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Silver Nova
Silversea
Dec 21, 2026 - Dec 29, 2026 (8 Nights)
Bridgetown, Barbados • Soufrier Bay, St. Lucia • Bequia Island, Saint Vincent • Grenada • Fort-De-France, Martinique • St. Kitts • St. Thomas • San Juan, Puerto Rico
Average Starting Price
$4,200pp
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 9, 2028 - Jan 23, 2028 (14 Nights)
San Juan, Puerto Rico • Tortola • St. Kitts • Dominica • Grenada • Bridgetown, Barbados • San Juan, Puerto Rico • St. Thomas • Philipsburg, St. Maarten • St John's, Antigua • Bridgetown, Barbados • St. Lucia • San Juan, Puerto Rico
Average Starting Price
$1,318pp
Jim's Onboard Credit
Star Pride
Windstar Cruises
Mar 13, 2028 - Mar 27, 2028 (14 Nights)
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 • St. John • Basseterre, St. Kitts and Nevis • Gustavia, St. Barts • Philipsburg, St. Maarten • Great Harbor Jost Van Dyke, British Virgin Islands • Virgin Gorda, British Virgin Islands • San Juan, Puerto Rico
Average Starting Price
$4,014pp
Jim's Onboard Credit
Seabourn Ovation
Seabourn
Dec 11, 2027 - Dec 28, 2027 (17 Nights)
Bridgetown, Barbados • Rodney Bay, Saint Lucia • Scarborough (Tobago), Trinidad and Tobago • Willemstad, Curacao • Kralendijk, Bonaire • Bridgetown, Barbados • Grenada • Bequia Island, Saint Vincent • St. Pierre • Terre de Haut, Guadeloupe • St John's, Antigua • St. Kitts • Great Harbor Jost Van Dyke, British Virgin Islands • Road Bay, Anguilla • Philipsburg, St. Maarten
Average Starting Price
$11,343pp
Jim's Onboard Credit
29% OFF
MSC World Europa
MSC Cruises
Mar 23, 2027 - Apr 6, 2027 (14 Nights)
Bridgetown, Barbados • Grenada • Kingstown, Saint Vincent Island, Saint Vincent • Fort-De-France, Martinique • Pointe-à-Pitre, Guadeloupe • Philipsburg, St. Maarten • St John's, Antigua • St. Kitts • Roseau, Dominica • Fort-De-France, Martinique • Pointe-à-Pitre, Guadeloupe • Castries, St. Lucia • Bridgetown, Barbados
Average Starting Price
$1,918pp
Jim's Onboard Credit
Azamara Quest
Azamara
Dec 19, 2027 - Jan 5, 2028 (17 Nights)
San Juan, Puerto Rico • Virgin Gorda, British Virgin Islands • St John's, Antigua • Portsmouth, Dominica • Port Elizabeth (Bequia), Saint Vincent and the Grenadines • Grenada • Scarborough (Tobago), Trinidad and Tobago • Bridgetown, Barbados • Kralendijk, Bonaire • Willemstad, Curacao • Oranjestad, Aruba • Puerto Plata, Dominican Republic • Nassau • Miami
Average Starting Price
$4,929pp
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!

Crown Princess
Princess Cruises
Jan 31, 2027 - Feb 14, 2027 (14 Nights)
San Juan, Puerto Rico • St. Thomas • Pointe-à-Pitre, Guadeloupe • Dominica • Grenada • Bridgetown, Barbados • San Juan, Puerto Rico • St. Thomas • Philipsburg, St. Maarten • St John's, Antigua • Dominica • Bridgetown, Barbados • San Juan, Puerto Rico
Average Starting Price
$1,332pp
Jim's Onboard Credit
49% OFF
MSC World Asia
MSC Cruises
Dec 14, 2027 - Dec 28, 2027 (14 Nights)
Bridgetown, Barbados • Kingstown, Saint Vincent Island, Saint Vincent • Grenada • Fort-De-France, Martinique • Pointe-à-Pitre, Guadeloupe • Philipsburg, St. Maarten • St John's, Antigua • St. Kitts • Roseau, Dominica • Fort-De-France, Martinique • Pointe-à-Pitre, Guadeloupe • Kingstown, Saint Vincent Island, Saint Vincent • Bridgetown, Barbados
Average Starting Price
$2,399pp
Jim's Onboard Credit
Wind Star
Windstar Cruises
Nov 24, 2026 - Dec 5, 2026 (11 Nights)
Bridgetown, Barbados • Bequia Island, Saint Vincent • Grenada • Kralendijk, Bonaire • Willemstad, Curacao • Oranjestad, Aruba • Cartagena, Colombia • Panama Canal, Panama • Colon, Panama
Average Starting Price
$5,201pp
Jim's Onboard Credit
54% OFF
MSC Opera
MSC Cruises
Apr 5, 2027 - Apr 12, 2027 (7 Nights)
La Romana, Dominican Republic • Catalina Island, Dominican Republic • Oranjestad, Aruba • Willemstad, Curacao • Kralendijk, Bonaire • Grenada • La Romana, Dominican Republic
Average Starting Price
$759pp
Jim's Onboard Credit
Vision of the Seas
Royal Caribbean
Apr 2, 2028 - Apr 9, 2028 (7 Nights)
San Juan, Puerto Rico • St. Thomas • St John's, Antigua • Kingstown, Saint Vincent Island, Saint Vincent • Grenada • Bridgetown, Barbados • San Juan, Puerto Rico
Average Starting Price
$852pp
Jim's Onboard Credit
Star Legend
Windstar Cruises
Jan 31, 2028 - Feb 14, 2028 (14 Nights)
San Juan, Puerto Rico • St. John • Gustavia, St. Barts • Philipsburg, St. Maarten • 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
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