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October 2026

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Scarlet Lady

Virgin Voyages

Nov 12, 2027 - Nov 20, 2027 (8 Nights)

San Juan, Puerto Rico • Tortola • Basseterre, St. Kitts and Nevis • Bridgetown, Barbados • Castries, St. Lucia • Roseau, Dominica • Philipsburg, St. Maarten • San Juan, Puerto Rico

Average Starting Price

$1,112pp

Jim's Onboard Credit

Celebrity Constellation

Celebrity Cruises

Mar 27, 2027 - Apr 3, 2027 (7 Nights)

San Juan, Puerto Rico • Tortola • Basseterre, St. Kitts and Nevis • Roseau, Dominica • Castries, St. Lucia • Bridgetown, Barbados • San Juan, Puerto Rico

Average Starting Price

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

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

Average Starting Price

Jan 13, 2028 - Jan 24, 2028 (11 Nights)

Cape Liberty • Philipsburg, St. Maarten • Castries, St. Lucia • Bridgetown, Barbados • Basseterre, St. Kitts and Nevis • Cape Liberty

Average Starting Price

Dec 6, 2027 - Jan 3, 2028 (28 Nights)

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

Average Starting Price

Jan 16, 2028 - Jan 23, 2028 (7 Nights)

San Juan, Puerto Rico • Bequia Island, Saint Vincent • Castries, St. Lucia • Bridgetown, Barbados • St John's, Antigua • Basseterre, St. Kitts and Nevis • San Juan, Puerto Rico

Average Starting Price

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

Fort Lauderdale • St. Kitts • Dominica • Bridgetown, Barbados • Pointe-à-Pitre, Guadeloupe • Philipsburg, St. Maarten • San Juan, Puerto Rico • Amber Cove, Dominican Republic • Fort Lauderdale

Average Starting Price

$1,324pp

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!

Azamara Quest

Azamara

Oct 28, 2027 - Nov 14, 2027 (17 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

Average Starting Price

Mar 19, 2027 - Mar 27, 2027 (8 Nights)

San Juan, Puerto Rico • St. Thomas • Bridgetown, Barbados • Kingstown, Saint Vincent Island, Saint Vincent • Roseau, Dominica • Philipsburg, St. Maarten • San Juan, Puerto Rico

Average Starting Price

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!

Norwegian Pearl

Norwegian Cruise Line

Jan 3, 2028 - Jan 15, 2028 (12 Nights)

Philadelphia • Philipsburg, St. Maarten • Bridgetown, Barbados • St. Lucia • St John's, Antigua • San Juan, Puerto Rico • Puerto Plata, Dominican Republic • Philadelphia

Average Starting Price

$898pp

Jim's Onboard Credit

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