Balanced pace
9 ports in 14 nights
A steady alternation between time onboard and time ashore.
Southern Caribbean cruises
Southern Caribbean Loop via Georgetown, Grand Cayman, Montego Bay & Oranjestad
Georgetown, Grand Cayman · Montego Bay · Oranjestad · Willemstad · Kralendijk · Saint George's · Fort-de-France · Basseterre, Saint Kitts · Philipsburg
Balanced route with a steady mix of port days and sea days. Covers Cayman Islands, Jamaica, Aruba, Curaçao, and more.
14 nights
Miami
Southern Caribbean
9 ports
5 sea days
What this trip feels like
Balanced, varied and easy to pace
This route gives you a steady mix of ship time and 9 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
Georgetown, Grand Cayman · Montego Bay · Oranjestad + more
Frequent changes of scenery across the itinerary.
Easy logistics
Round-trip from Miami
No open-jaw flights or separate arrival and departure transfers.
Port experience
Georgetown, Grand Cayman · 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 $330/night, with most departures landing in the $310-$346/night band across 1 tracked sailing.
Typical price
$330/night
$4,619 total
Normal range
$310-$346/night
$4,339-$4,841 total
Lowest recent fare
$311/night
$4,349 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
14 nights · 9 port calls · 5 sea days · 9 countries
9 port calls across Cayman Islands, Jamaica, Aruba, Curaçao · Neither especially port-heavy nor sea-day heavy for this trip length.
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Disembark in Miami
Disembarkation ports can vary by sailing
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Embark port
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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 South Friars Bay + Saint-Barthélemy
Southern Caribbean: South Friars Bay, Saint-Barthélemy & Castries
0 nights · 11 ports · 0 sea days
−14 nights +2 ports
Much more time ashore in a shorter trip.
Compare this route →
From $7,469
More variety
Add Rodney Bay + Curaçao
Southern Caribbean: Rodney Bay, Curaçao & Oranjestad
0 nights · 10 ports · 10 countries
−14 nights +1 country
A much broader Southern Caribbean experience.
Compare this route →
From $7,649
Longer trip
Make it 22 nights
Southern Caribbean: Bridgetown, Port-of-Spain & Santarém
22 nights · 7 ports · 15 sea days
+8 nights +10 sea days
More time onboard without changing the trip's overall pace much.
Compare this route →
From $11,242