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, Puerto Rico×
Sort by: Recommended

Search Cruises

Nieuw Statendam
Holland America Line
Feb 28, 2027 - Mar 14, 2027 (14 Nights)
Fort Lauderdale • Nassau • Grand Turk • Amber Cove, Dominican Republic • Relaxaway Half Moon Cay • Fort Lauderdale • Grand Turk • San Juan, Puerto Rico • St. Thomas • Relaxaway Half Moon Cay • Fort Lauderdale
Average Starting Price
$2,714pp
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 I
Explora Journeys
Feb 5, 2027 - Mar 1, 2027 (24 Nights)
San Juan, Puerto Rico • Gustavia, St. Barts • St. Pierre • Bridgetown, Barbados • Port of Spain, Trinidad • Port of Spain, Trinidad • Macapa, , Brazil • Santarem, Brazil • Boca da Valeria (Amazon River), Brazil • Manaus, Brazil • Manaus, Brazil • Parintins, Brazil • Alter Do Chao, Brazil • Macapa, , Brazil • Devil's Island, France • Bequia Island, Saint Vincent • Bridgetown, Barbados • Castries, St. Lucia • Gustavia, St. Barts • Basseterre, St. Kitts and Nevis • San Juan, Puerto Rico
Average Starting Price
$17,100pp
Jim's Onboard Credit
60% OFF
Margaritaville at Sea Beachcomber
Margaritaville at Sea
Jul 3, 2027 - Jul 10, 2027 (7 Nights)
Miami • Philipsburg, St. Maarten • San Juan, Puerto Rico • Puerto Plata, Dominican Republic • Miami
Average Starting Price
$849pp
Jim's Onboard Credit
Seabourn Quest
Seabourn
Dec 28, 2027 - Jan 7, 2028 (10 Nights)
Miami • San Juan, Puerto Rico • St. Kitts • Little Bay, Montserrat • Saint Barthelemy, Gustavia • Great Harbor Jost Van Dyke, British Virgin Islands • Miami
Average Starting Price
$6,753pp
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!

EXPLORA III
Explora Journeys
Mar 7, 2027 - Mar 14, 2027 (7 Nights)
San Juan, Puerto Rico • Philipsburg, St. Maarten • Gustavia, St. Barts • Gustavia, St. Barts • Basseterre, St. Kitts and Nevis • Grand Turk • Miami
Average Starting Price
$6,785pp
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!

Crystal Symphony
Crystal Cruises
Mar 20, 2027 - Apr 2, 2027 (13 Nights)
Fort Lauderdale • San Juan, Puerto Rico • Marigot Bay, St. Martin, French West Indies • St John's, Antigua • Santa Cruz de la Palma, Spain • Santa Cruz de Tenerife, Spain • Canary Islands
Average Starting Price
$5,200pp
Jim's Onboard Credit
Brilliant Lady
Virgin Voyages
Feb 7, 2028 - Feb 17, 2028 (10 Nights)
Miami • Puerto Plata, Dominican Republic • San Juan, Puerto Rico • Tortola • St. Thomas • Basseterre, St. Kitts and Nevis • Philipsburg, St. Maarten • Miami
Average Starting Price
$1,390pp
Jim's Onboard Credit
Independence of the Seas
Royal Caribbean
Apr 18, 2027 - Apr 25, 2027 (7 Nights)
Miami • Perfect Day Cococay • San Juan, Puerto Rico • St. Thomas • Miami
Average Starting Price
$639pp
Jim's Onboard Credit
FREE Specialty Dining Meal
Star Legend
Windstar Cruises
Dec 20, 2027 - Dec 27, 2027 (7 Nights)
San Juan, Puerto Rico • St. John • Basseterre, St. Kitts and Nevis • Gustavia, St. Barts • Philipsburg, St. Maarten • Great Harbor Jost Van Dyke, British Virgin Islands • Virgin Gorda, British Virgin Islands • San Juan, Puerto Rico
Average Starting Price
$2,443pp
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!

Azamara Journey
Azamara
Dec 18, 2026 - Jan 5, 2027 (18 Nights)
San Juan, Puerto Rico • St. Thomas • Virgin Gorda, British Virgin Islands • St John's, Antigua • Gustavia, St. Barts • St. Pierre • Port Elizabeth (Bequia), Saint Vincent and the Grenadines • Scarborough (Tobago), Trinidad and Tobago • Mayreau Island, Saint Vincent and the Grenadines • Bridgetown, Barbados • Oranjestad, Aruba • Willemstad, Curacao • Castries, St. Lucia • Charlestown, Nevis • St. Croix • San Juan, Puerto Rico
Average Starting Price
$5,729pp
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!

Seabourn Ovation
Seabourn
Nov 20, 2026 - Nov 28, 2026 (8 Nights)
Miami • San Juan, Puerto Rico • Great Harbor Jost Van Dyke, British Virgin Islands • St. Kitts • Roseau, Dominica • Bequia Island, Saint Vincent • Bridgetown, Barbados
Average Starting Price
$4,368pp
Jim's Onboard Credit
Celebrity Summit
Celebrity Cruises
Nov 21, 2027 - Nov 28, 2027 (7 Nights)
San Juan, Puerto Rico • Roseau, Dominica • Bridgetown, Barbados • Castries, St. Lucia • St John's, Antigua • St. Thomas • San Juan, Puerto Rico
Average Starting Price
$619pp
Jim's Onboard Credit
 Back
Page 31 of 121
Next 
Filters 
Filters
X
Active filters (1)
Port: San Juan, Puerto Rico×
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