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October 2026

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Rotterdam

Holland America Line

Feb 12, 2028 - Feb 26, 2028 (14 Nights)

Fort Lauderdale • Nassau • Amber Cove, Dominican Republic • Grand Turk • Relaxaway Half Moon Cay • Fort Lauderdale • Grand Turk • San Juan, Puerto Rico • St. Thomas • Relaxaway Half Moon Cay • Fort Lauderdale

Average Starting Price

$3,559pp

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!

Viking Sky

Viking

Jan 13, 2029 - Feb 3, 2029 (21 Nights)

San Juan, Puerto Rico • Sail the Caribbean Sea • Bridgetown, Barbados • Sail the Atlantic Ocean • Iles du Salut (Ile Royale), French Guiana • Sail the Atlantic Ocean • Sail the Mouth of the Amazon River • Santarem, Brazil • Parintins, Brazil • Manaus, Brazil • Manaus, Brazil • Sail the Amazon River • Sail the Amazon River • Belem, Brazil • Sail the Atlantic Ocean • Sail the Atlantic Ocean • Scarborough (Tobago), Trinidad and Tobago • Castries, St. Lucia • St John's, Antigua • St. Thomas • San Juan, Puerto Rico

Average Starting Price

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

Miami • Road Bay, Anguilla • St. Thomas • St. John's • St. John • San Juan, Puerto Rico

Average Starting Price

Feb 7, 2027 - Feb 14, 2027 (7 Nights)

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

Average Starting Price

Jan 29, 2028 - Feb 12, 2028 (14 Nights)

Fort Lauderdale • Celebration Key • Amber Cove, Dominican Republic • San Juan, Puerto Rico • Grand Turk • Fort Lauderdale • Belize City • Roatan, Honduras • Cozumel • Celebration Key • Fort Lauderdale

Average Starting Price

$1,468pp

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!

Star Princess

Princess Cruises

Feb 27, 2028 - Mar 5, 2028 (7 Nights)

Port Canaveral (Orlando), Florida • Celebration Key • Amber Cove, Dominican Republic • San Juan, Puerto Rico • Grand Turk • Port Canaveral (Orlando), Florida

Average Starting Price

$719pp

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!

Allura

Oceania Cruises

Nov 17, 2026 - Dec 2, 2026 (15 Nights)

Barcelona, Spain • Malaga, Spain • Agadir, Morocco • Arrecife (Lanzarote), Spain • San Juan, Puerto Rico • Miami

Average Starting Price

30% OFF

Nov 9, 2026 - Nov 24, 2026 (15 Nights)

Lisbon, Portugal • Arrecife (Lanzarote), Spain • Las Palmas (Gran Canaria), Spain • Santa Cruz de la Palma, Spain • San Juan, Puerto Rico • San Juan, Puerto Rico • Puerto Plata, Dominican Republic • Miami

Average Starting Price

$2,765pp

Jim's Onboard Credit

Independence of the Seas

Royal Caribbean

Feb 7, 2027 - Feb 14, 2027 (7 Nights)

Miami • Perfect Day Cococay • San Juan, Puerto Rico • St. Thomas • Miami

Average Starting Price

$660pp

Jim's Onboard Credit

FREE Specialty Dining Meal

Norwegian Pearl

Norwegian Cruise Line

Mar 7, 2028 - Mar 17, 2028 (10 Nights)

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

Average Starting Price

Dec 20, 2026 - Dec 30, 2026 (10 Nights)

Fort Lauderdale • St. Thomas • Virgin Gorda, British Virgin Islands • St John's, Antigua • Marigot Bay, St. Martin, French West Indies • San Juan, Puerto Rico • Nassau • Fort Lauderdale

Average Starting Price

$6,000pp

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 Prima

Norwegian Cruise Line

Jan 1, 2028 - Jan 8, 2028 (7 Nights)

San Juan, Puerto Rico • Tortola • Oranjestad, Aruba • Willemstad, Curacao • St. Thomas • San Juan, Puerto Rico

Average Starting Price

$1,219pp

Jim's Onboard Credit

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