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October 2026

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Valiant Lady

Virgin Voyages

Feb 27, 2027 - Mar 6, 2027 (7 Nights)

San Juan, Puerto Rico • Oranjestad, Aruba • Willemstad, Curacao • Fort-De-France, Martinique • Basseterre, St. Kitts and Nevis • San Juan, Puerto Rico

Average Starting Price

Nov 29, 2026 - Dec 20, 2026 (21 Nights)

Fort Lauderdale • Philipsburg, St. Maarten • Fort-De-France, Martinique • Bridgetown, Barbados • Scarborough (Tobago), Trinidad and Tobago • Castries, St. Lucia • St. Kitts • Key West, Florida • Fort Lauderdale • Philipsburg, St. Maarten • St John's, Antigua • Tortola • San Juan, Puerto Rico • Relaxaway Half Moon Cay • Fort Lauderdale

Average Starting Price

$3,164pp

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

$4,700pp

Jim's Onboard Credit

26% OFF

Seven Seas Prestige

Regent Seven Seas Cruises

Nov 25, 2028 - Dec 9, 2028 (14 Nights)

Miami • Ocho Rios, Jamaica • Oranjestad, Aruba • Willemstad, Curacao • Kralendijk, Bonaire • Grenada • Kingstown, Saint Vincent Island, Saint Vincent • Fort-De-France, Martinique • Basseterre, St. Kitts and Nevis • 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

Dec 22, 2026 - Jan 5, 2027 (14 Nights)

Miami • George Town, Cayman Islands • Montego Bay, Jamaica • Oranjestad, Aruba • Willemstad, Curacao • Kralendijk, Bonaire • Fort-De-France, Martinique • Basseterre, St. Kitts and Nevis • Philipsburg, St. Maarten • Miami

Average Starting Price

$4,699pp

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!

Scarlet Lady

Virgin Voyages

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

San Juan, Puerto Rico • Philipsburg, St. Maarten • Bridgetown, Barbados • Fort-De-France, Martinique • Basseterre, St. Kitts and Nevis • St. Thomas • San Juan, Puerto Rico

Average Starting Price

Dec 10, 2026 - Dec 20, 2026 (10 Nights)

Miami • St. John • Philipsburg, St. Maarten • St. Kitts • Les Saintes, F.W.I. • Fort-De-France, Martinique • Little Bay, Montserrat • Great Harbor Jost Van Dyke, British Virgin Islands • San Juan, Puerto Rico

Average Starting Price

Nov 13, 2028 - Nov 25, 2028 (12 Nights)

Miami • St. Thomas • Gustavia, St. Barts • St John's, Antigua • Fort-De-France, Martinique • Roseau, Dominica • Basseterre, St. Kitts and Nevis • Tortola • Miami

Average Starting Price

Dec 12, 2027 - Jan 2, 2028 (21 Nights)

Fort Lauderdale • Relaxaway Half Moon Cay • Falmouth, Jamaica • George Town, Cayman Islands • Mahogany Bay, Honduras • Belize City • Cozumel • Fort Lauderdale • Relaxaway Half Moon Cay • Philipsburg, St. Maarten • Roseau, Dominica • Fort-De-France, Martinique • St. Kitts • St. Thomas • Fort Lauderdale

Average Starting Price

$5,169pp

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!

Rotterdam

Holland America Line

Feb 23, 2027 - Mar 16, 2027 (21 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 • Relaxaway Half Moon Cay • Falmouth, Jamaica • George Town, Cayman Islands • Mahogany Bay, Honduras • Belize City • Cozumel • Fort Lauderdale

Average Starting Price

$3,989pp

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 Ray

Silversea

Feb 7, 2027 - Feb 19, 2027 (12 Nights)

Miami • San Juan, Puerto Rico • St. John • St. Kitts • Gustavia, St. Barts • St John's, Antigua • Deshaies, Guadeloupe • Roseau, Dominica • Fort-De-France, Martinique • Bequia Island, Saint Vincent • Bridgetown, Barbados

Average Starting Price

$7,200pp

Jim's Onboard Credit

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