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Cruise Dates

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October 2026

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Windstar Cruises

Feb 7, 2028 - Feb 21, 2028 (14 Nights)

San Juan, Puerto Rico • Grenada • Bequia Island, Saint Vincent • Mayreau Island, Saint Vincent and the Grenadines • Les Saintes, F.W.I. • Marigot Bay, St. Martin, French West Indies • San Juan, Puerto Rico • St. John • Philipsburg, St. Maarten • Gustavia, St. Barts • Basseterre, St. Kitts and Nevis • Great Harbor Jost Van Dyke, British Virgin Islands • Virgin Gorda, British Virgin Islands • San Juan, Puerto Rico

Average Starting Price

Feb 6, 2028 - Feb 13, 2028 (7 Nights)

San Juan, Puerto Rico • Tortola • St. Kitts • Dominica • Grenada • Bridgetown, Barbados • San Juan, Puerto Rico

Average Starting Price

Mar 21, 2027 - Mar 29, 2027 (8 Nights)

Bridgetown, Barbados • Grenada • Castries, St. Lucia • Fort-De-France, Martinique • Gustavia, St. Barts • Gustavia, St. Barts • Virgin Gorda, British Virgin Islands • Miami • St. John • St John's, Antigua • Terre de Haut, Guadeloupe • Tortola • San Juan, Puerto Rico

Average Starting Price

Mar 27, 2028 - Apr 3, 2028 (7 Nights)

Average Starting Price

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

Bridgetown, Barbados • Grenada • Bequia Island, Saint Vincent • St. Pierre • Terre de Haut, Guadeloupe • St John's, Antigua • St. Kitts • Great Harbor Jost Van Dyke, British Virgin Islands • Road Bay, Anguilla • Philipsburg, St. Maarten

Average Starting Price

$7,383pp

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 Shadow

Silversea

Mar 10, 2029 - Mar 20, 2029 (10 Nights)

San Juan del sur, Nicaragua • Rodney Bay, Saint Lucia • Bridgetown, Barbados • Grenada • Canouan, Saint Vincent and the Grenadines • Bequia Island, Saint Vincent • Roseau, Dominica • Little Bay, Montserrat • St. Kitts • San Juan del sur, Nicaragua

Average Starting Price

23% OFF

Mar 7, 2027 - Mar 14, 2027 (7 Nights)

Pointe-à-Pitre, Guadeloupe • Castries, St. Lucia • Bridgetown, Barbados • Kingstown, Saint Vincent Island, Saint Vincent • Grenada • Fort-De-France, Martinique • Pointe-à-Pitre, Guadeloupe

Average Starting Price

Mar 7, 2027 - Mar 19, 2027 (12 Nights)

Bridgetown, Barbados • Bequia Island, Saint Vincent • Grenada • Willemstad, Curacao • Oranjestad, Aruba • Kralendijk, Bonaire • Virgin Gorda, British Virgin Islands • San Juan, Puerto Rico • Miami

Average Starting Price

Jan 17, 2027 - Jan 24, 2027 (7 Nights)

San Juan, Puerto Rico • Philipsburg, St. Maarten • Martinique • Grenada • St. Lucia • Bridgetown, Barbados • San Juan, Puerto Rico

Average Starting Price

50% OFF

Dec 26, 2027 - Jan 2, 2028 (7 Nights)

Pointe-à-Pitre, Guadeloupe • Kingstown, Saint Vincent Island, Saint Vincent • Bridgetown, Barbados • Castries, St. Lucia • Grenada • Fort-De-France, Martinique • Pointe-à-Pitre, Guadeloupe

Average Starting Price

49% OFF

Nov 29, 2027 - Dec 13, 2027 (14 Nights)

La Romana, Dominican Republic • Catalina Island, Dominican Republic • Virgin Gorda, British Virgin Islands • Philipsburg, St. Maarten • St. Kitts • St John's, Antigua • La Romana, Dominican Republic • Catalina Island, Dominican Republic • Oranjestad, Aruba • Willemstad, Curacao • Kralendijk, Bonaire • Grenada • La Romana, Dominican Republic

Average Starting Price

$1,372pp

Jim's Onboard Credit

30% OFF

Seven Seas Grandeur

Regent Seven Seas Cruises

Jan 18, 2029 - Jan 28, 2029 (10 Nights)

Bridgetown, Barbados • Grenada • Oranjestad, Aruba • Willemstad, Curacao • Kralendijk, Bonaire • Fort-De-France, Martinique • Castries, St. Lucia • Kingstown, Saint Vincent Island, Saint Vincent • Bridgetown, Barbados

Average Starting Price

$6,999pp

Jim's Onboard Credit

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