Connected Balcony parties
Sea Terrace cabins booked side by side turn into one long open-air party at sea — the signature CruisingBears night.
Caribbean Bear Cruises
Caribbean bear cruises for 2027.
Warm water, adults-only ships and a crew that already feels like family. Our hosted Caribbean sailings for bears, chubs, chasers and their admirers — with dates, ports, cabin prices and everything we run onboard.
Sailings
Hosted Caribbean sailings.
- HiBEARnation
Jan 25–Feb 4, 2027 · Virgin Voyages · Brilliant Lady · Eastern Caribbean
from $1,750
Ports
Where we drop anchor.
The HiBEARnation itinerary: eastern Caribbean ports, two-and-two sea days for the pool deck, and a private beach club finish.
- Miami, Florida · Embark
Mon, Jan 25 · Depart 5:00 PM. Embark times subject to change.
- At Sea
Tue, Jan 26 · A lazy sea day with the crew.
- At Sea
Wed, Jan 27 · Another lazy sea day to recharge before port days.
- Philipsburg, St. Maarten
Thu, Jan 28 · Arrive 8:00 AM · Depart 6:00 PM
- Road Town, Tortola, BVI
Fri, Jan 29 · Arrive 9:00 AM · Depart 6:00 PM
- Basseterre, St. Kitts
Sat, Jan 30 · Arrive 8:00 AM · Depart 6:00 PM
- St. John's, Antigua and Barbuda
Sun, Jan 31 · Arrive 8:00 AM · Depart 5:00 PM
- At Sea
Mon, Feb 1 · Sea day.
- At Sea
Tue, Feb 2 · Sea day.
- The Beach Club, Bimini, Bahamas
Wed, Feb 3 · Arrive 9:00 AM · Depart 6:00 PM
- Miami, Florida · Disembark
Thu, Feb 4 · Arrive 6:30 AM. Disembark times subject to change.
Onboard
Themed nights, our way.
Themed nights & takeovers
We claim a corner of the biggest nights aboard so you always know where the crew has landed.
Group dinners
Reserved tables across the ship's restaurants: no awkward solo seating, just good food with familiar faces.
Adults-only sailing
Virgin Voyages is 18+ across the whole ship. No kids — no kidding.
Shore Days
Island days with your people.
Beach days with the crew
Philipsburg, Tortola and Antigua are made for a bear-friendly stretch of sand — we point the group at one beach so nobody spends the day hunting for familiar faces.
Catamaran & snorkel runs
Small-boat sails and reef stops in the British Virgin Islands and St. Kitts: swim, float, and be back aboard before the evening party starts.
Island bars & local food
Rum shops in Basseterre, beach bars in St. John's, and easy walkable port towns for anyone who'd rather eat and browse than swim.
The Beach Club, Bimini
Virgin Voyages' private Bahamas beach day closes out the sailing — daybeds, DJs and a whole shoreline of our own people.
FAQ
Caribbean bear cruise questions.
When is the next Caribbean bear cruise?
HiBEARnation sails Jan 25 – Feb 4, 2027 roundtrip from Miami aboard Virgin Voyages' Brilliant Lady.
Which Caribbean ports does the cruise visit?
Philipsburg (St. Maarten), Road Town (Tortola, BVI), Basseterre (St. Kitts), St. John's (Antigua and Barbuda) and The Beach Club at Bimini, Bahamas, with sea days in between.
How much does a Caribbean bear cruise cost?
Cabins on HiBEARnation start from $1,750. Prices are quoted per room and move with availability, so early bookings get the best cabins.
Is it good for solo travelers?
Yes. The first days are built for solo bears — pre-cruise hotel meet & greet, welcome party and group dinners mean you're travelling with people you know by day two.
Is the ship adults only?
Yes. Every guest on Virgin Voyages must be 18 or older, so the whole sailing is kid-free.
Ready for the Caribbean?
Ask Matthew about cabins, solo rates and Connected Balcony neighbours.