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October 2026

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Valiant Lady

Virgin Voyages

Mar 13, 2027 - Mar 19, 2027 (6 Nights)

San Juan, Puerto Rico • Tortola • Basseterre, St. Kitts and Nevis • St John's, Antigua • Castries, St. Lucia • San Juan, Puerto Rico

Average Starting Price

Dec 6, 2027 - Jan 4, 2028 (29 Nights)

Miami • Oranjestad, Aruba • Willemstad, Curacao • Kralendijk, Bonaire • Grenada • Bridgetown, Barbados • Castries, St. Lucia • Pointe-à-Pitre, Guadeloupe • Tortola • Miami • George Town, Cayman Islands • Cartagena, Colombia • Panama Canal, Panama • Puntarenas, Costa Rica • Puerto Quetzal, Guatemala • Zihuatanejo (Ixtapa), Mexico • Manzanillo, Mexico • Ensenada • Los Angeles

Average Starting Price

Oct 28, 2027 - Nov 21, 2027 (24 Nights)

New York, New York • Hamilton, Bermuda • Hamilton, Bermuda • Hamilton, Bermuda • Philipsburg, St. Maarten • Tortola • San Juan, Puerto Rico • Virgin Gorda, British Virgin Islands • St. Thomas • St John's, Antigua • St. Pierre • Port Elizabeth (Bequia), Saint Vincent and the Grenadines • Grenada • Scarborough (Tobago), Trinidad and Tobago • Bridgetown, Barbados • Castries, St. Lucia • Roseau, Dominica • Basseterre, St. Kitts and Nevis • Charlestown, Nevis • Philipsburg, St. Maarten • Tortola • San Juan, Puerto Rico

Average Starting Price

$6,129pp

Jim's Onboard Credit

26% OFF

Seven Seas Prestige

Regent Seven Seas Cruises

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

Miami • St. Thomas • St John's, Antigua • Castries, St. Lucia • Pointe-à-Pitre, Guadeloupe • Basseterre, St. Kitts and Nevis • Tortola • Miami

Average Starting Price

Nov 28, 2027 - Dec 10, 2027 (12 Nights)

Miami • Oranjestad, Aruba • Willemstad, Curacao • Kralendijk, Bonaire • Grenada • Castries, St. Lucia • Pointe-à-Pitre, Guadeloupe • Philipsburg, St. Maarten • Miami

Average Starting Price

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

San Juan, Puerto Rico • St. John • St. Kitts • Castries, St. Lucia • St John's, Antigua • Great Harbor Jost Van Dyke, British Virgin Islands • San Juan, Puerto Rico

Average Starting Price

$3,800pp

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!

Celebrity Ascent

Celebrity Cruises

Apr 9, 2027 - Apr 19, 2027 (10 Nights)

Fort Lauderdale • Philipsburg, St. Maarten • Castries, St. Lucia • Grenada • Bridgetown, Barbados • St John's, Antigua • Fort Lauderdale

Average Starting Price

Dec 23, 2027 - Jan 4, 2028 (12 Nights)

Fort Lauderdale • Relaxaway Half Moon Cay • Philipsburg, St. Maarten • Fort-De-France, Martinique • Bridgetown, Barbados • Scarborough (Tobago), Trinidad and Tobago • Castries, St. Lucia • St. Kitts • Fort Lauderdale

Average Starting Price

$3,234pp

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 Sea

Viking

Nov 27, 2027 - Dec 7, 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

Nov 29, 2027 - Dec 9, 2027 (10 Nights)

Average Starting Price

Sep 18, 2027 - Sep 25, 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

Jan 7, 2027 - Jan 20, 2027 (13 Nights)

Miami • George Town, Cayman Islands • Falmouth, Jamaica • Oranjestad, Aruba • Willemstad, Curacao • Castries, St. Lucia • Pointe-à-Pitre, Guadeloupe • Tortola • Miami

Average Starting Price

$6,599pp

Jim's Onboard Credit

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