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Cruise Dates

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October 2026

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Rotterdam

Holland America Line

Jan 12, 2027 - Jan 23, 2027 (11 Nights)

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

Average Starting Price

$2,319pp

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

Dec 12, 2026 - Dec 19, 2026 (7 Nights)

San Juan, Puerto Rico • Philipsburg, St. Maarten • Bridgetown, Barbados • Castries, St. Lucia • Fort-De-France, Martinique • Basseterre, St. Kitts and Nevis • San Juan, Puerto Rico

Average Starting Price

49% OFF

May 13, 2027 - May 27, 2027 (14 Nights)

Bridgetown, Barbados • Fort-De-France, Martinique • Pointe-à-Pitre, Guadeloupe • Tortola • La Romana, Dominican Republic • Catalina Island, Dominican Republic • Virgin Gorda, British Virgin Islands • Philipsburg, St. Maarten • Fort-De-France, Martinique • St John's, Antigua • La Romana, Dominican Republic • Catalina Island, Dominican Republic • Bridgetown, Barbados

Average Starting Price

48% OFF

Nov 5, 2027 - Nov 27, 2027 (22 Nights)

Barcelona, Spain • Palma de Mallorca, Spain • Alicante, Spain • Malaga, Spain • Las Palmas (Gran Canaria), Spain • St John's, Antigua • Kingstown, Saint Vincent Island, Saint Vincent • Bridgetown, Barbados • Fort-De-France, Martinique • Pointe-à-Pitre, Guadeloupe • St John's, Antigua • Philipsburg, St. Maarten • St. Kitts • Roseau, Dominica • Fort-De-France, Martinique

Average Starting Price

22% OFF

Mar 28, 2027 - Apr 4, 2027 (7 Nights)

Pointe-à-Pitre, Guadeloupe • Philipsburg, St. Maarten • St John's, Antigua • St. Kitts • Roseau, Dominica • Fort-De-France, Martinique • Pointe-à-Pitre, Guadeloupe

Average Starting Price

Jan 27, 2029 - Feb 3, 2029 (7 Nights)

Philipsburg, St. Maarten • St. Kitts • Saint Barthelemy, Gustavia • Fort-De-France, Martinique • Terre de Haut, Guadeloupe • Grenada • Bridgetown, Barbados

Average Starting Price

Dec 18, 2027 - Dec 26, 2027 (8 Nights)

Bridgetown, Barbados • Castries, St. Lucia • Grenada • Bequia Island, Saint Vincent • Fort-De-France, Martinique • St John's, Antigua • Charlestown, Nevis • San Juan, Puerto Rico

Average Starting Price

$4,500pp

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!

Silver Spirit

Silversea

Jan 10, 2028 - Jan 22, 2028 (12 Nights)

Bridgetown, Barbados • Canouan, Saint Vincent and the Grenadines • Castries, St. Lucia • Kralendijk, Bonaire • Willemstad, Curacao • Oranjestad, Aruba • Gustavia, St. Barts • Charlestown, Nevis • Fort-De-France, Martinique • Grenada • Bridgetown, Barbados

Average Starting Price

Mar 15, 2028 - Apr 1, 2028 (17 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 • Grand Turk • Amber Cove, Dominican Republic • Relaxaway Half Moon Cay • Fort Lauderdale

Average Starting Price

$4,239pp

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!

31% OFF

Seven Seas Grandeur

Regent Seven Seas Cruises

Jan 25, 2028 - Feb 4, 2028 (10 Nights)

Bridgetown, Barbados • Kingstown, Saint Vincent Island, Saint Vincent • Castries, St. Lucia • Fort-De-France, Martinique • Pointe-à-Pitre, Guadeloupe • Gustavia, St. Barts • Basseterre, St. Kitts and Nevis • St John's, Antigua • Roseau, Dominica • Bridgetown, Barbados

Average Starting Price

Jan 2, 2027 - Jan 23, 2027 (21 Nights)

Fort Lauderdale • Relaxaway Half Moon Cay • Falmouth, Jamaica • George Town, Cayman Islands • Belize City • Cozumel • Key West, Florida • Fort Lauderdale • Philipsburg, St. Maarten • St John's, Antigua • Roseau, Dominica • Fort-De-France, Martinique • St. Kitts • San Juan, Puerto Rico • Relaxaway Half Moon Cay • Fort Lauderdale

Average Starting Price

$3,709pp

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!

Silver Nova

Silversea

Dec 21, 2026 - Dec 29, 2026 (8 Nights)

Bridgetown, Barbados • Soufrier Bay, St. Lucia • Bequia Island, Saint Vincent • Grenada • Fort-De-France, Martinique • St. Kitts • St. Thomas • San Juan, Puerto Rico

Average Starting Price

$4,200pp

Jim's Onboard Credit

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