Eastern Caribbean cruises

Eastern Caribbean Arc via Road Bay, Saint John's & Basseterre, Saint Kitts (Best Balance)

⚓ Road Bay · Saint John's · Basseterre, Saint Kitts · Grand Turk Island · Miami · Ocho Rios · Catalina Island · Jost Van Dyke · Philipsburg · Charlotte Amalie, Saint Thomas

Balanced itinerary with more sea time than port-packed variants. Covers Anguilla, Antigua and Barbuda, Saint Kitts and Nevis, and Turks and Caicos Islands and more.

San Juan Eastern Caribbean 10 ports 4 sea days

Itinerary pricing

What this itinerary usually costs

Typical pricing runs around $688/night. with most departures landing in the $595-$744/night band. across 1 tracked sailings.

Typical price

$688/night

$10,318 total

Normal range

$595-$744/night

$8,925-$11,160 total

Lowest recent fare

Building history

$10,460 total

Comparison set

1 sailings

Used for itinerary baseline

Best departures

Best upcoming sailings

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When should I go?

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December 2026
Cheapest
Median price/night
$744
1 sailing
Upcoming departures
8% above itinerary median
1 priced departures tracked

Route overview

How this route is built

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10 port calls · 4 sea days · 10 countries

10 port calls across Anguilla, Antigua and Barbuda, Saint Kitts and Nevis, Turks and Caicos Islands

  1. 1

    Embark in San Juan

    Embarkation ports can vary by sailing

  2. 2

    Road Bay

    Anguilla · Eastern Caribbean

  3. 3

    Saint John's

    Antigua and Barbuda · Eastern Caribbean

  4. 4

    Basseterre, Saint Kitts

    Saint Kitts and Nevis · Eastern Caribbean

  5. 5

    Grand Turk Island

    Turks and Caicos Islands · Eastern Caribbean

  6. 6

    Miami

    United States · US East Coast

  7. 7

    Ocho Rios

    Jamaica · Western Caribbean

  8. 8

    Catalina Island

    Dominican Republic · Eastern Caribbean

  9. 9

    Jost Van Dyke

    Virgin Islands, British · Eastern Caribbean

  10. 10

    Philipsburg

    Sint Maarten (Dutch part) · Eastern Caribbean

  11. 11

    Charlotte Amalie, Saint Thomas

    Virgin Islands, U.S. · Eastern Caribbean

  12. 12

    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.

Similar itineraries are still being assembled for comparison.

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.