Long-form pace
7 ports in 28 nights
Long ocean passages make onboard routines a major part of the experience.
Eastern Caribbean cruises
Eastern Caribbean Loop via New York, Road Town, Tortola & Basseterre, Saint Kitts
New York · Road Town, Tortola · Basseterre, Saint Kitts · Castries · Bridgetown · Philipsburg · New York
Extended 28-night voyage with 20 sea days and 7 ports. Covers United States, Virgin Islands, British, Saint Kitts and Nevis, Saint Lucia, and more.
28 nights
Southampton
Eastern Caribbean
7 ports
20 sea days
What this trip feels like
Expansive, immersive and built around life at sea
At 28 nights, this is a multi-month, world-cruise-style voyage rather than a conventional getaway. 20 sea days make the ship your home base between 7 ports across a wide arc of destinations. Expect long ocean passages and the planning commitment of an extended journey.
Broad destination variety
New York · Road Town, Tortola · Basseterre, Saint Kitts + more
Frequent changes of scenery across the itinerary.
Easy logistics
Round-trip from Southampton
No open-jaw flights or separate arrival and departure transfers.
Port experience
New York · 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 · Long-form travelers · Sea-day lovers · Multi-region exploration
Think twice if · You want a conventional one- or two-week cruise
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 $161/night, with most departures landing in the $142-$194/night band across 1 tracked sailing.
Typical price
$161/night
$4,518 total
Normal range
$142-$194/night
$3,988-$5,436 total
Lowest recent fare
$136/night
$3,795 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
28 nights · 7 port calls · 20 sea days · 6 countries
7 port calls across United States, Virgin Islands, British, Saint Kitts and Nevis, Saint Lucia · Leans more toward sea time than a port-packed 28-night route.
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Embark in Southampton
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Disembark in Southampton
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 Nassau + Half Moon Cay
Eastern Caribbean: Nassau, Half Moon Cay & Ocho Rios
28 nights · 18 ports · 10 sea days
Same length +11 ports
Much more time ashore without making the trip longer.
Compare this route →
From $4,179
More variety
Add Cozumel + Roatán
Eastern Caribbean: Cozumel, Roatán & Harvest Caye
0 nights · 21 ports · 19 countries
−28 nights +13 countries
A much broader Eastern Caribbean experience.
Compare this route →
From $8,649
Longer trip
Make it 40 nights
Eastern Caribbean: Ketchikan, Juneau & Victoria
40 nights · 18 ports · 22 sea days
+12 nights +2 sea days
More time onboard without changing the trip's overall pace much.
Compare this route →
From $3,016