Balanced pace
8 ports in 19 nights
A steady alternation between time onboard and time ashore.
Southern Caribbean cruises
Southern Caribbean Crossing via Tortola, South Friars Bay & Les Trois-Îlets
Tortola · South Friars Bay · Les Trois-Îlets · Port Elizabeth, New Jersey · Saint George's · Bridgetown · Castries · Funchal, Madeira
Balanced route with a steady mix of port days and sea days. Covers Virgin Islands, British, Saint Kitts and Nevis, Martinique, United States, and more. Includes anchorage-style calls.
19 nights
Philipsburg
Southern Caribbean
8 ports
10 sea days
What this trip feels like
Balanced, varied and easy to pace
This route gives you a steady mix of ship time and 8 ports. It suits travelers who want meaningful days ashore without turning every day into an early start and a tightly planned port call.
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 · A mix of ship and shore time · First-time visitors · Travelers who like a steady pace
Think twice if · You want either an all-ports itinerary or a mostly ship-focused escape
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.
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 1 tracked sailing.
Typical price
$559/night
$10,612 total
Normal range
$505-$636/night
$9,586-$12,077 total
Lowest recent fare
Building history
$8,909 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
19 nights · 8 port calls · 10 sea days · 8 countries
8 port calls across Virgin Islands, British, Saint Kitts and Nevis, Martinique, United States · Neither especially port-heavy nor sea-day heavy for this trip length.
-
1
Embark in Philipsburg
Embarkation ports can vary by sailing
-
2
-
3
-
4
-
5
-
6
-
7
-
8
-
9
-
10
Disembark in Lisboa
Disembarkation ports can vary by sailing
Loading route map
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.
More port time
Add Port Elizabeth, Bequia + Mayreau Island
Southern Caribbean: Port Elizabeth, Bequia, Mayreau Island & Kralendijk
18 nights · 12 ports · 6 sea days
−1 night +4 ports
Much more time ashore in a shorter trip.
Compare this route →
From $16,890
More variety
Add Oranjestad + Willemstad
Southern Caribbean: Oranjestad, Willemstad & Kralendijk
29 nights · 16 ports · 15 countries
+10 nights +7 countries
A much broader Southern Caribbean experience.
Compare this route →
From $13,799
Longer trip
Make it 22 nights
Southern Caribbean: Bridgetown, Port-of-Spain & Santarém
22 nights · 7 ports · 15 sea days
+3 nights +5 sea days
More time onboard without changing the trip's overall pace much.
Compare this route →
From $11,242