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

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!

Star Legend
Windstar Cruises
Dec 27, 2027 - Jan 10, 2028 (14 Nights)
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 • St. John • Gustavia, St. Barts • Basseterre, St. Kitts and Nevis • Philipsburg, St. Maarten • Great Harbor Jost Van Dyke, British Virgin Islands • Virgin Gorda, British Virgin Islands • San Juan, Puerto Rico
Average Starting Price
$4,504pp
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!

9% OFF
Crystal Serenity
Crystal Cruises
Dec 29, 2027 - Jan 8, 2028 (10 Nights)
San Juan, Puerto Rico • Marigot Bay, St. Martin, French West Indies • St. Kitts • Great Harbor Jost Van Dyke, British Virgin Islands • Cap Cana (Punta Cana), Dominican Republic • Montego Bay, Jamaica • George Town, Cayman Islands • Cozumel • Fort Lauderdale
Average Starting Price
$5,380pp
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
Jan 5, 2027 - Jan 14, 2027 (9 Nights)
San Juan, Puerto Rico • St. John • Great Harbor Jost Van Dyke, British Virgin Islands • Philipsburg, St. Maarten • St John's, Antigua • Basseterre, St. Kitts and Nevis • Tortola • Miami
Average Starting Price
$3,009pp
Jim's Onboard Credit
Vision of the Seas
Royal Caribbean
Nov 7, 2027 - Nov 14, 2027 (7 Nights)
San Juan, Puerto Rico • St. Thomas • Basseterre, St. Kitts and Nevis • Willemstad, Curacao • Oranjestad, Aruba • San Juan, Puerto Rico
Average Starting Price
$709pp
Jim's Onboard Credit
Celebrity Summit
Celebrity Cruises
Nov 14, 2027 - Nov 21, 2027 (7 Nights)
San Juan, Puerto Rico • Kingstown, Saint Vincent Island, Saint Vincent • Bridgetown, Barbados • Castries, St. Lucia • St John's, Antigua • St. Thomas • San Juan, Puerto Rico
Average Starting Price
$591pp
Jim's Onboard Credit
Seabourn Ovation
Seabourn
Nov 21, 2026 - Nov 28, 2026 (7 Nights)
San Juan, Puerto Rico • St. Barthelemy, F.W.I • St. Kitts • Les Trois-Îlets • Port Elizabeth, South Africa • Kralendijk, Bonaire • Oranjestad, Aruba
Average Starting Price
$3,469pp
Jim's Onboard Credit
9% OFF
Crystal Symphony
Crystal Cruises
Jan 3, 2028 - Jan 11, 2028 (8 Nights)
San Juan, Puerto Rico • Marigot Bay, St. Martin, French West Indies • St John's, Antigua • St. Kitts • Tortola • Samana, Dominican Republic • Grand Turk • Fort Lauderdale
Average Starting Price
$3,840pp
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!

Emerald Princess
Princess Cruises
Nov 28, 2027 - Dec 5, 2027 (7 Nights)
San Juan, Puerto Rico • Tortola • St. Kitts • Dominica • Grenada • Bridgetown, Barbados • San Juan, Puerto Rico
Average Starting Price
$804pp
Jim's Onboard Credit
Silver Shadow
Silversea
Feb 26, 2027 - Mar 5, 2027 (7 Nights)
San Juan, Puerto Rico • St. John • Gustavia, St. Barts • St. Kitts • St John's, Antigua • Little Bay, Montserrat • Great Harbor Jost Van Dyke, British Virgin Islands • San Juan, Puerto Rico
Average Starting Price
$4,350pp
Jim's Onboard Credit
Rhapsody of the Seas
Royal Caribbean
Dec 11, 2027 - Dec 18, 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
$729pp
Jim's Onboard Credit
Scarlet Lady
Virgin Voyages
Nov 20, 2027 - Nov 27, 2027 (7 Nights)
San Juan, Puerto Rico • Oranjestad, Aruba • Willemstad, Curacao • St John's, Antigua • Philipsburg, St. Maarten • San Juan, Puerto Rico
Average Starting Price
$973pp
Jim's Onboard Credit
 Back
Page 6 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