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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
Emerald Princess
Princess Cruises
Dec 19, 2027 - Jan 2, 2028 (14 Nights)
San Juan, Puerto Rico • St. Thomas • Philipsburg, St. Maarten • St John's, Antigua • St. Lucia • Bridgetown, Barbados • San Juan, Puerto Rico • Tortola • St. Kitts • Dominica • Grenada • Bridgetown, Barbados • San Juan, Puerto Rico
Average Starting Price
$1,613pp
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!

Nieuw Statendam
Holland America Line
Jan 24, 2027 - Jan 31, 2027 (7 Nights)
Fort Lauderdale • Grand Turk • San Juan, Puerto Rico • St. Thomas • Relaxaway Half Moon Cay • Fort Lauderdale
Average Starting Price
$1,389pp
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!

Vision of the Seas
Royal Caribbean
Dec 12, 2027 - Dec 19, 2027 (7 Nights)
San Juan, Puerto Rico • St. Thomas • Philipsburg, St. Maarten • Willemstad, Curacao • Oranjestad, Aruba • San Juan, Puerto Rico
Average Starting Price
$722pp
Jim's Onboard Credit
Vista
Oceania Cruises
Nov 13, 2028 - Dec 5, 2028 (22 Nights)
Miami • St. Thomas • Gustavia, St. Barts • St John's, Antigua • Fort-De-France, Martinique • Roseau, Dominica • Basseterre, St. Kitts and Nevis • Tortola • Miami • Key West, Florida • George Town, Cayman Islands • Santo Tomas de Castilla, Guatemala • Harvest Caye, Belize • Cozumel • Miami
Average Starting Price
$8,699pp
Jim's Onboard Credit
Celebrity Summit
Celebrity Cruises
Dec 19, 2027 - Dec 26, 2027 (7 Nights)
San Juan, Puerto Rico • Roseau, Dominica • Bridgetown, Barbados • Castries, St. Lucia • St John's, Antigua • St. Thomas • San Juan, Puerto Rico
Average Starting Price
$763pp
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
Jan 9, 2027 - Jan 16, 2027 (7 Nights)
San Juan, Puerto Rico • St. Thomas • Philipsburg, St. Maarten • St John's, Antigua • Castries, St. Lucia • Grenada • San Juan, Puerto Rico
Average Starting Price
$716pp
Jim's Onboard Credit
38% OFF
Carnival Firenze
Carnival Cruise Line
Jan 23, 2028 - Feb 6, 2028 (14 Nights)
Port Canaveral (Orlando), Florida • Fun Day at Sea • Fun Day at Sea • St. Thomas • St John's, Antigua • Pointe-à-Pitre, Guadeloupe • Martinique • Grenada • Bridgetown, Barbados • Fun Day at Sea • Philipsburg, St. Maarten • San Juan, Puerto Rico • Fun Day at Sea • Fun Day at Sea • Port Canaveral (Orlando), Florida
Average Starting Price
$974pp
Jim's Onboard Credit
62% OFF
Carnival Venezia
Carnival Cruise Line
Nov 15, 2026 - Nov 22, 2026 (7 Nights)
Port Canaveral (Orlando), Florida • Celebration Key • Fun Day at Sea • San Juan, Puerto Rico • St. Thomas • Fun Day at Sea • Fun Day at Sea • Port Canaveral (Orlando), Florida
Average Starting Price
$370pp
Jim's Onboard Credit
Norwegian Aura
Norwegian Cruise Line
Jun 26, 2027 - Jul 3, 2027 (7 Nights)
Miami • Puerto Plata, Dominican Republic • St. Thomas • Tortola • Great Stirrup Cay • Miami
Average Starting Price
$1,399pp
Jim's Onboard Credit
Allure of the Seas
Royal Caribbean
Dec 20, 2026 - Dec 27, 2026 (7 Nights)
Miami • Puerto Plata, Dominican Republic • San Juan, Puerto Rico • St. Thomas • Miami
Average Starting Price
$1,524pp
Jim's Onboard Credit
FREE Specialty Dining Meal

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 Beyond
Celebrity Cruises
Jan 31, 2027 - Feb 7, 2027 (7 Nights)
Fort Lauderdale • Puerto Plata, Dominican Republic • St. Thomas • Basseterre, St. Kitts and Nevis • Fort Lauderdale
Average Starting Price
$1,095pp
Jim's Onboard Credit
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