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October 2026

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Viking Sea

Viking

Dec 17, 2027 - Dec 27, 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

Feb 28, 2027 - Mar 7, 2027 (7 Nights)

Miami • Philipsburg, St. Maarten • St. Thomas • Puerto Plata, Dominican Republic • Miami

Average Starting Price

$977pp

Jim's Onboard Credit

FREE Specialty Dining Meal

Enchanted Princess

Princess Cruises

Jan 25, 2028 - Feb 5, 2028 (11 Nights)

Fort Lauderdale • St. Thomas • St. Kitts • St. Lucia • Bridgetown, Barbados • St John's, Antigua • Philipsburg, St. Maarten • Fort Lauderdale

Average Starting Price

34% OFF

Jun 5, 2027 - Jun 12, 2027 (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

$939pp

Jim's Onboard Credit

Norwegian Aqua

Norwegian Cruise Line

Sep 19, 2027 - Sep 26, 2027 (7 Nights)

Port Canaveral (Orlando), Florida • Puerto Plata, Dominican Republic • St. Thomas • Tortola • Great Stirrup Cay • Port Canaveral (Orlando), Florida

Average Starting Price

$1,039pp

Jim's Onboard Credit

20% OFF

Seven Seas Prestige

Regent Seven Seas Cruises

Mar 5, 2027 - Mar 17, 2027 (12 Nights)

Miami • St. Thomas • Basseterre, St. Kitts and Nevis • Roseau, Dominica • Castries, St. Lucia • Bridgetown, Barbados • Pointe-à-Pitre, Guadeloupe • Tortola • Miami

Average Starting Price

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

Fort Lauderdale • Grand Turk • San Juan, Puerto Rico • St. Thomas • Relaxaway Half Moon Cay • Fort Lauderdale

Average Starting Price

$1,489pp

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!

EXPLORA IV

Explora Journeys

Dec 23, 2027 - Dec 30, 2027 (7 Nights)

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

Average Starting Price

$4,685pp

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!

Viking Sky

Viking

Dec 19, 2027 - Dec 29, 2027 (10 Nights)

Average Starting Price

Jan 29, 2028 - Feb 7, 2028 (9 Nights)

Fort Lauderdale • St. Thomas • St John's, Antigua • Castries, St. Lucia • Philipsburg, St. Maarten • Fort Lauderdale

Average Starting Price

$1,191pp

Jim's Onboard Credit

Norwegian Prima

Norwegian Cruise Line

Nov 27, 2027 - Dec 4, 2027 (7 Nights)

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

Average Starting Price

37% OFF

Jun 5, 2027 - Jun 13, 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

$929pp

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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