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Southern Caribbean cruises

Southern Caribbean Loop via Saint Thomas, Philipsburg & Antigua

Saint Thomas · Philipsburg · Antigua · Castries · Bridgetown

Balanced itinerary with more sea time than port-packed variants. Covers Virgin Islands, U.S., Sint Maarten (Dutch part), Antigua and Barbuda, Saint Lucia, and more.

14 nights San Juan Southern Caribbean 5 ports 9 sea days
Compare departures Explore the route

What this trip feels like

Easygoing, familiar and ship-focused

9 sea days give you plenty of uninterrupted time onboard, while Saint Thomas, Philipsburg, and Antigua provide the trip's main day ashore. You're choosing this route for an easy break with minimal logistics, not destination variety.

Relaxed pace

5 ports in 14 nights

Plenty of uninterrupted ship time.

Broad destination variety

Saint Thomas · Philipsburg · Antigua + 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 · First-time cruisers · Ship-focused trips · Easy short getaways

Think twice if · You want a port-intensive Southern Caribbean itinerary

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 → Saint George's → San Juan

Feb 21 · 14 nights

$1,426 inside · $102/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 $142/night, with most departures landing in the $118-$156/night band across 1 tracked sailing.

Typical price

$142/night

$1,988 total

Normal range

$118-$156/night

$1,646-$2,178 total

Lowest recent fare

$102/night

$1,426 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 →

14 nights · 5 port calls · 9 sea days · 5 countries

5 port calls across Virgin Islands, U.S., Sint Maarten (Dutch part), Antigua and Barbuda, Saint Lucia · Leans more toward sea time than a port-packed 14-night route.

  1. 1

    Embark in San Juan

    Embarkation ports can vary by sailing

  2. 2

    Saint Thomas

    Virgin Islands, U.S. · Eastern Caribbean

  3. 3

    Philipsburg

    Sint Maarten (Dutch part) · Eastern Caribbean

  4. 4

    Antigua

    Antigua and Barbuda · Eastern Caribbean

  5. 5

    Castries

    Saint Lucia · Southern Caribbean

  6. 6

    Bridgetown

    Barbados · Southern Caribbean

  7. 7

    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.