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Viking Sky
Viking
Dec 29, 2027 - Jan 8, 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!

Seabourn Quest
Seabourn
Dec 20, 2026 - Jan 5, 2027 (16 Nights)
Miami • San Juan, Puerto Rico • Road Bay, Anguilla • St. Kitts • Marigot Bay, St. Martin, French West Indies • Terre de Haut, Guadeloupe • Fort-De-France, Martinique • Rodney Bay, Saint Lucia • Roseau, Dominica • Little Bay, Montserrat • St John's, Antigua • Great Harbor Jost Van Dyke, British Virgin Islands • Miami
Average Starting Price
$11,163pp
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!

Silver Spirit
Silversea
Nov 12, 2028 - Nov 24, 2028 (12 Nights)
Miami • San Juan del sur, Nicaragua • Road Bay, Anguilla • St. Kitts • Roseau, Dominica • Gustavia, St. Barts • St John's, Antigua • Virgin Gorda, British Virgin Islands • Miami
Average Starting Price
$4,700pp
Jim's Onboard Credit
Vista
Oceania Cruises
Dec 16, 2028 - Dec 28, 2028 (12 Nights)
Miami • St. Thomas • Gustavia, St. Barts • St John's, Antigua • Fort-De-France, Martinique • Roseau, Dominica • Basseterre, St. Kitts and Nevis • Nassau • Miami
Average Starting Price
$5,499pp
Jim's Onboard Credit
26% OFF
Seven Seas Grandeur
Regent Seven Seas Cruises
Dec 27, 2028 - Jan 8, 2029 (12 Nights)
Miami • Oranjestad, Aruba • Willemstad, Curacao • Kralendijk, Bonaire • Scarborough (Tobago), Trinidad and Tobago • Kingstown, Saint Vincent Island, Saint Vincent • Fort-De-France, Martinique • Roseau, Dominica • Castries, St. Lucia • Bridgetown, Barbados
Average Starting Price
$8,549pp
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!

Vision of the Seas
Royal Caribbean
Mar 21, 2027 - Mar 28, 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
$850pp
Jim's Onboard Credit
FREE Specialty Dining Meal
Celebrity Ascent
Celebrity Cruises
Feb 5, 2027 - Feb 15, 2027 (10 Nights)
Fort Lauderdale • Philipsburg, St. Maarten • Castries, St. Lucia • Grenada • Roseau, Dominica • St John's, Antigua • Fort Lauderdale
Average Starting Price
$1,671pp
Jim's Onboard Credit
9% OFF
Crystal Serenity
Crystal Cruises
Feb 12, 2028 - Feb 29, 2028 (17 Nights)
Fort Lauderdale • Tortola • Gustavia, St. Barts • Roseau, Dominica • St. Kitts • San Juan, Puerto Rico • St John's, Antigua • Pointe-à-Pitre, Guadeloupe • Castries, St. Lucia • Grenada • Kralendijk, Bonaire • Willemstad, Curacao • Oranjestad, Aruba • Cartagena, Colombia
Average Starting Price
$7,770pp
Jim's Onboard Credit
Eurodam
Holland America Line
Dec 22, 2027 - Jan 12, 2028 (21 Nights)
Fort Lauderdale • Relaxaway Half Moon Cay • Philipsburg, St. Maarten • Roseau, Dominica • Fort-De-France, Martinique • St. Kitts • St. Thomas • Fort Lauderdale • Relaxaway Half Moon Cay • Montego Bay, Jamaica • George Town, Cayman Islands • Mahogany Bay, Honduras • Belize City • Cozumel • Fort Lauderdale
Average Starting Price
$5,259pp
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!

Sonata
Oceania Cruises
Jan 30, 2029 - Feb 22, 2029 (23 Nights)
Miami • Puerto Plata, Dominican Republic • Kralendijk, Bonaire • Willemstad, Curacao • Oranjestad, Aruba • Cartagena, Colombia • Limon, Costa Rica • Panama Canal, Panama • Panama City (Fuerte Amador), Panama • Panama City (Fuerte Amador), Panama • Panama City (Fuerte Amador), Panama • Panama Canal, Panama • Oranjestad, Aruba • Grenada • Roseau, Dominica • Basseterre, St. Kitts and Nevis • Tortola • Miami
Average Starting Price
$11,699pp
Jim's Onboard Credit
29% OFF
Seven Seas Prestige
Regent Seven Seas Cruises
Jan 9, 2029 - Jan 19, 2029 (10 Nights)
Miami • Puerto Plata, Dominican Republic • San Juan, Puerto Rico • Gustavia, St. Barts • Roseau, Dominica • St John's, Antigua • Tortola • Miami
Average Starting Price
$7,299pp
Jim's Onboard Credit
Rotterdam
Holland America Line
Feb 13, 2027 - Mar 6, 2027 (21 Nights)
Fort Lauderdale • Key West, Florida • George Town, Cayman Islands • Ocho Rios, Jamaica • Mahogany Bay, Honduras • Belize City • Cozumel • Fort Lauderdale • Philipsburg, St. Maarten • St John's, Antigua • Roseau, Dominica • Fort-De-France, Martinique • St. Kitts • San Juan, Puerto Rico • Relaxaway Half Moon Cay • Fort Lauderdale
Average Starting Price
$4,109pp
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!

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