SeaDream I • SeaDream Yacht Club
14-night Eastern Caribbean Arc via Jost Van Dyke
Oct 24, 2027 → Nov 7, 2027 • Málaga → San Juan
From $5,366
$383/night
Great deal
↓63% below typical
Eastern Caribbean Cruises
Eastern Caribbean cruises include 1,173 itineraries, 2,206 upcoming sailings, and 44 ports. Explore the route patterns, ships, and departure options that define this region.
1,173
Itineraries
2,206
Upcoming sailings
44
Ports
27
Cruise lines
Best value departures
Departures in Eastern Caribbean that are currently pricing well below their typical tracked rate.
SeaDream I • SeaDream Yacht Club
14-night Transatlantic Crossing via Málaga & San Juan
Oct 28, 2028 → Nov 11, 2028 • Málaga → San Juan
From $4,883
$349/night
Great deal
↓66% below typical
Valiant Lady • Virgin Voyages
12-night Eastern Caribbean Arc via Kings Wharf, Bimini & Frederiksted, Saint Croix
Oct 19, 2026 → Oct 31, 2026 • New York → San Juan
From $1,068
$89/night
Great deal
↓37% below typical
Queen Elizabeth • Cunard Line
40-night Eastern Caribbean Arc via Endicott Arm, Panama Canal & Cruz Bay, Saint John
Sep 17, 2026 → Oct 27, 2026 • Seattle → Miami
From $3,016
$75/night
Great deal
↓49% below typical
Explore 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
Start with the route patterns that define this region.
Eastern Caribbean Loop via Puerto Plata & Great Stirrup Cay (Private Island Focus)
Eastern Caribbean • Next: Jun 6
From $779
148 upcoming sailings
8 ships
View itinerary →
Eastern Caribbean Loop via Coco Cay & Charlotte Amalie, Saint Thomas (Private Island Focus)
Eastern Caribbean • Next: Jun 21
From $916
55 upcoming sailings
4 ships
View itinerary →
Eastern Caribbean Loop via Philipsburg & Coco Cay (Private Island Focus)
Eastern Caribbean • Next: Jun 27
From $1,233
48 upcoming sailings
2 ships
View itinerary →
Eastern Caribbean Loop via Celebration Key & San Juan (Private Island Focus)
Eastern Caribbean • Next: Nov 1
From $504
34 upcoming sailings
5 ships
View itinerary →
Eastern Caribbean Loop via Tortola, Philipsburg & Saint John's (Port-Heavy)
Eastern Caribbean • Next: Jun 6
From $548
31 upcoming sailings
2 ships
View itinerary →
Eastern Caribbean Loop via Celebration Key & Puerto Plata (Private Island Focus)
Eastern Caribbean • Next: Jun 21
From $373
30 upcoming sailings
6 ships
View itinerary →
Eastern Caribbean Loop via Half Moon Cay & Grand Turk Island (Best Balance)
Eastern Caribbean • Next: Oct 31
From $554
30 upcoming sailings
2 ships
View itinerary →
Eastern Caribbean Loop via Puerto Plata & Charlotte Amalie, Saint Thomas (Best Balance)
Eastern Caribbean • Next: Nov 7
From $818
29 upcoming sailings
3 ships
View itinerary →
Eastern Caribbean Loop via Charlotte Amalie, Saint Thomas, Frederiksted, Saint Croix & Philipsburg (Port-Heavy)
Eastern Caribbean • Next: Jun 13
From $532
28 upcoming sailings
2 ships
View itinerary →
Eastern Caribbean Loop via Tortola & Disney Castaway Cay (Private Island Focus)
Eastern Caribbean • Next: Jun 6
From $1,553
27 upcoming sailings
1 ship
View itinerary →
Eastern Caribbean Loop via Charlotte Amalie, Saint Thomas, Frederiksted, Saint Croix & Philipsburg (Port-Heavy)
