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Eastern Caribbean cruises

Eastern Caribbean Arc via Tortola, Road Bay & South Friars Bay

Tortola · Road Bay · Falmouth · South Friars Bay · Terre-de-Haut (Les Saintes) · Oranjestad · Curaçao · Bonaire

Port-heavy Eastern Caribbean itinerary. Covers Virgin Islands, British, Anguilla, Antigua and Barbuda, Saint Kitts and Nevis, and more. Includes anchorage-style calls.

11 nights Philipsburg Eastern Caribbean 8 ports 3 sea days
Compare departures Explore the route

What this trip feels like

Active, varied and destination-focused

With 8 ports across 11 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

8 ports in 11 nights

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

Broad destination variety

Tortola · Road Bay · Falmouth + more

Frequent changes of scenery across the itinerary.

Route logistics

Sails from Philipsburg

Check the exact departure and arrival ports before arranging flights.

Port experience

Tortola · 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
Seabourn

Seabourn Ovation

Philipsburg → Tortola → Bonaire → Bridgetown

Dec 28 · 11 nights

About average

$5,779 balcony · $525/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 $540/night, with most departures landing in the $494-$585/night band across 1 tracked sailing.

Typical price

$540/night

$5,938 total

Normal range

$494-$585/night

$5,439-$6,440 total

Lowest recent fare

Building history

$5,439 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 →

11 nights · 8 port calls · 3 sea days · 8 countries

8 port calls across Virgin Islands, British, Anguilla, Antigua and Barbuda, Saint Kitts and Nevis · More port-intensive than many 11-night alternatives.

  1. 1

    Embark in Philipsburg

    Embarkation ports can vary by sailing

  2. 2

    Tortola

    Virgin Islands, British · Eastern Caribbean

  3. 3

    Road Bay

    Anguilla · Eastern Caribbean

  4. 4

    Falmouth

    Antigua and Barbuda · Eastern Caribbean

  5. 5

    South Friars Bay

    Saint Kitts and Nevis · Eastern Caribbean

    Anchorage
  6. 6

    Terre-de-Haut (Les Saintes)

    Guadeloupe · Eastern Caribbean

  7. 7

    Oranjestad

    Aruba · ABC Islands

  8. 8

    Curaçao

    Curaçao · ABC Islands

  9. 9

    Bonaire

    Bonaire, Sint Eustatius and Saba · Southern Caribbean

  10. 10

    Disembark in Bridgetown

    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.