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October 2026

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Azamara Journey

Azamara

Dec 12, 2026 - Dec 18, 2026 (6 Nights)

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

Average Starting Price

21% OFF

Mar 9, 2027 - Mar 23, 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 • Castries, St. Lucia • Bridgetown, Barbados

Average Starting Price

Jan 29, 2028 - Feb 5, 2028 (7 Nights)

Bridgetown, Barbados • Bequia Island, Saint Vincent • Fort-De-France, Martinique • Gustavia, St. Barts • Roseau, Dominica • Grenada • Castries, St. Lucia • Bridgetown, Barbados

Average Starting Price

9% OFF

Jan 30, 2028 - Feb 12, 2028 (13 Nights)

Manaus, Brazil • Parintins, Brazil • Alter Do Chao, Brazil • Cruising the Amazon River • Devil's Island, France • Bridgetown, Barbados • Roseau, Dominica • Gustavia, St. Barts • Fort Lauderdale

Average Starting Price

$6,200pp

Jim's Onboard Credit

31% OFF

Seven Seas Grandeur

Regent Seven Seas Cruises

Jan 25, 2028 - Feb 4, 2028 (10 Nights)

Bridgetown, Barbados • Kingstown, Saint Vincent Island, Saint Vincent • Castries, St. Lucia • Fort-De-France, Martinique • Pointe-à-Pitre, Guadeloupe • Gustavia, St. Barts • Basseterre, St. Kitts and Nevis • St John's, Antigua • Roseau, Dominica • Bridgetown, Barbados

Average Starting Price

Nov 10, 2026 - Nov 21, 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

$1,969pp

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!

Celebrity Constellation

Celebrity Cruises

Nov 17, 2026 - Nov 28, 2026 (11 Nights)

San Juan, Puerto Rico • Tortola • St John's, Antigua • Castries, St. Lucia • Grenada • Bridgetown, Barbados • Kingstown, Saint Vincent Island, Saint Vincent • Fort-De-France, Martinique • Roseau, Dominica • San Juan, Puerto Rico

Average Starting Price

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

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

Average Starting Price

Feb 11, 2029 - Feb 22, 2029 (11 Nights)

Panama City (Fuerte Amador), Panama • Panama Canal, Panama • Oranjestad, Aruba • Grenada • Roseau, Dominica • Basseterre, St. Kitts and Nevis • Tortola • 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

Jan 3, 2029 - Jan 13, 2029 (10 Nights)

Average Starting Price

Dec 19, 2027 - Jan 3, 2028 (15 Nights)

Philipsburg, St. Maarten • St John's, Antigua • Gustavia, St. Barts • Road Bay, Anguilla • Soper's Hole, Tortola • Great Harbor Jost Van Dyke, British Virgin Islands • Great Harbor Jost Van Dyke, British Virgin Islands • Virgin Gorda, British Virgin Islands • Charlestown, Nevis • Philipsburg, St. Maarten • Charlestown, Nevis • Roseau, Dominica • Mayreau Island, Saint Vincent and the Grenadines • Les Saintes, F.W.I. • Basseterre, St. Kitts and Nevis • Gustavia, St. Barts • Philipsburg, St. Maarten

Average Starting Price

$4,545pp

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!

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