Eastern Caribbean • Next: May 1
From $674
23 upcoming sailings
2 ships
View itinerary →
Eastern Caribbean Loop via Half Moon Cay & San Juan (Best Balance)
Eastern Caribbean • Next: Jul 11
From $526
22 upcoming sailings
1 ship
View itinerary →
Eastern Caribbean Loop via Puerto Plata & Ocean Cay (Private Island Focus)
Eastern Caribbean • Next: Jun 27
From $568
21 upcoming sailings
1 ship
View itinerary →
Eastern Caribbean Loop: Catalina Island, Bridgetown & Fort-de-France (Port-Heavy)
Eastern Caribbean • Next: Nov 16
From $628
20 upcoming sailings
1 ship
View itinerary →
Eastern Caribbean Loop via Princess Cays & Puerto Plata (Private Island Focus)
Eastern Caribbean • Next: Apr 3
From $833
19 upcoming sailings
3 ships
View itinerary →
Eastern Caribbean Loop via Grand Turk Island (Best Balance)
Eastern Caribbean • Next: Jun 15
From $422
16 upcoming sailings
4 ships
View itinerary →
Eastern Caribbean Loop: Antigua & La Romana (Best Balance)
Eastern Caribbean • Next: Apr 23
From $629
16 upcoming sailings
1 ship
View itinerary →
Eastern Caribbean Loop: Catalina Island, Spanish Town & Philipsburg (Port-Heavy)
Eastern Caribbean • Next: Apr 19
From $629
16 upcoming sailings
1 ship
View itinerary →
Eastern Caribbean Loop: Pointe-à-Pitre, Road Town, Tortola & La Romana (Port-Heavy)
Eastern Caribbean • Next: Apr 16
From $630
16 upcoming sailings
1 ship
View itinerary →
Eastern Caribbean Loop via Tortola, Basseterre, Saint Kitts & Bridgetown (Port-Heavy)
Eastern Caribbean • Next: Nov 22
From $1,259
16 upcoming sailings
1 ship
View itinerary →
Eastern Caribbean Loop: Basseterre, Saint Kitts & Road Bay (Best Balance)
Eastern Caribbean • Next: Nov 20
From $5,866
16 upcoming sailings
1 ship
View itinerary →
Eastern Caribbean Loop via Puerto Plata & Grand Turk Island (Best Balance)
Eastern Caribbean • Next: May 16
From $381
15 upcoming sailings
4 ships
View itinerary →
Eastern Caribbean Loop via Saint Thomas & Celebration Key (Private Island Focus)
Eastern Caribbean • Next: Jul 25
From $557
15 upcoming sailings
3 ships
View itinerary →
Eastern Caribbean Loop via Pointe-à-Pitre, Philipsburg & Saint John's (Port-Heavy)
Eastern Caribbean • Next: Dec 19
From $643
15 upcoming sailings
3 ships
View itinerary →
Price intelligence
Get a quick feel for how pricing behaves across Eastern Caribbean.
Median future price
$1,259
Cheapest currently available
$209
Tracked priced sailings
1,909
Median price by departure month
June 2026
$1,379
July 2026
$1,409
August 2026
$1,074
September 2026
$909
October 2026
$1,068
November 2026
$1,155
December 2026
$1,421
January 2027
$1,096
Cheapest embarkation ports for Eastern Caribbean cruises
Fort-de-France
20 priced sailings
From
$209
La Romana
18 priced sailings
From
$209
Miami
552 priced sailings
From
$373
Port Canaveral
375 priced sailings
From
$381
Fort Lauderdale
274 priced sailings
From
$387
San Juan
282 priced sailings
From
$431
Norfolk
34 priced sailings
From
$554
Tampa
3 priced sailings
From
$739
Pointe-à-Pitre
10 priced sailings
From
$759
Baltimore
11 priced sailings
From
$899
Upcoming sailings
Exact departures coming up soon in Eastern Caribbean.
