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Norwegian Prima
Norwegian Cruise Line
Mar 11, 2028 - Mar 18, 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
$1,239pp
Jim's Onboard Credit
Emerald Princess
Princess Cruises
Feb 27, 2028 - Mar 12, 2028 (14 Nights)
San Juan, Puerto Rico • St. Thomas • Philipsburg, St. Maarten • St John's, Antigua • St. Lucia • Bridgetown, Barbados • San Juan, Puerto Rico • Tortola • St. Kitts • Dominica • Grenada • Bridgetown, Barbados • San Juan, Puerto Rico
Average Starting Price
$1,738pp
Jim's Onboard Credit
Viking Sea
Viking
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!

Seabourn Ovation
Seabourn
Dec 18, 2027 - Dec 28, 2027 (10 Nights)
Bridgetown, Barbados • Grenada • Bequia Island, Saint Vincent • St. Pierre • Terre de Haut, Guadeloupe • St John's, Antigua • St. Kitts • Great Harbor Jost Van Dyke, British Virgin Islands • Road Bay, Anguilla • Philipsburg, St. Maarten
Average Starting Price
$7,383pp
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 Shadow
Silversea
Feb 3, 2029 - Feb 10, 2029 (7 Nights)
San Juan del sur, Nicaragua • St. John • St John's, Antigua • Road Bay, Anguilla • St. Kitts • Gustavia, St. Barts • Great Harbor Jost Van Dyke, British Virgin Islands • San Juan del sur, Nicaragua
Average Starting Price
$3,900pp
Jim's Onboard Credit
Wind Surf
Windstar Cruises
Jan 9, 2028 - Jan 23, 2028 (14 Nights)
Philipsburg, St. Maarten • Charlestown, Nevis • Roseau, Dominica • Mayreau Island, Saint Vincent and the Grenadines • Les Saintes, F.W.I. • Basseterre, St. Kitts and Nevis • Gustavia, St. Barts • Philipsburg, St. Maarten • St John's, Antigua • Road Bay, Anguilla • Soper's Hole, Tortola • Great Harbor Jost Van Dyke, British Virgin Islands • Great Harbor Jost Van Dyke, British Virgin Islands • Virgin Gorda, British Virgin Islands • Gustavia, St. Barts • Philipsburg, St. Maarten
Average Starting Price
$4,250pp
Jim's Onboard Credit
Celebrity Eclipse
Celebrity Cruises
Apr 10, 2028 - Apr 22, 2028 (12 Nights)
Fort Lauderdale • Grand Turk • Oranjestad, Aruba • Willemstad, Curacao • Castries, St. Lucia • Basseterre, St. Kitts and Nevis • St. Thomas • Fort Lauderdale
Average Starting Price
$1,760pp
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!

Enchanted Princess
Princess Cruises
Dec 17, 2026 - Dec 27, 2026 (10 Nights)
Fort Lauderdale • Relaxaway Half Moon Cay • Amber Cove, Dominican Republic • San Juan, Puerto Rico • Philipsburg, St. Maarten • St John's, Antigua • St. Kitts • Fort Lauderdale
Average Starting Price
$1,179pp
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!

Caribbean Princess
Princess Cruises
Dec 15, 2028 - Dec 22, 2028 (7 Nights)
Bridgetown, Barbados • San Juan, Puerto Rico • St. Thomas • St. Kitts • Martinique • Grenada • Bridgetown, Barbados
Average Starting Price
$775pp
Jim's Onboard Credit
49% OFF
MSC Opera
MSC Cruises
Jan 3, 2028 - Jan 17, 2028 (14 Nights)
La Romana, Dominican Republic • Catalina Island, Dominican Republic • Oranjestad, Aruba • Willemstad, Curacao • Kralendijk, Bonaire • Grenada • La Romana, Dominican Republic • Catalina Island, Dominican Republic • Virgin Gorda, British Virgin Islands • Philipsburg, St. Maarten • St. Kitts • St John's, Antigua • La Romana, Dominican Republic
Average Starting Price
$1,712pp
Jim's Onboard Credit
Sky Princess
Princess Cruises
Jan 28, 2029 - Feb 11, 2029 (14 Nights)
Fort Lauderdale • Belize City • Roatan, Honduras • Cozumel • Celebration Key • Fort Lauderdale • Amber Cove, Dominican Republic • San Juan, Puerto Rico • St. Kitts • Fort Lauderdale
Average Starting Price
$1,484pp
Jim's Onboard Credit
31% OFF
MSC World Europa
MSC Cruises
Jan 30, 2027 - Feb 6, 2027 (7 Nights)
Fort-De-France, Martinique • Pointe-à-Pitre, Guadeloupe • Philipsburg, St. Maarten • St John's, Antigua • St. Kitts • Roseau, Dominica • Fort-De-France, Martinique
Average Starting Price
$959pp
Jim's Onboard Credit
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