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Celebrity Summit
Celebrity Cruises
Dec 12, 2027 - Dec 19, 2027 (7 Nights)
San Juan, Puerto Rico • Kingstown, Saint Vincent Island, Saint Vincent • Bridgetown, Barbados • Fort-De-France, Martinique • St John's, Antigua • St. Thomas • San Juan, Puerto Rico
Average Starting Price
$660pp
Jim's Onboard Credit
Star Pride
Windstar Cruises
Sep 27, 2027 - Oct 22, 2027 (25 Nights)
Montreal, Quebec • Tadoussac, Canada • Saguenay, Quebec • Scenic Cruising Saguenay Fjord • Cap aux Meules, Quebec • St. Pierre • St John's, Newfoundland • St John's, Newfoundland • Saint-Anthony, Newfoundland • Red Bay, Canada • Bonne Bay, Newfoundland • Havre-Saint-Pierre, Quebec • Quebec City, Quebec • Cruising St. Lawrence River • Montreal, Quebec • Cruising St. Lawrence River • Quebec City, Quebec • Gaspe, Quebec • Sydney, Nova Scotia • Sydney, Nova Scotia • Halifax, Nova Scotia • Halifax, Nova Scotia • Bar Harbor, Maine • Portland, Australia • Boston
Average Starting Price
$18,916pp
Jim's Onboard Credit
Vista
Oceania Cruises
Dec 16, 2028 - Jan 7, 2029 (22 Nights)
Miami • St. Thomas • Gustavia, St. Barts • St John's, Antigua • Fort-De-France, Martinique • Roseau, Dominica • Basseterre, St. Kitts and Nevis • Nassau • Miami • Key West, Florida • George Town, Cayman Islands • Santo Tomas de Castilla, Guatemala • Harvest Caye, Belize • Cozumel • Miami
Average Starting Price
$10,149pp
Jim's Onboard Credit
Vision of the Seas
Royal Caribbean
Dec 19, 2027 - Dec 27, 2027 (8 Nights)
San Juan, Puerto Rico • St. Thomas • St John's, Antigua • Roseau, Dominica • Grenada • Bridgetown, Barbados • Philipsburg, St. Maarten • San Juan, Puerto Rico
Average Starting Price
$1,129pp
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!

Silver Nova
Silversea
Dec 11, 2028 - Dec 21, 2028 (10 Nights)
Fort Lauderdale • Grand Turk • Road Bay, Anguilla • St John's, Antigua • Gustavia, St. Barts • St. John • Fort Lauderdale
Average Starting Price
$5,800pp
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!

Celebrity Constellation
Celebrity Cruises
Dec 26, 2026 - Jan 2, 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
$1,244pp
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 9, 2028 (7 Nights)
San Juan, Puerto Rico • Philipsburg, St. Maarten • St. Thomas • St John's, Antigua • St. Lucia • Bridgetown, Barbados • San Juan, Puerto Rico
Average Starting Price
$739pp
Jim's Onboard Credit
9% OFF
Crystal Serenity
Crystal Cruises
Feb 12, 2028 - Feb 29, 2028 (17 Nights)
Fort Lauderdale • Tortola • Gustavia, St. Barts • Roseau, Dominica • St. Kitts • San Juan, Puerto Rico • St John's, Antigua • Pointe-à-Pitre, Guadeloupe • Castries, St. Lucia • Grenada • Kralendijk, Bonaire • Willemstad, Curacao • Oranjestad, Aruba • Cartagena, Colombia
Average Starting Price
$7,770pp
Jim's Onboard Credit
Valiant Lady
Virgin Voyages
Nov 14, 2026 - Nov 20, 2026 (6 Nights)
San Juan, Puerto Rico • Tortola • St John's, Antigua • Castries, St. Lucia • Basseterre, St. Kitts and Nevis • San Juan, Puerto Rico
Average Starting Price
$774pp
Jim's Onboard Credit
Celebrity Xcel
Celebrity Cruises
Dec 6, 2026 - Dec 13, 2026 (7 Nights)
Miami • Nassau • St. Thomas • St John's, Antigua • Miami
Average Starting Price
$922pp
Jim's Onboard Credit
EXPLORA I
Explora Journeys
Dec 13, 2026 - Dec 20, 2026 (7 Nights)
Miami • St. John • St John's, Antigua • Terre de Haut, Guadeloupe • Philipsburg, St. Maarten • San Juan, Puerto Rico
Average Starting Price
$4,385pp
Jim's Onboard Credit
46% OFF
MSC World Europa
MSC Cruises
Apr 11, 2027 - Apr 28, 2027 (17 Nights)
Pointe-à-Pitre, Guadeloupe • Philipsburg, St. Maarten • St. Kitts • St John's, Antigua • Santa Cruz de Tenerife, Spain • Barcelona, Spain • Marseille (Provence), France • Genoa (Portofino), Italy • La Spezia, Italy • Rome (Civitavecchia), Italy
Average Starting Price
$1,139pp
Jim's Onboard Credit
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