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Valiant Lady
Virgin Voyages
Nov 28, 2026 - Dec 5, 2026 (7 Nights)
San Juan, Puerto Rico • St. Thomas • Tortola • Basseterre, St. Kitts and Nevis • St John's, Antigua • Philipsburg, St. Maarten • San Juan, Puerto Rico
Average Starting Price
$763pp
Jim's Onboard Credit
Norwegian Epic
Norwegian Cruise Line
Dec 31, 2027 - Jan 7, 2028 (7 Nights)
Port Canaveral (Orlando), Florida • Puerto Plata, Dominican Republic • St. Thomas • Tortola • Great Stirrup Cay • Port Canaveral (Orlando), Florida
Average Starting Price
$1,339pp
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 Constellation
Celebrity Cruises
Dec 19, 2026 - Dec 26, 2026 (7 Nights)
San Juan, Puerto Rico • Tortola • Basseterre, St. Kitts and Nevis • Roseau, Dominica • Castries, St. Lucia • Bridgetown, Barbados • San Juan, Puerto Rico
Average Starting Price
$558pp
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!

Brilliant Lady
Virgin Voyages
Jan 11, 2027 - Jan 21, 2027 (10 Nights)
Miami • Philipsburg, St. Maarten • Tortola • St. Croix • San Juan, Puerto Rico • Puerto Plata, Dominican Republic • Bimini • Miami
Average Starting Price
$990pp
Jim's Onboard Credit
EXPLORA I
Explora Journeys
Dec 13, 2026 - Dec 27, 2026 (14 Nights)
Miami • St. John • St John's, Antigua • Terre de Haut, Guadeloupe • Philipsburg, St. Maarten • San Juan, Puerto Rico • Basseterre, St. Kitts and Nevis • Tortola • Gustavia, St. Barts • Gustavia, St. Barts • Road Bay, Anguilla • Miami
Average Starting Price
$9,335pp
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
Jul 8, 2027 - Jul 22, 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
$2,058pp
Jim's Onboard Credit
EXPLORA III
Explora Journeys
Jan 5, 2027 - Jan 13, 2027 (8 Nights)
Miami • St. John • Gustavia, St. Barts • St John's, Antigua • Tortola • Basseterre, St. Kitts and Nevis • San Juan, Puerto Rico
Average Starting Price
$7,240pp
Jim's Onboard Credit
Norwegian Aqua
Norwegian Cruise Line
Jun 27, 2027 - Jul 4, 2027 (7 Nights)
Port Canaveral (Orlando), Florida • Puerto Plata, Dominican Republic • St. Thomas • Tortola • Great Stirrup Cay • Port Canaveral (Orlando), Florida
Average Starting Price
$1,279pp
Jim's Onboard Credit
Norwegian Escape
Norwegian Cruise Line
Feb 26, 2027 - Mar 5, 2027 (7 Nights)
Port Canaveral (Orlando), Florida • Puerto Plata, Dominican Republic • St. Thomas • Tortola • Great Stirrup Cay • Port Canaveral (Orlando), Florida
Average Starting Price
$539pp
Jim's Onboard Credit
Grandeur of the Seas
Royal Caribbean
Oct 9, 2027 - Oct 16, 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
$670pp
Jim's Onboard Credit
Allura
Oceania Cruises
Dec 28, 2026 - Jan 7, 2027 (10 Nights)
Miami • St. Thomas • Philipsburg, St. Maarten • Gustavia, St. Barts • Basseterre, St. Kitts and Nevis • Tortola • Miami
Average Starting Price
$6,499pp
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!

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