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Caribbean Princess
Princess Cruises
Jan 2, 2029 - Jan 12, 2029 (10 Nights)
Bridgetown, Barbados • Oranjestad, Aruba • Willemstad, Curacao • San Juan, Puerto Rico • St. Thomas • St. Kitts • Dominica • Grenada • Bridgetown, Barbados
Average Starting Price
$1,219pp
Jim's Onboard Credit
Norwegian Aqua
Norwegian Cruise Line
Nov 15, 2026 - Nov 22, 2026 (7 Nights)
Miami • Puerto Plata, Dominican Republic • St. Thomas • Tortola • Great Stirrup Cay • Miami
Average Starting Price
$509pp
Jim's Onboard Credit
Regal Princess
Princess Cruises
Feb 5, 2029 - Feb 19, 2029 (14 Nights)
Fort Lauderdale • Relaxaway Half Moon Cay • Amber Cove, Dominican Republic • Grand Turk • Fort Lauderdale • Philipsburg, St. Maarten • St. Thomas • San Juan, Puerto Rico • Amber Cove, Dominican Republic • Fort Lauderdale
Average Starting Price
$1,974pp
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!

71% OFF
Carnival Vista
Carnival Cruise Line
Dec 18, 2026 - Dec 26, 2026 (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
$397pp
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
Jul 23, 2028 - Jul 30, 2028 (7 Nights)
Port Canaveral (Orlando), Florida • Puerto Plata, Dominican Republic • St. Thomas • Tortola • Great Stirrup Cay • Port Canaveral (Orlando), Florida
Average Starting Price
$1,319pp
Jim's Onboard Credit
Crown Princess
Princess Cruises
Jan 3, 2027 - Jan 10, 2027 (7 Nights)
San Juan, Puerto Rico • St. Thomas • St. Kitts • Dominica • Grenada • Bridgetown, Barbados • San Juan, Puerto Rico
Average Starting Price
$989pp
Jim's Onboard Credit
47% OFF
MSC Meraviglia
MSC Cruises
Dec 5, 2026 - Dec 19, 2026 (14 Nights)
Miami • San Juan, Puerto Rico • St. Kitts • St. Thomas • Amber Cove, Dominican Republic • Miami • Grand Turk • Ocean Cay • Nassau • Miami
Average Starting Price
$1,125pp
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!

Star Princess
Princess Cruises
Nov 11, 2028 - Nov 25, 2028 (14 Nights)
Fort Lauderdale • Belize City • Roatan, Honduras • Cozumel • Celebration Key • Fort Lauderdale • Relaxaway Half Moon Cay • St. Thomas • Philipsburg, St. Maarten • Fort Lauderdale
Average Starting Price
$2,044pp
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!

Star of the Seas
Royal Caribbean
Mar 7, 2027 - Mar 14, 2027 (7 Nights)
Port Canaveral (Orlando), Florida • Perfect Day Cococay • St. Thomas • Philipsburg, St. Maarten • Port Canaveral (Orlando), Florida
Average Starting Price
$1,480pp
Jim's Onboard Credit
FREE Specialty Dining Meal

Jim's Ship Pick
This is the BEST ship I’ve EVER sailed on! It rarely felt crowded, the food was incredible, the shows were absolutely phenomenal, and there’s something for everyone!

Norwegian Prima
Norwegian Cruise Line
Jan 31, 2027 - Feb 7, 2027 (7 Nights)
San Juan, Puerto Rico • Willemstad, Curacao • Philipsburg, St. Maarten • St. Thomas • Tortola • San Juan, Puerto Rico
Average Starting Price
$889pp
Jim's Onboard Credit
Viking Sea
Viking
Jan 19, 2029 - Jan 29, 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
$4,999pp
Jim's Onboard Credit
Emerald Princess
Princess Cruises
Mar 5, 2028 - Mar 19, 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 • St. Lucia • Bridgetown, Barbados • San Juan, Puerto Rico
Average Starting Price
$1,883pp
Jim's Onboard Credit
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