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Cruise Dates

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October 2026

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Vision of the Seas

Royal Caribbean

Feb 14, 2027 - Feb 21, 2027 (7 Nights)

San Juan, Puerto Rico • Tortola • St John's, Antigua • Philipsburg, St. Maarten • St. Croix • Basseterre, St. Kitts and Nevis • San Juan, Puerto Rico

Average Starting Price

$548pp

Jim's Onboard Credit

FREE Specialty Dining Meal

EXPLORA III

Explora Journeys

Nov 15, 2026 - Nov 29, 2026 (14 Nights)

San Juan, Puerto Rico • Road Bay, Anguilla • St John's, Antigua • St. Croix • Catalina Island, Dominican Republic • Puerto Plata, Dominican Republic • Miami • St. John • St John's, Antigua • Terre de Haut, Guadeloupe • Philipsburg, St. Maarten • San Juan, Puerto Rico

Average Starting Price

Nov 15, 2026 - Nov 25, 2026 (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

33% OFF

Jan 2, 2027 - Jan 9, 2027 (7 Nights)

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

Average Starting Price

Mar 12, 2028 - Mar 19, 2028 (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

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 Shadow

Silversea

Dec 30, 2028 - Jan 6, 2029 (7 Nights)

San Juan del sur, Nicaragua • Great Harbor Jost Van Dyke, British Virgin Islands • St John's, Antigua • Les Saintes, F.W.I. • Road Bay, Anguilla • Gustavia, St. Barts • St. Kitts • San Juan del sur, Nicaragua

Average Starting Price

Jan 15, 2028 - Jan 29, 2028 (14 Nights)

Bridgetown, Barbados • Castries, St. Lucia • Little Bay, Montserrat • St John's, Antigua • St. Kitts • Great Harbor Jost Van Dyke, British Virgin Islands • Philipsburg, St. Maarten • Soper's Hole, Tortola • St. Kitts • Trois Ilets, Martinique • Bequia Island, Saint Vincent • Grenada • Bridgetown, Barbados

Average Starting Price

Jan 2, 2027 - Jan 9, 2027 (7 Nights)

San Juan, Puerto Rico • St. Thomas • St. Croix • Philipsburg, St. Maarten • St John's, Antigua • Roseau, Dominica • San Juan, Puerto Rico

Average Starting Price

$697pp

Jim's Onboard Credit

FREE Specialty Dining Meal

Enchanted Princess

Princess Cruises

Dec 17, 2026 - Dec 27, 2026 (10 Nights)

Fort Lauderdale • Relaxaway Half Moon Cay • Amber Cove, Dominican Republic • San Juan, Puerto Rico • Philipsburg, St. Maarten • St John's, Antigua • St. Kitts • Fort Lauderdale

Average Starting Price

$1,179pp

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!

Wind Surf

Windstar Cruises

Feb 13, 2028 - Feb 27, 2028 (14 Nights)

Philipsburg, St. Maarten • St John's, Antigua • Road Bay, Anguilla • Soper's Hole, Tortola • Great Harbor Jost Van Dyke, British Virgin Islands • Great Harbor Jost Van Dyke, British Virgin Islands • Virgin Gorda, British Virgin Islands • Gustavia, St. Barts • 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

Dec 27, 2026 - Jan 10, 2027 (14 Nights)

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

Average Starting Price

$1,938pp

Jim's Onboard Credit

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