Port-forward pace
5 ports in 7–14 nights
Most days put a destination at the center of the plan.
Southern Caribbean cruises
Southern Caribbean Arc via Tortola, South Friars Bay & Les Trois-Îlets
Tortola · South Friars Bay · Les Trois-Îlets · Port Elizabeth, New Jersey · Saint George's
Port-heavy Southern Caribbean itinerary. Covers Virgin Islands, British, Saint Kitts and Nevis, Martinique, United States, and more. Includes anchorage-style calls.
7–14 nights
Philipsburg
Southern Caribbean
5 ports
2 sea days
What this trip feels like
Active, varied and destination-focused
With 5 ports across 7–14 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.
Broad destination variety
Tortola · South Friars Bay · Les Trois-Îlets + more
Frequent changes of scenery across the itinerary.
Route logistics
Sails from Philipsburg
Check the exact departure and arrival ports before arranging flights.
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
Seabourn Ovation
Philipsburg → Tortola → Rodney Bay → Bridgetown
Dec 5 · 14 nights
About average
$6,319 balcony · $451/night
Cheapest upcoming
Seabourn Ovation
Philipsburg → Tortola → Saint George's → Bridgetown
Dec 4 · 7 nights
About average
$3,824 balcony · $546/night
All departures
All upcoming departures
Compare all sailings for this itinerary.
Itinerary pricing
What this itinerary usually costs
Typical pricing runs around $559/night, with most departures landing in the $505-$636/night band across 10 tracked sailings.
Typical price
$559/night
$4,114 total
Normal range
$505-$636/night
$3,763-$4,624 total
Lowest recent fare
Building history
$3,569 total
Comparison set
10 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
7–14 nights · 5 port calls · 2 sea days · 5 countries
5 port calls across Virgin Islands, British, Saint Kitts and Nevis, Martinique, United States · More port-intensive than many 7-night alternatives.
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Embark in Philipsburg
Embarkation ports can vary by sailing
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Disembark in Bridgetown or 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.
More port time
Add Saint John's + Castries
Southern Caribbean: Saint John's, Castries & Saint George's
9 nights · 6 ports · 3 sea days
+2 nights +1 port
Much more time ashore for only two extra nights.
Compare this route →
From $689
More variety
Add Georgetown, South Carolina + Falmouth
Southern Caribbean: Georgetown, South Carolina, Falmouth & Oranjestad
14 nights · 8 ports · 8 countries
+7 nights +3 countries
A much broader Southern Caribbean experience.
Compare this route →
From $5,025
Longer trip
Make it 19 nights
Southern Caribbean: Paita, Cartagena & Curaçao
19 nights · 6 ports · 13 sea days
+12 nights +11 sea days
More time onboard without changing the trip's overall pace much.
Compare this route →
From $9,079