Cruise destination
Compare Caribbean sailings by cruise line, ship, departure date, port, and price.
734 sailing listings in the recorded comparison · recorded Sep 22, 2026 at 10:35 UTCPhoto by Hugh Whyte on Unsplash
Eastern, Western and Southern Caribbean itineraries offer different combinations of islands and days at sea. Choose the calls you care about before comparing the length of the voyage. This comparison also includes the Bahamas and Bermuda, so two sailings shown together may cover quite different stretches of water. A familiar departure port does not tell you which islands the ship will visit.
Check the number of stops, the hours in each port and any return visits to the same location. If your priority is time ashore, compare those details rather than assuming that a longer cruise always gives you more island time. For a trip built around one particular call, read the operator's itinerary-change terms and consider whether you would still want the voyage if that stop changed.
Weather deserves its own check, particularly during the Atlantic hurricane season. Monthly climate references describe typical conditions at a reference location, not the weather along every route. A lower listed median is not evidence of a safer or calmer crossing. Compare the cabin, included services and itinerary first, then use the dated fare comparison to understand the prices represented on this page.
Known for: Beach & Snorkeling · Island Hopping · Year-Round Sun · Family Friendly · Rum Cocktails
In depth: Best time to cruise Bahamas · Best time to cruise Bermuda · Best time to cruise Panama Canal
Caribbean · comparison coverage
Data recorded ; calculated Sep 22, 2026 at 10:36 UTC.
Our Caribbean comparison covers itineraries with a verified Caribbean Sea call or a verified call in the Bahamas or Bermuda.
Departures from through . Months combine all matching years in this window.
727 of 734
listings with a comparable USD fare
7
listings without a comparable USD fare
Fares are USD per person per night. These starting-fare comparisons mix cabin types, ships and trip lengths. Compare actual cabins and conditions on the individual sailing pages.
Itinerary geography was checked across 40,086 market candidates: 37,416 unresolved and 1,936 conflicting. Those candidates are not included in this destination’s figures and are not a count of missing Caribbean sailings.
Recorded listings · monthly comparison
Compare recorded monthly fares and seasonal conditions.
Among well-served months in this comparison, January has the lowest median listed fare at $96 per person per night and July the highest at $153. Adjacent months with limited choice are shown separately and may have lower fares. These are different future departures, not a price history for the same cruise. Roughly December through April you get 85°F sun, the calmest water of the year, and no hurricane season to dodge.
CruiseCaptain — corroborated USD listed fares, per person per night; recorded Sep 22, 2026
Each dot represents a sampled listed fare for one sailing and cabin category. The table’s monthly medians use the full eligible snapshot, not only the dots shown. These are different future departures, not repeated prices for an identical cruise.
734 sailing listings in the comparison window · dots show 364 priced listings after sampling and validation · calculated Sep 22, 2026
Departure window: 2026-09-22 to before 2028-03-22.
The 18-month comparison contains 734 active sailing listings with a positive trip length; 727 have a listed cabin fare and 7 have none. The seasonal comparison uses 734 sailing listings in well-served months and their adjacent shoulder months; 0 sailing listings fall outside that seasonal selection. Counts represent supplier sailing listings, not necessarily distinct voyages. Current verified itinerary links are checked separately.
Lowest and highest labels compare well-served (core) months only. Adjacent months with limited choice can have lower medians. The score weights listed price 35%, reference weather 30%, editorial seasonal experience 25% and fewer sailing listings 10%. Listing counts do not measure passenger occupancy or crowds; this score is a comparison aid, not a forecast. Equal inputs receive equal scores.
For each sailing listing, we divide its lowest usable corroborated USD cabin fare by trip length, then take the median within each calendar month across departure years. Cabin medians use only listings priced in that category: inside, oceanview, balcony or suite. Missing fares are excluded from medians, never treated as free cruises. The dots are a bounded sample; chart lines smooth that sample by cabin over nearby departure dates, with monthly medians as a fallback.
Prices are displayed in US dollars per person. Occupancy, taxes, fees and inclusions follow the source listing and are not independently standardized in this comparison. Check the sailing and supplier before booking. The calculation date is not the time every supplier last refreshed its fare; this aggregate does not include individual quote timestamps.
