Grandeur of the Seas
Colón (Panama Canal) → Kingstown → Tortola → San Juan
Apr 24 · 7 nights
Good value
$933 balcony · $133/night
10% below typical · 6-month low
Eastern Caribbean Cruises
Explore Philipsburg, San Juan, Puerto Plata, Basseterre, Saint Kitts, and Saint Thomas and dozens of Eastern Caribbean ports.
Browse nearly 2,291 upcoming sailings across 1,200+ itineraries.
1,230 itineraries · 2,291 sailings · 45 ports
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Best value departures
Departures in Eastern Caribbean that are currently pricing well below their typical tracked rate.
SeaDream II
Lisboa → Philipsburg → San Juan
Nov 14 · 13 nights
About average
$5,041 oceanview · $388/night
Norwegian Escape
Port Canaveral → Puerto Plata → Great Stirrup Cay → Port Canaveral
Nov 27 · 7 nights
Exceptional value
$529 inside · $76/night
27% below typical · 6-month low
SeaDream I
Málaga → Jost Van Dyke → San Juan
Oct 24 · 14 nights
About average
$5,565 oceanview · $398/night
Featured departures
Upcoming Eastern Caribbean cruises worth comparing
Upcoming departures with complete itinerary, availability, and current pricing data.
Grandeur of the Seas
Colón (Panama Canal) → Kingstown → Tortola → San Juan
Apr 24 · 7 nights
Good value
$933 balcony · $133/night
10% below typical · 6-month low
Norwegian Getaway
Port Canaveral → Puerto Plata → Great Stirrup Cay → Port Canaveral
Nov 11 · 5 nights
Good value
$359 inside · $72/night
20% below typical · 6-month low
Carnival Vista
Port Canaveral → Puerto Plata → Celebration Key → Port Canaveral
Sep 13 · 6 nights
Good value
$420 inside · $70/night
24% below typical · 3-month low
Celebrity Eclipse
Fort Lauderdale → Philipsburg → Basseterre, Saint Kitts → Fort Lauderdale
Dec 14 · 9 nights
Good value
$725 inside · $81/night
20% below typical · 6-month low
Freedom of the Seas
Miami → Nassau → Costa Maya (Mahahual) → Miami
Jan 9 · 5 nights
Good value
$398 inside · $80/night
12% below typical · 6-month low
Norwegian Escape
Port Canaveral → Puerto Plata → Great Stirrup Cay → Port Canaveral
Dec 11 · 7 nights
Good value
$629 inside · $90/night
14% below typical · 30-day low
Harmony of the Seas
Port Canaveral → Coco Cay → Philipsburg → Port Canaveral
Mar 4 · 7 nights
About average
$947 inside · $135/night
Independence of the Seas
Miami → Oranjestad → Grand Turk Island → Cape Liberty, NJ (NYC)
May 10 · 9 nights
Exceptional value
$679 inside · $75/night
26% below typicalExplore Eastern Caribbean cruise routes
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.
Popular Eastern Caribbean cruise itineraries
Eastern Caribbean Loop via Puerto Plata & Great Stirrup Cay
From $529
$529
·
126 upcoming sailings
·
8 ships
126 upcoming sailings
8 ships
View itinerary →
Eastern Caribbean Loop via Coco Cay & Charlotte Amalie, Saint Thomas
From $916
$916
·
54 upcoming sailings
·
4 ships
54 upcoming sailings
4 ships
View itinerary →
Eastern Caribbean Loop: Grand Turk Island & Bimini
From $645
$645
·
43 upcoming sailings
·
3 ships
43 upcoming sailings
3 ships
View itinerary →
Eastern Caribbean Loop via Philipsburg & Coco Cay
From $1,146
$1,146
·
42 upcoming sailings
·
2 ships
42 upcoming sailings
2 ships
View itinerary →
Eastern Caribbean Loop: Puerto Plata & Bimini
From $595
$595
·
35 upcoming sailings
·
4 ships
35 upcoming sailings
4 ships
View itinerary →
Eastern Caribbean Loop via Celebration Key & San Juan
From $504
$504
·
34 upcoming sailings
·
5 ships
34 upcoming sailings
5 ships
View itinerary →
Eastern Caribbean Loop via Half Moon Cay & Grand Turk Island
From $542
$542
·
30 upcoming sailings
·
2 ships
30 upcoming sailings
2 ships
View itinerary →
