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!

Crown Princess

Princess Cruises

Jan 22, 2027 - Jan 29, 2027 (7 Nights)

Bridgetown, Barbados • San Juan, Puerto Rico • St. Thomas • Philipsburg, St. Maarten • St John's, Antigua • St. Lucia • Bridgetown, Barbados

Average Starting Price

Feb 19, 2029 - Mar 5, 2029 (14 Nights)

Fort Lauderdale • Relaxaway Half Moon Cay • Amber Cove, Dominican Republic • Grand Turk • Fort Lauderdale • Philipsburg, St. Maarten • St. Thomas • San Juan, Puerto Rico • Amber Cove, Dominican Republic • Fort Lauderdale

Average Starting Price

$1,974pp

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!

Star Pride

Windstar Cruises

Mar 6, 2028 - Mar 20, 2028 (14 Nights)

Oranjestad, Aruba • Willemstad, Curacao • Kralendijk, Bonaire • Gustavia, St. Barts • 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

Dec 13, 2026 - Dec 20, 2026 (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

Jan 28, 2029 - Feb 11, 2029 (14 Nights)

Fort Lauderdale • Belize City • Roatan, Honduras • Cozumel • Celebration Key • Fort Lauderdale • Amber Cove, Dominican Republic • San Juan, Puerto Rico • St. Kitts • Fort Lauderdale

Average Starting Price

$1,484pp

Jim's Onboard Credit

Norwegian Prima

Norwegian Cruise Line

Dec 6, 2026 - Dec 13, 2026 (7 Nights)

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

Average Starting Price

60% OFF

Apr 3, 2027 - Apr 10, 2027 (7 Nights)

Miami • Puerto Plata, Dominican Republic • San Juan, Puerto Rico • Ocean Cay • Miami

Average Starting Price

$634pp

Jim's Onboard Credit

Jim Sr's Ship Pick
This ship never felt crowded - and the Pizza & Burger spot was a total win!

Crown Princess

Princess Cruises

Jan 15, 2027 - Jan 22, 2027 (7 Nights)

Bridgetown, Barbados • San Juan, Puerto Rico • Philipsburg, St. Maarten • Martinique • Grenada • St. Lucia • Bridgetown, Barbados

Average Starting Price

Nov 22, 2026 - Dec 6, 2026 (14 Nights)

Fort Lauderdale • Celebration Key • Grand Turk • Nassau • Fort Lauderdale • Philipsburg, St. Maarten • San Juan, Puerto Rico • Amber Cove, Dominican Republic • Grand Turk • Fort Lauderdale

Average Starting Price

$1,160pp

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!

Sky Princess

Princess Cruises

Feb 25, 2029 - Mar 4, 2029 (7 Nights)

Fort Lauderdale • Amber Cove, Dominican Republic • San Juan, Puerto Rico • St. Kitts • Fort Lauderdale

Average Starting Price

$725pp

Jim's Onboard Credit

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