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October 2026

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Star Pride

Windstar Cruises

Jan 10, 2027 - Jan 17, 2027 (7 Nights)

San Juan, Puerto Rico • St. John • Basseterre, St. Kitts and Nevis • Gustavia, St. Barts • Philipsburg, St. Maarten • Great Harbor Jost Van Dyke, British Virgin Islands • Virgin Gorda, British Virgin Islands • San Juan, Puerto Rico

Average Starting Price

Feb 26, 2028 - Mar 4, 2028 (7 Nights)

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

Average Starting Price

Feb 12, 2028 - Mar 4, 2028 (21 Nights)

Fort Lauderdale • Philipsburg, St. Maarten • St John's, Antigua • Roseau, Dominica • Fort-De-France, Martinique • St. Kitts • St. Thomas • Relaxaway Half Moon Cay • Fort Lauderdale • Relaxaway Half Moon Cay • Cabo Rojo, Dominican Republic • Kralendijk, Bonaire • Willemstad, Curacao • Oranjestad, Aruba • Fort Lauderdale

Average Starting Price

$5,094pp

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!

Norwegian Bliss

Norwegian Cruise Line

Mar 6, 2028 - Mar 18, 2028 (12 Nights)

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

Average Starting Price

Dec 18, 2028 - Dec 28, 2028 (10 Nights)

Miami • San Juan, Puerto Rico • Road Bay, Anguilla • Little Bay, Montserrat • St. Kitts • Great Harbor Jost Van Dyke, British Virgin Islands • Miami

Average Starting Price

$7,418pp

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!

Celebrity Beyond

Celebrity Cruises

Dec 20, 2026 - Dec 27, 2026 (7 Nights)

Fort Lauderdale • Basseterre, St. Kitts and Nevis • San Juan, Puerto Rico • Perfect Day Cococay • Fort Lauderdale

Average Starting Price

49% OFF

Nov 29, 2027 - Dec 13, 2027 (14 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 • Catalina Island, Dominican Republic • Oranjestad, Aruba • Willemstad, Curacao • Kralendijk, Bonaire • Grenada • La Romana, Dominican Republic

Average Starting Price

$1,372pp

Jim's Onboard Credit

Norwegian Prima

Norwegian Cruise Line

Jan 15, 2028 - Jan 22, 2028 (7 Nights)

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

Average Starting Price

Jan 31, 2028 - Feb 7, 2028 (7 Nights)

San Juan, Puerto Rico • St. John • Gustavia, St. Barts • Philipsburg, St. Maarten • Basseterre, St. Kitts and Nevis • Great Harbor Jost Van Dyke, British Virgin Islands • Virgin Gorda, British Virgin Islands • San Juan, Puerto Rico

Average Starting Price

Apr 9, 2028 - Apr 16, 2028 (7 Nights)

San Juan, Puerto Rico • St. Thomas • Basseterre, St. Kitts and Nevis • Willemstad, Curacao • Oranjestad, Aruba • San Juan, Puerto Rico

Average Starting Price

$902pp

Jim's Onboard Credit

16% OFF

Seven Seas Voyager

Regent Seven Seas Cruises

Feb 26, 2028 - Mar 18, 2028 (21 Nights)

Rio de Janeiro, Brazil • Recife, Brazil • Macapa, , Brazil • Alter Do Chao, Brazil • Boca da Valeria (Amazon River), Brazil • Manaus, Brazil • Manaus, Brazil • Parintins, Brazil • Santarem, Brazil • Macapa, , Brazil • Castries, St. Lucia • Basseterre, St. Kitts and Nevis • Miami

Average Starting Price

Dec 12, 2026 - Jan 2, 2027 (21 Nights)

Fort Lauderdale • Relaxaway Half Moon Cay • Falmouth, Jamaica • George Town, Cayman Islands • Mahogany Bay, Honduras • Belize City • Cozumel • Fort Lauderdale • Philipsburg, St. Maarten • St. Kitts • Roseau, Dominica • Castries, St. Lucia • St John's, Antigua • St. Thomas • Relaxaway Half Moon Cay • Fort Lauderdale

Average Starting Price

$3,604pp

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!

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