Eastern Caribbean Loop via Puerto Plata & Charlotte Amalie, Saint Thomas
From $768
$768
·
29 upcoming sailings
·
3 ships
29 upcoming sailings
3 ships
View itinerary →
Eastern Caribbean Loop: Puerto Plata, Ocean Cay & Cozumel
From $1,151
$1,151
·
26 upcoming sailings
·
1 ship
26 upcoming sailings
1 ship
View itinerary →
Eastern Caribbean Loop via Celebration Key & Puerto Plata
From $366
$366
·
24 upcoming sailings
·
6 ships
24 upcoming sailings
6 ships
View itinerary →
Eastern Caribbean Loop via Tortola, Philipsburg & Saint John's
From $477
$477
·
23 upcoming sailings
·
2 ships
23 upcoming sailings
2 ships
View itinerary →
Eastern Caribbean Loop via Charlotte Amalie, Saint Thomas, Frederiksted, Saint Croix & Philipsburg
From $650
$650
·
23 upcoming sailings
·
2 ships
23 upcoming sailings
2 ships
View itinerary →
Eastern Caribbean Loop via Charlotte Amalie, Saint Thomas, Frederiksted, Saint Croix & Philipsburg
From $501
$501
·
21 upcoming sailings
·
2 ships
21 upcoming sailings
2 ships
View itinerary →
Eastern Caribbean Loop: Catalina Island, Bridgetown & Fort-de-France
From $643
$643
·
21 upcoming sailings
·
1 ship
21 upcoming sailings
1 ship
View itinerary →
Eastern Caribbean Loop via Half Moon Cay & San Juan
From $483
$483
·
20 upcoming sailings
·
1 ship
20 upcoming sailings
1 ship
View itinerary →
Eastern Caribbean Loop via Puerto Plata & Ocean Cay
From $780
$780
·
19 upcoming sailings
·
1 ship
19 upcoming sailings
1 ship
View itinerary →
Eastern Caribbean Loop via Tortola & Disney Castaway Cay
From $1,732
$1,732
·
19 upcoming sailings
·
1 ship
19 upcoming sailings
1 ship
View itinerary →
Eastern Caribbean Loop via Princess Cays & Puerto Plata
Price unavailable
Price unavailable
·
19 upcoming sailings
·
3 ships
19 upcoming sailings
3 ships
View itinerary →
Eastern Caribbean Loop: Catalina Island, Spanish Town & Philipsburg
From $645
$645
·
17 upcoming sailings
·
1 ship
17 upcoming sailings
1 ship
View itinerary →
Eastern Caribbean Loop: Grand Turk Island & San Juan
From $749
$749
·
17 upcoming sailings
·
5 ships
17 upcoming sailings
5 ships
View itinerary →
Eastern Caribbean Loop: Pointe-à-Pitre, Philipsburg & Saint John's
From $820
$820
·
17 upcoming sailings
·
4 ships
17 upcoming sailings
4 ships
View itinerary →
Eastern Caribbean Loop: Antigua & La Romana
From $629
$629
·
16 upcoming sailings
·
1 ship
16 upcoming sailings
1 ship
View itinerary →
Eastern Caribbean Loop: Pointe-à-Pitre, Road Town, Tortola & La Romana
From $630
$630
·
16 upcoming sailings
·
1 ship
16 upcoming sailings
1 ship
View itinerary →
Eastern Caribbean Loop via Tortola, Basseterre, Saint Kitts & Bridgetown
From $999
$999
·
16 upcoming sailings
·
1 ship
16 upcoming sailings
1 ship
View itinerary →
Price intelligence
Get a quick feel for how pricing behaves across Eastern Caribbean.
Median future price
$1,189
Cheapest currently available
$349
Tracked priced sailings
1,668
Median price by departure month
September 2026
$754
October 2026
$1,095
November 2026
$1,091
December 2026
$1,352
January 2027
$1,159
February 2027
$1,181
March 2027
$1,040
April 2027
$827
Cheapest embarkation ports for Eastern Caribbean cruises
Port Canaveral
279 priced sailings
From
$349
Fort Lauderdale
176 priced sailings
From
$362
Miami
577 priced sailings
From
$366
San Juan
215 priced sailings
From
$406
Norfolk
33 priced sailings
From
$542
Fort-de-France
16 priced sailings
From
$629
La Romana
14 priced sailings
From
$643
Philadelphia
19 priced sailings
From
$739
Pointe-à-Pitre
10 priced sailings
From
$743
Tampa
3 priced sailings
From
$791
Top ports
The ports most central to cruising in Eastern Caribbean.
