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Eastern Caribbean cruises

Eastern Caribbean Loop via Philipsburg & San Juan

Philipsburg · San Juan · Samana · Bimini

Balanced route with a steady mix of port days and sea days. Covers Sint Maarten (Dutch part), Puerto Rico, Dominican Republic, and Bahamas.

8 nights Miami Eastern Caribbean 4 ports 4 sea days
Compare departures Explore the route

What this trip feels like

Balanced, varied and easy to pace

This route gives you a steady mix of ship time and 4 ports. It suits travelers who want meaningful days ashore without turning every day into an early start and a tightly planned port call.

Balanced pace

4 ports in 8 nights

A steady alternation between time onboard and time ashore.

Broad destination variety

Philipsburg · San Juan · Samana + more

Frequent changes of scenery across the itinerary.

Easy logistics

Round-trip from Miami

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

Port experience

Philipsburg · 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 · A mix of ship and shore time · First-time visitors · Travelers who like a steady pace

Think twice if · You want either an all-ports itinerary or a mostly ship-focused escape

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
Virgin Voyages

Resilient Lady

Miami → Philipsburg → Bimini → Miami

Nov 20 · 8 nights

About average

$952 inside · $119/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 $129/night, with most departures landing in the $119-$129/night band across 1 tracked sailing.

Typical price

$129/night

$1,032 total

Normal range

$119-$129/night

$952-$1,032 total

Lowest recent fare

$119/night

$952 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 →

8 nights · 4 port calls · 4 sea days · 4 countries

4 port calls across Sint Maarten (Dutch part), Puerto Rico, Dominican Republic, Bahamas · Neither especially port-heavy nor sea-day heavy for this trip length.

  1. 1

    Embark in Miami

    Embarkation ports can vary by sailing

  2. 2

    Philipsburg

    Sint Maarten (Dutch part) · Eastern Caribbean

  3. 3

    San Juan

    Puerto Rico · Eastern Caribbean

  4. 4

    Samana

    Dominican Republic · Eastern Caribbean

  5. 5

    Bimini

    Bahamas · Bahamas

  6. 6

    Disembark in Miami

    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.