Raw fares come from third-party feeds. CruiseCaptain’s contribution is tracking, normalization and analysis. These recorded-fare comparisons are descriptive: differences in lines, ships, cabins and routes can explain monthly gaps. They do not establish when to book or predict a future price.
Select a month to pin its column — the spotlight below follows.
Higher score, deeper bar — a better all-round month on price, weather & listing volume. – means too few priced listings to score; greyed months are outside the seasonal comparison.
Climate reference: Meteostat 1991–2020 monthly climate normals (nearest station), San Juan (18.47, -66.11). These representative conditions are separate from the recorded fare comparison and are not a sailing forecast.
Daylight reference: Computed for San Juan (18.5°N), sea level. Daylight changes with the itinerary’s latitude; these figures describe the reference location.
lowest core median
peak-season sun, whales arrive
January has 100 sailing listings in the comparison window, including 99 with a listed cabin fare. The median listed fare is $96 per person per night. This is the lowest median among well-served months. San Juan climate reference: average daytime high 83°F, 4.0 inches of monthly rain and 11.0 hours of daylight. High season is here.
$96/night median
100 sailing listings
well-served month
humpbacks breeding, dry skies
February has 101 sailing listings in the comparison window, including 101 with a listed cabin fare. The median listed fare is $116 per person per night. San Juan climate reference: average daytime high 84°F, 2.4 inches of monthly rain and 11.4 hours of daylight. The sweet spot: the heart of the dry season (2.4"), 84°F, flat seas, and humpbacks breaching off the Dominican Republic.
$116/night median
101 sailing listings
well-served month
whales linger, spring-break buzz
March has 88 sailing listings in the comparison window, including 86 with a listed cabin fare. The median listed fare is $122 per person per night. San Juan climate reference: average daytime high 85°F, 2.1 inches of monthly rain and 11.9 hours of daylight. The driest month of all (2.1"), 85°F and calm.
$122/night median
88 sailing listings
well-served month
turtles begin nesting
April has 31 sailing listings in the comparison window, including 31 with a listed cabin fare. The median listed fare is $118 per person per night. San Juan climate reference: average daytime high 86°F, 4.5 inches of monthly rain and 12.4 hours of daylight. The dry season holds, the water stays warm, and hurricanes are still months off.
$118/night median
31 sailing listings
well-served month
turtle nesting, warm seas
May has 28 sailing listings in the comparison window, including 28 with a listed cabin fare. The median listed fare is $119 per person per night. San Juan climate reference: average daytime high 87°F, 5.3 inches of monthly rain and 12.9 hours of daylight. Warming to 87°F with the first afternoon showers, but calm and uncrowded.
$119/night median
28 sailing listings
well-served month
hurricane season begins
June has 26 sailing listings in the comparison window, including 26 with a listed cabin fare. The median listed fare is $144 per person per night. San Juan climate reference: average daytime high 89°F, 4.5 inches of monthly rain and 13.1 hours of daylight. Atlantic hurricane season opens June 1.
$144/night median
26 sailing listings
highest core median
school’s-out crowds
July has 31 sailing listings in the comparison window, including 31 with a listed cabin fare. The median listed fare is $153 per person per night. This is the highest median among well-served months. San Juan climate reference: average daytime high 89°F, 6.0 inches of monthly rain and 13.0 hours of daylight. 89°F, humid, and named storms now a real possibility.
$153/night median
31 sailing listings
well-served month
storm season ramps
August has 30 sailing listings in the comparison window, including 30 with a listed cabin fare. The median listed fare is $141 per person per night. San Juan climate reference: average daytime high 89°F, 6.3 inches of monthly rain and 12.6 hours of daylight.
$141/night median
30 sailing listings
well-served month
hurricane peak
September has 32 sailing listings in the comparison window, including 31 with a listed cabin fare. The median listed fare is $120 per person per night. San Juan climate reference: average daytime high 89°F, 6.4 inches of monthly rain and 12.1 hours of daylight.
