Eastern Caribbean cruises

Eastern Caribbean Loop via Grand Turk Island, Ocean Cay & Philipsburg (Best Balance)

⚓ Grand Turk Island · Ocean Cay · Nassau · Miami · Philipsburg · Basseterre, Saint Kitts · Charlotte Amalie, Saint Thomas · Puerto Plata

Balanced route with a steady mix of port days and sea days. Covers Turks and Caicos Islands, Bahamas, United States, and Sint Maarten (Dutch part) and more. Includes private-island style stops.

☾14 nights Miami Eastern Caribbean 8 ports 6 sea days

Itinerary pricing

What this itinerary usually costs

Typical pricing runs around $127/night. with most departures landing in the $74-$150/night band. across 2 tracked sailings.

Typical price

$127/night

$1,777 total

Normal range

$74-$150/night

$1,037-$2,100 total

Lowest recent fare

$28/night

$398 total

Comparison set

2 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.

All departures

All upcoming departures

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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.

November 2026
Cheapest
Median price/night
$28
1 sailing
Upcoming departures
68% below itinerary median
1 priced departures tracked
February 2027
Priciest
Median price/night
$85
1 sailing
Upcoming departures
48% below itinerary median
1 priced departures tracked

Route overview

How this route is built

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14 nights · 8 port calls · 6 sea days · 7 countries

8 port calls across Turks and Caicos Islands, Bahamas, United States, Sint Maarten (Dutch part) · Neither especially port-heavy nor sea-day heavy for this trip length.

  1. 1

    Embark in Miami

    Embarkation ports can vary by sailing

  2. 2

    Grand Turk Island

    Turks and Caicos Islands · Eastern Caribbean

  3. 3

    Ocean Cay

    Bahamas · Bahamas

    Private
  4. 4

    Nassau

    Bahamas · Bahamas

  5. 5

    Miami

    United States · US East Coast

  6. 6

    Philipsburg

    Sint Maarten (Dutch part) · Eastern Caribbean

  7. 7

    Basseterre, Saint Kitts

    Saint Kitts and Nevis · Eastern Caribbean

  8. 8

    Charlotte Amalie, Saint Thomas

    Virgin Islands, U.S. · Eastern Caribbean

  9. 9

    Puerto Plata

    Dominican Republic · Eastern Caribbean

  10. 10

    Disembark in Miami

    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.