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October 2026

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Seabourn Ovation

Seabourn

Mar 6, 2027 - Mar 13, 2027 (7 Nights)

Philipsburg, St. Maarten • Soper's Hole, Tortola • St. Kitts • Trois Ilets, Martinique • Bequia Island, Saint Vincent • Grenada • Bridgetown, Barbados

Average Starting Price

Jan 19, 2029 - Jan 31, 2029 (12 Nights)

Panama City (Fuerte Amador), Panama • Panama Canal, Panama • Limon, Costa Rica • George Town, Cayman Islands • Ocho Rios, Jamaica • La Romana, Dominican Republic • Tortola • San Juan, Puerto Rico • Miami

Average Starting Price

$4,999pp

Jim's Onboard Credit

Norwegian Prima

Norwegian Cruise Line

Feb 21, 2027 - Feb 28, 2027 (7 Nights)

San Juan, Puerto Rico • Tortola • St. Kitts • Bridgetown, Barbados • St. Lucia • Philipsburg, St. Maarten • St. Thomas • San Juan, Puerto Rico

Average Starting Price

$1,099pp

Jim's Onboard Credit

Norwegian Escape

Norwegian Cruise Line

Sep 17, 2028 - Sep 24, 2028 (7 Nights)

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

Average Starting Price

Dec 18, 2027 - Dec 26, 2027 (8 Nights)

Port Canaveral (Orlando), Florida • Tortola • St. Thomas • San Juan, Puerto Rico • Disney Castaway Cay, Bahamas • Port Canaveral (Orlando), Florida

Average Starting Price

$4,123pp

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 Aqua

Norwegian Cruise Line

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

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

Average Starting Price

49% OFF

Aug 5, 2027 - Aug 19, 2027 (14 Nights)

Bridgetown, Barbados • Fort-De-France, Martinique • Pointe-à-Pitre, Guadeloupe • Tortola • La Romana, Dominican Republic • Catalina Island, Dominican Republic • Virgin Gorda, British Virgin Islands • Philipsburg, St. Maarten • Fort-De-France, Martinique • St John's, Antigua • La Romana, Dominican Republic • Catalina Island, Dominican Republic • Bridgetown, Barbados

Average Starting Price

Mar 21, 2027 - Apr 5, 2027 (15 Nights)

Bridgetown, Barbados • Grenada • Castries, St. Lucia • Fort-De-France, Martinique • Gustavia, St. Barts • Gustavia, St. Barts • Virgin Gorda, British Virgin Islands • Miami • St. John • St John's, Antigua • Terre de Haut, Guadeloupe • Tortola • San Juan, Puerto Rico

Average Starting Price

$13,370pp

Jim's Onboard Credit

27% OFF

Seven Seas Grandeur

Regent Seven Seas Cruises

Feb 24, 2028 - Mar 5, 2028 (10 Nights)

Bridgetown, Barbados • Castries, St. Lucia • Fort-De-France, Martinique • Roseau, Dominica • Pointe-à-Pitre, Guadeloupe • Gustavia, St. Barts • Philipsburg, St. Maarten • Tortola • Miami

Average Starting Price

$6,849pp

Jim's Onboard Credit

Norwegian Luna

Norwegian Cruise Line

Mar 5, 2028 - Mar 12, 2028 (7 Nights)

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

Average Starting Price

Feb 20, 2028 - Feb 27, 2028 (7 Nights)

San Juan, Puerto Rico • Tortola • St. Kitts • Martinique • Grenada • Bridgetown, Barbados • San Juan, Puerto Rico

Average Starting Price

Jan 3, 2028 - Jan 9, 2028 (6 Nights)

Philipsburg, St. Maarten • Road Bay, Anguilla • Gustavia, St. Barts • Great Harbor Jost Van Dyke, British Virgin Islands • Virgin Gorda, British Virgin Islands • Soper's Hole, Tortola • Philipsburg, St. Maarten

Average Starting Price

$2,108pp

Jim's Onboard Credit

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