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Port: St. Thomas, U.S. Virgin Islands×
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Hero of the Seas
Royal Caribbean
Jan 29, 2028 - Feb 5, 2028 (7 Nights)
Miami • Philipsburg, St. Maarten • St. Thomas • Perfect Day Cococay • Miami
Average Starting Price
$1,590pp
Jim's Onboard Credit
Star Princess
Princess Cruises
Dec 30, 2028 - Jan 6, 2029 (7 Nights)
Fort Lauderdale • Relaxaway Half Moon Cay • St. Thomas • Philipsburg, St. Maarten • Fort Lauderdale
Average Starting Price
$1,225pp
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 Pearl
Norwegian Cruise Line
Dec 23, 2026 - Jan 3, 2027 (11 Nights)
Philadelphia • Philipsburg, St. Maarten • St. Thomas • Tortola • San Juan, Puerto Rico • Puerto Plata, Dominican Republic • Philadelphia
Average Starting Price
$1,269pp
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!

Vision of the Seas
Royal Caribbean
Jan 9, 2028 - Jan 16, 2028 (7 Nights)
San Juan, Puerto Rico • St. Thomas • St John's, Antigua • Philipsburg, St. Maarten • Roseau, Dominica • Bridgetown, Barbados • San Juan, Puerto Rico
Average Starting Price
$815pp
Jim's Onboard Credit
Caribbean Princess
Princess Cruises
Dec 28, 2028 - Jan 7, 2029 (10 Nights)
San Juan, Puerto Rico • St. Thomas • Philipsburg, St. Maarten • St John's, Antigua • Martinique • Bridgetown, Barbados • Oranjestad, Aruba • Willemstad, Curacao • San Juan, Puerto Rico
Average Starting Price
$1,650pp
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!

Emerald Princess
Princess Cruises
Jan 2, 2028 - Jan 16, 2028 (14 Nights)
San Juan, Puerto Rico • Philipsburg, St. Maarten • St. Thomas • St John's, Antigua • St. Lucia • Bridgetown, Barbados • San Juan, Puerto Rico • Tortola • St. Kitts • Dominica • Grenada • Bridgetown, Barbados • San Juan, Puerto Rico
Average Starting Price
$1,378pp
Jim's Onboard Credit
Norwegian Aura
Norwegian Cruise Line
Sep 4, 2027 - Sep 11, 2027 (7 Nights)
Miami • Puerto Plata, Dominican Republic • St. Thomas • Tortola • Great Stirrup Cay • Miami
Average Starting Price
$1,049pp
Jim's Onboard Credit
47% OFF
MSC Seashore
MSC Cruises
Jan 29, 2028 - Feb 6, 2028 (8 Nights)
Miami • Philipsburg, St. Maarten • St. Kitts • St. Thomas • Puerto Plata, Dominican Republic • Miami
Average Starting Price
$728pp
Jim's Onboard Credit
58% OFF
Carnival Magic
Carnival Cruise Line
Mar 6, 2027 - Mar 14, 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!

Viking Sea
Viking
Jan 25, 2027 - Feb 4, 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
Zuiderdam
Holland America Line
Dec 5, 2026 - Dec 19, 2026 (14 Nights)
Miami • Grand Turk • San Juan, Puerto Rico • St. Thomas • Relaxaway Half Moon Cay • Miami • Relaxaway Half Moon Cay • Ocho Rios, Jamaica • George Town, Cayman Islands • Cozumel • Miami
Average Starting Price
$2,034pp
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!

Star of the Seas
Royal Caribbean
Sep 12, 2027 - Sep 19, 2027 (7 Nights)
Port Canaveral (Orlando), Florida • Perfect Day Cococay • Samana, Dominican Republic • St. Thomas • Port Canaveral (Orlando), Florida
Average Starting Price
$1,488pp
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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