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 24, 2028 - Nov 9, 2028 (46 Nights)
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 • The Seabourn Juan Fernandez Experience • The Seabourn Juan Fernandez Experience • The Seabourn Juan Fernandez Experience • Scenic Cruising Reloncavi Sound • Puerto Montt, Chile • Scenic Cruising Moraleda Channel • Scenic Cruising Darwin Channel • Scenic Cruising Baker Channel • Transit The English Narrows • Caleta Tortel, Chile • Scenic Cruising Eyre Fjord • Scenic Cruising Wide Channel • Pio XI Glacier, Chile • Scenic Cruising Peel Fjord • Scenic Cruising Smyth Channel • Brujo Glacier, Chile • Magellan Strait • Punta Arenas, Chile • Punta Arenas, Chile • The Seabourn Antarctic Experience • The Seabourn Antarctic Experience • The Seabourn Antarctic Experience • The Seabourn Antarctic Experience • The Seabourn Antarctic Experience • Ushuaia, Argentina • Ushuaia, Argentina
Average Starting Price
$40,708pp
Jim's Onboard Credit
Regal Princess
Princess Cruises
Jan 9, 2028 - Jan 16, 2028 (7 Nights)
Miami • St. Kitts • San Juan, Puerto Rico • Amber Cove, Dominican Republic • Miami
Average Starting Price
$569pp
Jim's Onboard Credit
47% OFF
MSC World America
MSC Cruises
Aug 21, 2027 - Aug 28, 2027 (7 Nights)
Miami • Puerto Plata, Dominican Republic • San Juan, Puerto Rico • Ocean Cay • Miami
Average Starting Price
$874pp
Jim's Onboard Credit

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

Sky Princess
Princess Cruises
Jan 23, 2028 - Feb 6, 2028 (14 Nights)
Fort Lauderdale • Relaxaway Half Moon Cay • San Juan, Puerto Rico • Grand Turk • Amber Cove, Dominican Republic • Fort Lauderdale • Relaxaway Half Moon Cay • Falmouth, Jamaica • George Town, Cayman Islands • Cozumel • Fort Lauderdale
Average Starting Price
$1,228pp
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!

9% OFF
Crystal Serenity
Crystal Cruises
Mar 10, 2028 - Mar 20, 2028 (10 Nights)
Fort Lauderdale • Grand Turk • Marigot Bay, St. Martin, French West Indies • St John's, Antigua • St. Kitts • San Juan, Puerto Rico • Nassau • Fort Lauderdale
Average Starting Price
$5,110pp
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!

Grandeur of the Seas
Royal Caribbean
Sep 4, 2027 - Sep 11, 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
$705pp
Jim's Onboard Credit
Sonata
Oceania Cruises
Nov 1, 2028 - Nov 16, 2028 (15 Nights)
Lisbon, Portugal • Portimão, Portugal • Funchal, Portugal • Santa Cruz de Tenerife, Spain • Santa Cruz de la Palma, Spain • San Juan, Puerto Rico • Miami
Average Starting Price
$5,299pp
Jim's Onboard Credit
Rhapsody of the Seas
Royal Caribbean
Feb 12, 2028 - Feb 19, 2028 (7 Nights)
San Juan, Puerto Rico • St. Thomas • Philipsburg, St. Maarten • St John's, Antigua • Basseterre, St. Kitts and Nevis • St. Croix • San Juan, Puerto Rico
Average Starting Price
$758pp
Jim's Onboard Credit
Viking Sky
Viking
Dec 24, 2028 - Jan 3, 2029 (10 Nights)
San Juan, Puerto Rico • St. Thomas • Basseterre, St. Kitts and Nevis • Castries, St. Lucia • Bridgetown, Barbados • Roseau, Dominica • St John's, Antigua • Philipsburg, St. Maarten • St. Croix • San Juan, Puerto Rico
Average Starting Price
$3,799pp
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!

Rotterdam
Holland America Line
Feb 13, 2027 - Mar 6, 2027 (21 Nights)
Fort Lauderdale • Key West, Florida • George Town, Cayman Islands • Ocho Rios, Jamaica • Mahogany Bay, Honduras • Belize City • Cozumel • Fort Lauderdale • Philipsburg, St. Maarten • St John's, Antigua • Roseau, Dominica • Fort-De-France, Martinique • St. Kitts • San Juan, Puerto Rico • Relaxaway Half Moon Cay • Fort Lauderdale
Average Starting Price
$4,109pp
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!

EXPLORA II
Explora Journeys
Mar 19, 2028 - Apr 4, 2028 (16 Nights)
Miami • San Juan, Puerto Rico • St John's, Antigua • Funchal, Portugal • Cadiz, Spain • Malaga, Spain • Barcelona, Spain
Average Starting Price
$7,110pp
Jim's Onboard Credit
35% OFF
Carnival Festivale
Carnival Cruise Line
Apr 1, 2028 - Apr 9, 2028 (8 Nights)
Port Canaveral (Orlando), Florida • Fun Day at Sea • Fun Day at Sea • St. Thomas • San Juan, Puerto Rico • Amber Cove, Dominican Republic • Fun Day at Sea • Celebration Key • Port Canaveral (Orlando), Florida
Average Starting Price
$1,016pp
Jim's Onboard Credit
 Back
Page 74 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