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Valiant Lady
Virgin Voyages
Jan 29, 2027 - Feb 6, 2027 (8 Nights)
San Juan, Puerto Rico • Oranjestad, Aruba • Willemstad, Curacao • Kralendijk, Bonaire • Fort-De-France, Martinique • Philipsburg, St. Maarten • San Juan, Puerto Rico
Average Starting Price
$1,352pp
Jim's Onboard Credit
Celebrity Constellation
Celebrity Cruises
Feb 6, 2027 - Feb 13, 2027 (7 Nights)
San Juan, Puerto Rico • St. Thomas • St John's, Antigua • Roseau, Dominica • Castries, St. Lucia • Grenada • San Juan, Puerto Rico
Average Starting Price
$768pp
Jim's Onboard Credit
Norwegian Prima
Norwegian Cruise Line
Dec 25, 2027 - Jan 1, 2028 (7 Nights)
San Juan, Puerto Rico • St. Kitts • Bridgetown, Barbados • St John's, Antigua • Philipsburg, St. Maarten • Tortola • St. Thomas • San Juan, Puerto Rico
Average Starting Price
$1,959pp
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
Star Legend
Windstar Cruises
Jan 17, 2028 - Jan 31, 2028 (14 Nights)
San Juan, Puerto Rico • St. John • Philipsburg, St. Maarten • Gustavia, St. Barts • Basseterre, St. Kitts and Nevis • Great Harbor Jost Van Dyke, British Virgin Islands • Virgin Gorda, British Virgin Islands • San Juan, Puerto Rico • Grenada • Bequia Island, Saint Vincent • Mayreau Island, Saint Vincent and the Grenadines • Les Saintes, F.W.I. • Marigot Bay, St. Martin, French West Indies • San Juan, Puerto Rico
Average Starting Price
$4,014pp
Jim's Onboard Credit
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!

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
$1,443pp
Jim's Onboard Credit
Viking Sky
Viking
Feb 27, 2028 - Mar 9, 2028 (11 Nights)
San Juan, Puerto Rico • Sail the Atlantic Ocean • Sail the Atlantic Ocean • Sail the Atlantic Ocean • Sail the Atlantic Ocean • Sail the North Atlantic Ocean • Sail the North Atlantic Ocean • Santa Cruz de la Palma, Spain • Santa Cruz de Tenerife, Spain • Funchal, Portugal • Sail the North Atlantic Ocean • Lisbon, Portugal
Average Starting Price
$3,299pp
Jim's Onboard Credit
Rhapsody of the Seas
Royal Caribbean
Jan 15, 2028 - Jan 22, 2028 (7 Nights)
San Juan, Puerto Rico • St. Thomas • Roseau, Dominica • St John's, Antigua • Philipsburg, St. Maarten • St. Croix • San Juan, Puerto Rico
Average Starting Price
$757pp
Jim's Onboard Credit
Grandeur of the Seas
Royal Caribbean
Oct 16, 2027 - Oct 23, 2027 (7 Nights)
San Juan, Puerto Rico • St. Thomas • St. Croix • Philipsburg, St. Maarten • Castries, St. Lucia • Bridgetown, Barbados • San Juan, Puerto Rico
Average Starting Price
$732pp
Jim's Onboard Credit
Scarlet Lady
Virgin Voyages
Jan 22, 2028 - Jan 29, 2028 (7 Nights)
San Juan, Puerto Rico • Oranjestad, Aruba • Castries, St. Lucia • St John's, Antigua • Philipsburg, St. Maarten • San Juan, Puerto Rico
Average Starting Price
$833pp
Jim's Onboard Credit
Star Pride
Windstar Cruises
Nov 29, 2027 - Dec 6, 2027 (7 Nights)
San Juan, Puerto Rico • Catalina Island, Dominican Republic • Santa Domingo, Dominican Republic • Cartagena, Colombia • Cartagena, Colombia • Panama Canal, Panama • Colon, Panama
Average Starting Price
$2,416pp
Jim's Onboard Credit
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