Philipsburg
607 itineraries
1122 sailings
San Juan
647 itineraries
974 sailings
Puerto Plata
380 itineraries
829 sailings
Basseterre, Saint Kitts
488 itineraries
744 sailings
Saint Thomas
275 itineraries
529 sailings
Tortola
218 itineraries
494 sailings
Charlotte Amalie, Saint Thomas
193 itineraries
458 sailings
Grand Turk Island
216 itineraries
439 sailings
Antigua
271 itineraries
403 sailings
Saint John's
160 itineraries
304 sailings
Saint-Barthélemy
170 itineraries
224 sailings
Spanish Town (Virgin Gorda)
87 itineraries
198 sailings
Pointe-à-Pitre
85 itineraries
196 sailings
La Romana
52 itineraries
159 sailings
Catalina Island
45 itineraries
155 sailings
Frederiksted, Saint Croix
46 itineraries
123 sailings
Jost Van Dyke
91 itineraries
116 sailings
Terre-de-Haut (Les Saintes)
72 itineraries
116 sailings
Road Town, Tortola
52 itineraries
116 sailings
Cruz Bay, Saint John
109 itineraries
108 sailings
Samana
54 itineraries
83 sailings
South Friars Bay
41 itineraries
80 sailings
Road Bay
57 itineraries
76 sailings
Little Bay
36 itineraries
59 sailings
Ships sailing this region
Ships with strong presence in Eastern Caribbean.
MSC Opera
MSC Cruises
148 sailings
$629
Seabourn Ovation
Seabourn
64 sailings
$3,599
Emerald Sakara
Emerald Cruises
63 sailings
$4,365
Carnival Magic
Carnival Cruise Line
58 sailings
$366
MSC Meraviglia
MSC Cruises
56 sailings
$659
Emerald Princess
Princess Cruises
54 sailings
Regal Princess
Princess Cruises
54 sailings
Arvia
P&O Cruises
52 sailings
$1,215
Resilient Lady
Virgin Voyages
50 sailings
$645
Star of the Seas
Royal Caribbean International
48 sailings
$1,022
MSC World America
MSC Cruises
47 sailings
$780
Rhapsody of the Seas
Royal Caribbean International
46 sailings
$468
Norwegian Prima
Norwegian Cruise Line
45 sailings
$469
Valiant Lady
Virgin Voyages
41 sailings
$595
Norwegian Aqua
Norwegian Cruise Line
37 sailings
$659
Star Princess
Princess Cruises
35 sailings
Rotterdam
Holland America
34 sailings
$1,054
Grandeur of the Seas
Royal Caribbean International
32 sailings
$472
Cruise lines in Eastern Caribbean
The operators with the broadest footprint here.
Royal Caribbean International
20 ships
·
349 upcoming sailings
From $349
MSC Cruises
13 ships
·
342 upcoming sailings
From $629
Princess Cruises
12 ships
·
263 upcoming sailings
From $614
Norwegian Cruise Line
17 ships
·
224 upcoming sailings
From $469
Carnival Cruise Line
17 ships
·
217 upcoming sailings
From $366
Celebrity Cruises
9 ships
·
131 upcoming sailings
From $362
Virgin Voyages
4 ships
·
130 upcoming sailings
From $595
Holland America
7 ships
·
97 upcoming sailings
From $549
Emerald Cruises
3 ships
·
83 upcoming sailings
From $4,365
P&O Cruises
3 ships
·
82 upcoming sailings
From $1,215
Seabourn
4 ships
·
77 upcoming sailings
From $3,569
Silversea Cruises
5 ships
·
47 upcoming sailings
From $8,450
About Eastern Caribbean cruises
A quick guide to what cruising this region typically looks like.
Eastern Caribbean is one of the core cruise regions on Jibhop, with 1,230 itineraries, 2,291 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, 14 nights, and 8 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 September 2026. 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.
Frequently asked questions
Common questions about cruising in Eastern Caribbean.
What kinds of cruises are available in Eastern Caribbean?
Eastern Caribbean currently has 1,230 itineraries and 2,291 upcoming sailings on Jibhop, spanning a range of route shapes, ship types, and cruise lines.
How much do Eastern Caribbean cruises cost?
Based on currently tracked pricing, the median future sailing price in Eastern Caribbean is about $1,189. Exact pricing varies by ship, itinerary, season, and cabin type.
When is the cheapest time to cruise Eastern Caribbean?
Based on currently tracked pricing, September 2026 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.
Should I browse itineraries or sailings first?
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.