Port-forward pace
10 ports in 14 nights
Most days put a destination at the center of the plan.
Eastern Caribbean cruises
Eastern Caribbean Loop via Road Bay, Saint John's & Cruz Bay, Saint John
Road Bay · Saint John's · Frederiksted, Saint Croix · Catalina Island · Puerto Plata · Miami · Cruz Bay, Saint John · Terre-de-Haut (Les Saintes) · Philipsburg
Port-heavy Eastern Caribbean itinerary. Covers Anguilla, Antigua and Barbuda, Virgin Islands, U.S., Dominican Republic, and more.
14 nights
San Juan
Eastern Caribbean
10 ports
4 sea days
What this trip feels like
Active, varied and destination-focused
With 10 ports across 14 nights, this trip keeps the focus on time ashore. Expect more destination variety and a busier rhythm, with the ship serving as the link between port days.
Broad destination variety
Road Bay · Saint John's · Frederiksted, Saint Croix + more
Frequent changes of scenery across the itinerary.
Easy logistics
Round-trip from San Juan
No open-jaw flights or separate arrival and departure transfers.
Port experience
Road Bay · Pick your date carefully
Cruise traffic varies substantially by date, so your specific port day can feel very different depending on when you visit.
Best for · Destination-led trips · Active days ashore · Travelers who prefer variety
Think twice if · You want long, uninterrupted stretches of time onboard
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.
Itinerary pricing
What this itinerary usually costs
Typical pricing runs around $697/night, with most departures landing in the $640-$790/night band across 1 tracked sailing.
Typical price
$697/night
$9,760 total
Normal range
$640-$790/night
$8,960-$11,060 total
Lowest recent fare
$638/night
$8,925 total
Comparison set
1 sailings
Used for itinerary baseline
When should I go?
Not enough departures yet to identify a reliable cheaper season.
Route overview
How this route is built
14 nights · 10 port calls · 4 sea days · 7 countries
10 port calls across Anguilla, Antigua and Barbuda, Virgin Islands, U.S., Dominican Republic · More port-intensive than many 14-night alternatives.
-
1
Embark in San Juan
Embarkation ports can vary by sailing
-
2
-
3
-
4
-
5
-
6
-
7
-
8
-
9
-
10
-
11
-
12
Disembark in San Juan
Disembarkation ports can vary by sailing
Loading route map
Render your Mapbox or Leaflet map here from the supplied route and port JSON.
Embark port
Disembark port
Port of call
Other routes to consider
Not quite the right itinerary? Compare routes that trade a little simplicity for more ports, different destinations, or a longer trip.
More port time
Add Kingstown + Saint George
Eastern Caribbean: Kingstown, Saint George & Fort-de-France
14 nights · 11 ports · 3 sea days
Same length +1 port
Much more time ashore without making the trip longer.
Compare this route →
From $1,662
More variety
Add Ketchikan + Juneau
Eastern Caribbean: Ketchikan, Juneau & Victoria
40 nights · 18 ports · 12 countries
+26 nights +5 countries
A much broader Eastern Caribbean experience.
Compare this route →
From $3,016
Longer trip
Make it 33 nights
Eastern Caribbean: Los Angeles, Cabo San Lucas & Puerto Quetzal
33 nights · 13 ports · 20 sea days
+19 nights +16 sea days
More time onboard without changing the trip's overall pace much.
Compare this route →
From $2,242