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Port: St. Thomas, U.S. Virgin Islands×
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Viking Sea
Viking
Feb 16, 2028 - Feb 26, 2028 (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
$4,499pp
Jim's Onboard Credit
Hero of the Seas
Royal Caribbean
Dec 30, 2027 - Jan 8, 2028 (9 Nights)
Miami • St. Thomas • Basseterre, St. Kitts and Nevis • Philipsburg, St. Maarten • San Juan, Puerto Rico • Perfect Day Cococay • Miami
Average Starting Price
$3,825pp
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!

37% OFF
Carnival Magic
Carnival Cruise Line
Dec 18, 2027 - Dec 26, 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
$956pp
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!

Vista
Oceania Cruises
Dec 16, 2028 - Jan 7, 2029 (22 Nights)
Miami • St. Thomas • Gustavia, St. Barts • St John's, Antigua • Fort-De-France, Martinique • Roseau, Dominica • Basseterre, St. Kitts and Nevis • Nassau • Miami • Key West, Florida • George Town, Cayman Islands • Santo Tomas de Castilla, Guatemala • Harvest Caye, Belize • Cozumel • Miami
Average Starting Price
$10,149pp
Jim's Onboard Credit
Icon of the Seas
Royal Caribbean
Apr 10, 2027 - Apr 17, 2027 (7 Nights)
Miami • Philipsburg, St. Maarten • St. Thomas • Perfect Day Cococay • Miami
Average Starting Price
$1,353pp
Jim's Onboard Credit
FREE Specialty Dining Meal
Vision of the Seas
Royal Caribbean
Dec 19, 2027 - Dec 27, 2027 (8 Nights)
San Juan, Puerto Rico • St. Thomas • St John's, Antigua • Roseau, Dominica • Grenada • Bridgetown, Barbados • Philipsburg, St. Maarten • San Juan, Puerto Rico
Average Starting Price
$1,129pp
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 Sky
Viking
Feb 17, 2028 - Feb 27, 2028 (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
$4,499pp
Jim's Onboard Credit
Emerald Princess
Princess Cruises
Dec 12, 2027 - Dec 26, 2027 (14 Nights)
San Juan, Puerto Rico • Tortola • St. Kitts • Martinique • Dominica • 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
$1,458pp
Jim's Onboard Credit
Norwegian Pearl
Norwegian Cruise Line
Jan 3, 2027 - Jan 13, 2027 (10 Nights)
Philadelphia • San Juan, Puerto Rico • San Juan, Puerto Rico • Tortola • St. Thomas • Philadelphia
Average Starting Price
$629pp
Jim's Onboard Credit
Celebrity Constellation
Celebrity Cruises
Jan 2, 2027 - Jan 9, 2027 (7 Nights)
San Juan, Puerto Rico • St. Thomas • Basseterre, St. Kitts and Nevis • Roseau, Dominica • Castries, St. Lucia • Bridgetown, Barbados • San Juan, Puerto Rico
Average Starting Price
$811pp
Jim's Onboard Credit
Celebrity Summit
Celebrity Cruises
Dec 26, 2027 - Jan 2, 2028 (7 Nights)
San Juan, Puerto Rico • St. Thomas • Bridgetown, Barbados • Castries, St. Lucia • St John's, Antigua • Philipsburg, St. Maarten • San Juan, Puerto Rico
Average Starting Price
$1,159pp
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!

Nieuw Statendam
Holland America Line
Jan 17, 2027 - Jan 31, 2027 (14 Nights)
Fort Lauderdale • Nassau • Relaxaway Half Moon Cay • Grand Turk • Amber Cove, Dominican Republic • Fort Lauderdale • Grand Turk • San Juan, Puerto Rico • St. Thomas • Relaxaway Half Moon Cay • Fort Lauderdale
Average Starting Price
$2,489pp
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!

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