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Cruise Dates

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November 2026

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Wind Surf

Windstar Cruises

Mar 27, 2027 - Apr 19, 2027 (23 Nights)

Philipsburg, St. Maarten • Funchal, Portugal • Porto Santo (Madeira), Portugal • Lisbon, Portugal • Cadiz, Spain • Gibraltar • Malaga, Spain • Almeria, Spain • Cartagena, Spain • Palma de Mallorca, Spain • Barcelona, Spain

Average Starting Price

Mar 12, 2028 - Mar 19, 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 19, 2028 - Apr 2, 2028 (14 Nights)

Miami • Relaxaway Half Moon Cay • San Juan, Puerto Rico • Philipsburg, St. Maarten • Miami • Belize City • Roatan, Honduras • Cozumel • Celebration Key • Miami

Average Starting Price

$1,583pp

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!

Seabourn Ovation

Seabourn

Feb 27, 2027 - Mar 6, 2027 (7 Nights)

Bridgetown, Barbados • Castries, St. Lucia • Little Bay, Montserrat • St John's, Antigua • St. Kitts • Great Harbor Jost Van Dyke, British Virgin Islands • Philipsburg, St. Maarten

Average Starting Price

Apr 16, 2028 - Apr 23, 2028 (7 Nights)

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

Average Starting Price

$2,117pp

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!

Rhapsody of the Seas

Royal Caribbean

Jan 2, 2027 - Jan 9, 2027 (7 Nights)

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

Average Starting Price

$697pp

Jim's Onboard Credit

FREE Specialty Dining Meal

Enchanted Princess

Princess Cruises

Jan 13, 2029 - Jan 23, 2029 (10 Nights)

Fort Lauderdale • Amber Cove, Dominican Republic • San Juan, Puerto Rico • St. Kitts • St John's, Antigua • St. Lucia • Philipsburg, St. Maarten • Fort Lauderdale

Average Starting Price

Dec 8, 2028 - Dec 15, 2028 (7 Nights)

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

Average Starting Price

55% OFF

Jan 2, 2027 - Jan 10, 2027 (8 Nights)

Miami • Philipsburg, St. Maarten • St. Kitts • St. Thomas • Amber Cove, Dominican Republic • Miami

Average Starting Price

Dec 23, 2026 - Dec 30, 2026 (7 Nights)

Port Canaveral (Orlando), Florida • Philipsburg, St. Maarten • San Juan, Puerto Rico • Perfect Day Cococay • Port Canaveral (Orlando), Florida

Average Starting Price

$2,023pp

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!

48% OFF