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Crown Princess
Princess Cruises
Jan 3, 2027 - Jan 17, 2027 (14 Nights)
San Juan, Puerto Rico • St. Thomas • St. Kitts • Dominica • Grenada • Bridgetown, Barbados • San Juan, Puerto Rico • St. Thomas • Philipsburg, St. Maarten • St John's, Antigua • St. Lucia • Bridgetown, Barbados • San Juan, Puerto Rico
Average Starting Price
$1,606pp
Jim's Onboard Credit
Norwegian Escape
Norwegian Cruise Line
Dec 30, 2026 - Jan 6, 2027 (7 Nights)
Port Canaveral (Orlando), Florida • Puerto Plata, Dominican Republic • St. Thomas • Tortola • Great Stirrup Cay • Port Canaveral (Orlando), Florida
Average Starting Price
$1,039pp
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!

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
Norwegian Prima
Norwegian Cruise Line
Feb 14, 2027 - Feb 21, 2027 (7 Nights)
San Juan, Puerto Rico • Tortola • Bridgetown, Barbados • St. Kitts • Philipsburg, St. Maarten • St. Thomas • San Juan, Puerto Rico
Average Starting Price
$1,009pp
Jim's Onboard Credit
Star Princess
Princess Cruises
Dec 2, 2028 - Dec 16, 2028 (14 Nights)
Fort Lauderdale • Belize City • Roatan, Honduras • Cozumel • Celebration Key • Fort Lauderdale • Relaxaway Half Moon Cay • St. Thomas • Philipsburg, St. Maarten • Fort Lauderdale
Average Starting Price
$2,044pp
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!

Rotterdam
Holland America Line
Dec 1, 2026 - Dec 12, 2026 (11 Nights)
Fort Lauderdale • Philipsburg, St. Maarten • St John's, Antigua • Roseau, Dominica • Castries, St. Lucia • St. Kitts • St. Thomas • Relaxaway Half Moon Cay • Fort Lauderdale
Average Starting Price
$2,024pp
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!

Emerald Princess
Princess Cruises
Feb 13, 2028 - Feb 27, 2028 (14 Nights)
San Juan, Puerto Rico • St. Thomas • Philipsburg, St. Maarten • Dominica • St. Lucia • Bridgetown, Barbados • San Juan, Puerto Rico • Tortola • St. Kitts • Martinique • Grenada • Bridgetown, Barbados • San Juan, Puerto Rico
Average Starting Price
$1,483pp
Jim's Onboard Credit
Viking Sea
Viking
Jan 9, 2029 - Jan 19, 2029 (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
$4,999pp
Jim's Onboard Credit
Vision of the Seas
Royal Caribbean
Mar 5, 2028 - Mar 12, 2028 (7 Nights)
San Juan, Puerto Rico • St. Thomas • St John's, Antigua • Roseau, Dominica • Castries, St. Lucia • Bridgetown, Barbados • San Juan, Puerto Rico
Average Starting Price
$765pp
Jim's Onboard Credit
Disney Treasure
Disney Cruise Line
Feb 12, 2028 - Feb 19, 2028 (7 Nights)
Port Canaveral (Orlando), Florida • Tortola • St. Thomas • Disney Castaway Cay, Bahamas • Port Canaveral (Orlando), Florida
Average Starting Price
$2,404pp
Jim's Onboard Credit
63% OFF
Carnival Celebration
Carnival Cruise Line
Jan 3, 2027 - Jan 10, 2027 (7 Nights)
Miami • Fun Day at Sea • Fun Day at Sea • St. Thomas • Amber Cove, Dominican Republic • Fun Day at Sea • Celebration Key • Miami
Average Starting Price
$371pp
Jim's Onboard Credit
Norwegian Aura
Norwegian Cruise Line
Sep 30, 2028 - Oct 7, 2028 (7 Nights)
Miami • Puerto Plata, Dominican Republic • St. Thomas • Tortola • Great Stirrup Cay • Miami
Average Starting Price
$1,199pp
Jim's Onboard Credit
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