Celebrity Beyond • Celebrity Cruises
7-night Eastern Caribbean Loop via Coco Cay & San Juan
Jun 7, 2026 → Jun 14, 2026 • Miami ↔
From $1,298
$185/night
Typical price
↑10% above typical
Caribbean Princess • Princess Cruises
14-night Eastern Caribbean Arc via Nassau, Princess Cays & Puerto Plata
Jun 7, 2026 → Jun 21, 2026 • Port Canaveral ↔
From $1,665
$119/night
Typical price
↓9% below typical
Carnival Magic • Carnival Cruise Line
8-night Eastern Caribbean Loop via Princess Cays & San Juan
Jun 13, 2026 → Jun 21, 2026 • Miami ↔
From $989
$124/night
Typical price
↑7% above typical
Norwegian Luna • Norwegian Cruise Line
7-night Eastern Caribbean Loop via Puerto Plata & Great Stirrup Cay
Jun 13, 2026 → Jun 20, 2026 • Miami ↔
From $1,359
$194/night
Typical price
↑4% above typical
Rhapsody of the Seas • Royal Caribbean International
7-night Eastern Caribbean Loop via Charlotte Amalie, Saint Thomas, Frederiksted, Saint Croix & Philipsburg
Jun 13, 2026 → Jun 20, 2026 • San Juan ↔
From $1,684
$241/night
Priced high
↑37% above typical
Caribbean Princess • Princess Cruises
7-night Eastern Caribbean Loop via Grand Turk Island & Puerto Plata
Jun 14, 2026 → Jun 21, 2026 • Port Canaveral ↔
From $867
$124/night
Typical price
↓8% below typical
Norwegian Prima • Norwegian Cruise Line
7-night Eastern Caribbean Loop via Puerto Plata & Great Stirrup Cay
Jun 14, 2026 → Jun 21, 2026 • Port Canaveral ↔
From $1,379
$197/night
Typical price
↑5% above typical
Carnival Sunshine • Carnival Cruise Line
9-night Eastern Caribbean Loop via Puerto Plata & San Juan
Jun 14, 2026 → Jun 23, 2026 • Norfolk ↔
From $1,443
$160/night
Priced high
↑23% above typical
Caribbean Princess • Princess Cruises
14-night Eastern Caribbean Loop via Grand Turk Island & Puerto Plata
Jun 14, 2026 → Jun 28, 2026 • Port Canaveral ↔
From $1,766
$126/night
Typical price
↓7% below typical
Star of the Seas • Royal Caribbean International
7-night Eastern Caribbean Loop via Coco Cay & Charlotte Amalie, Saint Thomas
Jun 14, 2026 → Jun 21, 2026 • Port Canaveral ↔
From $3,694
$528/night
Priced high
↑72% above typical
Jewel of the Seas • Royal Caribbean International
4-night Eastern Caribbean Loop via Grand Turk Island
Jun 15, 2026 → Jun 19, 2026 • Fort Lauderdale ↔
From $699
$175/night
Norwegian Luna • Norwegian Cruise Line
7-night Eastern Caribbean Loop via Puerto Plata & Great Stirrup Cay
Jun 20, 2026 → Jun 27, 2026 • Miami ↔
From $1,409
$201/night
Typical price
↑8% above typical
Icon of the Seas • Royal Caribbean International
7-night Eastern Caribbean Loop via Philipsburg & Coco Cay
Jun 20, 2026 → Jun 27, 2026 • Miami ↔
From $1,537
$220/night
Rhapsody of the Seas • Royal Caribbean International
7-night Eastern Caribbean Loop via Tortola, Philipsburg & Saint John's
Jun 20, 2026 → Jun 27, 2026 • San Juan ↔
From $1,549
$221/night
Priced high
↑57% above typical
Disney Treasure • Disney Cruise Line
7-night Eastern Caribbean Loop via Tortola & Disney Castaway Cay
Jun 20, 2026 → Jun 27, 2026 • Port Canaveral ↔
From $2,331
$333/night
Typical price
↓4% below typical
