Jibhop
Eastern Caribbean cruises

Eastern Caribbean Loop via Puerto Plata & Cruz Bay, Saint John

Puerto Plata · San Juan · Cruz Bay, Saint John · Philipsburg

Balanced itinerary with more sea time than port-packed variants. Covers Dominican Republic, Puerto Rico, Virgin Islands, U.S., and Sint Maarten (Dutch part).

10 nights Philadelphia Eastern Caribbean 4 ports 6 sea days
Compare departures Explore the route

What this trip feels like

Easygoing, familiar and ship-focused

6 sea days give you plenty of uninterrupted time onboard, while Puerto Plata, San Juan, and Cruz Bay, Saint John provide the trip's main day ashore. You're choosing this route for an easy break with minimal logistics, not destination variety.

Relaxed pace

4 ports in 10 nights

Plenty of uninterrupted ship time.

Broad destination variety

Puerto Plata · San Juan · Cruz Bay, Saint John + more

Frequent changes of scenery across the itinerary.

Easy logistics

Round-trip from Philadelphia

No open-jaw flights or separate arrival and departure transfers.

Port experience

Puerto Plata · 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 · First-time cruisers · Ship-focused trips · Easy short getaways

Think twice if · You want a port-intensive Eastern Caribbean itinerary

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.

Best overall value
Norwegian Cruise Line

Norwegian Pearl

Philadelphia → Puerto Plata → Philipsburg → Philadelphia

Dec 13 · 10 nights

About average

$1,049 inside · $105/night

All departures

All upcoming departures

Compare all sailings for this itinerary.

Explore in full search view

Itinerary pricing

What this itinerary usually costs

Typical pricing runs around $96/night, with most departures landing in the $88-$126/night band across 1 tracked sailing.

Typical price

$96/night

$959 total

Normal range

$88-$126/night

$883-$1,261 total

Lowest recent fare

$105/night

$1,049 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

Compare sailings →

10 nights · 4 port calls · 6 sea days · 4 countries

4 port calls across Dominican Republic, Puerto Rico, Virgin Islands, U.S., Sint Maarten (Dutch part) · Leans more toward sea time than a port-packed 10-night route.

  1. 1

    Embark in Philadelphia

    Embarkation ports can vary by sailing

  2. 2

    Puerto Plata

    Dominican Republic · Eastern Caribbean

  3. 3

    San Juan

    Puerto Rico · Eastern Caribbean

  4. 4

    Cruz Bay, Saint John

    Virgin Islands, U.S. · Eastern Caribbean

  5. 5

    Philipsburg

    Sint Maarten (Dutch part) · Eastern Caribbean

  6. 6

    Disembark in Philadelphia

    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.

FAQ

What’s the best month to sail this itinerary?
It depends on weather and crowd levels. Use the sailing list to compare dates and prioritize port days with comfortable conditions.
Are these sailings all the same route?
They can be close but not identical. Look for differences in port order, arrival times, and sea day placement.
How should I choose between two similar sailings?
Compare: (1) ship, (2) port day timing, (3) number of sea days, (4) price vs cabin value, and (5) flight convenience.