Caribbean Cruises: Sailings, Embarkations & Ports of Call
176 ships from 28 cruise lines across 27 countries
Find your Caribbean sailing
Upcoming sailings calling in Caribbean, earliest departure first.
Caribbean cruises at a glance
Waterways Cruise lists 1,435 upcoming sailings on 176 ships from 28 cruise lines visiting Caribbean, calling at 80 places. Cruises can start in San Juan, Bridgetown, Philipsburg, Fort-de-France, Antigua, Cartagena and 9 more and end in Antigua, Barranquilla, Bridgetown, Cartagena, Fort-de-France, Iles des Saintes and 9 more.
Reviewed and fact-checked by J. Richard · About this page · About us
Why Book With Waterways Cruise?
Four decades of expertise, one dedicated advisor, and every detail handled, from your front door to the gangway and back.
Cruise Concierge
A dedicated advisor who learns your name, your travel style and your preferences, then stays with you from the first conversation to the day you return home. Not a call center. Never a stranger.
100% Custom‑Built
No cookie-cutter packages. Flights, hotels, transfers and shore days are designed from scratch around how you actually like to travel, then refined until the trip feels like yours.
40+ Years in Travel
Founded by J. Richard, a four-decade veteran of the travel industry, and focused solely on premium river and ocean cruising. Decades of ship and itinerary knowledge go into every recommendation.
Book With Total Confidence
A travel agency that is a proud member of Signature Travel Network, CLIA, ASTA and IATA.
9 Days San Juan, Puerto Rico Round Trip
Scarlet Lady
8 Days One-Way from Bridgetown to Philipsburg St Maarten
Emerald Sakara
23 Days One-Way from Civitavecchia-Rome to Fort Lauderdale
Enchanted Princess
15 Days One-Way from Barcelona to San Juan
Rhapsody Of The Seas
Ships by type: 165 ocean 5 river 11 expedition · a ship that visits several places here is counted once; an expedition ship that also sails as an ocean ship appears under both types.
Cruises in Caribbean by country
Compare Caribbean cruise lines
MSC Cruises has the most upcoming sailings among Caribbean cruise lines (117). Starting fares run from $104 per person. Most sailings last 6–25 nights, and the most common length is 7 nights.
Ocean cruise lines (25)
Ultra-luxury cruise lines (5)
| Cruise line | Upcoming sailings | Lowest starting fare | Typical length |
|---|---|---|---|
| Regent Seven Seas Cruises | 77 | $16,798 | 10–24 nights (typically 14) |
| Silversea Cruises | 72 | $3,950 | 8–25 nights (typically 12) |
| Seabourn Cruises | 62 | $2,889 | 10–81 nights (typically 14) |
| SeaDream Yacht Club | 60 | $8,499 | 6–13 nights (typically 7) |
| Ritz-Carlton Yacht Collection | 19 | $3,700 | 4–7 nights (typically 7) |
Luxury cruise lines (4)
| Cruise line | Upcoming sailings | Lowest starting fare | Typical length |
|---|---|---|---|
| Oceania Cruises | 92 | $2,400 | 10–36 nights (typically 14) |
| MSC Explora Journeys | 58 | $3,150 | 7–18 nights (typically 16) |
| Ponant Cruises | 27 | $3,330 | 7–12 nights (typically 7) |
| Scenic Cruises | 11 | $6,463 | 9–20 nights (typically 11) |
Premium cruise lines (7)
| Cruise line | Upcoming sailings | Lowest starting fare | Typical length |
|---|---|---|---|
| Azamara Cruises | 59 | $1,069 | 8–49 nights (typically 13) |
| Crystal Cruises | 58 | $1,980 | 8–32 nights (typically 10) |
| Windstar Cruises | 54 | $2,108 | 7–23 nights (typically 14) |
| Emerald Cruises | 48 | $2,995 | 6–16 nights (typically 7) |
| Viking Cruises | 28 | $2,999 | 11–62 nights (typically 13) |
| Hapag-Lloyd Cruises | 20 | $8,624 | 14–19 nights (typically 14) |
| Lindblad Expeditions | 1 | $7,449 | 7 nights |
Contemporary cruise lines (8)
| Cruise line | Upcoming sailings | Lowest starting fare | Typical length |
|---|---|---|---|
| MSC Cruises | 117 | $104 | 6–20 nights (typically 14) |
| Royal Caribbean | 106 | $266 | 4–11 nights (typically 7) |
| Norwegian Cruise Line | 105 | $299 | 4–15 nights (typically 7) |
