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Sonata
Oceania Cruises
Feb 11, 2029 - Feb 22, 2029 (11 Nights)
Panama City (Fuerte Amador), Panama • Panama Canal, Panama • Oranjestad, Aruba • Grenada • Roseau, Dominica • Basseterre, St. Kitts and Nevis • Tortola • Miami
Average Starting Price
$5,699pp
Jim's Onboard Credit
Emerald Princess
Princess Cruises
Feb 6, 2028 - Feb 20, 2028 (14 Nights)
San Juan, Puerto Rico • Tortola • St. Kitts • Dominica • Grenada • Bridgetown, Barbados • San Juan, Puerto Rico • St. Thomas • Philipsburg, St. Maarten • Dominica • St. Lucia • Bridgetown, Barbados • San Juan, Puerto Rico
Average Starting Price
$1,378pp
Jim's Onboard Credit
Seabourn Ovation
Seabourn
Mar 20, 2027 - Mar 27, 2027 (7 Nights)
Philipsburg, St. Maarten • Soper's Hole, Tortola • St. Kitts • Trois Ilets, Martinique • Bequia Island, Saint Vincent • Grenada • Bridgetown, Barbados
Average Starting Price
$5,948pp
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
31% OFF
MSC World Europa
MSC Cruises
Mar 6, 2027 - Mar 13, 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
$893pp
Jim's Onboard Credit
Crown Princess
Princess Cruises
Jan 10, 2027 - Jan 24, 2027 (14 Nights)
San Juan, Puerto Rico • St. Thomas • Philipsburg, St. Maarten • St John's, Antigua • St. Lucia • Bridgetown, Barbados • San Juan, Puerto Rico • Philipsburg, St. Maarten • Martinique • Grenada • St. Lucia • Bridgetown, Barbados • San Juan, Puerto Rico
Average Starting Price
$1,666pp
Jim's Onboard Credit
Silver Spirit
Silversea
Jan 29, 2028 - Feb 5, 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
51% OFF
MSC Opera
MSC Cruises
Mar 22, 2027 - Mar 29, 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
$949pp
Jim's Onboard Credit
49% OFF
MSC World Asia
MSC Cruises
Jan 11, 2028 - Jan 25, 2028 (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 • Castries, St. Lucia • Bridgetown, Barbados
Average Starting Price
$1,839pp
Jim's Onboard Credit
30% OFF
Seven Seas Grandeur
Regent Seven Seas Cruises
Jan 28, 2029 - Feb 7, 2029 (10 Nights)
Bridgetown, Barbados • Kingstown, Saint Vincent Island, Saint Vincent • Grenada • Castries, St. Lucia • Fort-De-France, Martinique • Gustavia, St. Barts • Basseterre, St. Kitts and Nevis • St John's, Antigua • Roseau, Dominica • Bridgetown, Barbados
Average Starting Price
$7,099pp
Jim's Onboard Credit
Star Legend
Windstar Cruises
Feb 21, 2028 - Feb 28, 2028 (7 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
Average Starting Price
$2,481pp
Jim's Onboard Credit
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