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Cruise Dates

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October 2026

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Scarlet Lady

Virgin Voyages

Apr 22, 2028 - May 4, 2028 (12 Nights)

San Juan, Puerto Rico • Philipsburg, St. Maarten • Funchal, Portugal • Tangier, Morocco • Barcelona, Spain

Average Starting Price

41% OFF

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

Fort-De-France, Martinique • Pointe-à-Pitre, Guadeloupe • Tortola • La Romana, Dominican Republic • Catalina Island, Dominican Republic • Virgin Gorda, British Virgin Islands • Philipsburg, St. Maarten • Fort-De-France, Martinique

Average Starting Price

Mar 13, 2028 - Mar 22, 2028 (9 Nights)

Bridgetown, Barbados • Grenada • Castries, St. Lucia • St. Pierre • Roseau, Dominica • Philipsburg, St. Maarten • Tortola • Miami

Average Starting Price

$3,149pp

Jim's Onboard Credit

Norwegian Prima

Norwegian Cruise Line

Apr 1, 2028 - Apr 8, 2028 (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

Dec 20, 2028 - Dec 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

$3,799pp

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!

Viking Sky

Viking

Dec 9, 2026 - Dec 22, 2026 (13 Nights)

Barcelona, Spain • Sail the Mediterranean Sea • Sail the Atlantic Ocean • Funchal, Portugal • Sail the Atlantic Ocean • Sail the Atlantic Ocean • Sail the Atlantic Ocean • Sail the Atlantic Ocean • Sail the Atlantic Ocean • Sail the Atlantic Ocean • Philipsburg, St. Maarten • Sail the Caribbean Sea • Sail the Caribbean Sea • Fort Lauderdale

Average Starting Price

Jan 3, 2028 - Jan 9, 2028 (6 Nights)

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

Average Starting Price

Feb 27, 2028 - Mar 5, 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

Mar 12, 2028 - Mar 26, 2028 (14 Nights)

Miami • Celebration Key • Amber Cove, Dominican Republic • San Juan, Puerto Rico • Grand Turk • Miami • Relaxaway Half Moon Cay • San Juan, Puerto Rico • Philipsburg, St. Maarten • Miami

Average Starting Price

$1,468pp

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!

Star of the Seas

Royal Caribbean

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

Port Canaveral (Orlando), Florida • Perfect Day Cococay • St. Thomas • Philipsburg, St. Maarten • Port Canaveral (Orlando), Florida

Average Starting Price

$1,788pp

Jim's Onboard Credit

Jim's Ship Pick
This is the BEST ship I’ve EVER sailed on! It rarely felt crowded, the food was incredible, the shows were absolutely phenomenal, and there’s something for everyone!