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Coral Princess
Princess Cruises
Dec 20, 2027 - Jan 3, 2028 (14 Nights)
Fort Lauderdale • Philipsburg, St. Maarten • St. Kitts • Dominica • St. Lucia • Bridgetown, Barbados • Grenada • Oranjestad, Aruba • Willemstad, Curacao • Fort Lauderdale
Average Starting Price
$1,364pp
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!

Odyssey of the Seas
Royal Caribbean
Jan 13, 2028 - Jan 24, 2028 (11 Nights)
Cape Liberty • Philipsburg, St. Maarten • Castries, St. Lucia • Bridgetown, Barbados • Basseterre, St. Kitts and Nevis • Cape Liberty
Average Starting Price
$1,485pp
Jim's Onboard Credit
46% OFF
MSC Meraviglia
MSC Cruises
Mar 27, 2027 - Apr 10, 2027 (14 Nights)
Miami • Philipsburg, St. Maarten • St. Kitts • St. Thomas • Amber Cove, Dominican Republic • Miami • Grand Turk • Ocean Cay • Nassau • Miami
Average Starting Price
$1,345pp
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!

Eurodam
Holland America Line
Dec 1, 2027 - Dec 12, 2027 (11 Nights)
Fort Lauderdale • Philipsburg, St. Maarten • St John's, Antigua • Roseau, Dominica • Fort-De-France, Martinique • St. Kitts • St. Thomas • Relaxaway Half Moon Cay • Fort Lauderdale
Average Starting Price
$2,754pp
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!

Celebrity Constellation
Celebrity Cruises
Mar 13, 2027 - Mar 20, 2027 (7 Nights)
San Juan, Puerto Rico • St. Thomas • Basseterre, St. Kitts and Nevis • Roseau, Dominica • Castries, St. Lucia • Bridgetown, Barbados • San Juan, Puerto Rico
Average Starting Price
$713pp
Jim's Onboard Credit
Valiant Lady
Virgin Voyages
Mar 13, 2027 - Mar 19, 2027 (6 Nights)
San Juan, Puerto Rico • Tortola • Basseterre, St. Kitts and Nevis • St John's, Antigua • Castries, St. Lucia • San Juan, Puerto Rico
Average Starting Price
$894pp
Jim's Onboard Credit
31% OFF
Carnival Horizon
Carnival Cruise Line
Jan 27, 2029 - Feb 10, 2029 (14 Nights)
Galveston • Fun Day at Sea • Fun Day at Sea • Fun Day at Sea • Amber Cove, Dominican Republic • San Juan, Puerto Rico • St. Kitts • St. Lucia • Grenada • Fun Day at Sea • Fun Day at Sea • Montego Bay, Jamaica • Fun Day at Sea • Fun Day at Sea • Galveston
Average Starting Price
$1,321pp
Jim's Onboard Credit
Zuiderdam
Holland America Line
Mar 28, 2027 - Apr 17, 2027 (20 Nights)
Miami • Relaxaway Half Moon Cay • Cabo Rojo, Dominican Republic • Kralendijk, Bonaire • Willemstad, Curacao • Oranjestad, Aruba • Miami • Philipsburg, St. Maarten • St John's, Antigua • Castries, St. Lucia • St. Kitts • St. Thomas • Relaxaway Half Moon Cay • Miami
Average Starting Price
$3,644pp
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!

71% OFF
MSC Poesia
MSC Cruises
Nov 12, 2026 - Nov 22, 2026 (10 Nights)
Miami • St. Thomas • St. Kitts • Philipsburg, St. Maarten • St John's, Antigua • San Juan, Puerto Rico • Puerto Plata, Dominican Republic • Miami
Average Starting Price
$498pp
Jim's Onboard Credit
Silver Nova
Silversea
Jan 9, 2028 - Jan 20, 2028 (11 Nights)
Miami • San Juan, Puerto Rico • Soper's Hole, Tortola • Gustavia, St. Barts • St. Kitts • St John's, Antigua • St. John • Miami
Average Starting Price
$6,300pp
Jim's Onboard Credit
Regal Princess
Princess Cruises
Jan 2, 2028 - Jan 16, 2028 (14 Nights)
Miami • Belize City • Roatan, Honduras • Cozumel • Celebration Key • Miami • St. Kitts • San Juan, Puerto Rico • Amber Cove, Dominican Republic • Miami
Average Starting Price
$1,113pp
Jim's Onboard Credit
Crown Princess
Princess Cruises
Mar 14, 2027 - Mar 21, 2027 (7 Nights)
San Juan, Puerto Rico • St. Thomas • St. Kitts • Dominica • Grenada • Bridgetown, Barbados • San Juan, Puerto Rico
Average Starting Price
$1,024pp
Jim's Onboard Credit
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