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Emerald Princess
Princess Cruises
Dec 19, 2027 - Dec 26, 2027 (7 Nights)
San Juan, Puerto Rico • St. Thomas • Philipsburg, St. Maarten • St John's, Antigua • St. Lucia • Bridgetown, Barbados • San Juan, Puerto Rico
Average Starting Price
$739pp
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!

EXPLORA I
Explora Journeys
Jan 11, 2027 - Jan 20, 2027 (9 Nights)
Miami • Puerto Plata, Dominican Republic • Cayo Levantado, Dominican Republic • San Juan, Puerto Rico • St. Thomas • Virgin Gorda, British Virgin Islands • Miami
Average Starting Price
$5,460pp
Jim's Onboard Credit
Vision of the Seas
Royal Caribbean
Dec 19, 2027 - Dec 27, 2027 (8 Nights)
San Juan, Puerto Rico • St. Thomas • St John's, Antigua • Roseau, Dominica • Grenada • Bridgetown, Barbados • Philipsburg, St. Maarten • San Juan, Puerto Rico
Average Starting Price
$1,129pp
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!

Disney Fantasy
Disney Cruise Line
Apr 15, 2028 - Apr 23, 2028 (8 Nights)
Fort Lauderdale • Disney Lookout Cay at Lighthouse Point, Bahamas • San Juan, Puerto Rico • St John's, Antigua • Philipsburg, St. Maarten • Fort Lauderdale
Average Starting Price
$2,870pp
Jim's Onboard Credit
Viking Sky
Viking
Feb 27, 2028 - Mar 9, 2028 (11 Nights)
San Juan, Puerto Rico • Sail the Atlantic Ocean • Sail the Atlantic Ocean • Sail the Atlantic Ocean • Sail the Atlantic Ocean • Sail the North Atlantic Ocean • Sail the North Atlantic Ocean • Santa Cruz de la Palma, Spain • Santa Cruz de Tenerife, Spain • Funchal, Portugal • Sail the North Atlantic Ocean • Lisbon, Portugal
Average Starting Price
$3,299pp
Jim's Onboard Credit
56% OFF
Margaritaville at Sea Beachcomber
Margaritaville at Sea
Apr 3, 2027 - Apr 10, 2027 (7 Nights)
Miami • St. Thomas • San Juan, Puerto Rico • Puerto Plata, Dominican Republic • Miami
Average Starting Price
$579pp
Jim's Onboard Credit
9% OFF
Crystal Serenity
Crystal Cruises
Feb 12, 2028 - Mar 10, 2028 (27 Nights)
Fort Lauderdale • Tortola • Gustavia, St. Barts • Roseau, Dominica • St. Kitts • San Juan, Puerto Rico • St John's, Antigua • Pointe-à-Pitre, Guadeloupe • Castries, St. Lucia • Grenada • Kralendijk, Bonaire • Willemstad, Curacao • Oranjestad, Aruba • Cartagena, Colombia • Cartagena, Colombia • Colon, Panama • Limon, Costa Rica • Roatan, Honduras • Santo Tomas de Castilla, Guatemala • Belize City • Cozumel • Fort Lauderdale
Average Starting Price
$12,610pp
Jim's Onboard Credit
Harmony of the Seas
Royal Caribbean
Dec 30, 2027 - Jan 8, 2028 (9 Nights)
Port Canaveral (Orlando), Florida • Perfect Day Cococay • San Juan, Puerto Rico • Philipsburg, St. Maarten • Basseterre, St. Kitts and Nevis • St. Thomas • Port Canaveral (Orlando), Florida
Average Starting Price
$1,934pp
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!

33% OFF
Carnival Magic
Carnival Cruise Line
Dec 26, 2027 - Jan 3, 2028 (8 Nights)
Miami • Relaxaway Half Moon Cay • Fun Day at Sea • San Juan, Puerto Rico • Philipsburg, St. Maarten • St. Thomas • Fun Day at Sea • Fun Day at Sea • Miami
Average Starting Price
$1,155pp
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!

Regal Princess
Princess Cruises
Dec 19, 2027 - Dec 27, 2027 (8 Nights)
Miami • Amber Cove, Dominican Republic • San Juan, Puerto Rico • Philipsburg, St. Maarten • Tortola • Miami
Average Starting Price
$949pp
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 Summit
Celebrity Cruises
Jan 2, 2028 - Jan 6, 2028 (4 Nights)
San Juan, Puerto Rico • Philipsburg, St. Maarten • Fort Lauderdale
Average Starting Price
$481pp
Jim's Onboard Credit
Caribbean Princess
Princess Cruises
Nov 26, 2028 - Dec 1, 2028 (5 Nights)
San Juan, Puerto Rico • St. Thomas • Philipsburg, St. Maarten • St John's, Antigua • St. Lucia • Bridgetown, Barbados
Average Starting Price
$628pp
Jim's Onboard Credit
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