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Norwegian Escape
Norwegian Cruise Line
Feb 5, 2027 - Feb 12, 2027 (7 Nights)
Port Canaveral (Orlando), Florida • Puerto Plata, Dominican Republic • St. Thomas • Tortola • Great Stirrup Cay • Port Canaveral (Orlando), Florida
Average Starting Price
$749pp
Jim's Onboard Credit
Norwegian Prima
Norwegian Cruise Line
Mar 21, 2027 - Mar 28, 2027 (7 Nights)
San Juan, Puerto Rico • Tortola • St. Kitts • Bridgetown, Barbados • Philipsburg, St. Maarten • St. Thomas • San Juan, Puerto Rico
Average Starting Price
$1,319pp
Jim's Onboard Credit
Eurodam
Holland America Line
Feb 12, 2028 - Mar 4, 2028 (21 Nights)
Fort Lauderdale • Philipsburg, St. Maarten • St John's, Antigua • Roseau, Dominica • Fort-De-France, Martinique • St. Kitts • St. Thomas • Relaxaway Half Moon Cay • Fort Lauderdale • Relaxaway Half Moon Cay • Cabo Rojo, Dominican Republic • Kralendijk, Bonaire • Willemstad, Curacao • Oranjestad, Aruba • Fort Lauderdale
Average Starting Price
$5,094pp
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!

48% OFF
MSC Seashore
MSC Cruises
Dec 12, 2027 - Dec 26, 2027 (14 Nights)
Miami • Ocean Cay • Puerto Plata, Dominican Republic • Nassau • Miami • Philipsburg, St. Maarten • St. Kitts • St. Thomas • Puerto Plata, Dominican Republic • Miami
Average Starting Price
$1,597pp
Jim's Onboard Credit
Hero of the Seas
Royal Caribbean
Dec 23, 2027 - Dec 30, 2027 (7 Nights)
Miami • Perfect Day Cococay • San Juan, Puerto Rico • St. Thomas • Miami
Average Starting Price
$2,530pp
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 Sea
Viking
Feb 14, 2027 - Feb 24, 2027 (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
$6,799pp
Jim's Onboard Credit
Norwegian Luna
Norwegian Cruise Line
Jan 2, 2028 - Jan 9, 2028 (7 Nights)
Miami • Puerto Plata, Dominican Republic • St. Thomas • Tortola • Great Stirrup Cay • Miami
Average Starting Price
$1,019pp
Jim's Onboard Credit
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
Mar 21, 2027 - Mar 28, 2027 (7 Nights)
San Juan, Puerto Rico • St. Thomas • St. Croix • Philipsburg, St. Maarten • St John's, Antigua • Roseau, Dominica • San Juan, Puerto Rico
Average Starting Price
$850pp
Jim's Onboard Credit
FREE Specialty Dining Meal
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
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