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Rotterdam
Holland America Line
Dec 12, 2026 - Jan 2, 2027 (21 Nights)
Fort Lauderdale • Relaxaway Half Moon Cay • Falmouth, Jamaica • George Town, Cayman Islands • Mahogany Bay, Honduras • Belize City • Cozumel • Fort Lauderdale • Philipsburg, St. Maarten • St. Kitts • Roseau, Dominica • Castries, St. Lucia • St John's, Antigua • St. Thomas • Relaxaway Half Moon Cay • Fort Lauderdale
Average Starting Price
$3,604pp
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 Escape
Norwegian Cruise Line
Sep 17, 2028 - Sep 24, 2028 (7 Nights)
Port Canaveral (Orlando), Florida • Puerto Plata, Dominican Republic • St. Thomas • Tortola • Great Stirrup Cay • Port Canaveral (Orlando), Florida
Average Starting Price
$919pp
Jim's Onboard Credit
Crown Princess
Princess Cruises
Dec 28, 2028 - Jan 5, 2029 (8 Nights)
Fort Lauderdale • Amber Cove, Dominican Republic • St. Thomas • Philipsburg, St. Maarten • Tortola • Fort Lauderdale
Average Starting Price
$1,325pp
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!

53% OFF
Carnival Magic
Carnival Cruise Line
Dec 18, 2026 - Dec 26, 2026 (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
$586pp
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 Apex
Celebrity Cruises
Dec 5, 2026 - Dec 12, 2026 (7 Nights)
Port Canaveral (Orlando), Florida • Puerto Plata, Dominican Republic • St. Thomas • Basseterre, St. Kitts and Nevis • Port Canaveral (Orlando), Florida
Average Starting Price
$910pp
Jim's Onboard Credit
55% 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
$503pp
Jim's Onboard Credit
Star Princess
Princess Cruises
Nov 18, 2028 - Nov 25, 2028 (7 Nights)
Fort Lauderdale • Relaxaway Half Moon Cay • St. Thomas • Philipsburg, St. Maarten • Fort Lauderdale
Average Starting Price
$925pp
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 Xcel
Celebrity Cruises
Dec 27, 2026 - Jan 3, 2027 (7 Nights)
Miami • Nassau • St. Thomas • St John's, Antigua • Miami
Average Starting Price
$2,152pp
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!

Harmony of the Seas
Royal Caribbean
Mar 6, 2027 - Mar 13, 2027 (7 Nights)
Port Canaveral (Orlando), Florida • St. Thomas • Puerto Plata, Dominican Republic • Perfect Day Cococay • Port Canaveral (Orlando), Florida
Average Starting Price
$848pp
Jim's Onboard Credit
Icon of the Seas
Royal Caribbean
Dec 19, 2026 - Dec 26, 2026 (7 Nights)
Miami • Philipsburg, St. Maarten • St. Thomas • Perfect Day Cococay • Miami
Average Starting Price
$1,600pp
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!

Disney Treasure
Disney Cruise Line
Jan 2, 2028 - Jan 9, 2028 (7 Nights)
Port Canaveral (Orlando), Florida • Tortola • St. Thomas • Disney Castaway Cay, Bahamas • Port Canaveral (Orlando), Florida
Average Starting Price
$2,565pp
Jim's Onboard Credit
Emerald Princess
Princess Cruises
Jan 30, 2028 - Feb 6, 2028 (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
$684pp
Jim's Onboard Credit
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