Private destination routes
For a trip that includes a cruise-line private destination.
Puerto Plata · Saint Thomas · Tortola · Great Stirrup Cay
Explore this itinerary →
Caribbean
Eastern Caribbean Cruises
Routes here bring ports such as Philipsburg, San Juan, and Basseterre, Saint Kitts into reach. Choose how much time you want ashore versus on the ship, then compare departure ports and dates.
Popular trip length: 7 nights
Private destination options
Start with the route
Choose your kind of trip
A few different ways to explore Eastern Caribbean, drawn from itineraries with upcoming departures.
A shorter escape
For fitting a cruise into a few days away.
Grand Turk Island · Bimini
Explore this itinerary →A mix of ports and sea days
For balancing time ashore with time on board.
Half Moon Cay · Grand Turk Island · Puerto Plata
Explore this itinerary →Start and finish somewhere different
For combining a cruise with stays in two different places.
Antigua · Fort-de-France · Pointe-à-Pitre · Basseterre, Saint Kitts + 1 more
Explore this itinerary →Current sailings worth comparing
Departures in Eastern Caribbean whose cabin-level price history currently points to favorable pricing. Compare the fare and booking context on each sailing.
No departures in this region currently have favorable pricing based on Jibhop's price history.
Plan your dates and budget
When to go & what it costs
- $1,324
- $858–$2,639
- $179
Compare departure months
October 2026 has the lowest median nightly fare in the months shown; July 2027 has the highest.
Oct 2026
$76
Nov 2026
$106
Dec 2026
$153
Jan 2027
$130
Feb 2027
$135
Mar 2027
$134
Apr 2027
$121
May 2027
$125
Jun 2027
$143
Jul 2027
$170
Aug 2027
$141
Sep 2027
$116
Alerts
Get deal alerts for Eastern Caribbean
We'll email you when unusually cheap cruises appear in this region.
Where should I start?
Choose your departure port
Balance route choice and cruise fare with the cost of getting to the port.
Get to know Eastern Caribbean
Loading map...
Key ports
The ports most central to cruising in Eastern Caribbean.
Philipsburg
979 itineraries
1768 sailings
San Juan
1053 itineraries
1555 sailings
Basseterre, Saint Kitts
844 itineraries
1430 sailings
Puerto Plata
612 itineraries
1342 sailings
Grand Turk Island
406 itineraries
736 sailings
Saint Thomas
383 itineraries
715 sailings
More ports
Antigua
341 itineraries
638 sailings
Tortola
240 itineraries
621 sailings
Saint John's
343 itineraries
600 sailings
Charlotte Amalie, Saint Thomas
299 itineraries
573 sailings
Saint-Barthélemy
394 itineraries
556 sailings
Pointe-à-Pitre
222 itineraries
423 sailings
Spanish Town (Virgin Gorda)
203 itineraries
408 sailings
La Romana
117 itineraries
271 sailings
Jost Van Dyke
193 itineraries
261 sailings
Terre-de-Haut (Les Saintes)
155 itineraries
245 sailings
Road Town
150 itineraries
218 sailings
Catalina Island
65 itineraries
202 sailings
Cruz Bay, Saint John
185 itineraries
195 sailings
Road Bay
138 itineraries
188 sailings
Frederiksted, Saint Croix
60 itineraries
153 sailings
Samana
90 itineraries
131 sailings
Norman Island
78 itineraries
131 sailings
Road Town, Tortola
57 itineraries
124 sailings
Ships sailing this region
Ships with strong presence in Eastern Caribbean.
MSC Opera
MSC Cruises
178 sailings
$179
Arvia
P&O Cruises
106 sailings
$1,350
Regal Princess
Princess Cruises
98 sailings
$509
Seabourn Ovation
Seabourn
86 sailings
$2,639
More ships
Emerald Sakara
Emerald Cruises
83 sailings
$3,968
Star Princess
Princess Cruises
76 sailings
$534
MSC World America
MSC Cruises
75 sailings
$468
MSC Meraviglia
MSC Cruises
73 sailings
$259
SeaDream I
SeaDream Yacht Club
72 sailings
$3,394
Costa Fascinosa
Costa Cruises
71 sailings
$507
Iona
P&O Cruises
71 sailings
$1,931
Sky Princess
Princess Cruises
61 sailings
$529
Allure of the Seas
Royal Caribbean International
58 sailings
$329
Carnival Vista
Carnival Cruise Line
58 sailings
$340
Emerald Princess
Princess Cruises
57 sailings
$500
Valiant Lady
Virgin Voyages
57 sailings
$645
Costa Serena
Costa Cruises
56 sailings
$995
Carnival Magic
Carnival Cruise Line
54 sailings
$335
Cruise lines in Eastern Caribbean
Explore more itineraries
- Eastern Caribbean Loop: Puerto Plata & Great Stirrup Cay
- Eastern Caribbean Loop: Puerto Plata & Great Stirrup Cay
- Bahamas Loop from Port Canaveral: Coco Cay & Charlotte Amalie, Saint Thomas
- Eastern Caribbean Loop: Grand Turk Island & Bimini
- Eastern Caribbean Loop: Half Moon Cay & Grand Turk Island
- Eastern Caribbean Loop via Philipsburg & Coco Cay
- Eastern Caribbean Arc: Basseterre, Saint Kitts, Ocho Rios & Road Town, Tortola
- Bahamas Loop via Puerto Plata & Celebration Key
- Eastern Caribbean Loop: Basseterre, Saint Kitts, Roseau & Philipsburg
- Southern Caribbean Arc: San Juan, Saint Thomas & Castries
- Eastern Caribbean Loop: Pointe-à-Pitre, Philipsburg & Saint John's
- Eastern Caribbean Loop via Celebration Key & San Juan
More upcoming Eastern Caribbean cruises
Featured departures
More departures to explore
Upcoming departures with complete itinerary, availability, and current pricing data.
Allure of the Seas
Miami → Coco Cay → Charlotte Amalie, Saint Thomas → Miami
Nov 8, 2026 · 7 nights
$329 · $47/night
Norwegian Prima
San Juan → Philipsburg → Tortola → San Juan
Dec 27, 2026 · 7 nights
$1,419 · $203/night
Carnival Sunshine
Norfolk → Half Moon Cay → Puerto Plata → Norfolk
Oct 31, 2026 · 8 nights
$601 interior · $75/night
24% below typical · Price trending down
Norwegian Star
Miami → Puerto Plata → Alicante → Barcelona
Mar 1, 2027 · 15 nights
$739 · $49/night
About Eastern Caribbean cruises
Eastern Caribbean has 2,137 itineraries, 4,042 upcoming sailings, and calls across 54 ports.
The most common cruise lengths in Eastern Caribbean tend to be 7 nights, 14 nights, and 8 nights.
Based on currently tracked pricing, one of the more affordable departure periods appears to be October 2026.
Frequently asked questions
What kinds of cruises are available in Eastern Caribbean?
Eastern Caribbean currently has 2,137 itineraries and 4,042 upcoming sailings.
How much do Eastern Caribbean cruises cost?
The median future sailing price in Eastern Caribbean is about $1,324.
When is the cheapest time to cruise Eastern Caribbean?
October 2026 appears to be one of the more affordable departure periods.