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October 2026

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Azamara Journey

Azamara

Dec 12, 2026 - Dec 28, 2026 (16 Nights)

Bridgetown, Barbados • Castries, St. Lucia • Roseau, Dominica • Basseterre, St. Kitts and Nevis • Charlestown, Nevis • Philipsburg, St. Maarten • San Juan, Puerto Rico • St. Thomas • Virgin Gorda, British Virgin Islands • St John's, Antigua • Gustavia, St. Barts • St. Pierre • Port Elizabeth (Bequia), Saint Vincent and the Grenadines • Scarborough (Tobago), Trinidad and Tobago • Mayreau Island, Saint Vincent and the Grenadines • Bridgetown, Barbados

Average Starting Price

Dec 13, 2026 - Dec 27, 2026 (14 Nights)

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 • Grenada • Bequia Island, Saint Vincent • Mayreau Island, Saint Vincent and the Grenadines • Deshaies, Guadeloupe • Marigot Bay, St. Martin, French West Indies • San Juan, Puerto Rico

Average Starting Price

49% OFF

Dec 14, 2027 - Dec 28, 2027 (14 Nights)

Bridgetown, Barbados • Kingstown, Saint Vincent Island, Saint Vincent • Grenada • Fort-De-France, Martinique • Pointe-à-Pitre, Guadeloupe • Philipsburg, St. Maarten • St John's, Antigua • St. Kitts • Roseau, Dominica • Fort-De-France, Martinique • Pointe-à-Pitre, Guadeloupe • Kingstown, Saint Vincent Island, Saint Vincent • Bridgetown, Barbados

Average Starting Price

Nov 10, 2028 - Dec 18, 2028 (38 Nights)

Miami • San Juan, Puerto Rico • Carambola Beach, Saint Kitts and Nevis • Great Harbour, Jost Van Dyke, B.V.I • Miami • Basseterre, St. Kitts and Nevis • Port Elizabeth, South Africa • Saint Georges, Grenada • Port of Spain, Trinidad • Cruising the Amazon River • Macapa, , Brazil • Cruising the Amazon River • Cruising the Amazon River • Santarem, Brazil • Parintins, Brazil • Manaus, Brazil • Manaus, Brazil • Alter Do Chao, Brazil • Cruising the Amazon River • Devil's Island, France • Castries, St. Lucia • Gustavia, St. Barts • St. John • Miami

Average Starting Price

Jan 9, 2027 - Jan 16, 2027 (7 Nights)

San Juan, Puerto Rico • St. Croix • Philipsburg, St. Maarten • St John's, Antigua • Fort-De-France, Martinique • Basseterre, St. Kitts and Nevis • San Juan, Puerto Rico

Average Starting Price

$508pp

Jim's Onboard Credit

FREE Specialty Dining Meal

50% OFF

MSC Opera

MSC Cruises

Dec 27, 2027 - Jan 3, 2028 (7 Nights)

La Romana, Dominican Republic • Catalina Island, Dominican Republic • Virgin Gorda, British Virgin Islands • Philipsburg, St. Maarten • St. Kitts • St John's, Antigua • La Romana, Dominican Republic

Average Starting Price

$1,559pp

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!

Silver Ray

Silversea

Feb 26, 2027 - Mar 10, 2027 (12 Nights)

Bridgetown, Barbados • Bequia Island, Saint Vincent • Grenada • Fort-De-France, Martinique • Deshaies, Guadeloupe • Soufrier Bay, St. Lucia • St. Kitts • Philipsburg, St. Maarten • Gustavia, St. Barts • Road Bay, Anguilla • Miami

Average Starting Price

$6,500pp

Jim's Onboard Credit

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

Norwegian Bliss

Norwegian Cruise Line

Dec 23, 2026 - Jan 4, 2027 (12 Nights)

Manhattan • Puerto Plata, Dominican Republic • San Juan, Puerto Rico • St. Kitts • St. Thomas • Tortola • Philipsburg, St. Maarten • Manhattan

Average Starting Price

67% OFF

Dec 19, 2026 - Dec 27, 2026 (8 Nights)

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

Average Starting Price

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!

Vision of the Seas

Royal Caribbean

Nov 15, 2026 - Nov 22, 2026 (7 Nights)

San Juan, Puerto Rico • St. Thomas • St John's, Antigua • Philipsburg, St. Maarten • St. Croix • Basseterre, St. Kitts and Nevis • San Juan, Puerto Rico

Average Starting Price

$664pp

Jim's Onboard Credit

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