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Emerald Princess
Princess Cruises
Jan 16, 2028 - Jan 30, 2028 (14 Nights)
San Juan, Puerto Rico • St. Thomas • Philipsburg, St. Maarten • St John's, Antigua • Bridgetown, Barbados • St. Lucia • San Juan, Puerto Rico • St. Thomas • St. Kitts • Dominica • Grenada • Bridgetown, Barbados • San Juan, Puerto Rico
Average Starting Price
$1,308pp
Jim's Onboard Credit
12% OFF
MSC World Europa
MSC Cruises
Apr 4, 2027 - Apr 11, 2027 (7 Nights)
Pointe-à-Pitre, Guadeloupe • Castries, St. Lucia • Bridgetown, Barbados • Grenada • Kingstown, Saint Vincent Island, Saint Vincent • Fort-De-France, Martinique • Pointe-à-Pitre, Guadeloupe
Average Starting Price
$2,814pp
Jim's Onboard Credit
Azamara Quest
Azamara
Dec 5, 2027 - Dec 12, 2027 (7 Nights)
San Juan, Puerto Rico • Virgin Gorda, British Virgin Islands • St John's, Antigua • St. Pierre • Port Elizabeth (Bequia), Saint Vincent and the Grenadines • Grenada • Scarborough (Tobago), Trinidad and Tobago • Bridgetown, Barbados
Average Starting Price
$1,869pp
Jim's Onboard Credit
Crown Princess
Princess Cruises
Feb 14, 2027 - Feb 28, 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
$1,428pp
Jim's Onboard Credit
Celebrity Ascent
Celebrity Cruises
Dec 14, 2026 - Dec 24, 2026 (10 Nights)
Fort Lauderdale • Philipsburg, St. Maarten • Castries, St. Lucia • Grenada • Bridgetown, Barbados • St John's, Antigua • Fort Lauderdale
Average Starting Price
$8,267pp
Jim's Onboard Credit
49% OFF
MSC World Asia
MSC Cruises
Nov 30, 2027 - Dec 14, 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
$1,899pp
Jim's Onboard Credit
Vision of the Seas
Royal Caribbean
Feb 27, 2028 - Mar 5, 2028 (7 Nights)
San Juan, Puerto Rico • Bridgetown, Barbados • Grenada • Castries, St. Lucia • St John's, Antigua • St. Thomas • San Juan, Puerto Rico
Average Starting Price
$721pp
Jim's Onboard Credit
25% OFF
Seven Seas Grandeur
Regent Seven Seas Cruises
Mar 31, 2027 - Apr 14, 2027 (14 Nights)
Panama City (Fuerte Amador), Panama • Panama Canal, Panama • Cartagena, Colombia • Santa Marta, Colombia • Oranjestad, Aruba • Willemstad, Curacao • Kralendijk, Bonaire • Cruising the Caribbean Sea • Grenada • Castries, St. Lucia • Gustavia, St. Barts • Tortola • Atlantic Ocean cruising • Cruising the Bahamian Waters • Miami
Average Starting Price
$10,249pp
Jim's Onboard Credit
49% OFF
MSC Opera
MSC Cruises
Nov 22, 2027 - Dec 6, 2027 (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
$1,152pp
Jim's Onboard Credit
Silver Ray
Silversea
Dec 18, 2027 - Dec 26, 2027 (8 Nights)
Bridgetown, Barbados • Castries, St. Lucia • Grenada • Bequia Island, Saint Vincent • Fort-De-France, Martinique • St John's, Antigua • Charlestown, Nevis • San Juan, Puerto Rico
Average Starting Price
$4,500pp
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!

Star Legend
Windstar Cruises
Jan 17, 2028 - Jan 31, 2028 (14 Nights)
San Juan, Puerto Rico • St. John • Philipsburg, St. Maarten • Gustavia, St. Barts • Basseterre, St. Kitts and Nevis • 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 • Les Saintes, F.W.I. • Marigot Bay, St. Martin, French West Indies • San Juan, Puerto Rico
Average Starting Price
$4,014pp
Jim's Onboard Credit
Emerald Princess
Princess Cruises
Jan 9, 2028 - Jan 16, 2028 (7 Nights)
San Juan, Puerto Rico • Tortola • St. Kitts • Dominica • Grenada • Bridgetown, Barbados • San Juan, Puerto Rico
Average Starting Price
$669pp
Jim's Onboard Credit
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