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Celebrity Ascent
Celebrity Cruises
Dec 24, 2026 - Jan 4, 2027 (11 Nights)
Fort Lauderdale • Philipsburg, St. Maarten • St John's, Antigua • Castries, St. Lucia • Bridgetown, Barbados • Roseau, Dominica • Basseterre, St. Kitts and Nevis • Fort Lauderdale
Average Starting Price
$2,508pp
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!

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
Star Pride
Windstar Cruises
Dec 27, 2026 - Jan 10, 2027 (14 Nights)
San Juan, Puerto Rico • St. John • Gustavia, St. Barts • Basseterre, St. Kitts and Nevis • Philipsburg, St. Maarten • Great Harbor Jost Van Dyke, British Virgin Islands • Virgin Gorda, British Virgin Islands • San Juan, Puerto Rico • Grenada • Bequia Island, Saint Vincent • Mayreau Island, Saint Vincent and the Grenadines • Deshaies, Guadeloupe • Marigot Bay, St. Martin, French West Indies • San Juan, Puerto Rico
Average Starting Price
$7,094pp
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!

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
Grandeur of the Seas
Royal Caribbean
Nov 20, 2027 - Nov 27, 2027 (7 Nights)
San Juan, Puerto Rico • Tortola • Philipsburg, St. Maarten • St John's, Antigua • Basseterre, St. Kitts and Nevis • St. Croix • San Juan, Puerto Rico
Average Starting Price
$888pp
Jim's Onboard Credit
Seabourn Quest
Seabourn
Nov 18, 2028 - Dec 18, 2028 (30 Nights)
Miami • Basseterre, St. Kitts and Nevis • Port Elizabeth, South Africa • Saint Georges, Grenada • Port of Spain, Trinidad • Cruising the Amazon River • Macapa, , Brazil • Cruising the Amazon River • Cruising the Amazon River • Santarem, Brazil • Parintins, Brazil • Manaus, Brazil • Manaus, Brazil • Alter Do Chao, Brazil • Cruising the Amazon River • Devil's Island, France • Castries, St. Lucia • Gustavia, St. Barts • St. John • Miami
Average Starting Price
$17,159pp
Jim's Onboard Credit
Rhapsody of the Seas
Royal Caribbean
Jan 23, 2027 - Jan 30, 2027 (7 Nights)
San Juan, Puerto Rico • Tortola • Philipsburg, St. Maarten • St John's, Antigua • Basseterre, St. Kitts and Nevis • St. Croix • San Juan, Puerto Rico
Average Starting Price
$532pp
Jim's Onboard Credit
FREE Specialty Dining Meal
54% OFF
MSC Opera
MSC Cruises
Mar 29, 2027 - Apr 5, 2027 (7 Nights)
La Romana, Dominican Republic • Catalina Island, Dominican Republic • Virgin Gorda, British Virgin Islands • Philipsburg, St. Maarten • St. Kitts • St John's, Antigua • La Romana, Dominican Republic
Average Starting Price
$679pp
Jim's Onboard Credit
Eurodam
Holland America Line
Mar 15, 2028 - Mar 26, 2028 (11 Nights)
Fort Lauderdale • Philipsburg, St. Maarten • St John's, Antigua • Roseau, Dominica • Fort-De-France, Martinique • St. Kitts • St. Thomas • Relaxaway Half Moon Cay • Fort Lauderdale
Average Starting Price
$2,849pp
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!

Silver Spirit
Silversea
Feb 18, 2027 - Feb 28, 2027 (10 Nights)
Bridgetown, Barbados • Bequia Island, Saint Vincent • Grenada • Kralendijk, Bonaire • Willemstad, Curacao • St. Kitts • Castries, St. Lucia • Canouan, Saint Vincent and the Grenadines • Bridgetown, Barbados
Average Starting Price
$5,500pp
Jim's Onboard Credit
Star Legend
Windstar Cruises
Feb 14, 2028 - Feb 28, 2028 (14 Nights)
San Juan, Puerto Rico • St. John • Philipsburg, St. Maarten • Gustavia, St. Barts • Basseterre, St. Kitts and Nevis • Great Harbor Jost Van Dyke, British Virgin Islands • Virgin Gorda, British Virgin Islands • San Juan, Puerto Rico • Grenada • Bequia Island, Saint Vincent • Mayreau Island, Saint Vincent and the Grenadines • Les Saintes, F.W.I. • Marigot Bay, St. Martin, French West Indies • San Juan, Puerto Rico
Average Starting Price
$4,084pp
Jim's Onboard Credit
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
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