Eastern Caribbean cruises

Eastern Caribbean Arc: Cruz Bay, Saint John, Terre-de-Haut & Little Bay

Cruz Bay, Saint John · Terre-de-Haut (Les Saintes) · Tortola · San Juan · Saint-Barthélemy · Little Bay · Basseterre, Saint Kitts · Key West

Port-heavy Eastern Caribbean itinerary. Covers Virgin Islands, U.S., Guadeloupe, Virgin Islands, British, Puerto Rico, and more.

14 nights Miami Eastern Caribbean 10 ports 10 sea days

What this trip feels like

Port-intensive itinerary

Port-intensive itinerary with 10 port calls across 14 nights.

Port-forward pace

10 ports in 14 nights

Most days are port days.

Broad destination variety

Cruz Bay, Saint John · Terre-de-Haut (Les Saintes) · Tortola + more

Frequent port calls throughout the itinerary.

Easy logistics

Round-trip from Miami

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

Port experience

Cruz Bay, Saint John · 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

1 of 1 sailings with enough price history currently have favorable pricing. Median current fare is $670/night.

Median current fare

$670/night

$9,380 total

Lowest recent fare

$670/night

$9,380 total

Pricing signal

1 of 1 favorable

Price history for 1 of 1 sailings

Comparison set

1 sailings

Currently priced departures

When should I go?

Not enough departures yet to identify a reliable cheaper season.

Route overview

How this route is built

Compare sailings →

14 nights · 10 port calls · 10 sea days · 8 countries

10 port calls across Virgin Islands, U.S., Guadeloupe, Virgin Islands, British, Puerto Rico · More port-intensive than many 14-night alternatives.

  1. 1

    Embark in Miami

    Embarkation ports can vary by sailing

  2. 2

    Cruz Bay, Saint John

    Virgin Islands, U.S. · Eastern Caribbean

  3. 3

    Cruz Bay, Saint John

    Virgin Islands, U.S. · Eastern Caribbean

  4. 4

    Terre-de-Haut (Les Saintes)

    Guadeloupe · Eastern Caribbean

  5. 5

    Tortola

    Virgin Islands, British · Eastern Caribbean

  6. 6

    San Juan

    Puerto Rico · Eastern Caribbean

  7. 7

    Saint-Barthélemy

    Saint Barthélemy · Eastern Caribbean

  8. 8

    Saint-Barthélemy

    Saint Barthélemy · Eastern Caribbean

  9. 9

    Little Bay

    Montserrat · Eastern Caribbean

  10. 10

    Basseterre, Saint Kitts

    Saint Kitts and Nevis · Eastern Caribbean

  11. 11

    Key West

    United States · US East Coast

  12. 12

    Disembark in Miami

    Disembarkation ports can vary by sailing

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Embark port
Disembark port
Port of call

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