.

Before submitting, check that your email address is spelled correctly and belongs to an inbox you can access. A typo could make it difficult to receive promotion-related communication if your entry is selected.

Submit only after reviewing your details. The limit is one entry total, not one entry per day, week, email address, or device. Repeated submissions do not create a valid entry strategy and could conflict with the promotion limit.

There is no verified purchase requirement included in the available promotion facts. Follow the official page as presented, and do not assume that buying a product, sharing a post, tagging friends, or completing unlisted actions will improve your odds.

Use a one-entry strategy instead of waiting until the last minute

Because every eligible person receives only one entry, timing does not provide extra chances. Entering on the first day and entering later in the promotion each produce one allowed submission, provided the entry is received correctly and on time.

The practical advantage of entering early is avoiding deadline problems. A forgotten task, slow connection, closed browser tab, or time-zone mix-up can turn a planned entry into no entry at all. Once you have submitted successfully, make a private note that your one entry is complete.

Do not return each day to enter again. Instead, keep access to the email account used for the submission and make sure legitimate messages are not automatically disappearing into an unchecked folder.

The sweepstakes runs from September 1 through October 31, 2026. The final cutoff is October 31 at 11:59 p.m. ET. Entrants outside the Eastern time zone should convert that cutoff rather than assuming the promotion stays open until local midnight.

Check the state-by-state age rules before entering

The promotion is open to eligible residents of the United States and Washington, D.C. The minimum age depends on where an entrant lives.

Entrants must be at least 18 in most states. Residents of Alabama and Nebraska must be at least 19, while Mississippi residents must be at least 21. Your eligibility is based on the applicable residence and age requirements, not simply on being old enough to travel.

If you are close to the minimum age or expect to move during the entry period, review the official terms before submitting. An entry must satisfy the promotion requirements; reaching the required age after the deadline should not be assumed to fix an ineligible entry.

The prize is promoted as a trip for you and your bestie, but the travel companion does not have to submit a shared entry with you. The eligible entrant submits the entry, and one winner is selected. Any companion requirements should be reviewed during prize fulfillment if the travel option is chosen.

Plan around the passport and travel-voucher requirement

Both travelers need valid passports for the Sydney trip. That means a winner who chooses travel must be able to arrange international travel with a companion who also has the required documentation.

Do not wait for a possible win to consider passport timing. Check whether both passports are valid and whether their expiration dates could affect international travel. Passport applications and renewals can take time, and winning does not remove normal travel-document requirements.

The travel voucher must be redeemed by March 31, 2027. “Redeemed” is an important condition: the selected winner should promptly read the fulfillment instructions to understand what must be booked, confirmed, or completed by that date.

The random drawing is expected around November 5, 2026, leaving a limited window between winner selection and the voucher redemption date. Anyone considering the travel prize should be prepared to respond promptly, compare schedules with a companion, and follow the sponsor’s booking directions.

If passports, timing, or international travel make the vacation impractical, the winner has the verified option to choose the $4,999 cash payment. The winner should still review any paperwork, tax considerations, and acceptance deadlines provided with the official notification.

Watch for the winner message without falling for a scam

One potential winner is expected to be selected in a random drawing around November 5, 2026. That is an approximate drawing date, not a promise that a public announcement or message will appear at a specific hour.

After the entry period closes, monitor the email account used to enter. Check spam, junk, promotions, and filtered folders as well as the main inbox. Since email marketing signup is required, keep promotional messages separate from any communication that asks you to complete official winner-verification steps.

Treat unexpected messages cautiously. A real prize notification should be consistent with this promotion: one winner, a choice between the Sydney trip for two valued up to $4,999 and a $4,999 cash payment, and an entry originally made through the Naked Sundays promotion page.

Do not send money, buy gift cards, disclose banking passwords, or pay a surprise fee merely to receive a sweepstakes prize. Avoid clicking unfamiliar links in urgent messages. When in doubt, return independently to the official promotion page and use the sponsor information there to verify the communication.

Save a copy or screenshot of your submitted information for your own records, without posting personal details publicly. If selected, read the response instructions carefully and reply within any stated timeframe. With one winner and one entry total, the best approach is simple: enter once with accurate information, retain access to your email, and be ready to evaluate the travel-versus-cash choice.