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Star Legend
Windstar Cruises
Nov 27, 2026 - Dec 4, 2026 (7 Nights)
Bridgetown, Barbados • Anse Mitan, Martinique • Rodney Bay, Saint Lucia • Rodney Bay, Saint Lucia • Castries, St. Lucia • Scenic Cruising the Pitons • Mayreau Island, Saint Vincent and the Grenadines • Grenada • Bequia Island, Saint Vincent • Bridgetown, Barbados
Average Starting Price
$2,699pp
Jim's Onboard Credit
Crystal Symphony
Crystal Cruises
Jan 7, 2029 - May 7, 2029 (120 Nights)
Melbourne, Australia • Portland, Australia • Penneshaw (Kangaroo Island), Australia • Adelaide, Australia • Adelaide, Australia • Esperance, Australia • Albany, Australia • Busselton, Australia • Perth (Fremantle), Australia • Perth (Fremantle), Australia • Komodo (Rinca), Indonesia • Benoa (Bali), Indonesia • Benoa (Bali), Indonesia • Waingapu, Sumba, Indonesia • Kupang, Indonesia • Darwin, Australia • Cairns (Yorkeys Knob), Australia • Cairns (Yorkeys Knob), Australia • Airlie Beach, Qld, Australia • Brisbane, Australia • Sydney, Australia • Wellington, New Zealand • Gisborne, New Zealand • Tauranga, New Zealand • Auckland, New Zealand • Auckland, New Zealand • Waitangi (Bay of Islands), New Zealand • Suva, Fiji • Apia, Samoa • International Dateline • Raiatea, French Polynesia • Bora Bora, French Polynesia • Moorea, French Polynesia • Moorea, French Polynesia • Papeete, French Polynesia • Huahine, French Polynesia • Rangiroa, French Polynesia • Fakarava, French Polynesia • Adamstown, Pitcairn Islands • Hanga Roa (Rapa Nui), Chile • Hanga Roa (Rapa Nui), Chile • Robinson Crusoe Island, Chile • Valparaíso, Chile • Puerto Montt, Chile • Castro, Chile • Chacabuco, Chile • Laguna San Rafael, Chile • Cruising the Chilean Fjords • Cruising the Chilean Fjords • Punta Arenas, Chile • Ushuaia, Argentina • Ushuaia, Argentina • Port Stanley, Falkland Islands • Puerto Madryn, Argentina • Puerto Madryn, Argentina • Punta del Este, Uruguay • Buenos Aires, Argentina • Buenos Aires, Argentina • Montevideo, Uruguay • Montevideo, Uruguay • Balneario Camboriu, Brazil • Ilhabela, Brazil • Paraty, Brazil • Rio de Janeiro, Brazil • Rio de Janeiro, Brazil • Buzios, Brazil • Sao Salvador Da Bahia • Maceio, Brazil • Recife, Brazil • Santarem, Brazil • Boca de Valeria, Brazil • Manaus, Brazil • Manaus, Brazil • Parintins, Brazil • Alter Do Chao, Brazil • Devil's Island, France • Bridgetown, Barbados • Roseau, Dominica • St. Kitts • San Juan, Puerto Rico • Samana, Dominican Republic • Grand Turk • Fort Lauderdale
Average Starting Price
$74,100pp
Jim's Onboard Credit

Luke's Port Pick
Grand Turk has it all - stunning ship views, a pool, great snorkeling, and crystal-clear water! This port will always be my favorite!

Silver Spirit
Silversea
Jan 10, 2028 - Jan 22, 2028 (12 Nights)
Bridgetown, Barbados • Canouan, Saint Vincent and the Grenadines • Castries, St. Lucia • Kralendijk, Bonaire • Willemstad, Curacao • Oranjestad, Aruba • Gustavia, St. Barts • Charlestown, Nevis • Fort-De-France, Martinique • Grenada • Bridgetown, Barbados
Average Starting Price
$5,300pp
Jim's Onboard Credit
31% OFF
MSC World Europa
MSC Cruises
Mar 6, 2027 - Mar 13, 2027 (7 Nights)
Fort-De-France, Martinique • Pointe-à-Pitre, Guadeloupe • Castries, St. Lucia • Bridgetown, Barbados • Kingstown, Saint Vincent Island, Saint Vincent • Grenada • Fort-De-France, Martinique
Average Starting Price
$893pp
Jim's Onboard Credit
50% OFF
MSC World Asia
MSC Cruises
Dec 26, 2027 - Jan 2, 2028 (7 Nights)
Pointe-à-Pitre, Guadeloupe • Kingstown, Saint Vincent Island, Saint Vincent • Bridgetown, Barbados • Castries, St. Lucia • Grenada • Fort-De-France, Martinique • Pointe-à-Pitre, Guadeloupe
Average Starting Price
$1,789pp
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!

Norwegian Prima
Norwegian Cruise Line
Feb 19, 2028 - Feb 26, 2028 (7 Nights)
San Juan, Puerto Rico • Tortola • St. Kitts • Bridgetown, Barbados • Philipsburg, St. Maarten • St. Thomas • San Juan, Puerto Rico
Average Starting Price
$1,239pp
Jim's Onboard Credit
Caribbean Princess
Princess Cruises
Dec 28, 2028 - Jan 7, 2029 (10 Nights)
San Juan, Puerto Rico • St. Thomas • Philipsburg, St. Maarten • St John's, Antigua • Martinique • Bridgetown, Barbados • Oranjestad, Aruba • Willemstad, Curacao • San Juan, Puerto Rico
Average Starting Price
$1,650pp
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
Jan 2, 2028 - Jan 16, 2028 (14 Nights)
San Juan, Puerto Rico • Philipsburg, St. Maarten • St. Thomas • St John's, Antigua • St. Lucia • Bridgetown, Barbados • San Juan, Puerto Rico • Tortola • St. Kitts • Dominica • Grenada • Bridgetown, Barbados • San Juan, Puerto Rico
Average Starting Price
$1,378pp
Jim's Onboard Credit
Celebrity Constellation
Celebrity Cruises
Dec 5, 2026 - Dec 12, 2026 (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
$1,094pp
Jim's Onboard Credit
49% OFF
MSC Opera
MSC Cruises
Oct 22, 2027 - Oct 29, 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
$739pp
Jim's Onboard Credit
Celebrity Ascent
Celebrity Cruises
Apr 7, 2028 - Apr 17, 2028 (10 Nights)
Fort Lauderdale • Philipsburg, St. Maarten • Castries, St. Lucia • Bridgetown, Barbados • St John's, Antigua • Basseterre, St. Kitts and Nevis • Fort Lauderdale
Average Starting Price
$1,640pp
Jim's Onboard Credit
Azamara Journey
Azamara
Jan 25, 2027 - Feb 7, 2027 (13 Nights)
Bridgetown, Barbados • Scarborough (Tobago), Trinidad and Tobago • Iles du Salut (Ile Royale), French Guiana • Belem, Brazil • Recife, Brazil • Salvador da Bahia, Brazil • Buzios, Brazil • Rio de Janeiro, Brazil
Average Starting Price
$5,789pp
Jim's Onboard Credit
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