Cruise Search | Caribbean Breeze Travel

Ocean & RiverAllOcean OnlyOceanRiver OnlyRiver

Cruise Dates



October 2026



1 2 3 4 5 6 7 8 9 10 11 12 13 14 15 16 17 18 19 20 21 22 23 24 25 26 27 28 29 30 31

Nights

Clear All Filters

Rotterdam

Holland America Line

Feb 23, 2027 - Mar 6, 2027 (11 Nights)

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

$2,269pp

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!

Silver Dawn

Silversea

Jan 4, 2028 - Jan 15, 2028 (11 Nights)

San Juan, Puerto Rico • Great Harbor Jost Van Dyke, British Virgin Islands • Gustavia, St. Barts • St. Kitts • Fort-De-France, Martinique • Grenada • Kralendijk, Bonaire • Willemstad, Curacao • Oranjestad, Aruba • San Juan, Puerto Rico

Average Starting Price

34% OFF

Feb 13, 2027 - Feb 21, 2027 (8 Nights)

Miami • Philipsburg, St. Maarten • St. Kitts • St. Thomas • Amber Cove, Dominican Republic • Miami

Average Starting Price

Jan 31, 2028 - Feb 11, 2028 (11 Nights)

Miami • St. John • Gustavia, St. Barts • St John's, Antigua • Fort-De-France, Martinique • St. Kitts • San Juan, Puerto Rico • Miami

Average Starting Price

$6,300pp

Jim's Onboard Credit

Norwegian Prima

Norwegian Cruise Line

Dec 11, 2027 - Dec 18, 2027 (7 Nights)

San Juan, Puerto Rico • St. Thomas • St. Kitts • Philipsburg, St. Maarten • Bridgetown, Barbados • Tortola • San Juan, Puerto Rico

Average Starting Price

Mar 6, 2028 - Mar 17, 2028 (11 Nights)

Fort Lauderdale • St. Thomas • St John's, Antigua • Bridgetown, Barbados • Castries, St. Lucia • Roseau, Dominica • Basseterre, St. Kitts and Nevis • Fort Lauderdale

Average Starting Price

Feb 14, 2027 - Feb 21, 2027 (7 Nights)

San Juan, Puerto Rico • St. Thomas • St. Kitts • Dominica • Grenada • Bridgetown, Barbados • San Juan, Puerto Rico

Average Starting Price

Dec 27, 2027 - Jan 6, 2028 (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

$3,599pp

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!

Celebrity Constellation

Celebrity Cruises

Feb 13, 2027 - Feb 20, 2027 (7 Nights)

San Juan, Puerto Rico • Tortola • Basseterre, St. Kitts and Nevis • Roseau, Dominica • Castries, St. Lucia • Bridgetown, Barbados • San Juan, Puerto Rico

Average Starting Price

$626pp

Jim's Onboard Credit

33% OFF

Seven Seas Mariner

Regent Seven Seas Cruises

Oct 28, 2028 - Nov 7, 2028 (10 Nights)

Miami • San Juan, Puerto Rico • St. Thomas • Basseterre, St. Kitts and Nevis • St John's, Antigua • Gustavia, St. Barts • Miami

Average Starting Price

9% OFF

Jan 19, 2029 - Jan 27, 2029 (8 Nights)

Fort Lauderdale • Grand Turk • Samana, Dominican Republic • Great Harbor Jost Van Dyke, British Virgin Islands • St John's, Antigua • St. Kitts • Gustavia, St. Barts • San Juan, Puerto Rico

Average Starting Price

$5,170pp

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!

Seabourn Quest

Seabourn

Dec 18, 2027 - Dec 28, 2027 (10 Nights)

Miami • San Juan, Puerto Rico • Road Bay, Anguilla • Little Bay, Montserrat • St. Kitts • Great Harbor Jost Van Dyke, British Virgin Islands • Miami

Average Starting Price

$7,453pp

Jim's Onboard Credit

Page 21 of 83

Filters

Search Cruises