Enter to Win a 5-Night Virgin Voyages 2026 Cruise
Enter for the chance to win a 5-night Virgin Voyages 2026 sailing on Resilient Lady, visiting The Beach Club at Bimini.
At VV Insider, our goal has always been to help Sailors get more from Virgin Voyages through useful guides, timely updates, honest advice, and a growing community built around this incredible brand. Being able to offer our first-ever voyage giveaway feels like a pretty special moment.
To mark the occasion, and with the courtesy of The Cruise Boys, we are giving one lucky winner the chance to sail on a 5-night Virgin Voyages cruise aboard Resilient Lady on September 5, 2026.
The prize is a double-occupancy Insider cabin on the Grand Turk and Bimini Beach Club itinerary. It includes Virgin Voyages’ standard fare inclusions, plus taxes, gratuities, Wave of Pride Entertainment Pass and $25 in Sailor Loot. The winner can bring one guest or sail solo.
Itinerary Details
This 5-night Caribbean itinerary sails round-trip from Miami and includes two sea days, a call in Grand Turk, and a visit to Virgin Voyages’ Beach Club at Bimini before returning to Florida.
- Sat 5 Sep: Miami, Florida
- Sun 6 Sep: Sea Day
- Mon 7 Sep: Grand Turk, Turks and Caicos
- Tue 8 Sep: Sea Day
- Wed 9 Sep: The Beach Club at Bimini, Bahamas
- Thu 10 Sep: Miami, Florida

Waves of Pride Cruise
Note: Participation in this part of the voyage is completely optional, and all other aspects of the sailing follow a standard Virgin Voyages voyage.
The sailing is part of Waves of Pride, a new LGBTQ group cruise experience on Virgin Voyages that brings an extra layer of energy, celebration, and community to an already standout itinerary. It’s a sailing that promises sunshine, sea days and a real sense of occasion brought to you by special guests Roxxxy Andrews (from RuPaul’s Drag Race), Darcel Stevens, TP Lords and DJ Edil Hernandez.
As part of the prize, the winner’s cabin will also include the Waves of Pride entertainment fee for up to two sailors (a value of $99 each), meaning the winner will be able to fully enjoy the experience connected to this special group sailing.
So if you’ve been dreaming about stepping on board Resilient Lady, relaxing in the Caribbean, visiting Grand Turk, and spending the day at the Beach Club at Bimini, this is your chance.

What You’ll Win
- A 5-night Virgin Voyages cruise aboard Resilient Lady
- A double-occupancy Insider cabin (eligible to bid to upgrade at own expense)
- The September 5, 2026 sailing
- Calls in Grand Turk and The Beach Club at Bimini
- Virgin Voyages’ standard legacy fare inclusions
- Taxes and pre-paid gratuities included
- $25 Sailor Loot
- Waves of Pride entertainment fee included for up to two sailors
Enter using the Gleam widget below, then scroll down to read the full terms and conditions before taking part.
And from us, genuinely, thank you for being part of VV Insider. Launching our first voyage giveaway is something we’re really proud of and we’re very glad to be able to share it with the community that made it possible.
How to Enter
Use the options below to enter, anyone eligible can enter for free and complete as many actions as they choose. More actions mean more entries.
Form not working or having issues? Click here to enter.
Virgin Voyages 5-Night Cruise Giveaway
Terms and Conditions
1. Promoters: who is running this giveaway
This giveaway is jointly promoted by North East Digital Ltd (trading as VV Insider), Newcastle Upon Tyne, UK, and The Cruise Boys, LLC (trading as The Cruise Boys™ – powered by KVI Travel), Orlando FL, United States.
This giveaway is not sponsored by, endorsed by, administered by, or officially affiliated with Virgin Voyages or The Virgin Group.
2. Eligibility: who can and cannot enter
The giveaway is open to legal residents of the United States, Canada, the United Kingdom, and European Union member states, excluding Italy, who are aged 18 or over at the time of entry.
The giveaway is void where prohibited or restricted by law.
Employees, directors, contractors, agents, and immediate family members or members of the same household of VV Insider, The Cruise Boys, KVI Travel, Virgin Voyages, and any Registered First Mates (travel agents), as well as anyone professionally connected with the administration of this giveaway, are not eligible to enter.
3. No Purchase Necessary: free entry only
No purchase is necessary to enter or win. A purchase will not improve the chances of winning.
4. How to Enter: Gleam entry process and multiple entries
Entries must be submitted through the official Gleam giveaway widget published on this page.
Entrants may earn multiple entries by completing the actions listed in Gleam. Multiple entrants from the same household are permitted, but each entrant must use their own valid details and comply with these terms.
Use of automated methods, bots, scripts, or any other means intended to manipulate the entry process is prohibited and may result in disqualification.
5. Opening and Closing Dates: when the giveaway opens, closes, and is drawn
The giveaway opens at 19:30 UTC on April 7, 2026 (3:30 PM ET) and closes at 22:59 UTC on May 6, 2026 (6:59 PM ET).
