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49% OFF
MSC Opera
MSC Cruises
Dec 27, 2027 - Jan 10, 2028 (14 Nights)
La Romana, Dominican Republic • Catalina Island, Dominican Republic • Virgin Gorda, British Virgin Islands • Philipsburg, St. Maarten • St. Kitts • St John's, Antigua • La Romana, Dominican Republic • Catalina Island, Dominican Republic • Oranjestad, Aruba • Willemstad, Curacao • Kralendijk, Bonaire • Grenada • La Romana, Dominican Republic
Average Starting Price
$2,482pp
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 Spirit
Silversea
Feb 18, 2027 - Feb 28, 2027 (10 Nights)
Bridgetown, Barbados • Bequia Island, Saint Vincent • Grenada • Kralendijk, Bonaire • Willemstad, Curacao • St. Kitts • Castries, St. Lucia • Canouan, Saint Vincent and the Grenadines • Bridgetown, Barbados
Average Starting Price
$5,500pp
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
49% OFF
MSC World Asia
MSC Cruises
Jan 22, 2028 - Jan 29, 2028 (7 Nights)
Fort-De-France, Martinique • Pointe-à-Pitre, Guadeloupe • Castries, St. Lucia • Bridgetown, Barbados • Kingstown, Saint Vincent Island, Saint Vincent • Grenada • Fort-De-France, Martinique
Average Starting Price
$859pp
Jim's Onboard Credit
Emerald Princess
Princess Cruises
Feb 27, 2028 - Mar 12, 2028 (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 • Dominica • Grenada • Bridgetown, Barbados • San Juan, Puerto Rico
Average Starting Price
$1,738pp
Jim's Onboard Credit
Star Pride
Windstar Cruises
Dec 20, 2026 - Dec 27, 2026 (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
$4,231pp
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!

Seabourn Ovation
Seabourn
Jan 15, 2028 - Jan 29, 2028 (14 Nights)
Bridgetown, Barbados • Castries, St. Lucia • Little Bay, Montserrat • St John's, Antigua • St. Kitts • Great Harbor Jost Van Dyke, British Virgin Islands • Philipsburg, St. Maarten • Soper's Hole, Tortola • St. Kitts • Trois Ilets, Martinique • Bequia Island, Saint Vincent • Grenada • Bridgetown, Barbados
Average Starting Price
$9,508pp
Jim's Onboard Credit
29% OFF
MSC World Europa
MSC Cruises
Feb 23, 2027 - Mar 9, 2027 (14 Nights)
Bridgetown, Barbados • Kingstown, Saint Vincent Island, Saint Vincent • Grenada • Fort-De-France, Martinique • Pointe-à-Pitre, Guadeloupe • St John's, Antigua • Philipsburg, St. Maarten • 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
50% OFF
MSC Opera
MSC Cruises
Dec 20, 2027 - Jan 3, 2028 (14 Nights)
La Romana, Dominican Republic • Catalina Island, Dominican Republic • Oranjestad, Aruba • Willemstad, Curacao • Kralendijk, Bonaire • Grenada • La Romana, Dominican Republic • Catalina Island, Dominican Republic • Virgin Gorda, British Virgin Islands • Philipsburg, St. Maarten • St. Kitts • St John's, Antigua • La Romana, Dominican Republic
Average Starting Price
$2,692pp
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 Spirit
Silversea
Feb 5, 2028 - Feb 17, 2028 (12 Nights)
Bridgetown, Barbados • Canouan, Saint Vincent and the Grenadines • Fort-De-France, Martinique • Gustavia, St. Barts • Philipsburg, St. Maarten • Oranjestad, Aruba • Willemstad, Curacao • Kralendijk, Bonaire • Grenada • Castries, St. Lucia • Bridgetown, Barbados
Average Starting Price
$5,000pp
Jim's Onboard Credit
Crown Princess
Princess Cruises
Jan 3, 2027 - Jan 10, 2027 (7 Nights)
San Juan, Puerto Rico • St. Thomas • St. Kitts • Dominica • Grenada • Bridgetown, Barbados • San Juan, Puerto Rico
Average Starting Price
$959pp
Jim's Onboard Credit
49% OFF
MSC World Asia
MSC Cruises
Jan 23, 2028 - Jan 30, 2028 (7 Nights)
Pointe-à-Pitre, Guadeloupe • Castries, St. Lucia • Bridgetown, Barbados • Kingstown, Saint Vincent Island, Saint Vincent • Grenada • Fort-De-France, Martinique • Pointe-à-Pitre, Guadeloupe
Average Starting Price
$859pp
Jim's Onboard Credit
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