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Carnival Firenze
Carnival Cruise Line
Mar 8, 2027 - Mar 18, 2027 (10 Nights)
Miami • Fun Day at Sea • Fun Day at Sea • Philipsburg, St. Maarten • St. Kitts • St. Lucia • St John's, Antigua • St. Thomas • Fun Day at Sea • Fun Day at Sea • Miami
Average Starting Price
$844pp
Jim's Onboard Credit
Enchanted Princess
Princess Cruises
Dec 14, 2027 - Dec 24, 2027 (10 Nights)
Fort Lauderdale • St. Thomas • St. Kitts • St John's, Antigua • St. Lucia • Philipsburg, St. Maarten • Fort Lauderdale
Average Starting Price
$794pp
Jim's Onboard Credit
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!

EXPLORA III
Explora Journeys
Feb 5, 2027 - Feb 19, 2027 (14 Nights)
Miami • Philipsburg, St. Maarten • Gustavia, St. Barts • Basseterre, St. Kitts and Nevis • St. John • San Juan, Puerto Rico • St. Thomas • St John's, Antigua • Terre de Haut, Guadeloupe • Puerto Plata, Dominican Republic • Miami
Average Starting Price
$12,720pp
Jim's Onboard Credit
Norwegian Bliss
Norwegian Cruise Line
Dec 22, 2027 - Jan 3, 2028 (12 Nights)
Manhattan • Puerto Plata, Dominican Republic • San Juan, Puerto Rico • Tortola • St. Thomas • St. Kitts • Philipsburg, St. Maarten • Manhattan
Average Starting Price
$2,269pp
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!

38% OFF
Carnival Vista
Carnival Cruise Line
Mar 20, 2027 - Mar 28, 2027 (8 Nights)
Port Canaveral (Orlando), Florida • Fun Day at Sea • Fun Day at Sea • St. Thomas • Philipsburg, St. Maarten • San Juan, Puerto Rico • Fun Day at Sea • Grand Bahama Island • Port Canaveral (Orlando), Florida
Average Starting Price
$893pp
Jim's Onboard Credit
Rhapsody of the Seas
Royal Caribbean
Dec 24, 2027 - Dec 31, 2027 (7 Nights)
San Juan, Puerto Rico • St. Thomas • St John's, Antigua • Philipsburg, St. Maarten • St. Croix • Basseterre, St. Kitts and Nevis • San Juan, Puerto Rico
Average Starting Price
$1,079pp
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!

Scarlet Lady
Virgin Voyages
Dec 4, 2027 - Dec 11, 2027 (7 Nights)
San Juan, Puerto Rico • Oranjestad, Aruba • Willemstad, Curacao • St John's, Antigua • Philipsburg, St. Maarten • San Juan, Puerto Rico
Average Starting Price
$903pp
Jim's Onboard Credit
Coral Princess
Princess Cruises
Dec 19, 2026 - Dec 26, 2026 (7 Nights)
Fort Lauderdale • Relaxaway Half Moon Cay • San Juan, Puerto Rico • Philipsburg, St. Maarten • Fort Lauderdale
Average Starting Price
$729pp
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!

Symphony of the Seas
Royal Caribbean
Dec 26, 2027 - Jan 4, 2028 (9 Nights)
Fort Lauderdale • Puerto Plata, Dominican Republic • St. Thomas • Philipsburg, St. Maarten • San Juan, Puerto Rico • Perfect Day Cococay • Fort Lauderdale
Average Starting Price
$2,155pp
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!

Celebrity Xcel
Celebrity Cruises
Dec 26, 2027 - Jan 2, 2028 (7 Nights)
Fort Lauderdale • Philipsburg, St. Maarten • San Juan, Puerto Rico • Puerto Plata, Dominican Republic • Fort Lauderdale
Average Starting Price
$1,666pp
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
Mar 7, 2027 - Mar 14, 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
$671pp
Jim's Onboard Credit
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