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Valiant Lady
Virgin Voyages
Dec 19, 2026 - Dec 26, 2026 (7 Nights)
San Juan, Puerto Rico • Basseterre, St. Kitts and Nevis • Fort-De-France, Martinique • Oranjestad, Aruba • Willemstad, Curacao • San Juan, Puerto Rico
Average Starting Price
$903pp
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!

Silver Nova
Silversea
Dec 21, 2028 - Jan 3, 2029 (13 Nights)
Fort Lauderdale • San Juan del sur, Nicaragua • Gustavia, St. Barts • St. Kitts • Roseau, Dominica • Willemstad, Curacao • Oranjestad, Aruba • Oranjestad, Aruba • Fort Lauderdale
Average Starting Price
$8,700pp
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!

Emerald Princess
Princess Cruises
Dec 26, 2027 - Jan 2, 2028 (7 Nights)
San Juan, Puerto Rico • Tortola • St. Kitts • Dominica • Grenada • Bridgetown, Barbados • San Juan, Puerto Rico
Average Starting Price
$904pp
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 12, 2026 - Dec 19, 2026 (7 Nights)
San Juan, Puerto Rico • Tortola • Basseterre, St. Kitts and Nevis • Roseau, Dominica • Castries, St. Lucia • Grenada • San Juan, Puerto Rico
Average Starting Price
$503pp
Jim's Onboard Credit
Celebrity Eclipse
Celebrity Cruises
Jan 5, 2028 - Jan 17, 2028 (12 Nights)
Fort Lauderdale • George Town, Cayman Islands • Oranjestad, Aruba • Willemstad, Curacao • Castries, St. Lucia • Basseterre, St. Kitts and Nevis • San Juan, Puerto Rico • Puerto Plata, Dominican Republic • Fort Lauderdale
Average Starting Price
$1,538pp
Jim's Onboard Credit
EXPLORA I
Explora Journeys
Dec 20, 2026 - Jan 4, 2027 (15 Nights)
San Juan, Puerto Rico • Basseterre, St. Kitts and Nevis • Tortola • Gustavia, St. Barts • Gustavia, St. Barts • Road Bay, Anguilla • Miami • Puerto Plata, Dominican Republic • Catalina Island, Dominican Republic • St. John • New Year Fireworks SJU • New Year Fireworks SJU • Great Harbor Jost Van Dyke, British Virgin Islands • Basseterre, St. Kitts and Nevis • St. Thomas • San Juan, Puerto Rico
Average Starting Price
$12,365pp
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!

Enchanted Princess
Princess Cruises
Mar 7, 2027 - Mar 17, 2027 (10 Nights)
Fort Lauderdale • Relaxaway Half Moon Cay • Amber Cove, Dominican Republic • San Juan, Puerto Rico • Philipsburg, St. Maarten • St John's, Antigua • St. Kitts • Fort Lauderdale
Average Starting Price
$1,124pp
Jim's Onboard Credit

Jim's Port Pick
Half Moon Cay is one of my all-time favorite private islands - the sand is unbelievably soft, hands-down the best I’ve ever felt!

Wind Surf
Windstar Cruises
Nov 20, 2027 - Dec 5, 2027 (15 Nights)
Philipsburg, St. Maarten • Gustavia, St. Barts • St John's, Antigua • Deshaies, Guadeloupe • Road Bay, Anguilla • Soper's Hole, Tortola • Great Harbor Jost Van Dyke, British Virgin Islands • Great Harbor Jost Van Dyke, British Virgin Islands • Virgin Gorda, British Virgin Islands • Philipsburg, St. Maarten • Charlestown, Nevis • Roseau, Dominica • Mayreau Island, Saint Vincent and the Grenadines • Les Saintes, F.W.I. • Gustavia, St. Barts • Basseterre, St. Kitts and Nevis • Philipsburg, St. Maarten
Average Starting Price
$4,845pp
Jim's Onboard Credit
52% OFF
MSC World Europa
MSC Cruises
Apr 11, 2027 - Apr 24, 2027 (13 Nights)
Pointe-à-Pitre, Guadeloupe • Philipsburg, St. Maarten • St. Kitts • St John's, Antigua • Santa Cruz de Tenerife, Spain • Barcelona, Spain
Average Starting Price
$699pp
Jim's Onboard Credit
Star Pride
Windstar Cruises
Mar 13, 2028 - Mar 27, 2028 (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
26% OFF
Seven Seas Prestige
Regent Seven Seas Cruises
Nov 25, 2028 - Dec 9, 2028 (14 Nights)
Miami • Ocho Rios, Jamaica • Oranjestad, Aruba • Willemstad, Curacao • Kralendijk, Bonaire • Grenada • Kingstown, Saint Vincent Island, Saint Vincent • Fort-De-France, Martinique • Basseterre, St. Kitts and Nevis • Miami
Average Starting Price
$9,899pp
Jim's Onboard Credit
Grandeur of the Seas
Royal Caribbean
Jun 19, 2027 - Jun 26, 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
$796pp
Jim's Onboard Credit
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