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Southern Caribbean cruises

Southern Caribbean Loop via Saint Thomas, Pointe-à-Pitre & Roseau

Saint Thomas · Pointe-à-Pitre · Roseau · Saint George's · Bridgetown · San Juan · Saint Thomas · Philipsburg · Antigua · Roseau · Bridgetown

Port-heavy Southern Caribbean itinerary. Covers Virgin Islands, U.S., Guadeloupe, Dominica, Grenada, and more.

7 nights San Juan Southern Caribbean 11 ports
Compare departures Explore the route

What this trip feels like

Active, varied and destination-focused

With 11 ports across 7 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

11 ports in 7 nights

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

Broad destination variety

Saint Thomas · Pointe-à-Pitre · Roseau + 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

Saint Thomas · 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
Princess Cruises

Crown Princess

San Juan → Saint Thomas → Bridgetown → San Juan

Jan 31 · 7 nights

$793 inside · $113/night

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 $115/night, with most departures landing in the $107-$132/night band across 1 tracked sailing.

Typical price

$115/night

$802 total

Normal range

$107-$132/night

$748-$922 total

Lowest recent fare

$113/night

$793 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 →

7 nights · 11 port calls · 8 countries

11 port calls across Virgin Islands, U.S., Guadeloupe, Dominica, Grenada · More port-intensive than many 7-night alternatives.

  1. 1

    Embark in San Juan

    Embarkation ports can vary by sailing

  2. 2

    Saint Thomas

    Virgin Islands, U.S. · Eastern Caribbean

  3. 3

    Pointe-à-Pitre

    Guadeloupe · Eastern Caribbean

  4. 4

    Roseau

    Dominica · Southern Caribbean

  5. 5

    Saint George's

    Grenada · Southern Caribbean

  6. 6

    Bridgetown

    Barbados · Southern Caribbean

  7. 7

    San Juan

    Puerto Rico · Eastern Caribbean

  8. 8

    Saint Thomas

    Virgin Islands, U.S. · Eastern Caribbean

  9. 9

    Philipsburg

    Sint Maarten (Dutch part) · Eastern Caribbean

  10. 10

    Antigua

    Antigua and Barbuda · Eastern Caribbean

  11. 11

    Roseau

    Dominica · Southern Caribbean

  12. 12

    Bridgetown

    Barbados · Southern Caribbean

  13. 13

    Disembark in San Juan

    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.