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Celebrity Constellation
Celebrity Cruises
Nov 28, 2026 - Dec 5, 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
$960pp
Jim's Onboard Credit
Silver Nova
Silversea
Dec 21, 2026 - Dec 29, 2026 (8 Nights)
Bridgetown, Barbados • Soufrier Bay, St. Lucia • Bequia Island, Saint Vincent • Grenada • Fort-De-France, Martinique • St. Kitts • St. Thomas • San Juan, Puerto Rico
Average Starting Price
$4,200pp
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!

29% OFF
Seven Seas Grandeur
Regent Seven Seas Cruises
Feb 14, 2028 - Feb 24, 2028 (10 Nights)
Bridgetown, Barbados • Grenada • Kingstown, Saint Vincent Island, Saint Vincent • 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
$7,199pp
Jim's Onboard Credit
42% OFF
MSC Opera
MSC Cruises
Aug 13, 2027 - Aug 20, 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
$1,117pp
Jim's Onboard Credit
Celebrity Ascent
Celebrity Cruises
Jan 15, 2027 - Jan 25, 2027 (10 Nights)
Fort Lauderdale • Philipsburg, St. Maarten • Castries, St. Lucia • Grenada • Bridgetown, Barbados • St John's, Antigua • Fort Lauderdale
Average Starting Price
$3,641pp
Jim's Onboard Credit
Azamara Journey
Azamara
Jan 25, 2027 - Feb 17, 2027 (23 Nights)
Bridgetown, Barbados • Scarborough (Tobago), Trinidad and Tobago • Iles du Salut (Ile Royale), French Guiana • Belem, Brazil • Recife, Brazil • Salvador da Bahia, Brazil • At Sea Eclipse Viewing • Buzios, Brazil • Rio de Janeiro, Brazil • Rio de Janeiro, Brazil • Rio de Janeiro, Brazil • Paraty, Brazil • Ilhabela, Brazil • Santos (Sao Paulo), Brazil • Montevideo, Uruguay • Buenos Aires, Argentina • Buenos Aires, Argentina
Average Starting Price
$9,939pp
Jim's Onboard Credit
Seabourn Ovation
Seabourn
Nov 27, 2027 - Dec 11, 2027 (14 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 • Soper's Hole, Tortola • St. Kitts • Trois Ilets, Martinique • Bequia Island, Saint Vincent • Grenada • Bridgetown, Barbados
Average Starting Price
$8,408pp
Jim's Onboard Credit
Viking Sea
Viking
Nov 25, 2026 - Dec 5, 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
Seabourn Venture
Seabourn
Oct 9, 2027 - Nov 19, 2027 (41 Nights)
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
$33,714pp
Jim's Onboard Credit
Viking Sky
Viking
Jan 3, 2029 - Jan 13, 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
$4,999pp
Jim's Onboard Credit
Crown Princess
Princess Cruises
Jan 31, 2027 - Feb 7, 2027 (7 Nights)
San Juan, Puerto Rico • St. Thomas • Pointe-à-Pitre, Guadeloupe • Dominica • Grenada • Bridgetown, Barbados • San Juan, Puerto Rico
Average Starting Price
$599pp
Jim's Onboard Credit
Silver Shadow
Silversea
Feb 17, 2029 - Feb 27, 2029 (10 Nights)
San Juan del sur, Nicaragua • Rodney Bay, Saint Lucia • Grenada • Bridgetown, Barbados • Canouan, Saint Vincent and the Grenadines • Bequia Island, Saint Vincent • Roseau, Dominica • Little Bay, Montserrat • St. Kitts • San Juan del sur, Nicaragua
Average Starting Price
$5,400pp
Jim's Onboard Credit
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