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
Depart: San Juan×
Sort by: Recommended

Search Cruises

Disney Dream
Disney Cruise Line
Apr 23, 2027 - Apr 27, 2027 (4 Nights)
San Juan, Puerto Rico • Disney Lookout Cay at Lighthouse Point, Bahamas • Disney Castaway Cay, Bahamas • Fort Lauderdale
Average Starting Price
$1,568pp
Jim's Onboard Credit
Emerald Princess
Princess Cruises
Nov 21, 2027 - Nov 26, 2027 (5 Nights)
San Juan, Puerto Rico • St. Thomas • Philipsburg, St. Maarten • Dominica • St. Lucia • Bridgetown, Barbados
Average Starting Price
$497pp
Jim's Onboard Credit
Valiant Lady
Virgin Voyages
Apr 10, 2027 - Apr 15, 2027 (5 Nights)
San Juan, Puerto Rico • Grand Turk • Bimini • Miami
Average Starting Price
$795pp
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!

15% OFF
Allura
Oceania Cruises
Feb 19, 2027 - Feb 27, 2027 (8 Nights)
San Juan, Puerto Rico • St. Thomas • Philipsburg, St. Maarten • Basseterre, St. Kitts and Nevis • St John's, Antigua • Tortola • Miami
Average Starting Price
$3,740pp
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
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!

EXPLORA II
Explora Journeys
Dec 19, 2027 - Dec 26, 2027 (7 Nights)
San Juan, Puerto Rico • Tortola • Pointe-à-Pitre, Guadeloupe • Gustavia, St. Barts • St. John • Miami
Average Starting Price
$4,935pp
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!

Disney Fantasy
Disney Cruise Line
Dec 3, 2027 - Dec 10, 2027 (7 Nights)
San Juan, Puerto Rico • Oranjestad, Aruba • Willemstad, Curacao • Roseau, Dominica • St John's, Antigua • San Juan, Puerto Rico
Average Starting Price
$2,094pp
Jim's Onboard Credit
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
Scarlet Lady
Virgin Voyages
Nov 12, 2027 - Nov 20, 2027 (8 Nights)
San Juan, Puerto Rico • Tortola • Basseterre, St. Kitts and Nevis • Bridgetown, Barbados • Castries, St. Lucia • Roseau, Dominica • Philipsburg, St. Maarten • San Juan, Puerto Rico
Average Starting Price
$1,112pp
Jim's Onboard Credit
Crown Princess
Princess Cruises
Mar 21, 2027 - Mar 28, 2027 (7 Nights)
San Juan, Puerto Rico • St. Thomas • Philipsburg, St. Maarten • St John's, Antigua • St. Lucia • Bridgetown, Barbados • San Juan, Puerto Rico
Average Starting Price
$784pp
Jim's Onboard Credit
Star Pride
Windstar Cruises
Nov 1, 2027 - Nov 15, 2027 (14 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 • Grenada • Bequia Island, Saint Vincent • Mayreau Island, Saint Vincent and the Grenadines • Les Saintes, F.W.I. • Marigot Bay, St. Martin, French West Indies • San Juan, Puerto Rico
Average Starting Price
$4,224pp
Jim's Onboard Credit
 Back
Page 2 of 44
Next 
Filters 
Filters
X
Active filters (1)
Depart: 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