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October 2026

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Star Pride

Windstar Cruises

Nov 29, 2026 - Dec 6, 2026 (7 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

Average Starting Price

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

Feb 19, 2028 - Feb 26, 2028 (7 Nights)

San Juan, Puerto Rico • Oranjestad, Aruba • Willemstad, Curacao • St John's, Antigua • Philipsburg, St. Maarten • San Juan, Puerto Rico

Average Starting Price

58% OFF

Jan 23, 2027 - Jan 31, 2027 (8 Nights)

Miami • Relaxaway Half Moon Cay • Fun Day at Sea • San Juan, Puerto Rico • Philipsburg, St. Maarten • St. Thomas • Fun Day at Sea • Fun Day at Sea • Miami

Average Starting Price

$435pp

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!

Crown Princess

Princess Cruises

Jan 17, 2027 - Jan 24, 2027 (7 Nights)

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

Average Starting Price

Jan 16, 2027 - Jan 26, 2027 (10 Nights)

Fort Lauderdale • Celebration Key • Amber Cove, Dominican Republic • San Juan, Puerto Rico • Philipsburg, St. Maarten • St John's, Antigua • St. Kitts • Fort Lauderdale

Average Starting Price

31% OFF

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

Fort-De-France, Martinique • Pointe-à-Pitre, Guadeloupe • St John's, Antigua • Philipsburg, St. Maarten • St. Kitts • Roseau, Dominica • Fort-De-France, Martinique

Average Starting Price

49% OFF

Jan 1, 2028 - Jan 8, 2028 (7 Nights)

Fort-De-France, Martinique • Pointe-à-Pitre, Guadeloupe • Roseau, Dominica • Philipsburg, St. Maarten • St. Kitts • St John's, Antigua • Fort-De-France, Martinique

Average Starting Price

Jan 16, 2027 - Jan 23, 2027 (7 Nights)

Miami • Philipsburg, St. Maarten • St. Thomas • Perfect Day Cococay • Miami

Average Starting Price

$1,353pp

Jim's Onboard Credit

FREE Specialty Dining Meal

Eurodam

Holland America Line

Mar 15, 2028 - Mar 26, 2028 (11 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

Average Starting Price

$2,849pp

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!

Harmony of the Seas

Royal Caribbean

Dec 30, 2027 - Jan 8, 2028 (9 Nights)

Port Canaveral (Orlando), Florida • Perfect Day Cococay • San Juan, Puerto Rico • Philipsburg, St. Maarten • Basseterre, St. Kitts and Nevis • St. Thomas • Port Canaveral (Orlando), Florida

Average Starting Price

$2,046pp

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!

Vision of the Seas

Royal Caribbean

Nov 22, 2026 - Nov 29, 2026 (7 Nights)

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

Average Starting Price

$1,067pp

Jim's Onboard Credit

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