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Cruise Dates

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October 2026

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45% OFF

MSC Meraviglia

MSC Cruises

Feb 13, 2027 - Feb 27, 2027 (14 Nights)

Miami • Philipsburg, St. Maarten • St. Kitts • St. Thomas • Amber Cove, Dominican Republic • Miami • Nassau • Ocean Cay • Grand Turk • Miami

Average Starting Price

$1,155pp

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!

Viking Sky

Viking

Dec 14, 2028 - Dec 24, 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

Feb 19, 2028 - Feb 26, 2028 (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

Dec 12, 2026 - Dec 28, 2026 (16 Nights)

Bridgetown, Barbados • Castries, St. Lucia • Roseau, Dominica • Basseterre, St. Kitts and Nevis • Charlestown, Nevis • Philipsburg, St. Maarten • San Juan, Puerto Rico • St. Thomas • Virgin Gorda, British Virgin Islands • St John's, Antigua • Gustavia, St. Barts • St. Pierre • Port Elizabeth (Bequia), Saint Vincent and the Grenadines • Scarborough (Tobago), Trinidad and Tobago • Mayreau Island, Saint Vincent and the Grenadines • Bridgetown, Barbados

Average Starting Price

Dec 13, 2026 - Dec 27, 2026 (14 Nights)

San Juan, Puerto Rico • St. John • Gustavia, St. Barts • Basseterre, St. Kitts and Nevis • 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 • Deshaies, Guadeloupe • Marigot Bay, St. Martin, French West Indies • San Juan, Puerto Rico

Average Starting Price

Jan 26, 2027 - Feb 5, 2027 (10 Nights)

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

Average Starting Price

Feb 26, 2028 - Mar 4, 2028 (7 Nights)

San Juan, Puerto Rico • Philipsburg, St. Maarten • Bridgetown, Barbados • Fort-De-France, Martinique • Basseterre, St. Kitts and Nevis • St. Thomas • San Juan, Puerto Rico

Average Starting Price

44% OFF

Mar 11, 2028 - Mar 19, 2028 (8 Nights)

Miami • Relaxaway Half Moon Cay • Fun Day at Sea • San Juan, Puerto Rico • Philipsburg, St. Maarten • St. Thomas • Fun Day at Sea • Fun Day at Sea • Miami

Average Starting Price

$713pp

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!

Crown Princess

Princess Cruises

Jan 24, 2027 - Jan 31, 2027 (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

Dec 23, 2028 - Dec 30, 2028 (7 Nights)

San Juan del sur, Nicaragua • St. John • St John's, Antigua • Charlestown, Nevis • Philipsburg, St. Maarten • Gustavia, St. Barts • Virgin Gorda, British Virgin Islands • San Juan del sur, Nicaragua

Average Starting Price

$4,300pp

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!

49% OFF