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Eastern Caribbean cruises

Eastern Caribbean Loop via Philipsburg, Saint John's & South Friars Bay (Rare Variant)

⚓ Philipsburg · Saint John's · South Friars Bay · Norman Island · Spanish Town (Virgin Gorda)

Port-heavy Eastern Caribbean itinerary. Covers Sint Maarten (Dutch part), Antigua and Barbuda, Saint Kitts and Nevis, and Virgin Islands, British. Includes anchorage-style calls.

☾7 nights San Juan Eastern Caribbean 5 ports 2 sea days
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Itinerary pricing

What this itinerary usually costs

Typical pricing runs around $912/night. with most departures landing in the $880-$950/night band. across 1 tracked sailings.

Typical price

$912/night

$6,386 total

Normal range

$880-$950/night

$6,160-$6,652 total

Lowest recent fare

Building history

$6,563 total

Comparison set

1 sailings

Used for itinerary baseline

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
Emerald Cruises

Emerald Kaia • Emerald Cruises

7-night Eastern Caribbean Loop via Philipsburg, Saint John's & South Friars Bay

Dec 27, 2027 → Jan 3, 2028 • San Juan ↔

From $6,656

$951/night

Typical price

↑4% above typical

All departures

All upcoming departures

Compare all sailings for this itinerary.

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When should I go?

Scan monthly pricing to see which departure windows tend to look stronger or weaker for this itinerary.

December 2027
Cheapest
Median price/night
$951
1 sailing
Upcoming departures
Usually expensive
1 priced departures tracked

Route overview

How this route is built

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7 nights · 5 port calls · 2 sea days · 4 countries

5 port calls across Sint Maarten (Dutch part), Antigua and Barbuda, Saint Kitts and Nevis, Virgin Islands, British · More port-intensive than many 7-night alternatives.

  1. 1

    Embark in San Juan

    Embarkation ports can vary by sailing

  2. 2

    Philipsburg

    Sint Maarten (Dutch part) · Eastern Caribbean

  3. 3

    Saint John's

    Antigua and Barbuda · Eastern Caribbean

  4. 4

    South Friars Bay

    Saint Kitts and Nevis · Eastern Caribbean

    Anchorage
  5. 5

    Norman Island

    Virgin Islands, British · Eastern Caribbean

  6. 6

    Spanish Town (Virgin Gorda)

    Virgin Islands, British · Eastern Caribbean

  7. 7

    Disembark in San Juan

    Disembarkation ports can vary by sailing

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Embark port
Disembark port
Port of call

Alternatives

Compare nearby alternatives

Nearby options in the same planning set, with price and trip-shape tradeoffs called out so you can compare without restarting your search.

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.