Carnival Magic • Carnival Cruise Line
6-night Eastern Caribbean Loop via Celebration Key & Puerto Plata
Jun 21, 2026 → Jun 27, 2026 • Miami ↔
From $862
$144/night
Priced high
↑19% above typical
Caribbean Princess • Princess Cruises
7-night Eastern Caribbean Loop via Grand Turk Island & Puerto Plata
Jun 21, 2026 → Jun 28, 2026 • Port Canaveral ↔
From $954
$136/night
Typical price
↑1% above typical
Celebrity Beyond • Celebrity Cruises
7-night Eastern Caribbean Loop via Coco Cay & San Juan
Jun 21, 2026 → Jun 28, 2026 • Miami ↔
From $1,313
$188/night
Star of the Seas • Royal Caribbean International
7-night Eastern Caribbean Loop via Coco Cay & Charlotte Amalie, Saint Thomas
Jun 21, 2026 → Jun 28, 2026 • Port Canaveral ↔
From $1,342
$192/night
Great deal
↓31% below typical
Caribbean Princess • Princess Cruises
14-night Itinerary TCGDT-DOPOP-PRSJU-USPCV-BSNAS-P221398-DOPOP-TCGDT
Jun 21, 2026 → Jul 5, 2026 • Port Canaveral ↔
From $2,009
$144/night
Priced high
↑10% above typical
Adventure of the Seas • Royal Caribbean International
8-night Eastern Caribbean Loop via Coco Cay & San Juan
Jun 26, 2026 → Jul 4, 2026 • Port Canaveral ↔
From $2,759
$345/night
Priced high
↑38% above typical
MSC World America • MSC Cruises
7-night Eastern Caribbean Loop via Puerto Plata & Ocean Cay
Jun 27, 2026 → Jul 4, 2026 • Miami ↔
From $844
$121/night
Norwegian Luna • Norwegian Cruise Line
7-night Eastern Caribbean Loop via Puerto Plata & Great Stirrup Cay
Jun 27, 2026 → Jul 4, 2026 • Miami ↔
From $1,259
$180/night
Typical price
↓4% below typical
Carnival Vista • Carnival Cruise Line
8-night Eastern Caribbean Loop via Puerto Plata & Celebration Key
Jun 27, 2026 → Jul 5, 2026 • Port Canaveral ↔
From $1,326
$166/night
Priced high
↑20% above typical
Allure of the Seas • Royal Caribbean International
8-night Eastern Caribbean Loop via Basseterre, Saint Kitts & Coco Cay
Jun 27, 2026 → Jul 5, 2026 • Fort Lauderdale ↔
From $1,465
$183/night
Typical price
↑1% above typical
Rhapsody of the Seas • Royal Caribbean International
7-night Eastern Caribbean Loop via Charlotte Amalie, Saint Thomas, Frederiksted, Saint Croix & Philipsburg
Jun 27, 2026 → Jul 4, 2026 • San Juan ↔
From $1,479
$211/night
Icon of the Seas • Royal Caribbean International
7-night Eastern Caribbean Loop via Philipsburg & Coco Cay
Jun 27, 2026 → Jul 4, 2026 • Miami ↔
From $1,655
$237/night
Good value
↓20% below typical
Disney Destiny • Disney Cruise Line
7-night Eastern Caribbean Loop via Lighthouse Point, Florida & San Juan
Jun 27, 2026 → Jul 4, 2026 • Fort Lauderdale ↔
From $2,967
$424/night
Typical price
Norwegian Prima • Norwegian Cruise Line
7-night Eastern Caribbean Loop via Puerto Plata & Great Stirrup Cay
Jun 28, 2026 → Jul 5, 2026 • Port Canaveral ↔
From $1,329
$190/night
Typical price
↑2% above typical
Caribbean Princess • Princess Cruises
14-night Eastern Caribbean Arc via Nassau, Princess Cays & Puerto Plata
Jun 28, 2026 → Jul 12, 2026 • Port Canaveral ↔
From $1,893
$135/night
Typical price
Top ports
The ports most central to cruising in Eastern Caribbean.