The winner will be drawn at approximately 11:00 UTC on May 7, 2026 (7:00 AM ET).
Entries submitted after the closing time will not be counted.
6. The Prize: what the winner receives
There is one prize consisting of:
- One Insider cabin aboard Resilient Lady
- One sailing on the 5-night Grand Turk and Bimini Beach Club voyage departing September 5, 2026
- Double occupancy for up to two sailors
- Virgin Voyages’ standard fare inclusions
- Taxes and gratuities
- $25 Sailor Loot
- The Waves of Pride entertainment fee for up to two sailors
The approximate retail value of the prize is USD $2,000, or the GBP equivalent at the date of publication.
The winner may sail solo, but no substitute value, refund, credit, or additional compensation will be provided for any unused portion of the prize.
7. Prize Restrictions and Exclusions: what is not included
The prize is limited strictly to the sailing and cabin described above. No alternative sailing, date, cash alternative, transfer, exchange, or substitute prize will be offered except where required by law or if Virgin Voyages directly provides a replacement booking.
The prize does not include flights, hotels, ground transportation, visas, ESTA fees, passports, travel insurance, shore excursions, spa treatments, shopping, casino play, medical expenses, additional onboard purchases, or any other costs not expressly stated as included.
Cabin upgrades are not included, except through Virgin Voyages’ Level Upgrade bidding program where available and subject to Virgin Voyages’ rules.
8. Booking and Guest Details: how the cabin will be confirmed
The booking will be arranged by The Cruise Boys / KVI Travel after the prize is accepted.
The winner may travel alone or with one guest aged 18 or over.
Full sailor details must be provided no later than 10 days following contact with the winner. The second sailor may be changed up to that same deadline.
Once confirmed, the booking is non-transferable.
9. Virgin Voyages Terms Apply: ticket contract and booking conditions
The prize is subject to the applicable Virgin Voyages Ticket Contract and any booking conditions that apply in the winner’s jurisdiction. By accepting the prize, the winner and any guest agree to comply with those terms and all applicable travel requirements.
10. Travel Documents and Boarding: passports, visas, and boarding responsibility
The winner and any guest are solely responsible for ensuring they are legally able to travel and board the ship, including holding valid passports, visas, ESTA approvals, insurance where desired, and any other required documentation.
If the winner or any guest is unable to travel, fails to provide required details, or is denied boarding for any reason, the promoters are not responsible and no substitute, refund, compensation, or replacement prize will be offered.
11. Winner Selection: how the draw works
The winner will be selected at random using Gleam’s random draw functionality from all eligible entries received during the giveaway period.
The odds of winning depend on the total number of eligible entries received.
12. Winner Notification: how the winner will be contacted
The winner will be contacted using the email address provided in Gleam. The promoters may also attempt to contact the winner through an identifiable social media account where possible.
The winner must respond within 5 days of the first contact attempt. If the winner does not respond in time, declines the prize, or is found to be ineligible, the prize may be forfeited and a new winner may be drawn.
13. Canadian Residents: skill-testing question requirement
For residents of Canada, the selected entrant may be required to correctly answer a time-limited mathematical skill-testing question before being confirmed as the winner.
14. Publicity: use of winner’s first name and country
By accepting the prize, the winner agrees that the promoters may publish their first name and country of residence in connection with winner announcements, social media posts, and reasonable promotional activity related to the giveaway.
15. Entry Integrity and Disqualification: fraud, abuse, and rule breaches
The promoters reserve the right to disqualify any entrant or entry that they reasonably believe is fraudulent, incomplete, altered, abusive, deceptive, in breach of these terms, or generated through automated means.
16. Technical Issues: platform or submission problems
The promoters accept no responsibility for entries that are lost, delayed, corrupted, misdirected, incomplete, or not successfully submitted due to technical issues, platform failures, or any other reason beyond the promoters’ reasonable control.
17. Privacy: how entrant data will be used
Personal data supplied during the course of this giveaway will be used for the administration of the promotion and winner fulfillment. Entry into the giveaway does not automatically subscribe entrants to marketing unless explicitly stated otherwise.
Personal data will be handled in accordance with the VV Insider Privacy Policy. Gleam may also process personal data in connection with operating the giveaway platform.
18. Third-Party Platforms: platform disclaimer
This promotion is in no way sponsored, endorsed, administered by, or associated with Gleam, Facebook, Instagram, X, YouTube, or any other social platform used to promote it.
19. Changes, Cancellation, or Unavailability: what happens if plans change
If the sailing is cancelled, withdrawn, or becomes unavailable, no replacement sailing, date, or substitute prize will be offered unless Virgin Voyages directly provides a replacement booking.
The promoters reserve the right to amend, suspend, or cancel the giveaway where necessary due to circumstances beyond their reasonable control, provided that doing so is lawful.
20. Governing Law: which laws apply
These terms and conditions and any dispute arising from them shall be governed by the laws of England and Wales, unless mandatory consumer protections in the entrant’s place of residence apply.