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Viking Sea
Viking
Dec 10, 2028 - Dec 20, 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
$3,799pp
Jim's Onboard Credit
Star Pride
Windstar Cruises
Dec 27, 2026 - Jan 10, 2027 (14 Nights)
San Juan, Puerto Rico • St. John • Gustavia, St. Barts • Basseterre, St. Kitts and Nevis • Philipsburg, St. Maarten • 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 • Deshaies, Guadeloupe • Marigot Bay, St. Martin, French West Indies • San Juan, Puerto Rico
Average Starting Price
$7,094pp
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!

Silver Shadow
Silversea
Jan 6, 2029 - Jan 16, 2029 (10 Nights)
San Juan del sur, Nicaragua • Rodney Bay, Saint Lucia • Grenada • Bridgetown, Barbados • Canouan, Saint Vincent and the Grenadines • Bequia Island, Saint Vincent • Roseau, Dominica • Little Bay, Montserrat • St. Kitts • San Juan del sur, Nicaragua
Average Starting Price
$5,400pp
Jim's Onboard Credit
Rhapsody of the Seas
Royal Caribbean
Mar 25, 2028 - Apr 1, 2028 (7 Nights)
San Juan, Puerto Rico • St. Thomas • Philipsburg, St. Maarten • St John's, Antigua • Basseterre, St. Kitts and Nevis • St. Croix • San Juan, Puerto Rico
Average Starting Price
$788pp
Jim's Onboard Credit
Crown Princess
Princess Cruises
Jan 3, 2027 - Jan 17, 2027 (14 Nights)
San Juan, Puerto Rico • St. Thomas • St. Kitts • Dominica • Grenada • 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
$1,606pp
Jim's Onboard Credit
Norwegian Prima
Norwegian Cruise Line
Feb 7, 2027 - Feb 14, 2027 (7 Nights)
San Juan, Puerto Rico • Philipsburg, St. Maarten • St. Kitts • Bridgetown, Barbados • St. Lucia • St. Thomas • Tortola • San Juan, Puerto Rico
Average Starting Price
$1,269pp
Jim's Onboard Credit
Scarlet Lady
Virgin Voyages
Apr 22, 2028 - May 4, 2028 (12 Nights)
San Juan, Puerto Rico • Philipsburg, St. Maarten • Funchal, Portugal • Tangier, Morocco • Barcelona, Spain
Average Starting Price
$1,428pp
Jim's Onboard Credit
Emerald Princess
Princess Cruises
Feb 13, 2028 - Feb 20, 2028 (7 Nights)
San Juan, Puerto Rico • St. Thomas • Philipsburg, St. Maarten • Dominica • St. Lucia • Bridgetown, Barbados • San Juan, Puerto Rico
Average Starting Price
$739pp
Jim's Onboard Credit
Vision of the Seas
Royal Caribbean
Feb 20, 2028 - Feb 27, 2028 (7 Nights)
San Juan, Puerto Rico • St. Thomas • Philipsburg, St. Maarten • Oranjestad, Aruba • Willemstad, Curacao • San Juan, Puerto Rico
Average Starting Price
$781pp
Jim's Onboard Credit
Viking Sea
Viking
Dec 20, 2028 - Dec 30, 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
$3,799pp
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!

Star Pride
Windstar Cruises
Jan 3, 2027 - Jan 10, 2027 (7 Nights)
San Juan, Puerto Rico • Grenada • Bequia Island, Saint Vincent • Mayreau Island, Saint Vincent and the Grenadines • Deshaies, Guadeloupe • Marigot Bay, St. Martin, French West Indies • San Juan, Puerto Rico
Average Starting Price
$2,586pp
Jim's Onboard Credit
Silver Shadow
Silversea
Jan 27, 2029 - Feb 3, 2029 (7 Nights)
San Juan del sur, Nicaragua • Virgin Gorda, British Virgin Islands • St John's, Antigua • Les Saintes, F.W.I. • Philipsburg, St. Maarten • Gustavia, St. Barts • Charlestown, Nevis • San Juan del sur, Nicaragua
Average Starting Price
$3,900pp
Jim's Onboard Credit
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