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Viking Sky
Viking
Jan 18, 2028 - Jan 28, 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
Norwegian Pearl
Norwegian Cruise Line
Feb 2, 2027 - Feb 12, 2027 (10 Nights)
Philadelphia • Puerto Plata, Dominican Republic • San Juan, Puerto Rico • St. Thomas • Tortola • Philadelphia
Average Starting Price
$699pp
Jim's Onboard Credit
Nieuw Statendam
Holland America Line
Feb 14, 2027 - Feb 21, 2027 (7 Nights)
Fort Lauderdale • Grand Turk • San Juan, Puerto Rico • St. Thomas • Relaxaway Half Moon Cay • Fort Lauderdale
Average Starting Price
$1,539pp
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
Feb 24, 2027 - Mar 6, 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
48% OFF
MSC Seashore
MSC Cruises
Dec 18, 2027 - Dec 26, 2027 (8 Nights)
Miami • Philipsburg, St. Maarten • St. Kitts • St. Thomas • Puerto Plata, Dominican Republic • Miami
Average Starting Price
$1,098pp
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!

Crystal Symphony
Crystal Cruises
Nov 24, 2026 - Dec 3, 2026 (9 Nights)
Fort Lauderdale • St. Thomas • Tortola • Marigot Bay, St. Martin, French West Indies • San Juan, Puerto Rico • Puerto Plata, Dominican Republic • Fort Lauderdale
Average Starting Price
$4,200pp
Jim's Onboard Credit
Celebrity Constellation
Celebrity Cruises
Jan 23, 2027 - Jan 30, 2027 (7 Nights)
San Juan, Puerto Rico • St. Thomas • Philipsburg, St. Maarten • St John's, Antigua • Castries, St. Lucia • Bridgetown, Barbados • San Juan, Puerto Rico
Average Starting Price
$697pp
Jim's Onboard Credit
Celebrity Summit
Celebrity Cruises
Dec 5, 2027 - Dec 12, 2027 (7 Nights)
San Juan, Puerto Rico • Roseau, Dominica • Bridgetown, Barbados • Castries, St. Lucia • St John's, Antigua • St. Thomas • San Juan, Puerto Rico
Average Starting Price
$639pp
Jim's Onboard Credit
Celebrity Beyond
Celebrity Cruises
Jan 15, 2028 - Jan 23, 2028 (8 Nights)
Fort Lauderdale • St. Thomas • Philipsburg, St. Maarten • San Juan, Puerto Rico • Nassau • Fort Lauderdale
Average Starting Price
$1,229pp
Jim's Onboard Credit
Vision of the Seas
Royal Caribbean
Apr 4, 2027 - Apr 14, 2027 (10 Nights)
San Juan, Puerto Rico • St. Thomas • St. Croix • Philipsburg, St. Maarten • St John's, Antigua • Roseau, Dominica • Castries, St. Lucia • Basseterre, St. Kitts and Nevis • Miami
Average Starting Price
$1,109pp
Jim's Onboard Credit
FREE Specialty Dining Meal
Emerald Princess
Princess Cruises
Dec 5, 2027 - Dec 19, 2027 (14 Nights)
San Juan, Puerto Rico • St. Thomas • Philipsburg, St. Maarten • St John's, Antigua • St. Lucia • Bridgetown, Barbados • San Juan, Puerto Rico • Tortola • St. Kitts • Martinique • Dominica • Bridgetown, Barbados • San Juan, Puerto Rico
Average Starting Price
$1,428pp
Jim's Onboard Credit
30% OFF
Vista
Oceania Cruises
Dec 21, 2026 - Dec 28, 2026 (7 Nights)
Miami • Tortola • St. Thomas • Nassau • Miami
Average Starting Price
$3,010pp
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!

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