Western Caribbean cruises

Western Caribbean Loop via Cruz Bay, Saint John, Montego Bay & Cozumel

San Juan · Cruz Bay, Saint John · Castries · Bridgetown · Philipsburg · Road Town, Tortola · Miami · Georgetown, Grand Cayman · Montego Bay · Roatán · Costa Maya (Mahahual) · Cozumel

Port-heavy Western Caribbean itinerary. Covers Puerto Rico, Virgin Islands, U.S., Saint Lucia, Barbados, and more.

12–21 nights Miami Western Caribbean 12 ports

What this trip feels like

Active, varied and destination-focused

With 12 ports across 12–21 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

12 ports in 12–21 nights

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

Broad destination variety

San Juan · Cruz Bay, Saint John · Castries + 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

San Juan · 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.

All departures

All upcoming departures

Compare all sailings for this itinerary.

Itinerary pricing

What this itinerary usually costs

Typical pricing runs around $97/night, with most departures landing in the $88-$110/night band across 3 tracked sailings.

Typical price

$97/night

$2,046 total

Normal range

$88-$110/night

$1,844-$2,316 total

Lowest recent fare

Building history

$1,006 total

Comparison set

3 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 →

12–21 nights · 12 port calls · 11 countries

12 port calls across Puerto Rico, Virgin Islands, U.S., Saint Lucia, Barbados · More port-intensive than many 12-night alternatives.

  1. 1

    Embark in Miami

    Embarkation ports can vary by sailing

  2. 2

    San Juan

    Puerto Rico · Eastern Caribbean

  3. 3

    Cruz Bay, Saint John

    Virgin Islands, U.S. · Eastern Caribbean

  4. 4

    Castries

    Saint Lucia · Southern Caribbean

  5. 5

    Bridgetown

    Barbados · Southern Caribbean

  6. 6

    Philipsburg

    Sint Maarten (Dutch part) · Eastern Caribbean

  7. 7

    Road Town, Tortola

    Virgin Islands, British · Eastern Caribbean

  8. 8

    Miami

    United States · US East Coast

  9. 9

    Georgetown, Grand Cayman

    Cayman Islands · Western Caribbean

  10. 10

    Montego Bay

    Jamaica · Western Caribbean

  11. 11

    Roatán

    Honduras · Western Caribbean

  12. 12

    Costa Maya (Mahahual)

    Mexico · Western Caribbean

  13. 13

    Cozumel

    Mexico · Western Caribbean

  14. 14

    Disembark in Miami

    Disembarkation ports can vary by sailing

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Embark port
Disembark port
Port of call

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