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Norwegian Escape
Norwegian Cruise Line
Feb 12, 2027 - Feb 19, 2027 (7 Nights)
Port Canaveral (Orlando), Florida • Puerto Plata, Dominican Republic • St. Thomas • Tortola • Great Stirrup Cay • Port Canaveral (Orlando), Florida
Average Starting Price
$649pp
Jim's Onboard Credit
EXPLORA III
Explora Journeys
Dec 28, 2026 - Jan 13, 2027 (16 Nights)
San Juan, Puerto Rico • St John's, Antigua • Pointe-à-Pitre, Guadeloupe • St. John • New Year Fireworks SJU • New Year Fireworks SJU • Samana, Dominican Republic • Puerto Plata, Dominican Republic • Miami • St. John • Gustavia, St. Barts • St John's, Antigua • Tortola • Basseterre, St. Kitts and Nevis • San Juan, Puerto Rico
Average Starting Price
$26,135pp
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!

30% OFF
Allura
Oceania Cruises
Dec 12, 2026 - Dec 21, 2026 (9 Nights)
Miami • St. Thomas • Gustavia, St. Barts • Philipsburg, St. Maarten • Tortola • Miami
Average Starting Price
$3,290pp
Jim's Onboard Credit
Norwegian Prima
Norwegian Cruise Line
Mar 21, 2027 - Mar 28, 2027 (7 Nights)
San Juan, Puerto Rico • Tortola • St. Kitts • Bridgetown, Barbados • Philipsburg, St. Maarten • St. Thomas • San Juan, Puerto Rico
Average Starting Price
$1,319pp
Jim's Onboard Credit
Norwegian Luna
Norwegian Cruise Line
Dec 19, 2027 - Dec 26, 2027 (7 Nights)
Miami • Puerto Plata, Dominican Republic • St. Thomas • Tortola • Great Stirrup Cay • Miami
Average Starting Price
$1,599pp
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!

Vista
Oceania Cruises
Mar 2, 2029 - Mar 13, 2029 (11 Nights)
Miami • San Juan, Puerto Rico • St John's, Antigua • Castries, St. Lucia • Bridgetown, Barbados • Roseau, Dominica • Tortola • Miami
Average Starting Price
$4,999pp
Jim's Onboard Credit
Norwegian Pearl
Norwegian Cruise Line
Jan 3, 2027 - Jan 13, 2027 (10 Nights)
Philadelphia • San Juan, Puerto Rico • San Juan, Puerto Rico • Tortola • St. Thomas • Philadelphia
Average Starting Price
$629pp
Jim's Onboard Credit
Norwegian Aura
Norwegian Cruise Line
Sep 11, 2027 - Sep 18, 2027 (7 Nights)
Miami • Puerto Plata, Dominican Republic • St. Thomas • Tortola • Great Stirrup Cay • Miami
Average Starting Price
$1,099pp
Jim's Onboard Credit
Emerald Princess
Princess Cruises
Jan 2, 2028 - Jan 16, 2028 (14 Nights)
San Juan, Puerto Rico • Philipsburg, St. Maarten • St. Thomas • St John's, Antigua • St. Lucia • Bridgetown, Barbados • San Juan, Puerto Rico • Tortola • St. Kitts • Dominica • Grenada • Bridgetown, Barbados • San Juan, Puerto Rico
Average Starting Price
$1,378pp
Jim's Onboard Credit
49% OFF
MSC Opera
MSC Cruises
May 13, 2027 - May 27, 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
$1,748pp
Jim's Onboard Credit
28% OFF
Seven Seas Prestige
Regent Seven Seas Cruises
Dec 30, 2028 - Jan 9, 2029 (10 Nights)
Miami • St. Thomas • St John's, Antigua • Pointe-à-Pitre, Guadeloupe • Gustavia, St. Barts • Tortola • Miami
Average Starting Price
$7,599pp
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!

Sonata
Oceania Cruises
Jan 11, 2029 - Jan 23, 2029 (12 Nights)
Miami • St. Thomas • Philipsburg, St. Maarten • St John's, Antigua • Roseau, Dominica • Pointe-à-Pitre, Guadeloupe • Basseterre, St. Kitts and Nevis • Tortola • Miami
Average Starting Price
$6,199pp
Jim's Onboard Credit
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