Typical price
$723/night
$8,672 total
Eastern Caribbean cruises
Eastern Caribbean Loop via Philipsburg, Terre-de-Haut & Road Bay (Rare Variant)
⚓ Philipsburg · Terre-de-Haut (Les Saintes) · Saint George's · Castries · Puerto Plata · Miami · Charlotte Amalie, Saint Thomas · Road Bay · Saint-Pierre · Basseterre, Saint Kitts · Philipsburg
Port-heavy Eastern Caribbean itinerary. Covers Sint Maarten (Dutch part), Guadeloupe, Grenada, and Saint Lucia and more.
☾8 nights
San Juan
Eastern Caribbean
11 ports
Itinerary pricing
What this itinerary usually costs
Typical pricing runs around $723/night. with most departures landing in the $688-$744/night band. across 2 tracked sailings.
Normal range
$688-$744/night
$8,256-$8,925 total
Lowest recent fare
Building history
$5,360 total
Comparison set
2 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.
When should I go?
Scan monthly pricing to see which departure windows tend to look stronger or weaker for this itinerary.
January 2027
Cheapest
Median price/night
$788
2 sailings
Upcoming departures
Typical value
2 priced departures tracked
Route overview
How this route is built
8 nights · 11 port calls · 10 countries
11 port calls across Sint Maarten (Dutch part), Guadeloupe, Grenada, Saint Lucia · More port-intensive than many 8-night alternatives.
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Embark in San Juan
Embarkation ports can vary by sailing
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Disembark in San Juan or Miami
Disembarkation ports can vary by sailing
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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
Cheaper entry price than this itinerary
From $680
$140-$174/night typical
Eastern Caribbean Loop via Tortola & Disney Castaway Cay (Private Island Focus)
7 nights
Cheaper entry price than this itinerary
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
Cheaper entry price than this itinerary
From $709
$89-$156/night typical
Eastern Caribbean Loop via Philipsburg & Coco Cay (Private Island Focus)
7 nights
Cheaper entry price than this itinerary
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.