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Cruise Dates

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October 2026

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Silver Dawn

Silversea

Mar 14, 2028 - Mar 24, 2028 (10 Nights)

Miami • San Juan, Puerto Rico • Soper's Hole, Tortola • St. Kitts • St John's, Antigua • Virgin Gorda, British Virgin Islands • Miami

Average Starting Price

Jan 2, 2028 - Jan 9, 2028 (7 Nights)

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

Average Starting Price

9% OFF

Jan 18, 2028 - Feb 12, 2028 (25 Nights)

Fort Lauderdale • Tortola • Pointe-à-Pitre, Guadeloupe • Castries, St. Lucia • Scarborough (Tobago), Trinidad and Tobago • Santarem, Brazil • Boca da Valeria (Amazon River), Brazil • Manaus, Brazil • Manaus, Brazil • Parintins, Brazil • Alter Do Chao, Brazil • Devil's Island, France • Bridgetown, Barbados • Roseau, Dominica • Gustavia, St. Barts • Fort Lauderdale

Average Starting Price

$11,960pp

Jim's Onboard Credit

31% OFF

Seven Seas Grandeur

Regent Seven Seas Cruises

Jan 5, 2028 - Jan 15, 2028 (10 Nights)

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

Average Starting Price

Jan 4, 2027 - Jan 11, 2027 (7 Nights)

San Juan, Puerto Rico • Philipsburg, St. Maarten • St John's, Antigua • Little Bay, Montserrat • Tortola • Miami

Average Starting Price

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

San Juan, Puerto Rico • Tortola • Bridgetown, Barbados • Castries, St. Lucia • Roseau, Dominica • Philipsburg, St. Maarten • San Juan, Puerto Rico

Average Starting Price

Dec 29, 2027 - Jan 9, 2028 (11 Nights)

Miami • Key West, Florida • St. Thomas • Soper's Hole, Tortola • Gustavia, St. Barts • St John's, Antigua • St. John • Miami

Average Starting Price

$6,800pp

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 Getaway

Norwegian Cruise Line

Dec 14, 2026 - Dec 22, 2026 (8 Nights)

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

Average Starting Price

$639pp

Jim's Onboard Credit

Norwegian Gem

Norwegian Cruise Line

Nov 28, 2026 - Dec 10, 2026 (12 Nights)

Tampa • San Juan, Puerto Rico • Tortola • St. Kitts • Philipsburg, St. Maarten • St. Thomas • Falmouth, Jamaica • George Town, Cayman Islands • Tampa

Average Starting Price

$909pp

Jim's Onboard Credit

Norwegian Aura

Norwegian Cruise Line

Jul 24, 2027 - Jul 31, 2027 (7 Nights)

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

Average Starting Price

Oct 28, 2027 - Nov 6, 2027 (9 Nights)

New York, New York • Hamilton, Bermuda • Hamilton, Bermuda • Hamilton, Bermuda • Philipsburg, St. Maarten • Tortola • San Juan, Puerto Rico

Average Starting Price

Dec 6, 2027 - Jan 4, 2028 (29 Nights)

Miami • Oranjestad, Aruba • Willemstad, Curacao • Kralendijk, Bonaire • Grenada • Bridgetown, Barbados • Castries, St. Lucia • Pointe-à-Pitre, Guadeloupe • Tortola • Miami • George Town, Cayman Islands • Cartagena, Colombia • Panama Canal, Panama • Puntarenas, Costa Rica • Puerto Quetzal, Guatemala • Zihuatanejo (Ixtapa), Mexico • Manzanillo, Mexico • Ensenada • Los Angeles

Average Starting Price

$13,499pp

Jim's Onboard Credit

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