Philipsburg
577 itineraries
1105 sailings
San Juan
627 itineraries
992 sailings
Puerto Plata
369 itineraries
821 sailings
Basseterre, Saint Kitts
470 itineraries
729 sailings
Saint Thomas
263 itineraries
536 sailings
Tortola
212 itineraries
532 sailings
Charlotte Amalie, Saint Thomas
181 itineraries
480 sailings
Antigua
259 itineraries
374 sailings
Grand Turk Island
197 itineraries
371 sailings
Saint John's
147 itineraries
306 sailings
Saint-Barthélemy
156 itineraries
204 sailings
Spanish Town (Virgin Gorda)
84 itineraries
188 sailings
Pointe-à-Pitre
73 itineraries
165 sailings
La Romana
48 itineraries
150 sailings
Catalina Island
43 itineraries
145 sailings
Frederiksted, Saint Croix
46 itineraries
141 sailings
Road Town, Tortola
52 itineraries
110 sailings
Terre-de-Haut (Les Saintes)
64 itineraries
102 sailings
Cruz Bay, Saint John
107 itineraries
96 sailings
Jost Van Dyke
76 itineraries
92 sailings
Road Bay
54 itineraries
73 sailings
Samana
45 itineraries
66 sailings
Little Bay
34 itineraries
57 sailings
South Friars Bay
28 itineraries
55 sailings
Ships sailing this region
Ships with strong presence in Eastern Caribbean.
MSC Opera
MSC Cruises
139 sailings
$209
Carnival Magic
Carnival Cruise Line
68 sailings
$373
Regal Princess
Princess Cruises
65 sailings
$731
Emerald Sakara
Emerald Cruises
63 sailings
$5,302
Rhapsody of the Seas
Royal Caribbean International
61 sailings
$539
Star of the Seas
Royal Caribbean International
58 sailings
$1,311
MSC Meraviglia
MSC Cruises
56 sailings
$559
Emerald Princess
Princess Cruises
54 sailings
$695
Norwegian Prima
Norwegian Cruise Line
52 sailings
$569
Arvia
P&O Cruises
52 sailings
$1,417
Norwegian Luna
Norwegian Cruise Line
46 sailings
$909
Seabourn Ovation
Seabourn
42 sailings
$3,598
Celebrity Beyond
Celebrity Cruises
39 sailings
$693
Norwegian Aqua
Norwegian Cruise Line
37 sailings
$1,019
Icon of the Seas
Royal Caribbean International
36 sailings
$1,233
Star Princess
Princess Cruises
35 sailings
$612
Disney Treasure
Disney Cruise Line
35 sailings
$1,553
Carnival Celebration
Carnival Cruise Line
33 sailings
$478
Cruise lines in Eastern Caribbean
The operators with the broadest footprint here.
Royal Caribbean International
20 ships
·
392 upcoming sailings
From $422
Princess Cruises
12 ships
·
296 upcoming sailings
From $604
MSC Cruises
12 ships
·
290 upcoming sailings
From $209
Norwegian Cruise Line
17 ships
·
247 upcoming sailings
From $569
Carnival Cruise Line
17 ships
·
233 upcoming sailings
From $373
Celebrity Cruises
9 ships
·
137 upcoming sailings
From $387
Emerald Cruises
3 ships
·
83 upcoming sailings
From $5,076
P&O Cruises
3 ships
·
82 upcoming sailings
From $1,350
Seabourn
4 ships
·
52 upcoming sailings
From $3,598
Holland America
7 ships
·
51 upcoming sailings
From $614
Virgin Voyages
4 ships
·
51 upcoming sailings
From $763
Silversea Cruises
5 ships
·
47 upcoming sailings
From $8,000
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 1,173 itineraries, 2,206 upcoming sailings, and calls across 44 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 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.
Frequently asked questions
Common questions about cruising in Eastern Caribbean.
What kinds of cruises are available in Eastern Caribbean?
Eastern Caribbean currently has 1,173 itineraries and 2,206 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 $1,259. 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 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.
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.