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October 2026

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Celebrity Constellation

Celebrity Cruises

Dec 5, 2026 - Dec 12, 2026 (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

Jan 15, 2028 - Jan 25, 2028 (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

Jan 21, 2027 - Jan 29, 2027 (8 Nights)

Miami • St. Thomas • Road Bay, Anguilla • St. Pierre • Basseterre, St. Kitts and Nevis • Philipsburg, St. Maarten • San Juan, Puerto Rico

Average Starting Price

Jan 2, 2028 - Jan 22, 2028 (20 Nights)

Fort Lauderdale • Relaxaway Half Moon Cay • Montego Bay, Jamaica • George Town, Cayman Islands • Mahogany Bay, Honduras • Belize City • Cozumel • Fort Lauderdale • Philipsburg, St. Maarten • St John's, Antigua • Fort-De-France, Martinique • St. Kitts • San Juan, Puerto Rico • Relaxaway Half Moon Cay • Fort Lauderdale

Average Starting Price

$4,714pp

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!

Viking Vesta

Viking

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

Rome (Civitavecchia), Italy • Livorno, Italy • Livorno, Italy • Monte Carlo, Monaco • Marseille (Provence), France • Sete, France • Barcelona, Spain • Barcelona, Spain • Barcelona, Spain • Sail the Mediterranean Sea • 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 • Fort Lauderdale

Average Starting Price

46% OFF

Apr 11, 2027 - Apr 28, 2027 (17 Nights)

Pointe-à-Pitre, Guadeloupe • Philipsburg, St. Maarten • St. Kitts • St John's, Antigua • Santa Cruz de Tenerife, Spain • Barcelona, Spain • Marseille (Provence), France • Genoa (Portofino), Italy • La Spezia, Italy • Rome (Civitavecchia), Italy

Average Starting Price

49% OFF

Jul 8, 2027 - Jul 22, 2027 (14 Nights)

Bridgetown, Barbados • 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 • St John's, Antigua • La Romana, Dominican Republic • Catalina Island, Dominican Republic • Bridgetown, Barbados

Average Starting Price

Feb 27, 2027 - Mar 6, 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

$588pp

Jim's Onboard Credit

FREE Specialty Dining Meal

Grandeur of the Seas

Royal Caribbean

Sep 11, 2027 - Sep 18, 2027 (7 Nights)

San Juan, Puerto Rico • Tortola • Philipsburg, St. Maarten • St John's, Antigua • Basseterre, St. Kitts and Nevis • St. Croix • San Juan, Puerto Rico

Average Starting Price

Dec 26, 2027 - Jan 2, 2028 (7 Nights)

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

Average Starting Price

$1,813pp

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!

Crown Princess

Princess Cruises

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

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

Average Starting Price

Mar 20, 2028 - Mar 27, 2028 (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

$2,443pp

Jim's Onboard Credit

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