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Eastern Caribbean cruises

Eastern Caribbean Loop via Puerto Plata, San Juan & Philipsburg

Puerto Plata · San Juan · Philipsburg · Saint-Barthélemy · Saint John's · Tortola

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

10 nights Miami Eastern Caribbean 6 ports 4 sea days
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What this trip feels like

Balanced, varied and easy to pace

This route gives you a steady mix of ship time and 6 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

6 ports in 10 nights

A steady alternation between time onboard and time ashore.

Broad destination variety

Puerto Plata · San Juan · Philipsburg + 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

Puerto Plata · 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
Regent Seven Seas Cruises

Seven Seas Prestige

Miami → Puerto Plata → Tortola → Miami

Jan 17 · 10 nights

$7,772 balcony · $777/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 $715/night, with most departures landing in the $706-$773/night band across 1 tracked sailing.

Typical price

$715/night

$7,148 total

Normal range

$706-$773/night

$7,062-$7,734 total

Lowest recent fare

$777/night

$7,772 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 →

10 nights · 6 port calls · 4 sea days · 6 countries

6 port calls across Dominican Republic, Puerto Rico, Sint Maarten (Dutch part), Saint Barthélemy · 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

    Puerto Plata

    Dominican Republic · Eastern Caribbean

  3. 3

    San Juan

    Puerto Rico · Eastern Caribbean

  4. 4

    Philipsburg

    Sint Maarten (Dutch part) · Eastern Caribbean

  5. 5

    Saint-Barthélemy

    Saint Barthélemy · Eastern Caribbean

  6. 6

    Saint John's

    Antigua and Barbuda · Eastern Caribbean

  7. 7

    Tortola

    Virgin Islands, British · Eastern Caribbean

  8. 8

    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.