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Silver Spirit
Silversea
Feb 28, 2027 - Mar 7, 2027 (7 Nights)
Bridgetown, Barbados • Castries, St. Lucia • Gustavia, St. Barts • Road Bay, Anguilla • St John's, Antigua • Roseau, Dominica • Canouan, Saint Vincent and the Grenadines • Bridgetown, Barbados
Average Starting Price
$4,300pp
Jim's Onboard Credit
Rotterdam
Holland America Line
Dec 22, 2026 - Jan 12, 2027 (21 Nights)
Fort Lauderdale • Philipsburg, St. Maarten • St. Kitts • Roseau, Dominica • Castries, St. Lucia • St John's, Antigua • St. Thomas • Relaxaway Half Moon Cay • Fort Lauderdale • Relaxaway Half Moon Cay • Falmouth, Jamaica • George Town, Cayman Islands • Belize City • Cozumel • Key West, Florida • Fort Lauderdale
Average Starting Price
$3,689pp
Jim's Onboard Credit

Jim's Port Pick
Half Moon Cay is one of my all-time favorite private islands - the sand is unbelievably soft, hands-down the best I’ve ever felt!

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
$1,007pp
Jim's Onboard Credit
Rhapsody of the Seas
Royal Caribbean
Dec 19, 2026 - Dec 26, 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
$1,098pp
Jim's Onboard Credit
FREE Specialty Dining Meal

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 Sea
Viking
Jan 15, 2027 - Jan 25, 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
Viking Sky
Viking
Dec 24, 2028 - Jan 3, 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
$3,799pp
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!

Vision of the Seas
Royal Caribbean
Feb 7, 2027 - Feb 14, 2027 (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
$532pp
Jim's Onboard Credit
FREE Specialty Dining Meal
Wind Surf
Windstar Cruises
Mar 20, 2027 - Mar 27, 2027 (7 Nights)
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
$3,552pp
Jim's Onboard Credit
49% OFF
MSC World Asia
MSC Cruises
Dec 5, 2027 - Dec 12, 2027 (7 Nights)
Pointe-à-Pitre, Guadeloupe • St John's, Antigua • Philipsburg, St. Maarten • St. Kitts • Roseau, Dominica • Fort-De-France, Martinique • Pointe-à-Pitre, Guadeloupe
Average Starting Price
$889pp
Jim's Onboard Credit
Silver Shadow
Silversea
Mar 10, 2029 - Mar 20, 2029 (10 Nights)
San Juan del sur, Nicaragua • Rodney Bay, Saint Lucia • Bridgetown, Barbados • Grenada • 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
$4,900pp
Jim's Onboard Credit
Seabourn Ovation
Seabourn
Dec 12, 2026 - Dec 19, 2026 (7 Nights)
Bridgetown, Barbados • St. Kitts • Terre de Haut, Guadeloupe • St. Pierre • Roseau, Dominica • Rodney Bay, Saint Lucia • Bridgetown, Barbados
Average Starting Price
$3,663pp
Jim's Onboard Credit
9% OFF
Crystal Symphony
Crystal Cruises
Apr 10, 2029 - May 27, 2029 (47 Nights)
Rio de Janeiro, Brazil • Buzios, Brazil • Salvador da Bahia, Brazil • Maceio, Brazil • Recife, Brazil • Santarem, Brazil • Boca da Valeria (Amazon River), 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 • Havre-Saint-Pierre, Quebec • Saint John, New Brunswick • Cork (Cobh), Ireland • Plymouth, England • Portsmouth, England
Average Starting Price
$18,370pp
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!

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