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Norwegian Prima
Norwegian Cruise Line
Mar 7, 2027 - Mar 14, 2027 (7 Nights)
San Juan, Puerto Rico • Tortola • St. Thomas • Oranjestad, Aruba • Willemstad, Curacao • San Juan, Puerto Rico
Average Starting Price
$1,289pp
Jim's Onboard Credit
Volendam
Holland America Line
Mar 11, 2028 - May 13, 2028 (63 Nights)
Sydney, Australia • Brisbane, Australia • Townsville, Australia • Cairns (Yorkeys Knob), Australia • Scenic Cruising Torres Strait • Darwin, Australia • Slawi Bay, Komodo • Benoa (Bali), Indonesia • Crossing the Equator • Singapore • Singapore • Phuket, Thailand • Colombo, Sri Lanka • Male, Maldives • Port Louis, Mauritius • La Possession, Reunion • Port Elizabeth, South Africa • Cape Town, South Africa • Cape Town, South Africa • Cape Town, South Africa • Luderitz, Namibia • Walvis Bay, Namibia • Crossing Null Island • Sekondi-Takoradi, Ghana • Abidjan, Ivory Coast • Praia, Cape Verde • Mindelo, Cape Verde • San Juan, Puerto Rico • Fort Lauderdale
Average Starting Price
$16,179pp
Jim's Onboard Credit
Independence of the Seas
Royal Caribbean
Apr 8, 2028 - Apr 15, 2028 (7 Nights)
Miami • Puerto Plata, Dominican Republic • Samana, Dominican Republic • San Juan, Puerto Rico • Miami
Average Starting Price
$1,040pp
Jim's Onboard Credit
35% OFF
Carnival Vista
Carnival Cruise Line
Dec 18, 2027 - Dec 26, 2027 (8 Nights)
Port Canaveral (Orlando), Florida • Fun Day at Sea • Fun Day at Sea • St. Thomas • Philipsburg, St. Maarten • San Juan, Puerto Rico • Fun Day at Sea • Celebration Key • Port Canaveral (Orlando), Florida
Average Starting Price
$1,084pp
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!

Viking Sea
Viking
Feb 4, 2027 - Feb 14, 2027 (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
$6,799pp
Jim's Onboard Credit
Star Legend
Windstar Cruises
Jan 31, 2028 - Feb 7, 2028 (7 Nights)
San Juan, Puerto Rico • St. John • Gustavia, St. Barts • Philipsburg, St. Maarten • Basseterre, St. Kitts and Nevis • 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
Enchanted Princess
Princess Cruises
Jan 6, 2027 - Jan 16, 2027 (10 Nights)
Fort Lauderdale • Celebration Key • Amber Cove, Dominican Republic • San Juan, Puerto Rico • St John's, Antigua • Philipsburg, St. Maarten • St. Kitts • Fort Lauderdale
Average Starting Price
$1,569pp
Jim's Onboard Credit
Valiant Lady
Virgin Voyages
Jan 2, 2027 - Jan 9, 2027 (7 Nights)
San Juan, Puerto Rico • Tortola • Bridgetown, Barbados • Castries, St. Lucia • St John's, Antigua • Philipsburg, St. Maarten • San Juan, Puerto Rico
Average Starting Price
$1,183pp
Jim's Onboard Credit
Celebrity Constellation
Celebrity Cruises
Jan 2, 2027 - Jan 9, 2027 (7 Nights)
San Juan, Puerto Rico • St. Thomas • Basseterre, St. Kitts and Nevis • Roseau, Dominica • Castries, St. Lucia • Bridgetown, Barbados • San Juan, Puerto Rico
Average Starting Price
$806pp
Jim's Onboard Credit
EXPLORA IV
Explora Journeys
Mar 4, 2028 - Mar 11, 2028 (7 Nights)
San Juan, Puerto Rico • St. Thomas • Cayo Levantado, Dominican Republic • Puerto Plata, Dominican Republic • Key West, Florida • Ocean Cay • Miami
Average Starting Price
$3,655pp
Jim's Onboard Credit
Vision of the Seas
Royal Caribbean
Mar 14, 2027 - Mar 21, 2027 (7 Nights)
San Juan, Puerto Rico • Tortola • St John's, Antigua • Roseau, Dominica • St. Croix • Basseterre, St. Kitts and Nevis • San Juan, Puerto Rico
Average Starting Price
$649pp
Jim's Onboard Credit
FREE Specialty Dining Meal
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!

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