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Southern Caribbean cruises

Southern Caribbean Loop via Tortola, Saint John's & Castries

Tortola · Saint John's · Castries · Saint George's · Bridgetown · Kingstown · Fort-de-France · Roseau

Port-heavy Southern Caribbean itinerary. Covers Virgin Islands, British, Antigua and Barbuda, Saint Lucia, Grenada, and more.

11 nights San Juan Southern Caribbean 8 ports 3 sea days
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What this trip feels like

Active, varied and destination-focused

With 8 ports across 11 nights, this trip keeps the focus on time ashore. Expect more destination variety and a busier rhythm, with the ship serving as the link between port days.

Port-forward pace

8 ports in 11 nights

Most days put a destination at the center of the plan.

Broad destination variety

Tortola · Saint John's · Castries + more

Frequent changes of scenery across the itinerary.

Easy logistics

Round-trip from San Juan

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

Port experience

Tortola · 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 · Destination-led trips · Active days ashore · Travelers who prefer variety

Think twice if · You want long, uninterrupted stretches of time onboard

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
Celebrity Cruises

Celebrity Constellation

San Juan → Tortola → Roseau → San Juan

Nov 17 · 11 nights

Priced high

$1,371 inside · $125/night

18% above typical · Strong mix of price and timing for this itinerary

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 $118/night, with most departures landing in the $92-$157/night band across 1 tracked sailing.

Typical price

$118/night

$1,296 total

Normal range

$92-$157/night

$1,017-$1,731 total

Lowest recent fare

Building history

$869 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 →

11 nights · 8 port calls · 3 sea days · 8 countries

8 port calls across Virgin Islands, British, Antigua and Barbuda, Saint Lucia, Grenada · More port-intensive than many 11-night alternatives.

  1. 1

    Embark in San Juan

    Embarkation ports can vary by sailing

  2. 2

    Tortola

    Virgin Islands, British · Eastern Caribbean

  3. 3

    Saint John's

    Antigua and Barbuda · Eastern Caribbean

  4. 4

    Castries

    Saint Lucia · Southern Caribbean

  5. 5

    Saint George's

    Grenada · Southern Caribbean

  6. 6

    Bridgetown

    Barbados · Southern Caribbean

  7. 7

    Kingstown

    Saint Vincent and the Grenadines · Southern Caribbean

  8. 8

    Fort-de-France

    Martinique · Southern Caribbean

  9. 9

    Roseau

    Dominica · Southern Caribbean

  10. 10

    Disembark in San Juan

    Disembarkation ports can vary by sailing

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Render your Mapbox or Leaflet map here from the supplied route and port JSON.

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.