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Emerald Princess
Princess Cruises
Dec 26, 2027 - Jan 2, 2028 (7 Nights)
San Juan, Puerto Rico • Tortola • St. Kitts • Dominica • Grenada • Bridgetown, Barbados • San Juan, Puerto Rico
Average Starting Price
$904pp
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!

33% OFF
Seven Seas Grandeur
Regent Seven Seas Cruises
Feb 4, 2028 - Feb 14, 2028 (10 Nights)
Bridgetown, Barbados • Willemstad, Curacao • Oranjestad, Aruba • Castries, St. Lucia • Pointe-à-Pitre, Guadeloupe • Basseterre, St. Kitts and Nevis • St John's, Antigua • Roseau, Dominica • Bridgetown, Barbados
Average Starting Price
$6,099pp
Jim's Onboard Credit
Caribbean Princess
Princess Cruises
Jan 14, 2029 - Jan 28, 2029 (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
$1,714pp
Jim's Onboard Credit
Celebrity Constellation
Celebrity Cruises
Dec 19, 2026 - Dec 26, 2026 (7 Nights)
San Juan, Puerto Rico • Tortola • Basseterre, St. Kitts and Nevis • Roseau, Dominica • Castries, St. Lucia • Bridgetown, Barbados • San Juan, Puerto Rico
Average Starting Price
$558pp
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 Nova
Silversea
Dec 9, 2026 - Dec 21, 2026 (12 Nights)
Lisbon, Portugal • Las Palmas (Gran Canaria), Spain • Mindelo, Cape Verde • Bridgetown, Barbados
Average Starting Price
$3,950pp
Jim's Onboard Credit
Celebrity Ascent
Celebrity Cruises
Mar 17, 2028 - Mar 27, 2028 (10 Nights)
Fort Lauderdale • Philipsburg, St. Maarten • Castries, St. Lucia • Bridgetown, Barbados • St John's, Antigua • Basseterre, St. Kitts and Nevis • Fort Lauderdale
Average Starting Price
$1,805pp
Jim's Onboard Credit
Viking Sea
Viking
Jan 15, 2027 - Jan 25, 2027 (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
$6,799pp
Jim's Onboard Credit
53% OFF
MSC Opera
MSC Cruises
Oct 25, 2027 - Nov 1, 2027 (7 Nights)
La Romana, Dominican Republic • Catalina Island, Dominican Republic • Bridgetown, Barbados • Fort-De-France, Martinique • Pointe-à-Pitre, Guadeloupe • Tortola • La Romana, Dominican Republic
Average Starting Price
$584pp
Jim's Onboard Credit
Seabourn Ovation
Seabourn
Nov 27, 2027 - Dec 4, 2027 (7 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
Average Starting Price
$4,768pp
Jim's Onboard Credit
Seabourn Venture
Seabourn
Oct 9, 2027 - Oct 25, 2027 (16 Nights)
Bridgetown, Barbados • Port of Spain, Trinidad • Devil's Island, France • Crossing the Equator • Fortaleza, Brazil • Natal, Brazil • Salvador, Brazil • Armacao dos Buzios, Brazil • Paraty, Brazil • Rio de Janeiro, Brazil
Average Starting Price
$10,623pp
Jim's Onboard Credit
Viking Sky
Viking
Dec 24, 2028 - Jan 3, 2029 (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!

Silver Ray
Silversea
Mar 20, 2028 - Apr 1, 2028 (12 Nights)
Bridgetown, Barbados • Bequia Island, Saint Vincent • Castries, St. Lucia • Fort-De-France, Martinique • Roseau, Dominica • St John's, Antigua • St. Kitts • Gustavia, St. Barts • Great Harbor Jost Van Dyke, British Virgin Islands • San Juan, Puerto Rico • Miami
Average Starting Price
$6,400pp
Jim's Onboard Credit
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