Cruise Search | Caribbean Breeze Travel

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!

Silver Spirit

Silversea

Feb 17, 2028 - Feb 29, 2028 (12 Nights)

Bridgetown, Barbados • Bequia Island, Saint Vincent • Castries, St. Lucia • Oranjestad, Aruba • Kralendijk, Bonaire • Willemstad, Curacao • Gustavia, St. Barts • St John's, Antigua • Fort-De-France, Martinique • Grenada • Bridgetown, Barbados

Average Starting Price

$4,500pp

Jim's Onboard Credit

33% OFF

Seven Seas Grandeur

Regent Seven Seas Cruises

Feb 4, 2028 - Feb 14, 2028 (10 Nights)

Bridgetown, Barbados • Willemstad, Curacao • Oranjestad, Aruba • Castries, St. Lucia • Pointe-à-Pitre, Guadeloupe • Basseterre, St. Kitts and Nevis • St John's, Antigua • Roseau, Dominica • Bridgetown, Barbados

Average Starting Price

Dec 1, 2026 - Dec 12, 2026 (11 Nights)

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

$1,924pp

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!

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

Apr 7, 2028 - Apr 17, 2028 (10 Nights)

Fort Lauderdale • Philipsburg, St. Maarten • Castries, St. Lucia • Bridgetown, Barbados • St John's, Antigua • Basseterre, St. Kitts and Nevis • Fort Lauderdale

Average Starting Price

Feb 21, 2027 - Feb 28, 2027 (7 Nights)

San Juan, Puerto Rico • St. Thomas • St. Croix • Philipsburg, St. Maarten • St John's, Antigua • Roseau, Dominica • San Juan, Puerto Rico

Average Starting Price

$609pp

Jim's Onboard Credit

FREE Specialty Dining Meal

EXPLORA III

Explora Journeys

Dec 28, 2026 - Jan 5, 2027 (8 Nights)

San Juan, Puerto Rico • St John's, Antigua • Pointe-à-Pitre, Guadeloupe • St. John • New Year Fireworks SJU • New Year Fireworks SJU • Samana, Dominican Republic • Puerto Plata, Dominican Republic • Miami

Average Starting Price

Jan 5, 2027 - Jan 15, 2027 (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

$6,799pp

Jim's Onboard Credit

27% OFF

Seven Seas Mariner

Regent Seven Seas Cruises

Oct 14, 2028 - Nov 7, 2028 (24 Nights)

Average Starting Price

Jan 16, 2029 - Jan 27, 2029 (11 Nights)

San Juan del sur, Nicaragua • Oranjestad, Aruba • Willemstad, Curacao • Kralendijk, Bonaire • Canouan, Saint Vincent and the Grenadines • Castries, St. Lucia • Les Saintes, F.W.I. • St John's, Antigua • Road Bay, Anguilla • San Juan del sur, Nicaragua

Average Starting Price

$6,000pp

Jim's Onboard Credit

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