Typical price
$111/night
$779 total
Eastern Caribbean cruises
Eastern Caribbean Loop via Tortola, Philipsburg & Saint John's (Port-Heavy)
⚓ Tortola · Philipsburg · Saint John's · Basseterre, Saint Kitts · Frederiksted, Saint Croix
Port-heavy Eastern Caribbean itinerary. Covers Virgin Islands, British, Sint Maarten (Dutch part), Antigua and Barbuda, and Saint Kitts and Nevis and more.
☾7 nights
San Juan
Eastern Caribbean
5 ports
2 sea days
Itinerary pricing
What this itinerary usually costs
Typical pricing runs around $111/night. with most departures landing in the $96-$127/night band. across 30 tracked sailings.
Normal range
$96-$127/night
$671-$889 total
Lowest recent fare
Building history
$506 total
Comparison set
30 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 30 upcoming departures.
When should I go?
Scan monthly pricing to see which departure windows tend to look stronger or weaker for this itinerary.
June 2026
Median price/night
$221
1 sailing
Upcoming departures
57% above itinerary median
1 priced departures tracked
July 2026
Priciest
Median price/night
$248
2 sailings
Upcoming departures
67% above itinerary median
2 priced departures tracked
August 2026
Median price/night
$107
3 sailings
Upcoming departures
24% below itinerary median
3 priced departures tracked
September 2026
Median price/night
$98
2 sailings
Upcoming departures
Typical value
2 priced departures tracked
October 2026
Median price/night
$87
2 sailings
Upcoming departures
Typical value
2 priced departures tracked
November 2026
Median price/night
$81
1 sailing
Upcoming departures
24% below itinerary median
1 priced departures tracked
December 2026
Median price/night
$85
1 sailing
Upcoming departures
33% below itinerary median
1 priced departures tracked
January 2027
Median price/night
$85
1 sailing
Upcoming departures
18% below itinerary median
1 priced departures tracked
February 2027
Cheapest
Median price/night
$80
2 sailings
Upcoming departures
27% below itinerary median
2 priced departures tracked
May 2027
Median price/night
$126
2 sailings
Upcoming departures
Typical value
2 priced departures tracked
June 2027
Median price/night
$142
2 sailings
Upcoming departures
Typical value
2 priced departures tracked
July 2027
Median price/night
$143
3 sailings
Upcoming departures
Typical value
3 priced departures tracked
August 2027
Median price/night
$104
2 sailings
Upcoming departures
Typical value
2 priced departures tracked
September 2027
Median price/night
$91
2 sailings
Upcoming departures
14% below itinerary median
2 priced departures tracked
October 2027
Median price/night
$95
2 sailings
Upcoming departures
Typical value
2 priced departures tracked
November 2027
Median price/night
$112
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 · 5 countries
5 port calls across Virgin Islands, British, Sint Maarten (Dutch part), Antigua and Barbuda, Saint Kitts and Nevis · 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
Loading route map
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
Higher typical pricing for similar trip length
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
Higher typical pricing for similar trip length
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.