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Cruise Dates

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October 2026

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Emerald Princess

Princess Cruises

Jan 23, 2028 - Jan 30, 2028 (7 Nights)

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

Average Starting Price

Jan 30, 2028 - Feb 6, 2028 (7 Nights)

San Juan, Puerto Rico • Bridgetown, Barbados • Grenada • Kingstown, Saint Vincent Island, Saint Vincent • St John's, Antigua • St. Thomas • San Juan, Puerto Rico

Average Starting Price

Oct 2, 2027 - Oct 9, 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

Jan 5, 2027 - Jan 15, 2027 (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

Apr 3, 2028 - Apr 19, 2028 (16 Nights)

San Juan, Puerto Rico • Lisbon, Portugal • Brest, France • Amsterdam, Netherlands

Average Starting Price

Jan 30, 2027 - Feb 6, 2027 (7 Nights)

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

Average Starting Price

$553pp

Jim's Onboard Credit

FREE Specialty Dining Meal

Silver Shadow

Silversea

Feb 27, 2029 - Mar 10, 2029 (11 Nights)

San Juan del sur, Nicaragua • Gustavia, St. Barts • St John's, Antigua • Les Saintes, F.W.I. • Castries, St. Lucia • Canouan, Saint Vincent and the Grenadines • Kralendijk, Bonaire • Willemstad, Curacao • Oranjestad, Aruba • San Juan del sur, Nicaragua

Average Starting Price

Jan 17, 2027 - Jan 31, 2027 (14 Nights)

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

Mar 25, 2028 - Apr 1, 2028 (7 Nights)

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

Average Starting Price

$973pp

Jim's Onboard Credit

Norwegian Prima

Norwegian Cruise Line

Feb 19, 2028 - Feb 26, 2028 (7 Nights)

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

Average Starting Price

Dec 26, 2026 - Jan 2, 2027 (7 Nights)

San Juan, Puerto Rico • Philipsburg, St. Maarten • Fort-De-France, Martinique • Bridgetown, Barbados • Castries, St. Lucia • St John's, Antigua • San Juan, Puerto Rico

Average Starting Price

$1,533pp

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!

Celebrity Constellation

Celebrity Cruises

Nov 17, 2026 - Nov 28, 2026 (11 Nights)

San Juan, Puerto Rico • Tortola • St John's, Antigua • Castries, St. Lucia • Grenada • Bridgetown, Barbados • Kingstown, Saint Vincent Island, Saint Vincent • Fort-De-France, Martinique • Roseau, Dominica • San Juan, Puerto Rico

Average Starting Price

$1,296pp

Jim's Onboard Credit

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