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Emerald Princess
Princess Cruises
Feb 20, 2028 - Mar 5, 2028 (14 Nights)
San Juan, Puerto Rico • Tortola • St. Kitts • Martinique • 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
$1,558pp
Jim's Onboard Credit
Seabourn Ovation
Seabourn
Mar 20, 2027 - Apr 8, 2027 (19 Nights)
Philipsburg, St. Maarten • Soper's Hole, Tortola • St. Kitts • Trois Ilets, Martinique • Bequia Island, Saint Vincent • Grenada • Bridgetown, Barbados • Castries, St. Lucia • Funchal, Portugal • Portimão, Portugal • Lisbon, Portugal
Average Starting Price
$10,898pp
Jim's Onboard Credit
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
19% OFF
MSC World Europa
MSC Cruises
Feb 21, 2027 - Feb 28, 2027 (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
$1,638pp
Jim's Onboard Credit
Silver Spirit
Silversea
Jan 22, 2028 - Jan 29, 2028 (7 Nights)
Bridgetown, Barbados • Bequia Island, Saint Vincent • Fort-De-France, Martinique • Gustavia, St. Barts • Roseau, Dominica • Grenada • Castries, St. Lucia • Bridgetown, Barbados
Average Starting Price
$3,700pp
Jim's Onboard Credit
49% OFF
MSC World Asia
MSC Cruises
Jan 9, 2028 - Jan 16, 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
49% OFF
MSC Opera
MSC Cruises
Dec 20, 2027 - Dec 27, 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
$1,279pp
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 3, 2027 - Jan 8, 2027 (5 Nights)
San Juan, Puerto Rico • St. Thomas • St. Kitts • Dominica • Grenada • Bridgetown, Barbados
Average Starting Price
$680pp
Jim's Onboard Credit
Emerald Princess
Princess Cruises
Feb 13, 2028 - Feb 27, 2028 (14 Nights)
San Juan, Puerto Rico • St. Thomas • Philipsburg, St. Maarten • Dominica • St. Lucia • Bridgetown, Barbados • San Juan, Puerto Rico • Tortola • St. Kitts • Martinique • Grenada • Bridgetown, Barbados • San Juan, Puerto Rico
Average Starting Price
$1,508pp
Jim's Onboard Credit
Star Pride
Windstar Cruises
Dec 6, 2026 - Dec 13, 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
$3,006pp
Jim's Onboard Credit
Seabourn Ovation
Seabourn
Mar 13, 2027 - Mar 27, 2027 (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
$11,618pp
Jim's Onboard Credit
20% OFF
MSC World Europa
MSC Cruises
Feb 20, 2027 - Feb 27, 2027 (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
$1,573pp
Jim's Onboard Credit
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