Explore Philipsburg, San Juan, Puerto Plata, Basseterre, Saint Kitts, and Saint Thomas and dozens of Eastern Caribbean ports.
Browse nearly 2,294 upcoming sailings across 1,200+ itineraries.
1,206 itineraries · 2,294 sailings · 45 ports
Alerts
We'll email you when unusually cheap cruises appear in this region.
Departures in Eastern Caribbean that are currently pricing well below their typical tracked rate.
SeaDream I • SeaDream Yacht Club
Oct 24, 2027 → Nov 7, 2027 • Málaga → San Juan
From $5,409
$386/night
↓62% below typical
SeaDream I • SeaDream Yacht Club
Oct 28, 2028 → Nov 11, 2028 • Málaga → San Juan
From $4,922
$352/night
↓66% below typical
Valiant Lady • Virgin Voyages
Oct 19, 2026 → Oct 31, 2026 • New York → San Juan
From $1,068
$89/night
↓37% below typical
Icon of the Seas • Royal Caribbean International
Aug 22, 2026 → Aug 29, 2026 • Miami ↔
From $1,255
$179/night
↓39% below typical
See representative route shapes, major ports, and where the most sailings cluster.
Interactive map
Render your Mapbox or Leaflet map here from the supplied route and port JSON.
Start with the route patterns that define this region.
Eastern Caribbean • Next: Jul 25
From $729
138 upcoming sailings
2 ships
View itinerary →
Eastern Caribbean • Next: Nov 1
From $916
54 upcoming sailings
2 ships
View itinerary →
Eastern Caribbean • Next: Jul 25
From $645
47 upcoming sailings
2 ships
View itinerary →
Eastern Caribbean • Next: Aug 1
From $1,145
46 upcoming sailings
2 ships
View itinerary →
Eastern Caribbean • Next: Aug 3
From $595
39 upcoming sailings
2 ships
View itinerary →
Eastern Caribbean • Next: Nov 1
From $504
34 upcoming sailings
2 ships
View itinerary →
Eastern Caribbean • Next: Oct 31
From $565
30 upcoming sailings
2 ships
View itinerary →
Eastern Caribbean • Next: Nov 7
From $873
29 upcoming sailings
2 ships
View itinerary →
Eastern Caribbean • Next: Aug 2
From $356
27 upcoming sailings
2 ships
View itinerary →
Eastern Caribbean • Next: Aug 1
From $549
27 upcoming sailings
2 ships
View itinerary →
Eastern Caribbean • Next: Jul 25
From $531
25 upcoming sailings
2 ships
View itinerary →
Eastern Caribbean • Next: May 1
From $674
23 upcoming sailings
2 ships
View itinerary →
Eastern Caribbean • Next: Aug 1
From $1,553
23 upcoming sailings
2 ships
View itinerary →
Eastern Caribbean • Next: Aug 8
From $487
21 upcoming sailings
2 ships
View itinerary →
Eastern Caribbean • Next: Nov 16
Price unavailable
20 upcoming sailings
2 ships
View itinerary →
Eastern Caribbean • Next: Aug 22
Price unavailable
20 upcoming sailings
2 ships
View itinerary →
Eastern Caribbean • Next: Apr 3
Price unavailable
19 upcoming sailings
2 ships
View itinerary →
Eastern Caribbean • Next: Dec 19
From $794
17 upcoming sailings
2 ships
View itinerary →
Eastern Caribbean • Next: Nov 22
From $1,259
16 upcoming sailings
2 ships
View itinerary →
Eastern Caribbean • Next: Nov 20
From $5,763
16 upcoming sailings
2 ships
View itinerary →
Eastern Caribbean • Next: Apr 23
Price unavailable
16 upcoming sailings
2 ships
View itinerary →
Eastern Caribbean • Next: Apr 19
Price unavailable
16 upcoming sailings
2 ships
View itinerary →
Eastern Caribbean • Next: Apr 16
Price unavailable
16 upcoming sailings
2 ships
View itinerary →
Eastern Caribbean • Next: May 16
From $379
15 upcoming sailings
2 ships
View itinerary →
Get a quick feel for how pricing behaves across Eastern Caribbean.
The ports most central to cruising in Eastern Caribbean.
Ships with strong presence in Eastern Caribbean.
The operators with the broadest footprint here.
A quick guide to what cruising this region typically looks like.
Eastern Caribbean is one of the core cruise regions on Jibhop, with 1,206 itineraries, 2,294 upcoming sailings, and calls across 45 ports. That makes it a strong region for comparing route shapes, ships, and departure options rather than just browsing raw inventory.
The most common cruise lengths in Eastern Caribbean tend to be 7 nights, 8 nights, and 5 nights, which gives you a good sense of how this region is usually packaged by cruise lines.
Based on currently tracked pricing, one of the more affordable departure periods appears to be May 2028. That does not mean every sailing in that month is cheap, but it is a useful signal when you are comparing options across the calendar.
The best way to browse this page is usually to start with the popular itineraries section, then use the map and the ports list to narrow your thinking. Once you know which route pattern you like, the individual sailing pages are where exact departure dates and prices become most useful.
Common questions about cruising in Eastern Caribbean.
Eastern Caribbean currently has 1,206 itineraries and 2,294 upcoming sailings on Jibhop, spanning a range of route shapes, ship types, and cruise lines.
Based on currently tracked pricing, the median future sailing price in Eastern Caribbean is about $1,154. Exact pricing varies by ship, itinerary, season, and cabin type.
Based on currently tracked pricing, May 2028 appears to be one of the more affordable departure periods. That is a directional signal rather than a guarantee, since individual sailings can still vary a lot.
Usually it is better to start with itineraries so you can understand the route patterns that define Eastern Caribbean. Once you know which route you like, compare exact sailings for dates, ships, and pricing.