BlackburyLuxury cruise specialists

Beyond cruising

Friendship Beach on Bequia in the Grenadines, palms over a quiet bay

Luxury cruises

December to April. Christmas and New Year sailings book 12 months ahead.7 nights from Barbados, St Maarten or Miami; 10 to 14 to reach the ABC islands or Panama.

Caribbean

Winter sun for the whole family, on ships that make Christmas and half-term easy.

Photo: qwesy qwesy · CC BY 3.0

Luxury Caribbean cruises in the winter months, from the quiet Grenadines to the French islands, with Christmas and New Year sailings that suit three-generation groups.

The Caribbean is the winter answer: guaranteed warmth, calm seas, and a week that works for a seven-year-old and a seventy-year-old at the same time. The luxury lines favour the smaller islands — the Grenadines, St Barths, Anguilla, the British Virgin Islands — where yachts anchor off empty beaches rather than queueing at a cruise pier.

Christmas and New Year sailings are the big multigenerational occasion, and they sell first. If you are thinking about a family Christmas at sea, the time to start is January of the same year.

Highlights

  • The Grenadines: Bequia, Mustique, Tobago Cays
  • St Barths and Anguilla from a yacht marina
  • British Virgin Islands anchorages
  • Christmas and New Year family sailings
  • Pre-cruise nights in Barbados or Antigua to soften the flight
Best time
December to April. Christmas and New Year sailings book 12 months ahead.
Best months
DecJanFebMarApr
How long
7 nights from Barbados, St Maarten or Miami; 10 to 14 to reach the ABC islands or Panama.
Guide price
From £4,000 pp

Planning figure for a typical week in a veranda suite. Final price depends on sailing date, ship, suite and availability.

Start Planning

For families

Explora and Ritz-Carlton for children's programmes, water sports and connecting suites.

For grandparents

Regent and Seabourn for warm, easy, inclusive weeks; Silversea for yacht-size ports.

Best cruise lines here

Who we'd shortlist for Caribbean

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

How to choose

How to choose the right Caribbean cruise

Derived from our own ratings of the lines above, not from brochures.

Start with ship size

Explora Journeys and Regent Seven Seas Cruises are mid-size; The Ritz-Carlton Yacht Collection is yacht-style; Silversea and Seabourn are small-ship. Smaller ships reach the smaller harbours in Caribbean; larger ones carry more for children and more dining choice.

Decide how formal you want it

Explora Journeys and The Ritz-Carlton Yacht Collection keep it relaxed; Regent Seven Seas Cruises leans formal and traditional. Ask us which suits the party before anything else.

Match the ship to who's travelling

Explora Journeys and The Ritz-Carlton Yacht Collection rate highest with us for families here; Seabourn is effectively adults-only. Children's facilities vary more than brochures suggest; we will say which ships really have them.

If the table matters most

Silversea, Explora Journeys, The Ritz-Carlton Yacht Collection, Regent Seven Seas Cruises and Seabourn lead on food in our experience of Caribbean sailings.

Cruise ideas

Caribbean sailings we like

Planning figures per person.

Travelling with three generations?

Connecting suites, different activity levels, dining that works for everyone, and transfers that suit grandparents and toddlers alike. The best family suites go first, so start early.

Further reading

Before you decide on Caribbean

Our own planning notes: who a ship suits, how many cabins to book, when to go.

All articles →

Good to know

Caribbean cruise questions

Is a Caribbean cruise good for a family Christmas?

It is one of the best ways to do it: one booking, everyone together, warm weather and no cooking. Suites and connecting cabins for the festive sailings sell out early, so we advise starting the conversation in January or February.

How long is the flight?

Around 8 to 9 hours direct from London to Barbados or Antigua. We usually add a night or two before the cruise so nobody boards exhausted.

Planning something specific? Tell us what you're looking for.

Don't spend thirty hours comparing forty ships, cabins, dates, flights and hotels. Give us five minutes and we'll narrow it down to what is worth considering.

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