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Zuiderdam
Holland America Line
Dec 30, 2027 - Jan 6, 2028 (7 Nights)
Fort Lauderdale • Relaxaway Half Moon Cay • St. Thomas • San Juan, Puerto Rico • Grand Turk • Fort Lauderdale
Average Starting Price
$2,234pp
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!

Norwegian Aqua
Norwegian Cruise Line
Jun 27, 2027 - Jul 4, 2027 (7 Nights)
Port Canaveral (Orlando), Florida • Puerto Plata, Dominican Republic • St. Thomas • Tortola • Great Stirrup Cay • Port Canaveral (Orlando), Florida
Average Starting Price
$1,229pp
Jim's Onboard Credit
Grandeur of the Seas
Royal Caribbean
May 1, 2027 - May 8, 2027 (7 Nights)
San Juan, Puerto Rico • St. Thomas • St. Croix • Philipsburg, St. Maarten • Castries, St. Lucia • Bridgetown, Barbados • San Juan, Puerto Rico
Average Starting Price
$689pp
Jim's Onboard Credit
FREE Specialty Dining Meal
Norwegian Escape
Norwegian Cruise Line
Feb 26, 2027 - Mar 5, 2027 (7 Nights)
Port Canaveral (Orlando), Florida • Puerto Plata, Dominican Republic • St. Thomas • Tortola • Great Stirrup Cay • Port Canaveral (Orlando), Florida
Average Starting Price
$539pp
Jim's Onboard Credit
29% OFF
Seven Seas Prestige
Regent Seven Seas Cruises
Jan 19, 2029 - Jan 29, 2029 (10 Nights)
Miami • Tortola • St John's, Antigua • Castries, St. Lucia • Roseau, Dominica • St. Thomas • Miami
Average Starting Price
$7,499pp
Jim's Onboard Credit
Allura
Oceania Cruises
Dec 28, 2026 - Jan 7, 2027 (10 Nights)
Miami • St. Thomas • Philipsburg, St. Maarten • Gustavia, St. Barts • Basseterre, St. Kitts and Nevis • Tortola • Miami
Average Starting Price
$6,499pp
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!

Hero of the Seas
Royal Caribbean
Nov 20, 2027 - Nov 27, 2027 (7 Nights)
Miami • Philipsburg, St. Maarten • St. Thomas • Perfect Day Cococay • Miami
Average Starting Price
$2,287pp
Jim's Onboard Credit
Disney Treasure
Disney Cruise Line
Jun 19, 2027 - Jun 26, 2027 (7 Nights)
Port Canaveral (Orlando), Florida • Tortola • St. Thomas • Disney Castaway Cay, Bahamas • Port Canaveral (Orlando), Florida
Average Starting Price
$3,091pp
Jim's Onboard Credit
Norwegian Prima
Norwegian Cruise Line
Dec 18, 2027 - Dec 25, 2027 (7 Nights)
San Juan, Puerto Rico • Tortola • St. Kitts • Bridgetown, Barbados • St. Lucia • Philipsburg, St. Maarten • St. Thomas • San Juan, Puerto Rico
Average Starting Price
$1,809pp
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!

Viking Sky
Viking
Jan 28, 2028 - Feb 7, 2028 (10 Nights)
San Juan, Puerto Rico • St. Thomas • Basseterre, St. Kitts and Nevis • Castries, St. Lucia • Bridgetown, Barbados • Roseau, Dominica • St John's, Antigua • Philipsburg, St. Maarten • St. Croix • San Juan, Puerto Rico
Average Starting Price
$4,299pp
Jim's Onboard Credit
Independence of the Seas
Royal Caribbean
Mar 11, 2028 - Mar 18, 2028 (7 Nights)
Miami • St. Thomas • Samana, Dominican Republic • Perfect Day Cococay • Miami
Average Starting Price
$912pp
Jim's Onboard Credit
59% OFF
Carnival Magic
Carnival Cruise Line
Apr 17, 2027 - Apr 25, 2027 (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
$464pp
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!

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