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: Philipsburg×
Sort by: Recommended

Search Cruises

Norwegian Prima
Norwegian Cruise Line
Feb 14, 2027 - Feb 21, 2027 (7 Nights)
San Juan, Puerto Rico • Tortola • Bridgetown, Barbados • St. Kitts • Philipsburg, St. Maarten • St. Thomas • San Juan, Puerto Rico
Average Starting Price
$1,009pp
Jim's Onboard Credit
Star of the Seas
Royal Caribbean
Mar 7, 2027 - Mar 14, 2027 (7 Nights)
Port Canaveral (Orlando), Florida • Perfect Day Cococay • St. Thomas • Philipsburg, St. Maarten • Port Canaveral (Orlando), Florida
Average Starting Price
$1,480pp
Jim's Onboard Credit
FREE Specialty Dining Meal

Jim's Ship Pick
This is the BEST ship I’ve EVER sailed on! It rarely felt crowded, the food was incredible, the shows were absolutely phenomenal, and there’s something for everyone!

Star Princess
Princess Cruises
Oct 28, 2028 - Nov 11, 2028 (14 Nights)
Fort Lauderdale • Relaxaway Half Moon Cay • St. Thomas • Philipsburg, St. Maarten • Fort Lauderdale • Celebration Key • Amber Cove, Dominican Republic • San Juan, Puerto Rico • Grand Turk • Fort Lauderdale
Average Starting Price
$2,054pp
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!

47% OFF
MSC Seashore
MSC Cruises
Jan 23, 2028 - Feb 6, 2028 (14 Nights)
Miami • Puerto Plata, Dominican Republic • Ocean Cay • Nassau • Miami • Philipsburg, St. Maarten • St. Kitts • St. Thomas • Puerto Plata, Dominican Republic • Miami
Average Starting Price
$1,187pp
Jim's Onboard Credit
Rotterdam
Holland America Line
Nov 21, 2026 - Dec 12, 2026 (21 Nights)
Fort Lauderdale • Relaxaway Half Moon Cay • Falmouth, Jamaica • Mahogany Bay, Honduras • Belize City • Costa Maya • Cozumel • Fort Lauderdale • Philipsburg, St. Maarten • St John's, Antigua • Roseau, Dominica • Castries, St. Lucia • St. Kitts • St. Thomas • Relaxaway Half Moon Cay • Fort Lauderdale
Average Starting Price
$3,184pp
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!

Azamara Quest
Azamara
Nov 14, 2027 - Nov 21, 2027 (7 Nights)
Bridgetown, Barbados • Castries, St. Lucia • Roseau, Dominica • Basseterre, St. Kitts and Nevis • Charlestown, Nevis • Philipsburg, St. Maarten • Tortola • San Juan, Puerto Rico
Average Starting Price
$2,029pp
Jim's Onboard Credit
51% OFF
MSC Opera
MSC Cruises
Oct 18, 2027 - Oct 25, 2027 (7 Nights)
La Romana, Dominican Republic • Catalina Island, Dominican Republic • Virgin Gorda, British Virgin Islands • Philipsburg, St. Maarten • Fort-De-France, Martinique • St John's, Antigua • La Romana, Dominican Republic
Average Starting Price
$623pp
Jim's Onboard Credit
Emerald Princess
Princess Cruises
Jan 23, 2028 - Feb 6, 2028 (14 Nights)
San Juan, Puerto Rico • St. Thomas • St. Kitts • Dominica • Grenada • Bridgetown, Barbados • San Juan, Puerto Rico • St. Thomas • Philipsburg, St. Maarten • St John's, Antigua • St. Lucia • Bridgetown, Barbados • San Juan, Puerto Rico
Average Starting Price
$1,338pp
Jim's Onboard Credit
Grandeur of the Seas
Royal Caribbean
May 1, 2027 - May 8, 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
$656pp
Jim's Onboard Credit
FREE Specialty Dining Meal
Celebrity Ascent
Celebrity Cruises
Jan 4, 2027 - Jan 15, 2027 (11 Nights)
Fort Lauderdale • Philipsburg, St. Maarten • St John's, Antigua • Castries, St. Lucia • Bridgetown, Barbados • Roseau, Dominica • Basseterre, St. Kitts and Nevis • Fort Lauderdale
Average Starting Price
$3,433pp
Jim's Onboard Credit
Regal Princess
Princess Cruises
Feb 6, 2028 - Feb 13, 2028 (7 Nights)
Miami • Relaxaway Half Moon Cay • St. Thomas • Philipsburg, St. Maarten • Miami
Average Starting Price
$810pp
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!

Viking Sea
Viking
Nov 25, 2026 - Dec 5, 2026 (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
$4,499pp
Jim's Onboard Credit
 Back
Page 68 of 118
Next 
Filters 
Filters
X
Active filters (1)
Port: Philipsburg×
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