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Disney Fantasy
Disney Cruise Line
Dec 19, 2027 - Dec 26, 2027 (7 Nights)
Fort Lauderdale • Disney Lookout Cay at Lighthouse Point, Bahamas • Tortola • Philipsburg, St. Maarten • Fort Lauderdale
Average Starting Price
$3,214pp
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!

Crown Princess
Princess Cruises
Mar 14, 2027 - Mar 28, 2027 (14 Nights)
San Juan, Puerto Rico • St. Thomas • St. Kitts • Dominica • Grenada • Bridgetown, Barbados • San Juan, Puerto Rico • St. Thomas • Philipsburg, St. Maarten • St John's, Antigua • St. Lucia • Bridgetown, Barbados • San Juan, Puerto Rico
Average Starting Price
$1,751pp
Jim's Onboard Credit
Allure of the Seas
Royal Caribbean
Mar 14, 2027 - Mar 21, 2027 (7 Nights)
Miami • Perfect Day Cococay • San Juan, Puerto Rico • Philipsburg, St. Maarten • Miami
Average Starting Price
$1,020pp
Jim's Onboard Credit
FREE Specialty Dining Meal
Azamara Quest
Azamara
Oct 28, 2027 - Nov 21, 2027 (24 Nights)
New York, New York • Hamilton, Bermuda • Hamilton, Bermuda • Hamilton, Bermuda • Philipsburg, St. Maarten • Tortola • San Juan, Puerto Rico • Virgin Gorda, British Virgin Islands • St. Thomas • St John's, Antigua • St. Pierre • Port Elizabeth (Bequia), Saint Vincent and the Grenadines • Grenada • Scarborough (Tobago), Trinidad and Tobago • 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
$6,129pp
Jim's Onboard Credit
66% OFF
MSC Poesia
MSC Cruises
Nov 12, 2026 - Dec 3, 2026 (21 Nights)
Miami • St. Thomas • St. Kitts • Philipsburg, St. Maarten • St John's, Antigua • San Juan, Puerto Rico • Puerto Plata, Dominican Republic • Miami • Ocho Rios, Jamaica • Cartagena, Colombia • Colon, Panama • Limon, Costa Rica • Roatan, Honduras • Belize City • Miami
Average Starting Price
$9,300pp
Jim's Onboard Credit
28% OFF
Carnival Pride
Carnival Cruise Line
Jan 9, 2028 - Jan 23, 2028 (14 Nights)
Baltimore • Fun Day at Sea • Fun Day at Sea • Fun Day at Sea • St. Thomas • Philipsburg, St. Maarten • Dominica • St. Lucia • Bridgetown, Barbados • St John's, Antigua • Tortola • Fun Day at Sea • Fun Day at Sea • Fun Day at Sea • Baltimore
Average Starting Price
$1,506pp
Jim's Onboard Credit
Odyssey of the Seas
Royal Caribbean
Jan 24, 2028 - Feb 5, 2028 (12 Nights)
Cape Liberty • Basseterre, St. Kitts and Nevis • St John's, Antigua • Bridgetown, Barbados • Castries, St. Lucia • Philipsburg, St. Maarten • Cape Liberty
Average Starting Price
$1,785pp
Jim's Onboard Credit
Majestic Princess
Princess Cruises
Nov 19, 2026 - Dec 22, 2026 (33 Nights)
Fort Lauderdale • Philipsburg, St. Maarten • St. Lucia • Bridgetown, Barbados • Fortaleza, Brazil • Rio de Janeiro, Brazil • Montevideo, Uruguay • Buenos Aires, Argentina • Buenos Aires, Argentina • Buenos Aires, Argentina • Montevideo, Uruguay • Puerto Madryn, Argentina • Falkland Islands • Cape Horn, Chile • Ushuaia, Argentina • Beagle Channel, Argentina • Punta Arenas, Chile • Puerto Montt, Chile • Valparaíso, Chile
Average Starting Price
$3,671pp
Jim's Onboard Credit
Norwegian Pearl
Norwegian Cruise Line
Jan 3, 2028 - Jan 15, 2028 (12 Nights)
Philadelphia • Philipsburg, St. Maarten • Bridgetown, Barbados • St. Lucia • St John's, Antigua • San Juan, Puerto Rico • Puerto Plata, Dominican Republic • Philadelphia
Average Starting Price
$898pp
Jim's Onboard Credit
Star Pride
Windstar Cruises
Nov 8, 2027 - Nov 22, 2027 (14 Nights)
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 • St. John • Basseterre, St. Kitts and Nevis • Gustavia, St. Barts • Philipsburg, St. Maarten • Great Harbor Jost Van Dyke, British Virgin Islands • Virgin Gorda, British Virgin Islands • San Juan, Puerto Rico
Average Starting Price
$4,014pp
Jim's Onboard Credit
Celebrity Ascent
Celebrity Cruises
Mar 29, 2027 - Apr 9, 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
$1,837pp
Jim's Onboard Credit
Grandeur of the Seas
Royal Caribbean
Aug 28, 2027 - Sep 4, 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
$648pp
Jim's Onboard Credit
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