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October 2026

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Star Pride

Windstar Cruises

Nov 15, 2027 - Nov 22, 2027 (7 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

Average Starting Price

Feb 20, 2027 - Feb 27, 2027 (7 Nights)

San Juan, Puerto Rico • Tortola • Castries, St. Lucia • Bridgetown, Barbados • Roseau, Dominica • Philipsburg, St. Maarten • San Juan, Puerto Rico

Average Starting Price

$1,043pp

Jim's Onboard Credit

Celebrity Constellation

Celebrity Cruises

Feb 20, 2027 - Feb 27, 2027 (7 Nights)

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

Average Starting Price

Mar 12, 2028 - Mar 19, 2028 (7 Nights)

San Juan, Puerto Rico • Tortola • Gustavia, St. Barts • St. Croix • Ocean Cay • Miami

Average Starting Price

Dec 19, 2027 - Dec 27, 2027 (8 Nights)

San Juan, Puerto Rico • Virgin Gorda, British Virgin Islands • St John's, Antigua • Portsmouth, Dominica • Port Elizabeth (Bequia), Saint Vincent and the Grenadines • Grenada • Scarborough (Tobago), Trinidad and Tobago • Bridgetown, Barbados

Average Starting Price

$2,529pp

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!

Norwegian Prima

Norwegian Cruise Line

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

San Juan, Puerto Rico • Tortola • St. Thomas • Willemstad, Curacao • Oranjestad, Aruba • San Juan, Puerto Rico

Average Starting Price

Jan 3, 2027 - Jan 10, 2027 (7 Nights)

San Juan, Puerto Rico • St. John • Gustavia, St. Barts • St John's, Antigua • Little Bay, Montserrat • St. Kitts • Great Harbor Jost Van Dyke, British Virgin Islands • San Juan, Puerto Rico

Average Starting Price

Feb 10, 2028 - Feb 19, 2028 (9 Nights)

San Juan, Puerto Rico • Virgin Gorda, British Virgin Islands • Road Bay, Anguilla • Gustavia, St. Barts • St. Kitts • Deshaies, Guadeloupe • Fort-De-France, Martinique • St John's, Antigua • St. John • San Juan, Puerto Rico

Average Starting Price

Mar 6, 2027 - Mar 26, 2027 (20 Nights)

San Juan, Puerto Rico • Philipsburg, St. Maarten • Sail the Atlantic Ocean • Sail the Atlantic Ocean • Sail the Atlantic Ocean • Sail the Atlantic Ocean • Sail the Atlantic Ocean • Sail the Atlantic Ocean • Funchal, Portugal • Sail the Atlantic Ocean • Cadiz, Spain • Sail the Strait of Gibraltar • Valencia, Spain • Barcelona, Spain • Barcelona, Spain • Sete, France • Marseille (Provence), France • Monte Carlo, Monaco • Livorno, Italy • Livorno, Italy • Rome (Civitavecchia), Italy

Average Starting Price

Jan 28, 2028 - Feb 7, 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

Dec 5, 2026 - Dec 12, 2026 (7 Nights)

San Juan, Puerto Rico • Virgin Gorda, British Virgin Islands • St John's, Antigua • St. Pierre • Port Elizabeth (Bequia), Saint Vincent and the Grenadines • Grenada • Scarborough (Tobago), Trinidad and Tobago • Bridgetown, Barbados

Average Starting Price

Jan 10, 2028 - Jan 17, 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

$2,411pp

Jim's Onboard Credit

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