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Explora I leaving the port of Rhodes on a clear summer afternoon

Best for

The best luxury Caribbean cruises

Luxury Caribbean cruises shortlisted by Blackbury for families at Christmas, couples in search of small islands and grandparents who want warm, easy weeks.

Photo: Pjotr Mahhonin · CC BY-SA 4.0

The luxury Caribbean is the small islands: the Grenadines, St Barths, Anguilla, the BVIs. The ships that reach them are small or anchor well, and the festive sailings are the great multigenerational occasion of the year.

CriterionExplora JourneysThe Ritz-Carlton Yacht CollectionSilverseaRegent Seven Seas CruisesSeabourn
For a family ChristmasExplora II from Barbados through the Grenadines, 7 nights, from about £4,900 pp
For couplesRitz-Carlton Evrima or Ilma, St Barths and the BVIs, from about £6,500 pp
For grandparentsSeabourn or Regent from Barbados or St Maarten, inclusive and easy
WhenDecember to April; Christmas and New Year booked 12 months ahead

Stars are Blackbury's editorial opinion, not independent ratings or customer reviews.

Fly direct to Barbados or Antigua, add a night or two on the island, and board rested. For Christmas, start the conversation in January.

Which should you choose?

Tell us who's travelling and what matters most. We'll say which of these we'd book for you, and why.

The lines

Read the full verdict on each

Explora I leaving the port of Rhodes on a clear summer afternoon
Medium ships · Relaxed, contemporary

Explora Journeys

Modern, relaxed, generous with space, and genuinely happy to see children.

Best for families & grandparents
  • Best for: Three-generation groups who want modern comfort and plenty of room
  • Not for: You want a traditional, intimate ship
  • Included: dining across most venues; drinks and minibar
The Ritz-Carlton Yacht Collection's Evrima moored at Katajanokka in Helsinki
Yacht-style · Relaxed, residential luxury

The Ritz-Carlton Yacht Collection

Hotel-style luxury on yachts of roughly 300 to 450 guests, with a surprisingly warm welcome for children.

Best for couples & families
  • Best for: Design-led families and couples who want yacht privacy with real service
  • Not for: You want to go somewhere remote or spend two weeks at sea
  • Included: all-suite accommodation; dining and most drinks
Silver Endeavour in the Gerlache Strait, Antarctica, among ice and mountains
Small ships · Elegant; relaxed on the newest ships

Silversea

Butler-served suites, serious destinations, and one of the strongest expedition fleets afloat.

Best for grandparents & couples
  • Best for: Couples and well-travelled grandparents, and families with teenagers on an expedition
  • Not for: You need a kids' club or a big, lively pool scene
  • Included: butler service in every suite; drinks and dining
Seven Seas Grandeur, Regent's newest all-suite ship, at anchor
Medium ships · Elegant, traditional

Regent Seven Seas Cruises

The most inclusive fare at sea, on all-suite ships that take elegance seriously.

Best for grandparents & couples
  • Best for: Grandparents hosting adult children, and couples who want a fully inclusive, elegant week
  • Not for: Your party includes young children or you want a casual atmosphere
  • Included: all-suite accommodation; shore excursions in every port
Seabourn Ovation anchored off the pastel harbour of Portofino
Small ships · Understated, sociable, smart

Seabourn

Small, sociable, quietly luxurious ships, with a sister expedition fleet.

Best for grandparents & couples
  • Best for: Couples and adult groups who value calm, warmth and a small ship
  • Not for: You are bringing children
  • Included: all-suite accommodation; drinks and dining

Keep reading

Related comparisons

Not sure which ship is right for your family?

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