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Emerald Princess
Princess Cruises
Dec 26, 2027 - Jan 9, 2028 (14 Nights)
San Juan, Puerto Rico • Tortola • St. Kitts • Dominica • Grenada • Bridgetown, Barbados • San Juan, Puerto Rico • Philipsburg, St. Maarten • St. Thomas • St John's, Antigua • St. Lucia • Bridgetown, Barbados • San Juan, Puerto Rico
Average Starting Price
$1,613pp
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!

33% OFF
Carnival Magic
Carnival Cruise Line
Dec 26, 2027 - Jan 3, 2028 (8 Nights)
Miami • Relaxaway Half Moon Cay • Fun Day at Sea • San Juan, Puerto Rico • Philipsburg, St. Maarten • St. Thomas • Fun Day at Sea • Fun Day at Sea • Miami
Average Starting Price
$1,155pp
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!

Vision of the Seas
Royal Caribbean
Dec 27, 2027 - Jan 3, 2028 (7 Nights)
San Juan, Puerto Rico • St. Thomas • Kralendijk, Bonaire • Willemstad, Curacao • Oranjestad, Aruba • San Juan, Puerto Rico
Average Starting Price
$1,180pp
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!

Independence of the Seas
Royal Caribbean
Jan 10, 2027 - Jan 17, 2027 (7 Nights)
Miami • Perfect Day Cococay • San Juan, Puerto Rico • St. Thomas • Miami
Average Starting Price
$661pp
Jim's Onboard Credit
FREE Specialty Dining Meal
Norwegian Pearl
Norwegian Cruise Line
Nov 28, 2026 - Dec 8, 2026 (10 Nights)
Philadelphia • Tortola • St. Thomas • San Juan, Puerto Rico • Puerto Plata, Dominican Republic • Philadelphia
Average Starting Price
$699pp
Jim's Onboard Credit
Star Princess
Princess Cruises
Feb 10, 2029 - Feb 17, 2029 (7 Nights)
Fort Lauderdale • Relaxaway Half Moon Cay • St. Thomas • Philipsburg, St. Maarten • Fort Lauderdale
Average Starting Price
$1,025pp
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
Dec 26, 2026 - Jan 2, 2027 (7 Nights)
San Juan, Puerto Rico • St. Thomas • Philipsburg, St. Maarten • St John's, Antigua • Castries, St. Lucia • Bridgetown, Barbados • San Juan, Puerto Rico
Average Starting Price
$1,024pp
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!

Caribbean Princess
Princess Cruises
Jan 14, 2029 - Jan 28, 2029 (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
$1,714pp
Jim's Onboard Credit
Norwegian Aura
Norwegian Cruise Line
Aug 7, 2027 - Aug 14, 2027 (7 Nights)
Miami • Puerto Plata, Dominican Republic • St. Thomas • Tortola • Great Stirrup Cay • Miami
Average Starting Price
$1,099pp
Jim's Onboard Credit
Icon of the Seas
Royal Caribbean
Mar 27, 2027 - Apr 3, 2027 (7 Nights)
Miami • Philipsburg, St. Maarten • St. Thomas • Perfect Day Cococay • Miami
Average Starting Price
$1,393pp
Jim's Onboard Credit
FREE Specialty Dining Meal
51% OFF
Carnival Celebration
Carnival Cruise Line
Apr 24, 2027 - May 2, 2027 (8 Nights)
Miami • Celebration Key • Fun Day at Sea • Amber Cove, Dominican Republic • San Juan, Puerto Rico • St. Thomas • Fun Day at Sea • Fun Day at Sea • Miami
Average Starting Price
$625pp
Jim's Onboard Credit
34% OFF
Carnival Firenze
Carnival Cruise Line
Feb 26, 2027 - Mar 8, 2027 (10 Nights)
Miami • Fun Day at Sea • Fun Day at Sea • San Juan, Puerto Rico • St. Croix • St. Kitts • Philipsburg, St. Maarten • St. Thomas • Fun Day at Sea • Fun Day at Sea • Miami
Average Starting Price
$1,147pp
Jim's Onboard Credit
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