Caribbean Cruises
Island escapes & turquoise waters
Warm water, soft sand and a different island almost every morning. Whether you want a quick long-weekend getaway or a leisurely Southern Caribbean voyage, there's a ship, an itinerary and a beach with your name on it.
When to go
Sailings run year-round. December through April is peak season; hurricane season (June–November) often brings attractive promotions.
Popular ports
- Cozumel
- Grand Cayman
- St. Thomas
- St. Maarten
- Aruba
- Barbados
- Nassau
01
Eastern Caribbean
St. Thomas, St. Maarten and private-island beach days — great for first-time cruisers.
02
Western Caribbean
Cozumel, Roatán, Belize and Grand Cayman: Mayan ruins, reefs and snorkeling.
03
Southern Caribbean
Aruba, Curaçao, Barbados and St. Lucia — longer sailings to more remote islands.
Hand-picked by James
Featured Cruises
Featured
Celebrity Cruises
Celebrity Cruises
Celebrity Fall Sale: Caribbean
Book by Nov 5
Cruise perks
- 75% off 2nd guest
- 3rd, 4th & 5th guests sail free
- Instant savings per stateroom
- 50% off 2nd guest on refundable-deposit fares
Sun-soaked Caribbean sailings on Celebrity's modern ships, with Fall Sale perks on select departures.
Sails: Select sailings through May 2029
Celebrity Cruises
Final Rooms at Great Rates: Caribbean
Book by Oct 19
Cruise perks
- Classic Drinks package included
- Basic Wi-Fi included
- One-week-only rates
Limited-time rates on close-in Caribbean sailings, with the option of an Exciting Deals fare that bundles perks.
Sails: Select close-in sailings
More cruise lines
Royal Caribbean
October Monthlong Offer
Book by Nov 2
Cruise perks
- 60% off 2nd guest
- Kids 12 & under sail free (select sailings)
- 3rd & 4th guests sail free
Family-friendly sailings with Halloween theme nights and events all October long.
Sails: Sailings departing on or after Oct 7, 2026
Royal Caribbean
Early Booking Bonus
Book by Dec 31
Cruise perks
- Bonus onboard credit
Plan ahead on Royal Caribbean and earn onboard credit when booking at least 7 months before departure.
Sails: Sailings booked 7+ months out
Virgin Voyages
The Caribbean Sale
Cruise perks
- Bonus onboard credit
- Dining included
- Wi-Fi included
- Entertainment included
- Adults-only
Adults-only Caribbean voyages, including 4-night weekenders from Miami.
Sails: Select Caribbean sailings
Holland America Line
Save on Sunshine: Caribbean & Holiday
Book by Oct 21
Cruise perks
- Up to 50% off cruise fares
- Bonus onboard credit
- Kids sail free on select sailings
- Holiday sailings: one night of specialty dining
Caribbean, Mexico and Panama Canal cruises, plus festive holiday sailings.
Sails: Select sailings
Princess Cruises · Crown Princess
Caribbean Island Hopping
Book by Nov 5
Cruise perks
- Up to 45% off fares
- Instant savings
White-sand beaches, reefs and Mayan ruins with More Ashore late-night port stays. Featured: a 7-day Southern Caribbean Distinctive Voyage on Crown Princess.
Sails: Featured: March 7, 2027
Regent Seven Seas Cruises
First Class in Every Way: Caribbean
Book by Oct 31
Cruise perks
- Free roundtrip first-class air
- Private chauffeured transfers
All-inclusive luxury Caribbean voyages, including stops like Costa Maya.
Sails: Select 2027–2028 voyages
Prefer to talk it through? Call 209.480.1533.
Let’s plan your Caribbean cruise.
Tell James where you’d like to go.