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Southern Caribbean cruises

Southern Caribbean Arc via Road Town, Tortola, Philipsburg & Bridgetown

Road Town, Tortola · Philipsburg · Bridgetown · Castries · Roseau · Basseterre, Saint Kitts · New York · Southampton Parish Anchorage

Balanced itinerary with more sea time than port-packed variants. Covers Virgin Islands, British, Sint Maarten (Dutch part), Barbados, Saint Lucia, and more.

23 nights New York Southern Caribbean 8 ports 14 sea days
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What this trip feels like

Easygoing, familiar and ship-focused

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

Relaxed pace

8 ports in 23 nights

Plenty of uninterrupted ship time.

Broad destination variety

Road Town, Tortola · Philipsburg · Bridgetown + more

Frequent changes of scenery across the itinerary.

Route logistics

Sails from New York

Check the exact departure and arrival ports before arranging flights.

Port experience

Road Town, Tortola · Expect plenty of cruise traffic

This port regularly handles substantial cruise traffic, although conditions still vary by date.

Best for · First-time cruisers · Ship-focused trips · Easy short getaways

Think twice if · You want a port-intensive Southern 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

New York → Road Town, Tortola → New York → Southampton

Dec 19 · 23 nights

Exceptional value

$10,050 suite · $437/night

36% below typical

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 $161/night, with most departures landing in the $142-$194/night band across 1 tracked sailing.

Typical price

$161/night

$3,711 total

Normal range

$142-$194/night

$3,276-$4,465 total

Lowest recent fare

Building history

$2,768 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 →

23 nights · 8 port calls · 14 sea days · 8 countries

8 port calls across Virgin Islands, British, Sint Maarten (Dutch part), Barbados, Saint Lucia · Leans more toward sea time than a port-packed 23-night route.

  1. 1

    Embark in New York

    Embarkation ports can vary by sailing

  2. 2

    Road Town, Tortola

    Virgin Islands, British · Eastern Caribbean

  3. 3

    Philipsburg

    Sint Maarten (Dutch part) · Eastern Caribbean

  4. 4

    Bridgetown

    Barbados · Southern Caribbean

  5. 5

    Castries

    Saint Lucia · Southern Caribbean

  6. 6

    Roseau

    Dominica · Southern Caribbean

  7. 7

    Basseterre, Saint Kitts

    Saint Kitts and Nevis · Eastern Caribbean

  8. 8

    New York

    United States · US East Coast

  9. 9

    Southampton Parish Anchorage

    Bermuda · Bermuda

  10. 10

    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.