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October 2026

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Valiant Lady

Virgin Voyages

Mar 6, 2027 - Mar 13, 2027 (7 Nights)

San Juan, Puerto Rico • Philipsburg, St. Maarten • Bridgetown, Barbados • Castries, St. Lucia • St John's, Antigua • Tortola • San Juan, Puerto Rico

Average Starting Price

$1,113pp

Jim's Onboard Credit

Celebrity Constellation

Celebrity Cruises

Mar 6, 2027 - Mar 13, 2027 (7 Nights)

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

Average Starting Price

Dec 11, 2027 - Dec 22, 2027 (11 Nights)

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

Average Starting Price

$2,739pp

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!

Volendam

Holland America Line

Dec 11, 2027 - Jan 4, 2028 (24 Nights)

Fort Lauderdale • Relaxaway Half Moon Cay • Willemstad, Curacao • Cartagena, Colombia • Enter Panama Canal at Cristobal • Cruising Panama Canal And Gatun Lake • Gatun Lake, Panama • Cruising Gatun Lake And Panama Canal • Panama Canal, Panama • Colon, Panama • Limon, Costa Rica • George Town, Cayman Islands • Fort Lauderdale • Relaxaway Half Moon Cay • Philipsburg, St. Maarten • Fort-De-France, Martinique • Bridgetown, Barbados • Scarborough (Tobago), Trinidad and Tobago • Castries, St. Lucia • Basseterre, St. Kitts and Nevis • Fort Lauderdale

Average Starting Price

$6,189pp

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!

Hero of the Seas

Royal Caribbean

Sep 11, 2027 - Sep 18, 2027 (7 Nights)

Miami • Philipsburg, St. Maarten • St. Thomas • Perfect Day Cococay • Miami

Average Starting Price

Dec 3, 2027 - Dec 13, 2027 (10 Nights)

Fort Lauderdale • Philipsburg, St. Maarten • Castries, St. Lucia • Bridgetown, Barbados • St John's, Antigua • Basseterre, St. Kitts and Nevis • Fort Lauderdale

Average Starting Price

Nov 21, 2027 - Dec 22, 2027 (31 Nights)

Miami • Cozumel • Santo Tomas de Castilla, Guatemala • Harvest Caye, Belize • Costa Maya • Miami • Oranjestad, Aruba • Willemstad, Curacao • Kralendijk, Bonaire • Grenada • Castries, St. Lucia • Pointe-à-Pitre, Guadeloupe • Philipsburg, St. Maarten • Miami • Nassau • Puerto Plata, Dominican Republic • San Juan, Puerto Rico • Basseterre, St. Kitts and Nevis • St. Thomas • St John's, Antigua • Gustavia, St. Barts • Tortola • Miami

Average Starting Price

Dec 18, 2027 - Dec 28, 2027 (10 Nights)

Fort Lauderdale • Amber Cove, Dominican Republic • San Juan, Puerto Rico • St. Kitts • Martinique • Philipsburg, St. Maarten • Celebration Key • Fort Lauderdale

Average Starting Price

$1,174pp

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!

EXPLORA I

Explora Journeys

Mar 8, 2027 - Mar 24, 2027 (16 Nights)

Miami • San Juan, Puerto Rico • Philipsburg, St. Maarten • Funchal, Portugal • Cadiz, Spain • Malaga, Spain • Barcelona, Spain

Average Starting Price

Mar 6, 2027 - Mar 27, 2027 (21 Nights)

Fort Lauderdale • Relaxaway Half Moon Cay • Falmouth, Jamaica • George Town, Cayman Islands • Mahogany Bay, Honduras • Belize City • Cozumel • 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

$3,949pp

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!

Grandeur of the Seas

Royal Caribbean

May 29, 2027 - Jun 5, 2027 (7 Nights)

San Juan, Puerto Rico • St. Thomas • St. Croix • Philipsburg, St. Maarten • Castries, St. Lucia • Bridgetown, Barbados • San Juan, Puerto Rico

Average Starting Price

$798pp

Jim's Onboard Credit

FREE Specialty Dining Meal

Viking Sea

Viking

Dec 7, 2027 - Dec 17, 2027 (10 Nights)

San Juan, Puerto Rico • St. Thomas • Basseterre, St. Kitts and Nevis • Castries, St. Lucia • Bridgetown, Barbados • Roseau, Dominica • St John's, Antigua • Philipsburg, St. Maarten • St. Croix • San Juan, Puerto Rico

Average Starting Price

$4,299pp

Jim's Onboard Credit

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