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Resilient Lady
Virgin Voyages
Dec 19, 2026 - Dec 27, 2026 (8 Nights)
Miami • Puerto Plata, Dominican Republic • San Juan, Puerto Rico • Philipsburg, St. Maarten • Bimini • Miami
Average Starting Price
$1,272pp
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!

Crystal Symphony
Crystal Cruises
Dec 13, 2026 - Dec 20, 2026 (7 Nights)
San Juan, Puerto Rico • Great Harbor Jost Van Dyke, British Virgin Islands • St John's, Antigua • Marigot Bay, St. Martin, French West Indies • St. Thomas • Fort Lauderdale
Average Starting Price
$3,300pp
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
Silver Shadow
Silversea
Nov 18, 2026 - Nov 30, 2026 (12 Nights)
Miami • San Juan, Puerto Rico • St. John • Gustavia, St. Barts • St John's, Antigua • Little Bay, Montserrat • St. Kitts • Great Harbor Jost Van Dyke, British Virgin Islands • Miami
Average Starting Price
$7,400pp
Jim's Onboard Credit
Seabourn Quest
Seabourn
Dec 18, 2028 - Dec 28, 2028 (10 Nights)
Miami • San Juan, Puerto Rico • Road Bay, Anguilla • Little Bay, Montserrat • St. Kitts • Great Harbor Jost Van Dyke, British Virgin Islands • Miami
Average Starting Price
$7,418pp
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!

38% OFF
Carnival Festivale
Carnival Cruise Line
Dec 11, 2027 - Dec 19, 2027 (8 Nights)
Port Canaveral (Orlando), Florida • Fun Day at Sea • Amber Cove, Dominican Republic • San Juan, Puerto Rico • St. Thomas • Fun Day at Sea • Fun Day at Sea • Celebration Key • Port Canaveral (Orlando), Florida
Average Starting Price
$938pp
Jim's Onboard Credit
EXPLORA IV
Explora Journeys
Jan 29, 2028 - Feb 5, 2028 (7 Nights)
Miami • St. John • St John's, Antigua • Terre de Haut, Guadeloupe • Basseterre, St. Kitts and Nevis • San Juan, Puerto Rico
Average Starting Price
$3,655pp
Jim's Onboard Credit
46% OFF
Carnival Celebration
Carnival Cruise Line
Jan 16, 2028 - Jan 23, 2028 (7 Nights)
Miami • Fun Day at Sea • Fun Day at Sea • Philipsburg, St. Maarten • San Juan, Puerto Rico • Fun Day at Sea • Celebration Key • Miami
Average Starting Price
$559pp
Jim's Onboard Credit
Viking Sea
Viking
Feb 6, 2028 - Feb 16, 2028 (10 Nights)
San Juan, Puerto Rico • St. Thomas • Basseterre, St. Kitts and Nevis • Castries, St. Lucia • Bridgetown, Barbados • Roseau, Dominica • St John's, Antigua • Philipsburg, St. Maarten • St. Croix • San Juan, Puerto Rico
Average Starting Price
$4,299pp
Jim's Onboard Credit
EXPLORA III
Explora Journeys
Feb 12, 2027 - Feb 28, 2027 (16 Nights)
San Juan, Puerto Rico • St. Thomas • St John's, Antigua • Terre de Haut, Guadeloupe • Puerto Plata, Dominican Republic • Miami • Puerto Plata, Dominican Republic • Cayo Levantado, Dominican Republic • San Juan, Puerto Rico • Virgin Gorda, British Virgin Islands • Road Bay, Anguilla • Miami
Average Starting Price
$12,560pp
Jim's Onboard Credit
Star Legend
Windstar Cruises
Jan 17, 2028 - Jan 31, 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
$4,014pp
Jim's Onboard Credit
Silver Dawn
Silversea
Mar 3, 2028 - Mar 14, 2028 (11 Nights)
Miami • San Juan, Puerto Rico • Soper's Hole, Tortola • Gustavia, St. Barts • St John's, Antigua • St. Kitts • Great Harbor Jost Van Dyke, British Virgin Islands • Miami
Average Starting Price
$4,900pp
Jim's Onboard Credit
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