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Cruise Dates

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October 2026

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Norwegian Pearl

Norwegian Cruise Line

Nov 28, 2026 - Dec 8, 2026 (10 Nights)

Philadelphia • Tortola • St. Thomas • San Juan, Puerto Rico • Puerto Plata, Dominican Republic • Philadelphia

Average Starting Price

Dec 17, 2026 - Dec 27, 2026 (10 Nights)

Fort Lauderdale • Relaxaway Half Moon Cay • Amber Cove, Dominican Republic • San Juan, Puerto Rico • Philipsburg, St. Maarten • St John's, Antigua • St. Kitts • Fort Lauderdale

Average Starting Price

$1,179pp

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!

53% OFF

Carnival Magic

Carnival Cruise Line

Dec 18, 2026 - Dec 26, 2026 (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

$586pp

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!

Independence of the Seas

Royal Caribbean

Dec 13, 2026 - Dec 20, 2026 (7 Nights)

Miami • Perfect Day Cococay • San Juan, Puerto Rico • St. Thomas • Miami

Average Starting Price

$664pp

Jim's Onboard Credit

FREE Specialty Dining Meal

Valiant Lady

Virgin Voyages

Nov 14, 2026 - Nov 20, 2026 (6 Nights)

San Juan, Puerto Rico • Tortola • St John's, Antigua • Castries, St. Lucia • Basseterre, St. Kitts and Nevis • San Juan, Puerto Rico

Average Starting Price

47% OFF

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

Port Canaveral (Orlando), Florida • Celebration Key • Fun Day at Sea • San Juan, Puerto Rico • St. Thomas • Fun Day at Sea • Fun Day at Sea • Port Canaveral (Orlando), Florida

Average Starting Price

Jan 16, 2028 - Jan 30, 2028 (14 Nights)

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

Average Starting Price

$1,308pp

Jim's Onboard Credit

Celebrity Constellation

Celebrity Cruises

Dec 19, 2026 - Dec 26, 2026 (7 Nights)

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

Average Starting Price

$558pp

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!

Caribbean Princess

Princess Cruises

Nov 26, 2028 - Dec 3, 2028 (7 Nights)

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

Average Starting Price

Dec 20, 2026 - Jan 4, 2027 (15 Nights)

San Juan, Puerto Rico • Basseterre, St. Kitts and Nevis • Tortola • Gustavia, St. Barts • Gustavia, St. Barts • Road Bay, Anguilla • Miami • Puerto Plata, Dominican Republic • Catalina Island, Dominican Republic • St. John • New Year Fireworks SJU • New Year Fireworks SJU • Great Harbor Jost Van Dyke, British Virgin Islands • Basseterre, St. Kitts and Nevis • St. Thomas • San Juan, Puerto Rico

Average Starting Price

Nov 28, 2026 - Dec 5, 2026 (7 Nights)

Port Canaveral (Orlando), Florida • Philipsburg, St. Maarten • San Juan, Puerto Rico • Perfect Day Cococay • Port Canaveral (Orlando), Florida

Average Starting Price

Mar 7, 2027 - Mar 14, 2027 (7 Nights)

San Juan, Puerto Rico • St. Thomas • St. Croix • Philipsburg, St. Maarten • St John's, Antigua • Roseau, Dominica • San Juan, Puerto Rico

Average Starting Price

$670pp

Jim's Onboard Credit

FREE Specialty Dining Meal

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