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Eastern Caribbean cruises

Eastern Caribbean Loop via Key West & Saint Thomas

Key West · Saint Thomas · Saint-Barthélemy · Saint John's

Balanced itinerary with more sea time than port-packed variants. Covers United States, Virgin Islands, U.S., Saint Barthélemy, and Antigua and Barbuda.

11 nights Miami Eastern Caribbean 4 ports 7 sea days
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What this trip feels like

Easygoing, familiar and ship-focused

7 sea days give you plenty of uninterrupted time onboard, while Key West, Saint Thomas, and Saint-Barthélemy provide the trip's main day ashore. You're choosing this route for an easy break with minimal logistics, not destination variety.

Relaxed pace

4 ports in 11 nights

Plenty of uninterrupted ship time.

Broad destination variety

Key West · Saint Thomas · Saint-Barthélemy + 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

Saint Thomas · 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 · First-time cruisers · Ship-focused trips · Easy short getaways

Think twice if · You want a port-intensive Eastern Caribbean itinerary

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
Silversea Cruises

Silver Nova

Miami → Key West → Saint John's → Miami

Dec 29 · 11 nights

$9,400 balcony · $855/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 $625/night, with most departures landing in the $575-$736/night band across 1 tracked sailing.

Typical price

$625/night

$6,875 total

Normal range

$575-$736/night

$6,325-$8,100 total

Lowest recent fare

$855/night

$9,400 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 · 4 port calls · 7 sea days · 4 countries

4 port calls across United States, Virgin Islands, U.S., Saint Barthélemy, Antigua and Barbuda · Leans more toward sea time than a port-packed 11-night route.

  1. 1

    Embark in Miami

    Embarkation ports can vary by sailing

  2. 2

    Key West

    United States · US East Coast

  3. 3

    Saint Thomas

    Virgin Islands, U.S. · Eastern Caribbean

  4. 4

    Saint-Barthélemy

    Saint Barthélemy · Eastern Caribbean

  5. 5

    Saint John's

    Antigua and Barbuda · Eastern Caribbean

  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.