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Coral Princess
Princess Cruises
Nov 18, 2026 - Nov 28, 2026 (10 Nights)
Fort Lauderdale • St. Thomas • St. Kitts • Dominica • St John's, Antigua • Philipsburg, St. Maarten • Fort Lauderdale
Average Starting Price
$599pp
Jim's Onboard Credit
Allura
Oceania Cruises
Jan 27, 2027 - Feb 5, 2027 (9 Nights)
Miami • St. Thomas • Philipsburg, St. Maarten • Basseterre, St. Kitts and Nevis • Tortola • Miami
Average Starting Price
$5,799pp
Jim's Onboard Credit
Scarlet Lady
Virgin Voyages
Dec 18, 2027 - Dec 26, 2027 (8 Nights)
San Juan, Puerto Rico • Philipsburg, St. Maarten • St John's, Antigua • Roseau, Dominica • Oranjestad, Aruba • Willemstad, Curacao • San Juan, Puerto Rico
Average Starting Price
$1,192pp
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!

Rhapsody of the Seas
Royal Caribbean
Jan 8, 2028 - Jan 15, 2028 (7 Nights)
San Juan, Puerto Rico • St. Thomas • St. Croix • Philipsburg, St. Maarten • St John's, Antigua • Bridgetown, Barbados • San Juan, Puerto Rico
Average Starting Price
$833pp
Jim's Onboard Credit
Norwegian Bliss
Norwegian Cruise Line
Mar 1, 2027 - Mar 13, 2027 (12 Nights)
Manhattan • Puerto Plata, Dominican Republic • San Juan, Puerto Rico • St. Kitts • Tortola • Philipsburg, St. Maarten • St. Thomas • Manhattan
Average Starting Price
$1,859pp
Jim's Onboard Credit
49% OFF
MSC Opera
MSC Cruises
Oct 15, 2027 - Oct 22, 2027 (7 Nights)
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
Average Starting Price
$739pp
Jim's Onboard Credit
Crown Princess
Princess Cruises
Feb 28, 2027 - Mar 14, 2027 (14 Nights)
San Juan, Puerto Rico • Philipsburg, St. Maarten • Martinique • 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
$1,296pp
Jim's Onboard Credit
Grandeur of the Seas
Royal Caribbean
Sep 25, 2027 - Oct 2, 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
$606pp
Jim's Onboard Credit
29% OFF
Seven Seas Prestige
Regent Seven Seas Cruises
Dec 20, 2028 - Dec 30, 2028 (10 Nights)
Miami • Puerto Plata, Dominican Republic • San Juan, Puerto Rico • St. Thomas • Philipsburg, St. Maarten • Gustavia, St. Barts • Tortola • Miami
Average Starting Price
$7,399pp
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!

Celebrity Xcel
Celebrity Cruises
Feb 21, 2027 - Feb 28, 2027 (7 Nights)
Miami • Philipsburg, St. Maarten • Tortola • Puerto Plata, Dominican Republic • Miami
Average Starting Price
$1,176pp
Jim's Onboard Credit
Hero of the Seas
Royal Caribbean
Nov 6, 2027 - Nov 13, 2027 (7 Nights)
Miami • Philipsburg, St. Maarten • St. Thomas • Perfect Day Cococay • Miami
Average Starting Price
$1,705pp
Jim's Onboard Credit
Star Pride
Windstar Cruises
Nov 15, 2027 - Nov 22, 2027 (7 Nights)
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
$2,443pp
Jim's Onboard Credit
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