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Seabourn Ovation
Seabourn
Feb 6, 2027 - Feb 13, 2027 (7 Nights)
Bridgetown, Barbados • St. Kitts • St. Pierre • Roseau, Dominica • Terre de Haut, Guadeloupe • Rodney Bay, Saint Lucia • Bridgetown, Barbados
Average Starting Price
$5,963pp
Jim's Onboard Credit
Celebrity Constellation
Celebrity Cruises
Dec 19, 2026 - Dec 26, 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
$708pp
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!

Rhapsody of the Seas
Royal Caribbean
Nov 21, 2026 - Nov 28, 2026 (7 Nights)
San Juan, Puerto Rico • St. Thomas • St. Croix • Philipsburg, St. Maarten • St John's, Antigua • Roseau, Dominica • San Juan, Puerto Rico
Average Starting Price
$918pp
Jim's Onboard Credit
Viking Sea
Viking
Jan 25, 2027 - Feb 4, 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
Silver Shadow
Silversea
Jan 20, 2027 - Jan 30, 2027 (10 Nights)
Bridgetown, Barbados • Canouan, Saint Vincent and the Grenadines • Castries, St. Lucia • Trois Ilets, Martinique • Roseau, Dominica • Les Saintes, F.W.I. • Little Bay, Montserrat • St. Kitts • Gustavia, St. Barts • St. John • San Juan, Puerto Rico
Average Starting Price
$5,900pp
Jim's Onboard Credit
Vision of the Seas
Royal Caribbean
Feb 13, 2028 - Feb 20, 2028 (7 Nights)
San Juan, Puerto Rico • Roseau, Dominica • Bridgetown, Barbados • Kingstown, Saint Vincent Island, Saint Vincent • St John's, Antigua • St. Thomas • San Juan, Puerto Rico
Average Starting Price
$668pp
Jim's Onboard Credit
Wind Surf
Windstar Cruises
Dec 5, 2027 - Dec 19, 2027 (14 Nights)
Philipsburg, St. Maarten • Falmouth (English Harbour), Antigua & Barbuda • Road Bay, Anguilla • Soper's Hole, Tortola • Great Harbor Jost Van Dyke, British Virgin Islands • Great Harbor Jost Van Dyke, British Virgin Islands • Virgin Gorda, British Virgin Islands • Gustavia, St. Barts • Philipsburg, St. Maarten • Charlestown, Nevis • Roseau, Dominica • Mayreau Island, Saint Vincent and the Grenadines • Les Saintes, F.W.I. • Basseterre, St. Kitts and Nevis • Gustavia, St. Barts • Philipsburg, St. Maarten
Average Starting Price
$4,040pp
Jim's Onboard Credit
Viking Sky
Viking
Nov 14, 2028 - Nov 24, 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
$3,799pp
Jim's Onboard Credit
49% OFF
MSC World Asia
MSC Cruises
Dec 4, 2027 - Dec 11, 2027 (7 Nights)
Fort-De-France, Martinique • Pointe-à-Pitre, Guadeloupe • St John's, Antigua • Philipsburg, St. Maarten • St. Kitts • Roseau, Dominica • Fort-De-France, Martinique
Average Starting Price
$889pp
Jim's Onboard Credit
Azamara Journey
Azamara
Nov 14, 2026 - Nov 21, 2026 (7 Nights)
Bridgetown, Barbados • Castries, St. Lucia • Roseau, Dominica • Basseterre, St. Kitts and Nevis • Charlestown, Nevis • Philipsburg, St. Maarten • Tortola • San Juan, Puerto Rico
Average Starting Price
$3,099pp
Jim's Onboard Credit
Crystal Symphony
Crystal Cruises
Jan 7, 2029 - May 27, 2029 (140 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, Nova Scotia • 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 • Royal Naval Dockyard, Bermuda • Royal Naval Dockyard, Bermuda • New York, New York • Newport, Rhode Island • Boston • Halifax, Nova Scotia • Sydney, Nova Scotia • St. Pierre • Saint John, New Brunswick • Cork (Cobh), Ireland • Plymouth, England • Portsmouth, England
Average Starting Price
$79,200pp
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!

30% OFF
MSC World Europa
MSC Cruises
Mar 13, 2027 - Mar 20, 2027 (7 Nights)
Fort-De-France, Martinique • Pointe-à-Pitre, Guadeloupe • Philipsburg, St. Maarten • St John's, Antigua • St. Kitts • Roseau, Dominica • Fort-De-France, Martinique
Average Starting Price
$999pp
Jim's Onboard Credit
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