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Cruise Dates

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October 2026

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Norwegian Bliss

Norwegian Cruise Line

Nov 29, 2026 - Dec 11, 2026 (12 Nights)

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

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

Jan 14, 2029 - Jan 28, 2029 (14 Nights)

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

Average Starting Price

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

Port Canaveral (Orlando), Florida • Nassau • Perfect Day Cococay • San Juan, Puerto Rico • Puerto Plata, Dominican Republic • Port Canaveral (Orlando), Florida

Average Starting Price

Dec 20, 2026 - Dec 27, 2026 (7 Nights)

San Juan, Puerto Rico • Basseterre, St. Kitts and Nevis • Tortola • Gustavia, St. Barts • Gustavia, St. Barts • Road Bay, Anguilla • Miami

Average Starting Price

$5,600pp

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!

Regal Princess

Princess Cruises

Jan 9, 2028 - Jan 16, 2028 (7 Nights)

Miami • St. Kitts • San Juan, Puerto Rico • Amber Cove, Dominican Republic • Miami

Average Starting Price

May 6, 2028 - May 13, 2028 (7 Nights)

San Juan, Puerto Rico • Bridgetown, Barbados • Castries, St. Lucia • Roseau, Dominica • St John's, Antigua • San Juan, Puerto Rico

Average Starting Price

Sep 24, 2028 - Nov 9, 2028 (46 Nights)

Halifax, Nova Scotia • Hamilton, Bermuda • San Juan, Puerto Rico • Oranjestad, Aruba • Panama Canal Cruising • Panama City (Fuerte Amador), Panama • Panama City (Fuerte Amador), Panama • Guayaquil, Ecuador • Lima, Peru • Lima, Peru • General San Martin, Peru • Valparaíso, Chile • The Seabourn Juan Fernandez Experience • The Seabourn Juan Fernandez Experience • The Seabourn Juan Fernandez Experience • Scenic Cruising Reloncavi Sound • Puerto Montt, Chile • Scenic Cruising Moraleda Channel • Scenic Cruising Darwin Channel • Scenic Cruising Baker Channel • Transit The English Narrows • Caleta Tortel, Chile • Scenic Cruising Eyre Fjord • Scenic Cruising Wide Channel • Pio XI Glacier, Chile • Scenic Cruising Peel Fjord • Scenic Cruising Smyth Channel • Brujo Glacier, Chile • Magellan Strait • Punta Arenas, Chile • Punta Arenas, Chile • The Seabourn Antarctic Experience • The Seabourn Antarctic Experience • The Seabourn Antarctic Experience • The Seabourn Antarctic Experience • The Seabourn Antarctic Experience • Ushuaia, Argentina • Ushuaia, Argentina

Average Starting Price

Jan 23, 2028 - Feb 6, 2028 (14 Nights)

Fort Lauderdale • Relaxaway Half Moon Cay • San Juan, Puerto Rico • Grand Turk • Amber Cove, Dominican Republic • Fort Lauderdale • Relaxaway Half Moon Cay • Falmouth, Jamaica • George Town, Cayman Islands • Cozumel • Fort Lauderdale

Average Starting Price

$1,228pp

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!

9% OFF

Crystal Serenity

Crystal Cruises

Mar 10, 2028 - Mar 20, 2028 (10 Nights)

Fort Lauderdale • Grand Turk • Marigot Bay, St. Martin, French West Indies • St John's, Antigua • St. Kitts • San Juan, Puerto Rico • Nassau • Fort Lauderdale

Average Starting Price

$5,110pp

Jim's Onboard Credit

Luke's Port Pick
Grand Turk has it all - stunning ship views, a pool, great snorkeling, and crystal-clear water! This port will always be my favorite!

49% OFF