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October 2026

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Regal Princess

Princess Cruises

Nov 27, 2027 - Dec 12, 2027 (15 Nights)

Miami • Amber Cove, Dominican Republic • San Juan, Puerto Rico • Philipsburg, St. Maarten • Tortola • Miami • Relaxaway Half Moon Cay • St. Thomas • Philipsburg, St. Maarten • Miami

Average Starting Price

$1,383pp

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 Escape

Norwegian Cruise Line

Mar 26, 2027 - Apr 2, 2027 (7 Nights)

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

Average Starting Price

30% OFF

Nov 25, 2026 - Dec 7, 2026 (12 Nights)

Miami • St. Thomas • Philipsburg, St. Maarten • Gustavia, St. Barts • Fort-De-France, Martinique • Pointe-à-Pitre, Guadeloupe • St John's, Antigua • Tortola • Miami

Average Starting Price

Nov 28, 2027 - Dec 12, 2027 (14 Nights)

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

Average Starting Price

9% OFF

Jan 18, 2028 - Jan 30, 2028 (12 Nights)

Fort Lauderdale • Tortola • Pointe-à-Pitre, Guadeloupe • Castries, St. Lucia • Scarborough (Tobago), Trinidad and Tobago • Cruising the Amazon River • Santarem, Brazil • Boca de Valeria, Brazil • Manaus, Brazil

Average Starting Price

$6,820pp

Jim's Onboard Credit

Norwegian Bliss

Norwegian Cruise Line

Dec 10, 2027 - Dec 22, 2027 (12 Nights)

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

Average Starting Price

Jan 4, 2027 - Jan 20, 2027 (16 Nights)

San Juan, Puerto Rico • Philipsburg, St. Maarten • St John's, Antigua • Little Bay, Montserrat • Tortola • Miami • Puerto Plata, Dominican Republic • Cayo Levantado, Dominican Republic • San Juan, Puerto Rico • St. Thomas • Virgin Gorda, British Virgin Islands • Miami

Average Starting Price

1% OFF

Jan 10, 2027 - Jan 24, 2027 (14 Nights)

Baltimore • Fun Day at Sea • Fun Day at Sea • Fun Day at Sea • St. Thomas • Philipsburg, St. Maarten • Dominica • St. Lucia • Bridgetown, Barbados • St John's, Antigua • Tortola • Fun Day at Sea • Fun Day at Sea • Fun Day at Sea • Baltimore

Average Starting Price

Dec 27, 2026 - Jan 3, 2027 (7 Nights)

Fort Lauderdale • Disney Lookout Cay at Lighthouse Point, Bahamas • San Juan, Puerto Rico • Tortola • Fort Lauderdale

Average Starting Price

$3,668pp

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!

Norwegian Dawn

Norwegian Cruise Line

Jan 2, 2028 - Jan 14, 2028 (12 Nights)

Jacksonville • Great Stirrup Cay • Grand Bahama Island • Puerto Plata, Dominican Republic • Samana, Dominican Republic • Tortola • St John's, Antigua • Philipsburg, St. Maarten • San Juan, Puerto Rico • Jacksonville

Average Starting Price

Jan 23, 2028 - Jan 30, 2028 (7 Nights)

San Juan, Puerto Rico • Tortola • Pointe-à-Pitre, Guadeloupe • Gustavia, St. Barts • Ocean Cay • Miami

Average Starting Price

Jan 29, 2027 - Feb 12, 2027 (14 Nights)

San Juan, Puerto Rico • Tortola • St John's, Antigua • Providenciales, Turks and Caicos Islands • Key West, Florida • Miami • Philipsburg, St. Maarten • Gustavia, St. Barts • Basseterre, St. Kitts and Nevis • St. John • San Juan, Puerto Rico

Average Starting Price

$13,000pp

Jim's Onboard Credit

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