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Southern Caribbean cruises

Southern Caribbean Loop via New York, Saint Thomas & Bridgetown

New York · Saint Thomas · Bridgetown · Castries · Roseau · Basseterre, Saint Kitts · Road Town, Tortola · New York

Extended 28-night voyage with 19 sea days and 8 ports. Covers United States, Virgin Islands, U.S., Barbados, Saint Lucia, and more.

28 nights Southampton Southern Caribbean 8 ports 19 sea days
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What this trip feels like

Expansive, immersive and built around life at sea

At 28 nights, this is a multi-month, world-cruise-style voyage rather than a conventional getaway. 19 sea days make the ship your home base between 8 ports across a wide arc of destinations. Expect long ocean passages and the planning commitment of an extended journey.

Long-form pace

8 ports in 28 nights

Long ocean passages make onboard routines a major part of the experience.

Broad destination variety

New York · Saint Thomas · Bridgetown + more

Frequent changes of scenery across the itinerary.

Easy logistics

Round-trip from Southampton

No open-jaw flights or separate arrival and departure transfers.

Port experience

New York · Pick your date carefully

Cruise traffic varies substantially by date, so your specific port day can feel very different depending on when you visit.

Best for · Long-form travelers · Sea-day lovers · Multi-region exploration

Think twice if · You want a conventional one- or two-week cruise

Best departures

Best upcoming sailings

Start here. These departures surface first because they combine stronger pricing, useful timing, or a notable warning signal for this itinerary.

Best overall value
Cunard Line

Queen Mary 2

Southampton → New York → Road Town, Tortola → Southampton

Nov 17 · 28 nights

Good value

$4,062 inside · $145/night

23% below typical · 6-month low

All departures

All upcoming departures

Compare all sailings for this itinerary.

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Itinerary pricing

What this itinerary usually costs

Typical pricing runs around $150/night, with most departures landing in the $122-$199/night band across 1 tracked sailing.

Typical price

$150/night

$4,200 total

Normal range

$122-$199/night

$3,420-$5,574 total

Lowest recent fare

$145/night

$4,062 total

Comparison set

1 sailings

Used for itinerary baseline

When should I go?

Not enough departures yet to identify a reliable cheaper season.

Route overview

How this route is built

Compare sailings →

28 nights · 8 port calls · 19 sea days · 7 countries

8 port calls across United States, Virgin Islands, U.S., Barbados, Saint Lucia · Leans more toward sea time than a port-packed 28-night route.

  1. 1

    Embark in Southampton

    Embarkation ports can vary by sailing

  2. 2

    New York

    United States · US East Coast

  3. 3

    Saint Thomas

    Virgin Islands, U.S. · Eastern Caribbean

  4. 4

    Bridgetown

    Barbados · Southern Caribbean

  5. 5

    Castries

    Saint Lucia · Southern Caribbean

  6. 6

    Roseau

    Dominica · Southern Caribbean

  7. 7

    Basseterre, Saint Kitts

    Saint Kitts and Nevis · Eastern Caribbean

  8. 8

    Road Town, Tortola

    Virgin Islands, British · Eastern Caribbean

  9. 9

    New York

    United States · US East Coast

  10. 10

    Disembark in Southampton

    Disembarkation ports can vary by sailing

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Embark port
Disembark port
Port of call

Other routes to consider

Not quite the right itinerary? Compare routes that trade a little simplicity for more ports, different destinations, or a longer trip.

FAQ

What’s the best month to sail this itinerary?
It depends on weather and crowd levels. Use the sailing list to compare dates and prioritize port days with comfortable conditions.
Are these sailings all the same route?
They can be close but not identical. Look for differences in port order, arrival times, and sea day placement.
How should I choose between two similar sailings?
Compare: (1) ship, (2) port day timing, (3) number of sea days, (4) price vs cabin value, and (5) flight convenience.