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Cruise Dates

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October 2026

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EXPLORA III

Explora Journeys

Dec 6, 2026 - Dec 20, 2026 (14 Nights)

Miami • St. John • St John's, Antigua • Terre de Haut, Guadeloupe • Gustavia, St. Barts • San Juan, Puerto Rico • Road Bay, Anguilla • St John's, Antigua • Basseterre, St. Kitts and Nevis • Grand Turk • Miami

Average Starting Price

$8,330pp

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!

Wind Surf

Windstar Cruises

Dec 27, 2027 - Jan 3, 2028 (7 Nights)

Philipsburg, St. Maarten • Charlestown, Nevis • Roseau, Dominica • Mayreau Island, Saint Vincent and the Grenadines • Les Saintes, F.W.I. • Basseterre, St. Kitts and Nevis • Gustavia, St. Barts • Philipsburg, St. Maarten

Average Starting Price

$2,432pp

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

Dec 27, 2026 - Jan 4, 2027 (8 Nights)

Bridgetown, Barbados • Bequia Island, Saint Vincent • Fort-De-France, Martinique • Deshaies, Guadeloupe • St. Kitts • Grenada • Castries, St. Lucia • Bridgetown, Barbados

Average Starting Price

Nov 22, 2026 - Dec 6, 2026 (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 • Gustavia, St. Barts • Basseterre, St. Kitts and Nevis • Philipsburg, St. Maarten • Great Harbor Jost Van Dyke, British Virgin Islands • Virgin Gorda, British Virgin Islands • San Juan, Puerto Rico

Average Starting Price

9% OFF

Apr 10, 2029 - May 27, 2029 (47 Nights)

Rio de Janeiro, Brazil • Buzios, Brazil • Salvador da Bahia, Brazil • Maceio, Brazil • Recife, Brazil • Santarem, Brazil • Boca da Valeria (Amazon River), Brazil • Manaus, Brazil • Manaus, Brazil • Parintins, Brazil • Alter Do Chao, Brazil • Devil's Island, France • Bridgetown, Barbados • Roseau, Dominica • St. Kitts • San Juan, Puerto Rico • Samana, Dominican Republic • Grand Turk • Fort Lauderdale • Royal Naval Dockyard, Bermuda • Royal Naval Dockyard, Bermuda • New York, New York • Newport, Rhode Island • Boston • Halifax, Nova Scotia • Sydney, Nova Scotia • Havre-Saint-Pierre, Quebec • Saint John, New Brunswick • Cork (Cobh), Ireland • Plymouth, England • Portsmouth, England

Average Starting Price

$18,370pp

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!