| Princess Cruises | 103 | $444 | 6–23 nights (typically 7) |
| Holland America | 83 | $614 | 7–26 nights (typically 14) |
| Celebrity Cruises | 61 | $324 | 5–14 nights (typically 7) |
| Cunard | 44 | $699 | 12–37 nights (typically 14) |
| Virgin Voyages | 30 | $834 | 4–12 nights (typically 7) |
Other cruise lines (1)
| Cruise line | Upcoming sailings | Lowest starting fare | Typical length |
|---|---|---|---|
| Star Clippers | 32 | $1,450 | 7–22 nights (typically 7) |
River cruise lines (2)
Luxury cruise lines (1)
| Cruise line | Upcoming sailings | Lowest starting fare | Typical length |
|---|---|---|---|
| AmaWaterways | 4 | $4,484 | 7 nights |
Premium cruise lines (1)
| Cruise line | Upcoming sailings | Lowest starting fare | Typical length |
|---|---|---|---|
| Emerald Cruises | 4 | On request | 7–10 nights (typically 7) |
Cruise embarkation and disembarkation
Cruise embarkation (15)
Antigua · Barranquilla · Bridgetown · Cartagena · Fort-de-France · La Romana · Nassau · Oranjestad · Philipsburg · Pointe-à-Pitre · Portsmouth · San Cristóbal · San Juan · St Georges Grenada · Willemstad
Cruise disembarkation (15)
Antigua · Barranquilla · Bridgetown · Cartagena · Fort-de-France · Iles des Saintes · La Romana · Nassau · Oranjestad · Philipsburg · Pointe-à-Pitre · San Cristóbal · San Juan · St Georges Grenada · Willemstad
Cruise lines sailing in Caribbean (28)
Ocean cruise lines (26)
Ultra-luxury cruise lines (5)
Luxury cruise lines (4)
Premium cruise lines (8)
Contemporary cruise lines (8)
Other cruise lines (1)
River cruise lines (3)
Luxury cruise lines (1)
Premium cruise lines (1)
Contemporary cruise lines (1)
Plan your Caribbean cruise
Caribbean cruise ports
Cruise ports, what to see, history and practical advice.
Caribbean cruise ports →More cruise regions
Western Europe · Mediterranean · Northern Europe & the Baltics · British Isles · Africa · Canada & New England · Central America & Mexico · Florida
Frequently asked questions about Caribbean cruises
Can you start or end a cruise in Caribbean?
Yes. Cruises start in San Juan, Bridgetown, Philipsburg, Fort-de-France, Antigua, Cartagena, Oranjestad, San Cristóbal and 7 more. Cruises end in Antigua, Barranquilla, Bridgetown, Cartagena, Fort-de-France, Iles des Saintes, La Romana, Nassau and 7 more.
How many places do cruises visit in Caribbean?
80 Caribbean places are visited by 176 ships from 28 cruise lines.
Which cruise lines sail to Caribbean?
28 cruise lines sail to Caribbean, including AmaWaterways, Atlas Ocean Voyages, Azamara Cruises, Celebrity Cruises, CroisiEurope, Crystal Cruises and 22 more.
Created by the Waterways Cruise content team and reviewed and fact-checked by J. Richard, Sr. Cruise Travel Agent and Founder of Waterways Cruise.
Published October 4, 2026 · Last updated October 31, 2026
Fares, availability and itineraries change often. Confirm current details with your cruise line or a Waterways Cruise agent before you book.
Cruise Disclosure
Good to know: Prices are quoted per person based on double occupancy and include all applicable taxes and fees. Availability and prices can change quickly, so please continue through the booking process to confirm the latest availability and pricing before you pay.
We work hard to make sure everything on this website is accurate and up to date. However, some information may be incomplete or inaccurate, including details supplied by third parties or otherwise outside our control, and we cannot be held responsible for such errors. We work with 0 cruise line operators, that are providing cruises on 0 ships visiting 0 ports across 0 unique cruises, creating 0 itineraries. This is a great deal of data to continually update daily from our suppliers. If a pricing error, misrepresentation, or omission occurs, we reserve the right to adjust the pricing, correct the information, or cancel or decline any booking made in error, with notice to you. Thank you for your understanding!