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October 2026

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Allura

Oceania Cruises

Feb 19, 2027 - Mar 11, 2027 (20 Nights)

San Juan, Puerto Rico • St. Thomas • Philipsburg, St. Maarten • Basseterre, St. Kitts and Nevis • St John's, Antigua • Tortola • Miami • George Town, Cayman Islands • Falmouth, Jamaica • Oranjestad, Aruba • Willemstad, Curacao • Kralendijk, Bonaire • Cabo Rojo, Dominican Republic • Nassau • Miami

Average Starting Price

$11,349pp

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

Jan 7, 2029 - Jan 31, 2029 (24 Nights)

Miami • St. Thomas • Philipsburg, St. Maarten • Basseterre, St. Kitts and Nevis • Willemstad, Curacao • Oranjestad, Aruba • Cartagena, Colombia • Panama Canal, Panama • Panama City (Fuerte Amador), Panama • Panama City (Fuerte Amador), Panama • 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

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

Miami • Relaxaway Half Moon Cay • St. Thomas • Philipsburg, St. Maarten • Miami • Belize City • Roatan, Honduras • Cozumel • Celebration Key • Miami

Average Starting Price

$1,103pp

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!

Odyssey of the Seas

Royal Caribbean

Jan 3, 2027 - Jan 14, 2027 (11 Nights)

Cape Liberty • Philipsburg, St. Maarten • St John's, Antigua • Basseterre, St. Kitts and Nevis • St. Thomas • Cape Liberty

Average Starting Price

$1,463pp

Jim's Onboard Credit

FREE Specialty Dining Meal

Marina

Oceania Cruises

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

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

Average Starting Price

45% OFF

Sep 26, 2027 - Oct 3, 2027 (7 Nights)

Miami • Fun Day at Sea • Fun Day at Sea • St. Thomas • San Juan, Puerto Rico • Fun Day at Sea • Celebration Key • Miami

Average Starting Price

Jan 4, 2027 - Jan 20, 2027 (16 Nights)

San Juan, Puerto Rico • Philipsburg, St. Maarten • St John's, Antigua • Little Bay, Montserrat • Tortola • Miami • Puerto Plata, Dominican Republic • Cayo Levantado, Dominican Republic • San Juan, Puerto Rico • St. Thomas • Virgin Gorda, British Virgin Islands • Miami

Average Starting Price

Dec 1, 2027 - Dec 12, 2027 (11 Nights)

Fort Lauderdale • Philipsburg, St. Maarten • St John's, Antigua • Roseau, Dominica • Fort-De-France, Martinique • St. Kitts • St. Thomas • Relaxaway Half Moon Cay • Fort Lauderdale

Average Starting Price

$2,754pp

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!

42% OFF

Carnival Venezia

Carnival Cruise Line

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

Port Canaveral (Orlando), Florida • Celebration Key • Fun Day at Sea • San Juan, Puerto Rico • St. Thomas • Fun Day at Sea • Fun Day at Sea • Port Canaveral (Orlando), Florida

Average Starting Price

$669pp

Jim's Onboard Credit

Norwegian Bliss

Norwegian Cruise Line

Dec 22, 2027 - Jan 3, 2028 (12 Nights)

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

Average Starting Price

$2,269pp

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!

1% OFF

Carnival Pride

Carnival Cruise Line

Jan 10, 2027 - Jan 24, 2027 (14 Nights)

Baltimore • Fun Day at Sea • Fun Day at Sea • Fun Day at Sea • St. Thomas • Philipsburg, St. Maarten • Dominica • St. Lucia • Bridgetown, Barbados • St John's, Antigua • Tortola • Fun Day at Sea • Fun Day at Sea • Fun Day at Sea • Baltimore

Average Starting Price

$2,013pp

Jim's Onboard Credit

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