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Eastern Caribbean cruises

Eastern Caribbean Arc: Road Bay & Saint-Barthélemy

Road Bay · Saint-Barthélemy · Jost Van Dyke

Port-heavy Eastern Caribbean itinerary. Covers Anguilla, Saint Barthélemy, and Virgin Islands, British.

7 nights San Juan Eastern Caribbean 5 ports 1 sea day
Compare departures Explore the route

What this trip feels like

Active, varied and destination-focused

With 5 ports across 7 nights, this trip keeps the focus on time ashore. Expect more destination variety and a busier rhythm, with the ship serving as the link between port days.

Port-forward pace

5 ports in 7 nights

Most days put a destination at the center of the plan.

Broad destination variety

Road Bay · Saint-Barthélemy · Jost Van Dyke

Frequent changes of scenery across the itinerary.

Easy logistics

Round-trip from San Juan

No open-jaw flights or separate arrival and departure transfers.

Port experience

Road Bay · 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 · Destination-led trips · Active days ashore · Travelers who prefer variety

Think twice if · You want long, uninterrupted stretches of time onboard

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
SeaDream Yacht Club

SeaDream I

San Juan → Road Bay → Jost Van Dyke → San Juan

Apr 1 · 7 nights

About average

$4,851 oceanview · $693/night

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 $486/night, with most departures landing in the $350-$698/night band across 1 tracked sailing.

Typical price

$486/night

$3,402 total

Normal range

$350-$698/night

$2,449-$4,886 total

Lowest recent fare

$693/night

$4,851 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 →

7 nights · 5 port calls · 1 sea days · 3 countries

5 port calls across Anguilla, Saint Barthélemy, Virgin Islands, British · More port-intensive than many 7-night alternatives.

  1. 1

    Embark in San Juan

    Embarkation ports can vary by sailing

  2. 2

    Road Bay

    Anguilla · Eastern Caribbean

  3. 3

    Saint-Barthélemy

    Saint Barthélemy · Eastern Caribbean

  4. 4

    Saint-Barthélemy

    Saint Barthélemy · Eastern Caribbean

  5. 5

    Saint-Barthélemy

    Saint Barthélemy · Eastern Caribbean

  6. 6

    Jost Van Dyke

    Virgin Islands, British · Eastern Caribbean

  7. 7

    Disembark in San Juan

    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.