Caribbean Breeze Travel Logo
About UsMy BookingFeatured OffersSail With MeLet Jim HelpGuidesTransfer CruiseSearch Cruises
Search Cruises
Let's Find Your Cruise

Displayed prices are starting points! I often have better deals that are not reflected!

Filters 
Cruise Lines
Ships
Cruise Dates
By Month
By Date
2026
JanuaryJanFebruaryFebMarchMarAprilAprMayMayJuneJunJulyJulAugustAugSeptemberSepOctoberOctNovemberNovDecemberDec
2027
JanuaryJanFebruaryFebMarchMarAprilAprMayMayJuneJunJulyJulAugustAugSeptemberSepOctoberOctNovemberNovDecemberDec


October 2026

S
M
T
W
T
F
S
12345678910111213141516171819202122232425262728293031
Nights

to

Departure Ports
Regions
Ports of Call
Room Type
Clear All Filters
Port: San Juan×
Sort by: Recommended

Search Cruises

Norwegian Pearl
Norwegian Cruise Line
Nov 27, 2027 - Dec 8, 2027 (11 Nights)
Philadelphia • Puerto Plata, Dominican Republic • San Juan, Puerto Rico • St John's, Antigua • St. Lucia • Philipsburg, St. Maarten • Philadelphia
Average Starting Price
$1,203pp
Jim's Onboard Credit
Rhapsody of the Seas
Royal Caribbean
Nov 27, 2027 - Dec 4, 2027 (7 Nights)
San Juan, Puerto Rico • St. Thomas • St. Croix • Philipsburg, St. Maarten • Castries, St. Lucia • Basseterre, St. Kitts and Nevis • San Juan, Puerto Rico
Average Starting Price
$709pp
Jim's Onboard Credit
Regal Princess
Princess Cruises
Apr 10, 2027 - Apr 17, 2027 (7 Nights)
Fort Lauderdale • Relaxaway Half Moon Cay • San Juan, Puerto Rico • Philipsburg, St. Maarten • Fort Lauderdale
Average Starting Price
$795pp
Jim's Onboard Credit

Jim's Port Pick
Half Moon Cay is one of my all-time favorite private islands - the sand is unbelievably soft, hands-down the best I’ve ever felt!

Allure of the Seas
Royal Caribbean
Apr 11, 2027 - Apr 18, 2027 (7 Nights)
Miami • Perfect Day Cococay • San Juan, Puerto Rico • Philipsburg, St. Maarten • Miami
Average Starting Price
$979pp
Jim's Onboard Credit
FREE Specialty Dining Meal
Silver Ray
Silversea
Dec 26, 2027 - Jan 3, 2028 (8 Nights)
San Juan, Puerto Rico • St. John • St John's, Antigua • Fort-De-France, Martinique • St. Kitts • Great Harbor Jost Van Dyke, British Virgin Islands • Miami
Average Starting Price
$5,500pp
Jim's Onboard Credit

Phyllis' Holiday Pick
Best time of the year to cruise! I love spending the holidays cruising with my family! The ships are beautifully decorated, and ringing in New Year’s Eve at sea is an experience I’ll never forget!

Norwegian Dawn
Norwegian Cruise Line
Nov 29, 2027 - Dec 9, 2027 (10 Nights)
Jacksonville • Grand Bahama Island • Nassau • Puerto Plata, Dominican Republic • Samana, Dominican Republic • Tortola • San Juan, Puerto Rico • Jacksonville
Average Starting Price
$1,039pp
Jim's Onboard Credit
Zuiderdam
Holland America Line
Oct 30, 2027 - Nov 27, 2027 (28 Nights)
Miami • Nassau • Relaxaway Half Moon Cay • Ocho Rios, Jamaica • Santa Domingo, Dominican Republic • San Juan, Puerto Rico • St. Thomas • St John's, Antigua • Castries, St. Lucia • Port of Spain, Trinidad • Willemstad, Curacao • Oranjestad, Aruba • Santa Marta, Colombia • Cartagena, Colombia • Colon, Panama • Limon, Costa Rica • Belize City • Cozumel • Progreso, Mexico • Miami
Average Starting Price
$6,584pp
Jim's Onboard Credit

Jim's Port Pick
Half Moon Cay is one of my all-time favorite private islands - the sand is unbelievably soft, hands-down the best I’ve ever felt!

Celebrity Eclipse
Celebrity Cruises
Dec 4, 2027 - Dec 14, 2027 (10 Nights)
Fort Lauderdale • Grand Turk • San Juan, Puerto Rico • Basseterre, St. Kitts and Nevis • Oranjestad, Aruba • Willemstad, Curacao • Fort Lauderdale
Average Starting Price
$1,172pp
Jim's Onboard Credit

Luke's Port Pick
Grand Turk has it all - stunning ship views, a pool, great snorkeling, and crystal-clear water! This port will always be my favorite!

Scarlet Lady
Virgin Voyages
Apr 17, 2027 - Apr 24, 2027 (7 Nights)
Miami • San Juan, Puerto Rico • Puerto Plata, Dominican Republic • Bimini • Miami
Average Starting Price
$903pp
Jim's Onboard Credit
Hero of the Seas
Royal Caribbean
Dec 30, 2027 - Jan 8, 2028 (9 Nights)
Miami • St. Thomas • Basseterre, St. Kitts and Nevis • Philipsburg, St. Maarten • San Juan, Puerto Rico • Perfect Day Cococay • Miami
Average Starting Price
$3,825pp
Jim's Onboard Credit

Phyllis' Holiday Pick
Best time of the year to cruise! I love spending the holidays cruising with my family! The ships are beautifully decorated, and ringing in New Year’s Eve at sea is an experience I’ll never forget!

Celebrity Constellation
Celebrity Cruises
Apr 3, 2027 - Apr 16, 2027 (13 Nights)
San Juan, Puerto Rico • Philipsburg, St. Maarten • Tangier, Morocco • Malaga, Spain • Barcelona, Spain
Average Starting Price
$891pp
Jim's Onboard Credit
Legend of the Seas
Royal Caribbean
Jan 3, 2027 - Jan 9, 2027 (6 Nights)
Fort Lauderdale • Perfect Day Cococay • San Juan, Puerto Rico • Samana, Dominican Republic • Fort Lauderdale
Average Starting Price
$1,315pp
Jim's Onboard Credit
FREE Specialty Dining Meal
 Back
Page 8 of 122
Next 
Filters 
Filters
X
Active filters (1)
Port: San Juan×
Clear all filters
Cruise Lines
Ships
Cruise Dates
By Month
By Date
2026
JanFebMarAprMayJunJulAugSepOctNovDec
2027
JanFebMarAprMayJunJulAugSepOctNovDec
2028
JanFebMarAprMayJunJulAugSepOctNovDec


October 2026
November 2026

S
M
T
W
T
F
S
12345678910111213141516171819202122232425262728293031
Nights

to

Departure Ports
Regions
Ports of Call
Room Type
Show Results
Caribbean Breeze Travel Logo
Welcome to the CBT Family!
  • Open 24/7
  • [email protected]
Cruise SearchContact Us

Explore Cruises

  • Cruise Destinations
  • Departure Ports
  • Cruise Lines
  • Private Destinations

Your Booking

  • My Booking
  • Transfer Cruise

Help & Guides

  • Cruise Guides
  • FAQ
  • Contact Us
© 2026 Caribbean Breeze Travel · Family-owned since 2015Photo Credits