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Norwegian Jewel
Norwegian Cruise Line
Dec 23, 2026 - Jan 4, 2027 (12 Nights)
Miami • Great Stirrup Cay • Cabo Rojo, Dominican Republic • Oranjestad, Aruba • Willemstad, Curacao • Philipsburg, St. Maarten • Tortola • St. Thomas • Puerto Plata, Dominican Republic • Miami
Average Starting Price
$1,599pp
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!

74% 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
$448pp
Jim's Onboard Credit
Jewel of the Seas
Royal Caribbean
Dec 7, 2026 - Dec 16, 2026 (9 Nights)
Tampa • San Juan, Puerto Rico • Philipsburg, St. Maarten • St. Thomas • Puerto Plata, Dominican Republic • Tampa
Average Starting Price
$961pp
Jim's Onboard Credit
FREE Specialty Dining Meal
Enchanted Princess
Princess Cruises
Jan 4, 2028 - Jan 15, 2028 (11 Nights)
Fort Lauderdale • St. Thomas • St. Kitts • St. Lucia • Bridgetown, Barbados • St John's, Antigua • Philipsburg, St. Maarten • Fort Lauderdale
Average Starting Price
$1,134pp
Jim's Onboard Credit
Celebrity Reflection
Celebrity Cruises
Dec 28, 2026 - Jan 4, 2027 (7 Nights)
Fort Lauderdale • Puerto Plata, Dominican Republic • St. Thomas • St John's, Antigua • Fort Lauderdale
Average Starting Price
$1,895pp
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!

31% OFF
Carnival Horizon
Carnival Cruise Line
Jan 6, 2029 - Jan 20, 2029 (14 Nights)
Galveston • Fun Day at Sea • Fun Day at Sea • Ocho Rios, Jamaica • Fun Day at Sea • St. Croix • Philipsburg, St. Maarten • St. Kitts • St. Thomas • San Juan, Puerto Rico • Amber Cove, Dominican Republic • Fun Day at Sea • Fun Day at Sea • Fun Day at Sea • Galveston
Average Starting Price
$1,335pp
Jim's Onboard Credit
Coral Princess
Princess Cruises
Nov 8, 2026 - Nov 18, 2026 (10 Nights)
Fort Lauderdale • St John's, Antigua • Philipsburg, St. Maarten • Dominica • St. Kitts • St. Thomas • Fort Lauderdale
Average Starting Price
$749pp
Jim's Onboard Credit
Norwegian Breakaway
Norwegian Cruise Line
Nov 8, 2026 - Nov 22, 2026 (14 Nights)
Boston • St. Thomas • St. Lucia • Grenada • Willemstad, Curacao • Oranjestad, Aruba • George Town, Cayman Islands • New Orleans
Average Starting Price
$869pp
Jim's Onboard Credit
28% OFF
Carnival Pride
Carnival Cruise Line
Jan 9, 2028 - Jan 23, 2028 (14 Nights)
Baltimore • Fun Day at Sea • Fun Day at Sea • Fun Day at Sea • St. Thomas • Philipsburg, St. Maarten • Dominica • St. Lucia • Bridgetown, Barbados • St John's, Antigua • Tortola • Fun Day at Sea • Fun Day at Sea • Fun Day at Sea • Baltimore
Average Starting Price
$1,506pp
Jim's Onboard Credit
Oasis of the Seas
Royal Caribbean
Dec 28, 2026 - Jan 4, 2027 (7 Nights)
Fort Lauderdale • Perfect Day Cococay • St. Thomas • Philipsburg, St. Maarten • Fort Lauderdale
Average Starting Price
$1,698pp
Jim's Onboard Credit
FREE Specialty Dining Meal

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!

Hero of the Seas
Royal Caribbean
Sep 11, 2027 - Sep 18, 2027 (7 Nights)
Miami • Philipsburg, St. Maarten • St. Thomas • Perfect Day Cococay • Miami
Average Starting Price
$1,527pp
Jim's Onboard Credit
Norwegian Pearl
Norwegian Cruise Line
Mar 2, 2027 - Mar 12, 2027 (10 Nights)
Philadelphia • Puerto Plata, Dominican Republic • San Juan, Puerto Rico • St. Thomas • Tortola • Philadelphia
Average Starting Price
$889pp
Jim's Onboard Credit
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