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October 2026

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Crown Princess

Princess Cruises

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

San Juan, Puerto Rico • St. Thomas • Pointe-à-Pitre, Guadeloupe • Dominica • Grenada • Bridgetown, Barbados • San Juan, Puerto Rico

Average Starting Price

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

San Juan, Puerto Rico • Oranjestad, Aruba • Willemstad, Curacao • St John's, Antigua • Philipsburg, St. Maarten • San Juan, Puerto Rico

Average Starting Price

$903pp

Jim's Onboard Credit

Norwegian Prima

Norwegian Cruise Line

Jan 15, 2028 - Jan 22, 2028 (7 Nights)

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

Average Starting Price

Feb 7, 2028 - Feb 14, 2028 (7 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

Average Starting Price

Dec 19, 2026 - Dec 26, 2026 (7 Nights)

San Juan, Puerto Rico • Basseterre, St. Kitts and Nevis • Fort-De-France, Martinique • Oranjestad, Aruba • Willemstad, Curacao • San Juan, Puerto Rico

Average Starting Price

$903pp

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

Dec 12, 2026 - Dec 19, 2026 (7 Nights)

San Juan, Puerto Rico • Tortola • Basseterre, St. Kitts and Nevis • Roseau, Dominica • Castries, St. Lucia • Grenada • San Juan, Puerto Rico

Average Starting Price

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

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

Average Starting Price

Jan 16, 2028 - Jan 23, 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

Jan 15, 2027 - Jan 25, 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

May 1, 2027 - May 8, 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

$689pp

Jim's Onboard Credit

FREE Specialty Dining Meal

Star Pride

Windstar Cruises

Mar 20, 2028 - Apr 3, 2028 (14 Nights)

San Juan, Puerto Rico • St. John • Basseterre, St. Kitts and Nevis • Gustavia, St. Barts • Philipsburg, St. Maarten • Great Harbor Jost Van Dyke, British Virgin Islands • Virgin Gorda, British Virgin Islands • 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

Average Starting Price

Dec 13, 2026 - Dec 20, 2026 (7 Nights)

San Juan, Puerto Rico • Road Bay, Anguilla • St John's, Antigua • Basseterre, St. Kitts and Nevis • Grand Turk • Miami

Average Starting Price

$4,575pp

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!

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