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Eastern Caribbean cruises

Eastern Caribbean Loop via New York, Saint Thomas & Road Town, Tortola

New York · Saint Thomas · Road Town, Tortola · Basseterre, Saint Kitts · Philipsburg · New York

Balanced itinerary with more sea time than port-packed variants. Covers United States, Virgin Islands, U.S., Virgin Islands, British, Saint Kitts and Nevis, and more.

25 nights Southampton Eastern Caribbean 6 ports 18 sea days
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What this trip feels like

Easygoing, familiar and ship-focused

18 sea days give you plenty of uninterrupted time onboard, while New York, Saint Thomas, and Road Town, Tortola provide the trip's main day ashore. You're choosing this route for an easy break with minimal logistics, not destination variety.

Relaxed pace

6 ports in 25 nights

Plenty of uninterrupted ship time.

Broad destination variety

New York · Saint Thomas · Road Town, Tortola + 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 · First-time cruisers · Ship-focused trips · Easy short getaways

Think twice if · You want a port-intensive Eastern Caribbean itinerary

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
Cunard Line

Queen Mary 2

Southampton → New York → Philipsburg → Southampton

Nov 10 · 25 nights

Good value

$3,685 balcony · $147/night

14% below typical · 6-month low

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 $150/night, with most departures landing in the $122-$199/night band across 1 tracked sailing.

Typical price

$150/night

$3,750 total

Normal range

$122-$199/night

$3,054-$4,977 total

Lowest recent fare

$110/night

$2,754 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 →

25 nights · 6 port calls · 18 sea days · 5 countries

6 port calls across United States, Virgin Islands, U.S., Virgin Islands, British, Saint Kitts and Nevis · Leans more toward sea time than a port-packed 25-night route.

  1. 1

    Embark in Southampton

    Embarkation ports can vary by sailing

  2. 2

    New York

    United States · US East Coast

  3. 3

    Saint Thomas

    Virgin Islands, U.S. · Eastern Caribbean

  4. 4

    Road Town, Tortola

    Virgin Islands, British · Eastern Caribbean

  5. 5

    Basseterre, Saint Kitts

    Saint Kitts and Nevis · Eastern Caribbean

  6. 6

    Philipsburg

    Sint Maarten (Dutch part) · Eastern Caribbean

  7. 7

    New York

    United States · US East Coast

  8. 8

    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.

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.