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Cruise Dates

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October 2026

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Disney Treasure

Disney Cruise Line

May 8, 2027 - May 15, 2027 (7 Nights)

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

Average Starting Price

$2,442pp

Jim's Onboard Credit

Norwegian Luna

Norwegian Cruise Line

Nov 28, 2027 - Dec 5, 2027 (7 Nights)

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

Average Starting Price

Dec 3, 2026 - Dec 20, 2026 (17 Nights)

Fort Lauderdale • Tortola • Gustavia, St. Barts • Pointe-à-Pitre, Guadeloupe • Kingstown, Saint Vincent Island, Saint Vincent • Castries, St. Lucia • Fort-De-France, Martinique • St. Kitts • San Juan, Puerto Rico • Great Harbor Jost Van Dyke, British Virgin Islands • Marigot Bay, St. Martin, French West Indies • St. John • St. Thomas • Fort Lauderdale

Average Starting Price

$7,900pp

Jim's Onboard Credit

Norwegian Pearl

Norwegian Cruise Line

Feb 2, 2027 - Feb 12, 2027 (10 Nights)

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

Average Starting Price

Jan 5, 2028 - Mar 22, 2028 (77 Nights)

Miami • Cozumel • Belize City • Roatan, Honduras • Limon, Costa Rica • Bocas Del Toro, Panama • Panama Canal (Cruising) • Panama City (Fuerte Amador), Panama • Panama City (Fuerte Amador), Panama • Manta, Ecuador • Lima, Peru • Lima, Peru • General San Martin, Peru • La Serena (Coquimbo), Chile • Valparaíso, Chile • Puerto Montt, Chile • Castro, Chile • Chacabuco, Chile • Sailing In The Chilean Fjords • Sailing In The Chilean Fjords • Punta Arenas, Chile • Punta Arenas, Chile • Ushuaia, Argentina • Sailing Snow Island • Sailing Bransfield Strait • Sailing Gerlache Strait • Sailing Paradise Bay • Sailing Wilhelmina Bay • Sailing Penguin Island • Sailing King George Island • Port Stanley, Falkland Islands • Punta del Este, Uruguay • Montevideo, Uruguay • Montevideo, Uruguay • Buenos Aires, Argentina • Buenos Aires, Argentina • Buenos Aires, Argentina • Montevideo, Uruguay • Rio Grande Do Sul, Brazil • Porto Belo, Brazil • Sao Francisco do Sul, Brazil • Paranagua, brazil • Santos (Sao Paulo), Brazil • Ilhabela, Brazil • Paraty, Brazil • Rio de Janeiro, Brazil • Rio de Janeiro, Brazil • Rio de Janeiro, Brazil • Salvador da Bahia, Brazil • Salvador da Bahia, Brazil • Natal, Brazil • Belem, Brazil • Iles du Salut (Ile Royale), French Guiana • Scarborough (Tobago), Trinidad and Tobago • Bridgetown, Barbados • Saint George's, Grenada • Castries, St. Lucia • St. Pierre • Roseau, Dominica • Philipsburg, St. Maarten • Tortola • Miami

Average Starting Price

Mar 1, 2028 - Mar 11, 2028 (10 Nights)

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

Average Starting Price

$4,799pp

Jim's Onboard Credit

30% OFF

Seven Seas Grandeur

Regent Seven Seas Cruises

Dec 3, 2028 - Dec 13, 2028 (10 Nights)

Miami • St. Thomas • St John's, Antigua • Castries, St. Lucia • Gustavia, St. Barts • Tortola • Miami

Average Starting Price

30% OFF

Dec 21, 2026 - Dec 28, 2026 (7 Nights)

Miami • Tortola • St. Thomas • Nassau • Miami

Average Starting Price

$3,010pp

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!

Emerald Princess

Princess Cruises

Dec 12, 2027 - Dec 26, 2027 (14 Nights)

San Juan, Puerto Rico • Tortola • St. Kitts • Martinique • Dominica • 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

Dec 19, 2027 - Dec 27, 2027 (8 Nights)

Miami • Amber Cove, Dominican Republic • San Juan, Puerto Rico • Philipsburg, St. Maarten • Tortola • Miami

Average Starting Price

Nov 28, 2026 - Dec 5, 2026 (7 Nights)

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

Average Starting Price

$558pp

Jim's Onboard Credit

Norwegian Aura

Norwegian Cruise Line

Oct 9, 2027 - Oct 16, 2027 (7 Nights)

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

Average Starting Price

$1,099pp

Jim's Onboard Credit

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