Typical price
$117/night
$817 total
Eastern Caribbean cruises
Eastern Caribbean Loop via Charlotte Amalie, Saint Thomas, Frederiksted, Saint Croix & Philipsburg (Port-Heavy)
⚓ Charlotte Amalie, Saint Thomas · Frederiksted, Saint Croix · Philipsburg · Castries · Bridgetown
Port-heavy Eastern Caribbean itinerary. Covers Virgin Islands, U.S., Sint Maarten (Dutch part), Saint Lucia, and Barbados.
☾7 nights
San Juan
Eastern Caribbean
5 ports
2 sea days
Itinerary pricing
What this itinerary usually costs
Typical pricing runs around $117/night. with most departures landing in the $107-$130/night band. across 23 tracked sailings.
Normal range
$107-$130/night
$748-$907 total
Lowest recent fare
$96/night
$674 total
Comparison set
23 sailings
Used for itinerary baseline
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.
Showing 23 upcoming departures.
When should I go?
Scan monthly pricing to see which departure windows tend to look stronger or weaker for this itinerary.
May 2027
Median price/night
$130
3 sailings
Upcoming departures
11% above itinerary median
3 priced departures tracked
June 2027
Median price/night
$138
2 sailings
Upcoming departures
Typical value
2 priced departures tracked
July 2027
Priciest
Median price/night
$155
2 sailings
Upcoming departures
Typical value
2 priced departures tracked
August 2027
Median price/night
$115
2 sailings
Upcoming departures
Typical value
2 priced departures tracked
September 2027
Cheapest
Median price/night
$97
2 sailings
Upcoming departures
17% below itinerary median
2 priced departures tracked
October 2027
Median price/night
$105
3 sailings
Upcoming departures
10% below itinerary median
3 priced departures tracked
November 2027
Median price/night
$108
1 sailing
Upcoming departures
7% below itinerary median
1 priced departures tracked
December 2027
Median price/night
$104
1 sailing
Upcoming departures
Typical value
1 priced departures tracked
January 2028
Median price/night
$110
1 sailing
Upcoming departures
6% above itinerary median
1 priced departures tracked
February 2028
Median price/night
$121
2 sailings
Upcoming departures
Typical value
2 priced departures tracked
March 2028
Median price/night
$117
2 sailings
Upcoming departures
Typical value
2 priced departures tracked
April 2028
Median price/night
$126
2 sailings
Upcoming departures
Typical value
2 priced departures tracked
Route overview
How this route is built
7 nights · 5 port calls · 2 sea days · 4 countries
5 port calls across Virgin Islands, U.S., Sint Maarten (Dutch part), Saint Lucia, Barbados · More port-intensive than many 7-night alternatives.
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1
Embark in San Juan
Embarkation ports can vary by sailing
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2
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3
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4
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5
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6
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7
Disembark in San Juan
Disembarkation ports can vary by sailing
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Render your Mapbox or Leaflet map here from the supplied route and port JSON.
Embark port
Disembark port
Port of call
Alternatives
Compare nearby alternatives
Nearby options in the same planning set, with price and trip-shape tradeoffs called out so you can compare without restarting your search.
Eastern Caribbean Loop via Philipsburg & Charlotte Amalie, Saint Thomas (Best Balance)
7 nights
Higher typical pricing for similar trip length
From $680
$140-$174/night typical
Eastern Caribbean Loop via Tortola & Disney Castaway Cay (Private Island Focus)
7 nights
Higher typical pricing for similar trip length
From $1,553
$329-$422/night typical
Eastern Caribbean Loop via Nassau & San Juan (Rare Variant)
8 nights
Cheaper entry price than this itinerary
From $579
$73-$136/night typical
Eastern Caribbean Arc via Philipsburg & Saint John's (Best Balance)
0 nights
Higher typical pricing for similar trip length
From $709
$89-$156/night typical
Eastern Caribbean Loop via Philipsburg & Coco Cay (Private Island Focus)
7 nights
Higher typical pricing for similar trip length
From $1,233
$215-$250/night typical
Eastern Caribbean Loop via Philipsburg & Basseterre, Saint Kitts (Best Balance)
8 nights
Cheaper entry price than this itinerary
From $599
$73-$127/night typical
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.