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Norwegian Aqua
Norwegian Cruise Line
Mar 21, 2027 - Mar 28, 2027 (7 Nights)
Miami • Puerto Plata, Dominican Republic • St. Thomas • Tortola • Great Stirrup Cay • Miami
Average Starting Price
$1,109pp
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!

Norwegian Escape
Norwegian Cruise Line
Dec 4, 2026 - Dec 11, 2026 (7 Nights)
Port Canaveral (Orlando), Florida • Puerto Plata, Dominican Republic • St. Thomas • Tortola • Great Stirrup Cay • Port Canaveral (Orlando), Florida
Average Starting Price
$529pp
Jim's Onboard Credit
Disney Treasure
Disney Cruise Line
Dec 4, 2027 - Dec 11, 2027 (7 Nights)
Port Canaveral (Orlando), Florida • Tortola • St. Thomas • Disney Castaway Cay, Bahamas • Port Canaveral (Orlando), Florida
Average Starting Price
$2,522pp
Jim's Onboard Credit
Star Princess
Princess Cruises
Nov 18, 2028 - Dec 2, 2028 (14 Nights)
Fort Lauderdale • Relaxaway Half Moon Cay • St. Thomas • Philipsburg, St. Maarten • Fort Lauderdale • Celebration Key • Amber Cove, Dominican Republic • San Juan, Puerto Rico • Grand Turk • Fort Lauderdale
Average Starting Price
$2,024pp
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!

Norwegian Bliss
Norwegian Cruise Line
Dec 23, 2026 - Jan 4, 2027 (12 Nights)
Manhattan • Puerto Plata, Dominican Republic • San Juan, Puerto Rico • St. Kitts • St. Thomas • Tortola • Philipsburg, St. Maarten • Manhattan
Average Starting Price
$1,899pp
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!

Caribbean Princess
Princess Cruises
Dec 3, 2028 - Dec 10, 2028 (7 Nights)
San Juan, Puerto Rico • St. Thomas • St. Kitts • Martinique • Grenada • Bridgetown, Barbados • San Juan, Puerto Rico
Average Starting Price
$780pp
Jim's Onboard Credit
Norwegian Luna
Norwegian Cruise Line
Feb 6, 2028 - Feb 13, 2028 (7 Nights)
Miami • Puerto Plata, Dominican Republic • St. Thomas • Tortola • Great Stirrup Cay • Miami
Average Starting Price
$1,019pp
Jim's Onboard Credit
Emerald Princess
Princess Cruises
Jan 9, 2028 - Jan 23, 2028 (14 Nights)
San Juan, Puerto Rico • Tortola • St. Kitts • Dominica • Grenada • Bridgetown, Barbados • San Juan, Puerto Rico • St. Thomas • Philipsburg, St. Maarten • St John's, Antigua • Bridgetown, Barbados • St. Lucia • San Juan, Puerto Rico
Average Starting Price
$1,318pp
Jim's Onboard Credit
Vision of the Seas
Royal Caribbean
Jan 23, 2028 - Jan 30, 2028 (7 Nights)
San Juan, Puerto Rico • Kingstown, Saint Vincent Island, Saint Vincent • Grenada • Fort-De-France, Martinique • St John's, Antigua • St. Thomas • San Juan, Puerto Rico
Average Starting Price
$836pp
Jim's Onboard Credit
Viking Sea
Viking
Dec 30, 2028 - Jan 9, 2029 (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
$4,499pp
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!

48% OFF
MSC Seashore
MSC Cruises
Mar 5, 2028 - Mar 19, 2028 (14 Nights)
Miami • Nassau • Ocean Cay • George Town, Cayman Islands • Miami • Philipsburg, St. Maarten • St. Kitts • St. Thomas • Amber Cove, Dominican Republic • Miami
Average Starting Price
$1,837pp
Jim's Onboard Credit
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