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Southern Caribbean cruises

Southern Caribbean Arc: Spanish Town, South Friars Bay & Castries

Spanish Town (Virgin Gorda) · South Friars Bay · Castries · Terre-de-Haut (Les Saintes) · Saint George's · Bridgetown · Port Elizabeth, Bequia · Les Trois-Îlets · Antigua · South Friars Bay · Jost Van Dyke

Port-heavy Southern Caribbean itinerary. Covers Virgin Islands, British, Saint Kitts and Nevis, Saint Lucia, Guadeloupe, and more. Includes anchorage-style calls.

14 nights Philipsburg Southern Caribbean 11 ports 2 sea days
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What this trip feels like

Active, varied and destination-focused

With 11 ports across 14 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 14 nights

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

Broad destination variety

Spanish Town (Virgin Gorda) · South Friars Bay · Castries + more

Frequent changes of scenery across the itinerary.

Easy logistics

Round-trip from Philipsburg

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

Port experience

Spanish Town (Virgin Gorda) · 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
Seabourn

Seabourn Ovation

Philipsburg → Spanish Town (Virgin Gorda) → Jost Van Dyke → Philipsburg

Dec 30 · 14 nights

About average

$8,009 balcony · $572/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 $540/night, with most departures landing in the $494-$585/night band across 1 tracked sailing.

Typical price

$540/night

$7,558 total

Normal range

$494-$585/night

$6,922-$8,196 total

Lowest recent fare

$572/night

$8,009 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 · 11 port calls · 2 sea days · 9 countries

11 port calls across Virgin Islands, British, Saint Kitts and Nevis, Saint Lucia, Guadeloupe · More port-intensive than many 14-night alternatives.

  1. 1

    Embark in Philipsburg

    Embarkation ports can vary by sailing

  2. 2

    Spanish Town (Virgin Gorda)

    Virgin Islands, British · Eastern Caribbean

  3. 3

    South Friars Bay

    Saint Kitts and Nevis · Eastern Caribbean

    Anchorage
  4. 4

    Castries

    Saint Lucia · Southern Caribbean

  5. 5

    Terre-de-Haut (Les Saintes)

    Guadeloupe · Eastern Caribbean

  6. 6

    Saint George's

    Grenada · Southern Caribbean

  7. 7

    Bridgetown

    Barbados · Southern Caribbean

  8. 8

    Port Elizabeth, Bequia

    Saint Vincent and the Grenadines · Southern Caribbean

  9. 9

    Les Trois-Îlets

    Martinique · Southern Caribbean

  10. 10

    Antigua

    Antigua and Barbuda · Eastern Caribbean

  11. 11

    South Friars Bay

    Saint Kitts and Nevis · Eastern Caribbean

    Anchorage
  12. 12

    Jost Van Dyke

    Virgin Islands, British · Eastern Caribbean

  13. 13

    Disembark in Philipsburg

    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.