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Enchanted Princess
Princess Cruises
Dec 13, 2028 - Dec 23, 2028 (10 Nights)
Fort Lauderdale • Amber Cove, Dominican Republic • San Juan, Puerto Rico • St. Kitts • St John's, Antigua • Martinique • Philipsburg, St. Maarten • Fort Lauderdale
Average Starting Price
$1,300pp
Jim's Onboard Credit
Wind Surf
Windstar Cruises
Feb 13, 2028 - Feb 27, 2028 (14 Nights)
Philipsburg, St. Maarten • St John's, Antigua • 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
$4,250pp
Jim's Onboard Credit
21% OFF
MSC World Europa
MSC Cruises
Feb 14, 2027 - Feb 21, 2027 (7 Nights)
Pointe-à-Pitre, Guadeloupe • Philipsburg, St. Maarten • St John's, Antigua • St. Kitts • Roseau, Dominica • Fort-De-France, Martinique • Pointe-à-Pitre, Guadeloupe
Average Starting Price
$1,468pp
Jim's Onboard Credit
Crown Princess
Princess Cruises
Dec 27, 2026 - Jan 10, 2027 (14 Nights)
San Juan, Puerto Rico • St. Thomas • Philipsburg, St. Maarten • St John's, Antigua • St. Lucia • Bridgetown, Barbados • San Juan, Puerto Rico • St. Thomas • St. Kitts • Dominica • Grenada • Bridgetown, Barbados • San Juan, Puerto Rico
Average Starting Price
$1,938pp
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!

Crystal Symphony
Crystal Cruises
Jan 27, 2027 - Feb 9, 2027 (13 Nights)
Manaus, Brazil • Parintins, Brazil • Alter Do Chao, Brazil • Devil's Island, France • Bridgetown, Barbados • St John's, Antigua • Great Harbor Jost Van Dyke, British Virgin Islands • Fort Lauderdale
Average Starting Price
$7,900pp
Jim's Onboard Credit
49% OFF
MSC Opera
MSC Cruises
Aug 5, 2027 - Aug 19, 2027 (14 Nights)
Bridgetown, Barbados • Fort-De-France, Martinique • Pointe-à-Pitre, Guadeloupe • Tortola • La Romana, Dominican Republic • Catalina Island, Dominican Republic • Virgin Gorda, British Virgin Islands • Philipsburg, St. Maarten • Fort-De-France, Martinique • St John's, Antigua • La Romana, Dominican Republic • Catalina Island, Dominican Republic • Bridgetown, Barbados
Average Starting Price
$1,998pp
Jim's Onboard Credit
Celebrity Ascent
Celebrity Cruises
Dec 4, 2026 - Dec 14, 2026 (10 Nights)
Fort Lauderdale • Philipsburg, St. Maarten • Castries, St. Lucia • Grenada • Bridgetown, Barbados • St John's, Antigua • Fort Lauderdale
Average Starting Price
$6,724pp
Jim's Onboard Credit
Viking Sea
Viking
Dec 10, 2028 - Dec 20, 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
EXPLORA III
Explora Journeys
Nov 15, 2026 - Nov 22, 2026 (7 Nights)
San Juan, Puerto Rico • Road Bay, Anguilla • St John's, Antigua • St. Croix • Catalina Island, Dominican Republic • Puerto Plata, Dominican Republic • Miami
Average Starting Price
$5,215pp
Jim's Onboard Credit
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
$550pp
Jim's Onboard Credit
FREE Specialty Dining Meal
Silver Spirit
Silversea
Jan 4, 2027 - Jan 15, 2027 (11 Nights)
Bridgetown, Barbados • Castries, St. Lucia • Fort-De-France, Martinique • St John's, Antigua • Oranjestad, Aruba • Willemstad, Curacao • Kralendijk, Bonaire • Canouan, Saint Vincent and the Grenadines • Bequia Island, Saint Vincent • Bridgetown, Barbados
Average Starting Price
$5,500pp
Jim's Onboard Credit
Silver Shadow
Silversea
Jan 27, 2029 - Feb 3, 2029 (7 Nights)
San Juan del sur, Nicaragua • Virgin Gorda, British Virgin Islands • St John's, Antigua • Les Saintes, F.W.I. • Philipsburg, St. Maarten • Gustavia, St. Barts • Charlestown, Nevis • San Juan del sur, Nicaragua
Average Starting Price
$3,900pp
Jim's Onboard Credit
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