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October 2026

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Oosterdam

Holland America Line

Dec 11, 2027 - Jan 2, 2028 (22 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 • George Town, Cayman Islands • Cartagena, Colombia • Oranjestad, Aruba • Willemstad, Curacao • Relaxaway Half Moon Cay • Fort Lauderdale

Average Starting Price

$5,709pp

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!

Valiant Lady

Virgin Voyages

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

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

Sep 18, 2027 - Sep 25, 2027 (7 Nights)

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

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!

Sun Princess

Princess Cruises

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

Fort Lauderdale • Relaxaway Half Moon Cay • St. Thomas • Philipsburg, St. Maarten • Fort Lauderdale

Average Starting Price

$659pp

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!

Celebrity Ascent

Celebrity Cruises

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

31% OFF

Jan 15, 2028 - Jan 27, 2028 (12 Nights)

Baltimore • Fun Day at Sea • Fun Day at Sea • Fun Day at Sea • St. Croix • St John's, Antigua • Martinique • Philipsburg, St. Maarten • St. Thomas • Fun Day at Sea • Fun Day at Sea • Fun Day at Sea • Baltimore

Average Starting Price

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

Mar 1, 2027 - Mar 24, 2027 (23 Nights)

San Juan, Puerto Rico • St John's, Antigua • Road Bay, Anguilla • Virgin Gorda, British Virgin Islands • Grand Turk • Miami • San Juan, Puerto Rico • Philipsburg, St. Maarten • Funchal, Portugal • Cadiz, Spain • Malaga, Spain • Barcelona, Spain

Average Starting Price

$13,230pp

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!

Silver Dawn

Silversea

Dec 28, 2027 - Jan 4, 2028 (7 Nights)

San Juan, Puerto Rico • St. John • Philipsburg, St. Maarten • Roseau, Dominica • St. Kitts • Great Harbor Jost Van Dyke, British Virgin Islands • San Juan, Puerto Rico

Average Starting Price

$4,300pp

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!

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