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Norwegian Prima
Norwegian Cruise Line
Mar 4, 2028 - Mar 11, 2028 (7 Nights)
San Juan, Puerto Rico • Tortola • St. Kitts • Bridgetown, Barbados • St. Lucia • Philipsburg, St. Maarten • St. Thomas • San Juan, Puerto Rico
Average Starting Price
$1,239pp
Jim's Onboard Credit
42% OFF
MSC Opera
MSC Cruises
Sep 27, 2027 - Oct 4, 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
$698pp
Jim's Onboard Credit
Viking Sea
Viking
Nov 15, 2026 - Nov 25, 2026 (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
$4,499pp
Jim's Onboard Credit
Celebrity Ascent
Celebrity Cruises
Nov 13, 2026 - Nov 23, 2026 (10 Nights)
Fort Lauderdale • Philipsburg, St. Maarten • Castries, St. Lucia • Grenada • Bridgetown, Barbados • St John's, Antigua • Fort Lauderdale
Average Starting Price
$1,239pp
Jim's Onboard Credit
Seabourn Venture
Seabourn
Sep 16, 2027 - Nov 20, 2027 (65 Nights)
Kangerlussuaq, Greenland • Nuuk (Godthaab), Greenland • Pangnirtung, Nunavut • Kekerten Island, Nunavut • Lady Franklin Island, Canada • Monumental Island (Nunavut), Canada • Lower Savage Islands, Canada • Resolution Island, Nunavut, Canada • Nachvak Fiord, Torngat Mts, Canada • Ramah Bay, Torngat Mts, Canada • Rose Island, Bahamas • Hebron, Canada • Nain, Canada • Indian Harbour, Newfoundland • Battle Harbour, Labrador • L'Anse aux Meadows, Newfoundland • Halifax, Nova Scotia • Carambola Beach, Saint Kitts and Nevis • Little Bay, Montserrat • Rodney Bay, Saint Lucia • 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 • Camboriu, Brazil • Montevideo, Uruguay • The Seabourn Falkland Island Experience • The Seabourn Falkland Island Experience • Port Stanley, Falkland Islands • The Seabourn South Georgia Experience • The Seabourn South Georgia Experience • The Seabourn South Georgia Experience • The Seabourn Antarctic Experience • The Seabourn Antarctic Experience • The Seabourn Antarctic Experience • The Seabourn Antarctic Experience • The Seabourn Antarctic Experience • Ushuaia, Argentina • Ushuaia, Argentina
Average Starting Price
$59,423pp
Jim's Onboard Credit
Seabourn Ovation
Seabourn
Dec 18, 2027 - Dec 28, 2027 (10 Nights)
Bridgetown, Barbados • Grenada • Bequia Island, Saint Vincent • St. Pierre • Terre de Haut, Guadeloupe • St John's, Antigua • St. Kitts • Great Harbor Jost Van Dyke, British Virgin Islands • Road Bay, Anguilla • Philipsburg, St. Maarten
Average Starting Price
$7,383pp
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!

Azamara Journey
Azamara
Dec 12, 2026 - Dec 18, 2026 (6 Nights)
Bridgetown, Barbados • Castries, St. Lucia • Roseau, Dominica • Basseterre, St. Kitts and Nevis • Charlestown, Nevis • Philipsburg, St. Maarten • San Juan, Puerto Rico
Average Starting Price
$3,679pp
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
$1,676pp
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
Silver Spirit
Silversea
Feb 17, 2028 - Feb 29, 2028 (12 Nights)
Bridgetown, Barbados • Bequia Island, Saint Vincent • Castries, St. Lucia • Oranjestad, Aruba • Kralendijk, Bonaire • Willemstad, Curacao • Gustavia, St. Barts • St John's, Antigua • Fort-De-France, Martinique • Grenada • Bridgetown, Barbados
Average Starting Price
$4,500pp
Jim's Onboard Credit
29% OFF
MSC World Europa
MSC Cruises
Feb 9, 2027 - Feb 23, 2027 (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
$1,870pp
Jim's Onboard Credit
Azamara Quest
Azamara
Nov 14, 2027 - Nov 28, 2027 (14 Nights)
Bridgetown, Barbados • Castries, St. Lucia • Roseau, Dominica • Basseterre, St. Kitts and Nevis • Charlestown, Nevis • Philipsburg, St. Maarten • Tortola • 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
$4,019pp
Jim's Onboard Credit
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