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October 2026

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Norwegian Pearl

Norwegian Cruise Line

Jan 23, 2027 - Feb 2, 2027 (10 Nights)

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

Average Starting Price

$649pp

Jim's Onboard Credit

Norwegian Luna

Norwegian Cruise Line

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

Miami • Puerto Plata, Dominican Republic • St. Thomas • Tortola • Great Stirrup Cay • Miami

Average Starting Price

47% OFF

Dec 5, 2027 - Dec 18, 2027 (13 Nights)

Miami • St John's, Antigua • St. Thomas • Puerto Plata, Dominican Republic • Miami • Ocean Cay • Puerto Plata, Dominican Republic • Nassau • Miami

Average Starting Price

Feb 7, 2027 - Feb 21, 2027 (14 Nights)

Fort Lauderdale • Nassau • Amber Cove, Dominican Republic • Grand Turk • Relaxaway Half Moon Cay • Fort Lauderdale • Grand Turk • San Juan, Puerto Rico • St. Thomas • Relaxaway Half Moon Cay • Fort Lauderdale

Average Starting Price

$2,714pp

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!

Viking Sea

Viking

Jan 27, 2028 - Feb 6, 2028 (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

58% OFF

Jan 24, 2027 - Jan 31, 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

Dec 20, 2026 - Jan 10, 2027 (21 Nights)

Fort Lauderdale • St. Thomas • Virgin Gorda, British Virgin Islands • St John's, Antigua • San Juan, Puerto Rico • Samana, Dominican Republic • Nassau • Fort Lauderdale • Cozumel • Belize City • Santo Tomas de Castilla, Guatemala • Roatan, Honduras • George Town, Cayman Islands • Ocho Rios, Jamaica • Fort Lauderdale • Nassau • Fort Lauderdale

Average Starting Price

$11,500pp

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 Constellation

Celebrity Cruises

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

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

Average Starting Price

Mar 28, 2027 - Apr 4, 2027 (7 Nights)

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

Average Starting Price

$711pp

Jim's Onboard Credit

FREE Specialty Dining Meal

Emerald Princess

Princess Cruises

Dec 19, 2027 - Dec 26, 2027 (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 16, 2028 - Dec 28, 2028 (12 Nights)

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

Average Starting Price

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

San Juan, Puerto Rico • Kingstown, Saint Vincent Island, Saint Vincent • Bridgetown, Barbados • Fort-De-France, Martinique • St John's, Antigua • St. Thomas • San Juan, Puerto Rico

Average Starting Price

$660pp

Jim's Onboard Credit

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