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Cruise Dates

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October 2026

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Emerald Princess

Princess Cruises

Feb 20, 2028 - Mar 5, 2028 (14 Nights)

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

Average Starting Price

Nov 20, 2028 - Nov 30, 2028 (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 13, 2027 - Nov 20, 2027 (7 Nights)

San Juan, Puerto Rico • St. Thomas • St. Croix • Philipsburg, St. Maarten • Castries, St. Lucia • Bridgetown, Barbados • San Juan, Puerto Rico

Average Starting Price

Feb 27, 2028 - Mar 5, 2028 (7 Nights)

San Juan, Puerto Rico • Bridgetown, Barbados • Grenada • Castries, St. Lucia • St John's, Antigua • St. Thomas • San Juan, Puerto Rico

Average Starting Price

Dec 20, 2026 - Dec 27, 2026 (7 Nights)

San Juan, Puerto Rico • Grenada • Bequia Island, Saint Vincent • Mayreau Island, Saint Vincent and the Grenadines • Deshaies, Guadeloupe • Marigot Bay, St. Martin, French West Indies • San Juan, Puerto Rico

Average Starting Price

$4,231pp

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 7, 2028 - Dec 16, 2028 (9 Nights)

San Juan del sur, Nicaragua • Charlestown, Nevis • Philipsburg, St. Maarten • Les Saintes, F.W.I. • Roseau, Dominica • Trois Ilets, Martinique • Gustavia, St. Barts • St John's, Antigua • Soper's Hole, Tortola • San Juan del sur, Nicaragua

Average Starting Price

Apr 1, 2028 - Apr 8, 2028 (7 Nights)

San Juan, Puerto Rico • St. Thomas • St. Croix • Philipsburg, St. Maarten • Castries, St. Lucia • Bridgetown, Barbados • San Juan, Puerto Rico

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

Norwegian Prima

Norwegian Cruise Line

Jan 24, 2027 - Jan 31, 2027 (7 Nights)

San Juan, Puerto Rico • Tortola • St. Kitts • Bridgetown, Barbados • St. Lucia • Philipsburg, St. Maarten • St. Thomas • San Juan, Puerto Rico

Average Starting Price

Jan 9, 2029 - Jan 19, 2029 (10 Nights)

Average Starting Price

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

San Juan, Puerto Rico • St. Thomas • Philipsburg, St. Maarten • Dominica • St. Lucia • Bridgetown, Barbados • San Juan, Puerto Rico • Tortola • St. Kitts • Martinique • Grenada • Bridgetown, Barbados • San Juan, Puerto Rico

Average Starting Price

Nov 6, 2027 - Nov 13, 2027 (7 Nights)

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

Average Starting Price

$686pp

Jim's Onboard Credit

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