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Caribbean Princess
Princess Cruises
Dec 28, 2028 - Jan 7, 2029 (10 Nights)
San Juan, Puerto Rico • St. Thomas • Philipsburg, St. Maarten • St John's, Antigua • Martinique • Bridgetown, Barbados • Oranjestad, Aruba • Willemstad, Curacao • San Juan, Puerto Rico
Average Starting Price
$1,650pp
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!

48% OFF
MSC Seashore
MSC Cruises
Jul 18, 2027 - Jul 22, 2027 (4 Nights)
Port Canaveral (Orlando), Florida • Nassau • Ocean Cay • Ocean Cay • Port Canaveral (Orlando), Florida
Average Starting Price
$451pp
Jim's Onboard Credit
53% OFF
MSC Meraviglia
MSC Cruises
Jan 2, 2027 - Jan 10, 2027 (8 Nights)
Miami • Philipsburg, St. Maarten • St. Kitts • St. Thomas • Amber Cove, Dominican Republic • Miami
Average Starting Price
$518pp
Jim's Onboard Credit
Disney Treasure
Disney Cruise Line
Dec 18, 2027 - Dec 26, 2027 (8 Nights)
Port Canaveral (Orlando), Florida • Tortola • St. Thomas • San Juan, Puerto Rico • Disney Castaway Cay, Bahamas • Port Canaveral (Orlando), Florida
Average Starting Price
$4,123pp
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 Spirit
Silversea
Feb 18, 2027 - Feb 28, 2027 (10 Nights)
Bridgetown, Barbados • Bequia Island, Saint Vincent • Grenada • Kralendijk, Bonaire • Willemstad, Curacao • St. Kitts • Castries, St. Lucia • Canouan, Saint Vincent and the Grenadines • Bridgetown, Barbados
Average Starting Price
$6,600pp
Jim's Onboard Credit
Sun Princess
Princess Cruises
Jan 17, 2027 - Jan 24, 2027 (7 Nights)
Fort Lauderdale • Celebration Key • San Juan, Puerto Rico • Amber Cove, Dominican Republic • Fort Lauderdale
Average Starting Price
$789pp
Jim's Onboard Credit
43% OFF
Carnival Miracle
Carnival Cruise Line
Dec 21, 2026 - Dec 26, 2026 (5 Nights)
Galveston • Fun Day at Sea • Cozumel • Progreso, Mexico • Fun Day at Sea • Galveston
Average Starting Price
$669pp
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!

Star Legend
Windstar Cruises
Feb 16, 2027 - Feb 22, 2027 (6 Nights)
Panama City (Fuerte Amador), Panama • Panama Canal, Panama • Bocas Del Toro, Panama • Panama Canal, Panama • Cartagena, Colombia • Oranjestad, Aruba
Average Starting Price
$5,016pp
Jim's Onboard Credit
53% OFF
Carnival Sunshine
Carnival Cruise Line
Dec 18, 2026 - Dec 26, 2026 (8 Nights)
Norfolk, Virginia • Fun Day at Sea • Fun Day at Sea • Relaxaway Half Moon Cay • Grand Turk • Amber Cove, Dominican Republic • Fun Day at Sea • Fun Day at Sea • Norfolk, Virginia
Average Starting Price
$716pp
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!

29% OFF
Seven Seas Grandeur
Regent Seven Seas Cruises
Feb 14, 2028 - Feb 24, 2028 (10 Nights)
Bridgetown, Barbados • Grenada • Kingstown, Saint Vincent Island, Saint Vincent • Castries, St. Lucia • Fort-De-France, Martinique • Gustavia, St. Barts • Basseterre, St. Kitts and Nevis • St John's, Antigua • Roseau, Dominica • Bridgetown, Barbados
Average Starting Price
$7,199pp
Jim's Onboard Credit
38% OFF
Carnival Festivale
Carnival Cruise Line
Feb 5, 2028 - Feb 13, 2028 (8 Nights)
Port Canaveral (Orlando), Florida • Fun Day at Sea • Fun Day at Sea • St. Thomas • San Juan, Puerto Rico • Amber Cove, Dominican Republic • Fun Day at Sea • Celebration Key • Port Canaveral (Orlando), Florida
Average Starting Price
$914pp
Jim's Onboard Credit
Vision of the Seas
Royal Caribbean
Jan 23, 2028 - Jan 30, 2028 (7 Nights)
San Juan, Puerto Rico • Kingstown, Saint Vincent Island, Saint Vincent • Grenada • Fort-De-France, Martinique • St John's, Antigua • St. Thomas • San Juan, Puerto Rico
Average Starting Price
$836pp
Jim's Onboard Credit
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