Relaxed pace
6 ports in 21 nights
Plenty of uninterrupted ship time.
Eastern Caribbean cruises
Eastern Caribbean Loop via San Juan, Cruz Bay, Saint John & Castries
San Juan · Cruz Bay, Saint John · Castries · Bridgetown · Philipsburg · Road Town, Tortola
Balanced itinerary with more sea time than port-packed variants. Covers Puerto Rico, Virgin Islands, U.S., Saint Lucia, Barbados, and more.
21 nights
Miami
Eastern Caribbean
6 ports
15 sea days
What this trip feels like
Easygoing, familiar and ship-focused
15 sea days give you plenty of uninterrupted time onboard, while San Juan, Cruz Bay, Saint John, and Castries provide the trip's main day ashore. You're choosing this route for an easy break with minimal logistics, not destination variety.
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 · 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
Queen Elizabeth
Miami → San Juan → Road Town, Tortola → Miami
Oct 15 · 12 nights
Good value
$2,306 suite · $192/night
21% below typical · 30-day lowAll departures
All upcoming departures
Compare all sailings for this itinerary.
Itinerary pricing
What this itinerary usually costs
Typical pricing runs around $117/night, with most departures landing in the $89-$166/night band across 3 tracked sailings.
Typical price
$117/night
$1,399 total
Normal range
$89-$166/night
$1,066-$1,995 total
Lowest recent fare
Building history
$906 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
21 nights · 6 port calls · 15 sea days · 6 countries
6 port calls across Puerto Rico, Virgin Islands, U.S., Saint Lucia, Barbados · Leans more toward sea time than a port-packed 21-night route.
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Embarkation ports can vary by sailing
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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.
More port time
Add Nassau + Costa Maya
Eastern Caribbean: Nassau, Costa Maya (Mahahual) & Harvest Caye
20 nights · 13 ports · 7 sea days
−1 night +7 ports
Much more time ashore in a shorter trip.
Compare this route →
From $6,381
More variety
Add Ensenada + Cabo San Lucas
Eastern Caribbean: Ensenada, Cabo San Lucas & Acapulco
44 nights · 25 ports · 18 countries
+23 nights +12 countries
A much broader Eastern Caribbean experience.
Compare this route →
From $20,799
Longer trip
Make it 40 nights
Eastern Caribbean: Ketchikan, Juneau & Victoria
40 nights · 18 ports · 22 sea days
+19 nights +7 sea days
More time onboard without changing the trip's overall pace much.
Compare this route →
From $3,016