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Disney Treasure
Disney Cruise Line
Apr 8, 2028 - Apr 15, 2028 (7 Nights)
Port Canaveral (Orlando), Florida • Tortola • St. Thomas • Disney Castaway Cay, Bahamas • Port Canaveral (Orlando), Florida
Average Starting Price
$3,160pp
Jim's Onboard Credit
Norwegian Prima
Norwegian Cruise Line
Jan 17, 2027 - Jan 24, 2027 (7 Nights)
San Juan, Puerto Rico • Kralendijk, Bonaire • Philipsburg, St. Maarten • St. Thomas • Tortola • San Juan, Puerto Rico
Average Starting Price
$839pp
Jim's Onboard Credit
Star of the Seas
Royal Caribbean
Mar 5, 2028 - Mar 12, 2028 (7 Nights)
Port Canaveral (Orlando), Florida • Perfect Day Cococay • St. Thomas • Philipsburg, St. Maarten • Port Canaveral (Orlando), Florida
Average Starting Price
$1,788pp
Jim's Onboard Credit

Jim's Ship Pick
This is the BEST ship I’ve EVER sailed on! It rarely felt crowded, the food was incredible, the shows were absolutely phenomenal, and there’s something for everyone!

Norwegian Aura
Norwegian Cruise Line
Oct 21, 2028 - Oct 28, 2028 (7 Nights)
Miami • Puerto Plata, Dominican Republic • St. Thomas • Tortola • Great Stirrup Cay • Miami
Average Starting Price
$1,249pp
Jim's Onboard Credit
Vision of the Seas
Royal Caribbean
Dec 27, 2026 - Jan 3, 2027 (7 Nights)
San Juan, Puerto Rico • St. Thomas • St. Croix • St John's, Antigua • Roseau, Dominica • Philipsburg, St. Maarten • San Juan, Puerto Rico
Average Starting Price
$1,427pp
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!

Caribbean Princess
Princess Cruises
Dec 8, 2028 - Dec 15, 2028 (7 Nights)
Bridgetown, Barbados • San Juan, Puerto Rico • St. Thomas • Philipsburg, St. Maarten • St John's, Antigua • St. Lucia • Bridgetown, Barbados
Average Starting Price
$785pp
Jim's Onboard Credit
Regal Princess
Princess Cruises
Jan 8, 2029 - Jan 22, 2029 (14 Nights)
Fort Lauderdale • Relaxaway Half Moon Cay • Amber Cove, Dominican Republic • Grand Turk • Fort Lauderdale • Philipsburg, St. Maarten • St. Thomas • San Juan, Puerto Rico • Amber Cove, Dominican Republic • Fort Lauderdale
Average Starting Price
$1,774pp
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
Nov 22, 2026 - Nov 29, 2026 (7 Nights)
Miami • Puerto Plata, Dominican Republic • St. Thomas • Tortola • Great Stirrup Cay • Miami
Average Starting Price
$859pp
Jim's Onboard Credit
Norwegian Escape
Norwegian Cruise Line
Aug 6, 2028 - Aug 13, 2028 (7 Nights)
Port Canaveral (Orlando), Florida • Puerto Plata, Dominican Republic • St. Thomas • Tortola • Great Stirrup Cay • Port Canaveral (Orlando), Florida
Average Starting Price
$1,249pp
Jim's Onboard Credit
Disney Treasure
Disney Cruise Line
Jan 2, 2027 - Jan 9, 2027 (7 Nights)
Port Canaveral (Orlando), Florida • St. Thomas • Tortola • Disney Castaway Cay, Bahamas • Port Canaveral (Orlando), Florida
Average Starting Price
$1,924pp
Jim's Onboard Credit
Norwegian Prima
Norwegian Cruise Line
Mar 25, 2028 - Apr 1, 2028 (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
$1,259pp
Jim's Onboard Credit
Star of the Seas
Royal Caribbean
Jan 24, 2027 - Jan 31, 2027 (7 Nights)
Port Canaveral (Orlando), Florida • Perfect Day Cococay • St. Thomas • Philipsburg, St. Maarten • Port Canaveral (Orlando), Florida
Average Starting Price
$1,413pp
Jim's Onboard Credit

Jim's Ship Pick
This is the BEST ship I’ve EVER sailed on! It rarely felt crowded, the food was incredible, the shows were absolutely phenomenal, and there’s something for everyone!

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