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

Seabourn Pursuit
Seabourn
Sep 6, 2028 - Oct 18, 2028 (42 Nights)
Reykjavik, Iceland • Exploring The Outer Islands of Heimaey • Heimaey (Vestmannaeyjar), Iceland • Prince Christian Sound, Greenland • Prince Christian Sound, Greenland • Kangikitsok, Greenland • Qaqortoq (Julianehåb), Greenland • Hvalsey, Greenland • Brattahlid (Qassiarsuk), Greenland • Nain, Canada • Nachvak Fiord, Torngat Mts, Canada • Eclipse Channel, Labrador, Canada • Saglek Fjord, Labrador, Canada • Hopedale, Labrador • Indian Harbour, Newfoundland • L'Anse aux Meadows, Newfoundland • Red Bay, Canada • Norris Point, Newfoundland • Halifax, Nova Scotia • Hamilton, Bermuda • San Juan, Puerto Rico • Oranjestad, Aruba • Panama Canal Cruising • Panama City (Fuerte Amador), Panama • Panama City (Fuerte Amador), Panama • Guayaquil, Ecuador • Lima, Peru • Lima, Peru • General San Martin, Peru • Valparaíso, Chile
Average Starting Price
$33,113pp
Jim's Onboard Credit
Sky Princess
Princess Cruises
Jan 9, 2028 - Jan 23, 2028 (14 Nights)
Fort Lauderdale • Relaxaway Half Moon Cay • Falmouth, Jamaica • George Town, Cayman Islands • Cozumel • Fort Lauderdale • St. Kitts • San Juan, Puerto Rico • Amber Cove, Dominican Republic • Fort Lauderdale
Average Starting Price
$1,098pp
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!

Nieuw Statendam
Holland America Line
Jan 3, 2027 - Jan 17, 2027 (14 Nights)
Fort Lauderdale • Grand Turk • San Juan, Puerto Rico • St. Thomas • Relaxaway Half Moon Cay • Fort Lauderdale • Relaxaway Half Moon Cay • Ocho Rios, Jamaica • George Town, Cayman Islands • Cozumel • Fort Lauderdale
Average Starting Price
$2,284pp
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!

28% OFF
Carnival Venezia
Carnival Cruise Line
Dec 27, 2026 - Jan 3, 2027 (7 Nights)
Port Canaveral (Orlando), Florida • Celebration Key • Fun Day at Sea • San Juan, Puerto Rico • St. Thomas • Fun Day at Sea • Fun Day at Sea • Port Canaveral (Orlando), Florida
Average Starting Price
$1,310pp
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!

Rhapsody of the Seas
Royal Caribbean
Feb 27, 2027 - Mar 6, 2027 (7 Nights)
San Juan, Puerto Rico • St. Thomas • St. Croix • Philipsburg, St. Maarten • St John's, Antigua • Roseau, Dominica • San Juan, Puerto Rico
Average Starting Price
$588pp
Jim's Onboard Credit
FREE Specialty Dining Meal
53% OFF
MSC World America
MSC Cruises
May 15, 2027 - May 22, 2027 (7 Nights)
Miami • Puerto Plata, Dominican Republic • San Juan, Puerto Rico • Ocean Cay • Miami
Average Starting Price
$724pp
Jim's Onboard Credit

Jim Sr's Ship Pick
This ship never felt crowded - and the Pizza & Burger spot was a total win!

Grandeur of the Seas
Royal Caribbean
Oct 16, 2027 - Oct 23, 2027 (7 Nights)
San Juan, Puerto Rico • St. Thomas • St. Croix • Philipsburg, St. Maarten • Castries, St. Lucia • Bridgetown, Barbados • San Juan, Puerto Rico
Average Starting Price
$732pp
Jim's Onboard Credit
Eurodam
Holland America Line
Dec 19, 2026 - Dec 26, 2026 (7 Nights)
Fort Lauderdale • Grand Turk • San Juan, Puerto Rico • St. Thomas • Relaxaway Half Moon Cay • Fort Lauderdale
Average Starting Price
$1,289pp
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!

Zuiderdam
Holland America Line
Nov 28, 2026 - Dec 12, 2026 (14 Nights)
Miami • Relaxaway Half Moon Cay • Amber Cove, Dominican Republic • Grand Turk • Nassau • Miami • Grand Turk • San Juan, Puerto Rico • St. Thomas • Relaxaway Half Moon Cay • Miami
Average Starting Price
$2,004pp
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!

Star Pride
Windstar Cruises
Nov 29, 2027 - Dec 13, 2027 (14 Nights)
San Juan, Puerto Rico • Catalina Island, Dominican Republic • Santa Domingo, Dominican Republic • Cartagena, Colombia • Cartagena, Colombia • Panama Canal, Panama • Colon, Panama • Panama Canal, Panama • Panama City (Fuerte Amador), Panama • Panama City (Fuerte Amador), Panama • Isla Parida, Panama • Puerto Jimenez (Golfo Dulce), Costa Rica • Quepos, Costa Rica • Caldera, Costa Rica
Average Starting Price
$5,434pp
Jim's Onboard Credit
Rotterdam
Holland America Line
Feb 5, 2028 - Feb 12, 2028 (7 Nights)
Fort Lauderdale • Grand Turk • San Juan, Puerto Rico • St. Thomas • Relaxaway Half Moon Cay • Fort Lauderdale
Average Starting Price
$1,829pp
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!

Scarlet Lady
Virgin Voyages
Jan 15, 2028 - Jan 22, 2028 (7 Nights)
San Juan, Puerto Rico • St. Thomas • Bridgetown, Barbados • Kingstown, Saint Vincent Island, Saint Vincent • St John's, Antigua • Philipsburg, St. Maarten • San Juan, Puerto Rico
Average Starting Price
$833pp
Jim's Onboard Credit
 Back
Page 59 of 129
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