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Star Princess
Princess Cruises
Mar 19, 2028 - Mar 29, 2028 (10 Nights)
Port Canaveral (Orlando), Florida • San Juan, Puerto Rico • St. Kitts • St. Lucia • St John's, Antigua • St. Thomas • Port Canaveral (Orlando), Florida
Average Starting Price
$1,364pp
Jim's Onboard Credit
23% OFF
Seven Seas Prestige
Regent Seven Seas Cruises
Nov 4, 2027 - Nov 20, 2027 (16 Nights)
Barcelona, Spain • Malaga, Spain • Cadiz, Spain • Casablanca, Morocco • Agadir, Morocco • Arrecife (Lanzarote), Spain • San Juan, Puerto Rico • Miami
Average Starting Price
$11,599pp
Jim's Onboard Credit
Norwegian Prima
Norwegian Cruise Line
Jan 22, 2028 - Jan 29, 2028 (7 Nights)
San Juan, Puerto Rico • St. Thomas • St. Kitts • Bridgetown, Barbados • St John's, Antigua • Philipsburg, St. Maarten • Tortola • San Juan, Puerto Rico
Average Starting Price
$1,209pp
Jim's Onboard Credit
Norwegian Pearl
Norwegian Cruise Line
Jan 13, 2027 - Jan 23, 2027 (10 Nights)
Philadelphia • St. Thomas • Tortola • San Juan, Puerto Rico • Puerto Plata, Dominican Republic • Philadelphia
Average Starting Price
$629pp
Jim's Onboard Credit
31% OFF
Carnival Vista
Carnival Cruise Line
Dec 31, 2027 - Jan 8, 2028 (8 Nights)
Port Canaveral (Orlando), Florida • Fun Day at Sea • Fun Day at Sea • St. Thomas • San Juan, Puerto Rico • Amber Cove, Dominican Republic • Fun Day at Sea • Celebration Key • Port Canaveral (Orlando), Florida
Average Starting Price
$1,253pp
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!

Star Legend
Windstar Cruises
Feb 14, 2028 - Feb 21, 2028 (7 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
Average Starting Price
$2,443pp
Jim's Onboard Credit
Independence of the Seas
Royal Caribbean
Jan 10, 2027 - Jan 17, 2027 (7 Nights)
Miami • Perfect Day Cococay • San Juan, Puerto Rico • St. Thomas • Miami
Average Starting Price
$661pp
Jim's Onboard Credit
FREE Specialty Dining Meal
Volendam
Holland America Line
Mar 28, 2028 - May 13, 2028 (46 Nights)
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
$10,954pp
Jim's Onboard Credit
Enchanted Princess
Princess Cruises
Dec 27, 2026 - Jan 6, 2027 (10 Nights)
Fort Lauderdale • Grand Turk • Amber Cove, Dominican Republic • San Juan, Puerto Rico • St John's, Antigua • Philipsburg, St. Maarten • St. Kitts • Fort Lauderdale
Average Starting Price
$1,159pp
Jim's Onboard Credit

Luke's Port Pick
Grand Turk has it all - stunning ship views, a pool, great snorkeling, and crystal-clear water! This port will always be my favorite!

EXPLORA IV
Explora Journeys
Mar 11, 2028 - Mar 18, 2028 (7 Nights)
Miami • Providenciales, Turks and Caicos Islands • Gustavia, St. Barts • St John's, Antigua • Road Bay, Anguilla • San Juan, Puerto Rico
Average Starting Price
$4,020pp
Jim's Onboard Credit
56% OFF
Margaritaville at Sea Beachcomber
Margaritaville at Sea
Jan 16, 2027 - Jan 23, 2027 (7 Nights)
Miami • St. Thomas • San Juan, Puerto Rico • Puerto Plata, Dominican Republic • Miami
Average Starting Price
$569pp
Jim's Onboard Credit
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!

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