$120/night median
32 sailing listings
well-served month
late-season storms
October has 62 sailing listings in the comparison window, including 61 with a listed cabin fare. The median listed fare is $113 per person per night. San Juan climate reference: average daytime high 89°F, 5.1 inches of monthly rain and 11.6 hours of daylight. Hurricane risk fades through October but isn’t gone.
$113/night median
62 sailing listings
well-served month
seas settle
November has 102 sailing listings in the comparison window, including 101 with a listed cabin fare. The median listed fare is $100 per person per night. San Juan climate reference: average daytime high 86°F, 7.0 inches of monthly rain and 11.1 hours of daylight. The wettest month climatically (7"), but hurricanes wind down and the dry season returns late.
$100/night median
102 sailing listings
most core listings
dry season returns
December has 103 sailing listings in the comparison window, including 102 with a listed cabin fare. The median listed fare is $136 per person per night. This month has the most sailing listings among well-served months; listing counts do not measure passenger crowds. San Juan climate reference: average daytime high 84°F, 4.8 inches of monthly rain and 10.9 hours of daylight. Early December, before the school break, buys the same weather with thinner crowds.
$136/night median
103 sailing listings
This close to the equator, daylight barely moves. Reckon on about 11 hours in December and 13 at the June solstice. The seasonal signal in the Caribbean isn’t light; it’s rain and hurricanes, so watch those instead.
≈11 h · December to ≈13 h · June
9 hours a day in April
NASA POWER climatology (all-sky vs clear-sky shortwave; bright-sun via Angstrom-Prescott)
September and October, if you need a plan you can count on. They also carry the statistical peak of Atlantic hurricane season, which the National Hurricane Center centres on September 10. A storm rarely hits your exact port in your exact week, but itineraries do get rerouted, and it’s a gamble you’d be taking with eyes open. November is the wettest month by the numbers, but the hurricane risk is already fading.
The Caribbean hides a winter wildlife draw most cruisers miss. Humpback whales gather off the Dominican Republic from January to March to breed and calve, concentrating at Silver Bank and Samaná Bay.
Among well-served months in this comparison, January has the lowest median listed fare at $96 per person per night and July the highest at $153. Adjacent months with limited choice are shown separately and may have lower fares. These are different future departures, not a price history for the same cruise.
August through October carry the highest hurricane risk, peaking around September 10. Use the monthly table for recorded listed fares and departure choice, then compare the actual ships, routes, cabin quotes and travel dates. Weather guidance uses regional reference conditions and does not explain why a fare changes.
December through April is the dry season. Tropical storms are gone, rainfall drops to just over 2" a month at San Juan in February and March, and the seas are at their flattest, with daytime highs of 83–86°F.
December to May sits outside the June–November Atlantic hurricane season. Use the monthly table for recorded listed fares and departure choice, then compare the actual ships, routes, cabin quotes and travel dates. Weather guidance uses regional reference conditions and does not explain why a fare changes.
Use the actual sailing and cabin quote for a trip budget. These monthly medians mix itinerary lengths and cabin availability, so multiplying them by seven does not establish the price of a seven-night cruise. Check occupancy, currency, inclusions, taxes and fees on the selected quote.
It’s the strongest month overall: near the driest skies of the year (2.1–2.4" from February into March), calm seas, 84°F, no hurricane risk, and humpback whales breeding off the Dominican Republic. The weather earns it anyway. Use the monthly table for recorded listed fares and departure choice, then compare the actual ships, routes, cabin quotes and travel dates. Weather guidance uses regional reference conditions and does not explain why a fare changes.
Weather-wise, yes. The dry season is back, seas are calm, and it's outside hurricane season. Sail early December, before the holiday peak, for the best of both. Use the monthly table for recorded listed fares and departure choice, then compare the actual ships, routes, cabin quotes and travel dates. Weather guidance uses regional reference conditions and does not explain why a fare changes.
Among well-served months in this comparison, January has the lowest median listed fare at $96 per person per night and July the highest at $153. Adjacent months with limited choice are shown separately and may have lower fares. These are different future departures, not a price history for the same cruise.
20 itineraries verified in this checked batch. Checked Sep 22, 2026 against the comparison recorded Sep 22, 2026. New listings enter after the next comparison refresh.
Further checks may not find more sailings.
For more options, explore Caribbean cruises.
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