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Celebrity Constellation
Celebrity Cruises
Feb 20, 2027 - Feb 27, 2027 (7 Nights)
San Juan, Puerto Rico • St. Thomas • Philipsburg, St. Maarten • St John's, Antigua • Castries, St. Lucia • Bridgetown, Barbados • San Juan, Puerto Rico
Average Starting Price
$699pp
Jim's Onboard Credit
Celebrity Ascent
Celebrity Cruises
Mar 6, 2028 - Mar 17, 2028 (11 Nights)
Fort Lauderdale • St. Thomas • St John's, Antigua • Bridgetown, Barbados • Castries, St. Lucia • Roseau, Dominica • Basseterre, St. Kitts and Nevis • Fort Lauderdale
Average Starting Price
$1,991pp
Jim's Onboard Credit
CBT Exclusive
$$$ Savings
Seabourn Venture
Seabourn
Oct 1, 2027 - Nov 19, 2027 (49 Nights)
Halifax, Nova Scotia • St. Kitts • 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 • Parati • 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
$40,069pp
Jim's Onboard Credit
37% OFF
Carnival Firenze
Carnival Cruise Line
Mar 19, 2028 - Apr 2, 2028 (14 Nights)
Port Canaveral (Orlando), Florida • Fun Day at Sea • Fun Day at Sea • St. Thomas • St John's, Antigua • St. Lucia • Grenada • Bridgetown, Barbados • Fun Day at Sea • Philipsburg, St. Maarten • St. Croix • San Juan, Puerto Rico • Fun Day at Sea • Fun Day at Sea • Port Canaveral (Orlando), Florida
Average Starting Price
$1,037pp
Jim's Onboard Credit
Rhapsody of the Seas
Royal Caribbean
Feb 19, 2028 - Feb 26, 2028 (7 Nights)
San Juan, Puerto Rico • St. Thomas • St. Croix • Philipsburg, St. Maarten • Castries, St. Lucia • Bridgetown, Barbados • San Juan, Puerto Rico
Average Starting Price
$868pp
Jim's Onboard Credit
Scarlet Lady
Virgin Voyages
Jan 29, 2028 - Feb 5, 2028 (7 Nights)
San Juan, Puerto Rico • Philipsburg, St. Maarten • Bridgetown, Barbados • Fort-De-France, Martinique • Basseterre, St. Kitts and Nevis • St. Thomas • San Juan, Puerto Rico
Average Starting Price
$833pp
Jim's Onboard Credit
Norwegian Prima
Norwegian Cruise Line
Dec 18, 2027 - Dec 25, 2027 (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
$1,809pp
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!

Viking Sky
Viking
Jan 18, 2028 - Jan 28, 2028 (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
Viking Sea
Viking
Feb 24, 2027 - Mar 6, 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
Celebrity Eclipse
Celebrity Cruises
Jan 29, 2027 - Feb 8, 2027 (10 Nights)
Fort Lauderdale • St John's, Antigua • Castries, St. Lucia • Bridgetown, Barbados • Kingstown, Saint Vincent Island, Saint Vincent • Basseterre, St. Kitts and Nevis • Fort Lauderdale
Average Starting Price
$1,788pp
Jim's Onboard Credit
Azamara Journey
Azamara
Nov 7, 2026 - Nov 14, 2026 (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
$4,129pp
Jim's Onboard Credit
Emerald Princess
Princess Cruises
Nov 28, 2027 - Dec 12, 2027 (14 Nights)
San Juan, Puerto Rico • Tortola • 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
$1,508pp
Jim's Onboard Credit
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