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Crown Princess
Princess Cruises
Mar 5, 2027 - Mar 12, 2027 (7 Nights)
Bridgetown, Barbados • San Juan, Puerto Rico • St. Thomas • Philipsburg, St. Maarten • St John's, Antigua • St. Lucia • Bridgetown, Barbados
Average Starting Price
$1,539pp
Jim's Onboard Credit
Rhapsody of the Seas
Royal Caribbean
Dec 19, 2026 - Dec 26, 2026 (7 Nights)
San Juan, Puerto Rico • St. Thomas • St. Croix • Philipsburg, St. Maarten • St John's, Antigua • Roseau, Dominica • San Juan, Puerto Rico
Average Starting Price
$1,098pp
Jim's Onboard Credit
FREE Specialty Dining Meal

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!

49% OFF
MSC Opera
MSC Cruises
May 7, 2027 - May 14, 2027 (7 Nights)
Fort-De-France, Martinique • St John's, Antigua • La Romana, Dominican Republic • Catalina Island, Dominican Republic • Bridgetown, Barbados • Fort-De-France, Martinique
Average Starting Price
$919pp
Jim's Onboard Credit
27% OFF
MSC World Europa
MSC Cruises
Dec 29, 2026 - Jan 12, 2027 (14 Nights)
Bridgetown, Barbados • Kingstown, Saint Vincent Island, Saint Vincent • Grenada • Castries, St. Lucia • 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
$2,001pp
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
Dec 17, 2027 - Dec 24, 2027 (7 Nights)
Bridgetown, Barbados • San Juan, Puerto Rico • St. Thomas • Philipsburg, St. Maarten • St John's, Antigua • St. Lucia • Bridgetown, Barbados
Average Starting Price
$1,614pp
Jim's Onboard Credit
Vision of the Seas
Royal Caribbean
Jan 3, 2027 - Jan 10, 2027 (7 Nights)
San Juan, Puerto Rico • St. Thomas • St John's, Antigua • Roseau, Dominica • St. Croix • Basseterre, St. Kitts and Nevis • San Juan, Puerto Rico
Average Starting Price
$599pp
Jim's Onboard Credit
FREE Specialty Dining Meal
Seabourn Ovation
Seabourn
Feb 12, 2028 - Feb 19, 2028 (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
$5,368pp
Jim's Onboard Credit
50% OFF
MSC Opera
MSC Cruises
May 3, 2027 - May 10, 2027 (7 Nights)
La Romana, Dominican Republic • Catalina Island, Dominican Republic • Virgin Gorda, British Virgin Islands • Philipsburg, St. Maarten • Fort-De-France, Martinique • St John's, Antigua • La Romana, Dominican Republic
Average Starting Price
$875pp
Jim's Onboard Credit
Crown Princess
Princess Cruises
Feb 19, 2027 - Feb 26, 2027 (7 Nights)
Bridgetown, Barbados • San Juan, Puerto Rico • St. Thomas • Philipsburg, St. Maarten • St John's, Antigua • St. Lucia • Bridgetown, Barbados
Average Starting Price
$1,669pp
Jim's Onboard Credit
14% OFF
MSC World Europa
MSC Cruises
Dec 2, 2026 - Dec 15, 2026 (13 Nights)
Bridgetown, Barbados • 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
$4,494pp
Jim's Onboard Credit
Vision of the Seas
Royal Caribbean
Apr 16, 2028 - Apr 23, 2028 (7 Nights)
San Juan, Puerto Rico • St. Thomas • St John's, Antigua • Willemstad, Curacao • Oranjestad, Aruba • San Juan, Puerto Rico
Average Starting Price
$985pp
Jim's Onboard Credit
Emerald Princess
Princess Cruises
Dec 31, 2027 - Jan 7, 2028 (7 Nights)
Bridgetown, Barbados • San Juan, Puerto Rico • Philipsburg, St. Maarten • St. Thomas • St John's, Antigua • St. Lucia • Bridgetown, Barbados
Average Starting Price
$1,989pp
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!

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