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Silver Nova
Silversea
Dec 21, 2026 - Dec 29, 2026 (8 Nights)
Bridgetown, Barbados • Soufrier Bay, St. Lucia • Bequia Island, Saint Vincent • Grenada • Fort-De-France, Martinique • St. Kitts • St. Thomas • San Juan, Puerto Rico
Average Starting Price
$4,200pp
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 3, 2027 - Jan 17, 2027 (14 Nights)
Fort Lauderdale • Grand Turk • San Juan, Puerto Rico • St. Thomas • Relaxaway Half Moon Cay • Fort Lauderdale • Relaxaway Half Moon Cay • Ocho Rios, Jamaica • George Town, Cayman Islands • Cozumel • Fort Lauderdale
Average Starting Price
$2,284pp
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!

Rhapsody of the Seas
Royal Caribbean
Feb 27, 2027 - Mar 6, 2027 (7 Nights)
San Juan, Puerto Rico • St. Thomas • St. Croix • Philipsburg, St. Maarten • St John's, Antigua • Roseau, Dominica • San Juan, Puerto Rico
Average Starting Price
$588pp
Jim's Onboard Credit
FREE Specialty Dining Meal
Zuiderdam
Holland America Line
Dec 19, 2026 - Jan 2, 2027 (14 Nights)
Miami • Amber Cove, Dominican Republic • Grand Turk • Relaxaway Half Moon Cay • Key West, Florida • Miami • Grand Turk • San Juan, Puerto Rico • St. Thomas • Relaxaway Half Moon Cay • Miami
Average Starting Price
$2,389pp
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!

Rotterdam
Holland America Line
Feb 5, 2028 - Feb 12, 2028 (7 Nights)
Fort Lauderdale • Grand Turk • San Juan, Puerto Rico • St. Thomas • Relaxaway Half Moon Cay • Fort Lauderdale
Average Starting Price
$1,829pp
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 Epic
Norwegian Cruise Line
Feb 11, 2028 - Feb 18, 2028 (7 Nights)
Port Canaveral (Orlando), Florida • Puerto Plata, Dominican Republic • St. Thomas • Tortola • Great Stirrup Cay • Port Canaveral (Orlando), Florida
Average Starting Price
$859pp
Jim's Onboard Credit
Star of the Seas
Royal Caribbean
May 23, 2027 - May 30, 2027 (7 Nights)
Port Canaveral (Orlando), Florida • Perfect Day Cococay • St. Thomas • Philipsburg, St. Maarten • Port Canaveral (Orlando), Florida
Average Starting Price
$1,794pp
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!

Azamara Onward
Azamara
Dec 9, 2027 - Dec 22, 2027 (13 Nights)
Malaga, Spain • Tangier, Morocco • St. Thomas • Miami
Average Starting Price
$1,669pp
Jim's Onboard Credit

Jim's Ship Pick
One of my absolute favorite ships! Small, simple, and luxurious without feeling stuffy - and perfect for immersive, port-intensive cruises!

Harmony of the Seas
Royal Caribbean
Dec 23, 2027 - Dec 30, 2027 (7 Nights)
Port Canaveral (Orlando), Florida • Perfect Day Cococay • St. Thomas • Philipsburg, St. Maarten • Port Canaveral (Orlando), Florida
Average Starting Price
$1,420pp
Jim's Onboard Credit
CBT Exclusive
$$$ Savings

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!

Regal Princess
Princess Cruises
Feb 20, 2028 - Mar 5, 2028 (14 Nights)
Miami • Amber Cove, Dominican Republic • San Juan, Puerto Rico • Grand Turk • Celebration Key • Miami • Relaxaway Half Moon Cay • St. Thomas • Philipsburg, St. Maarten • Miami
Average Starting Price
$1,709pp
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!

Celebrity Apex
Celebrity Cruises
Feb 13, 2027 - Feb 20, 2027 (7 Nights)
Port Canaveral (Orlando), Florida • Puerto Plata, Dominican Republic • St. Thomas • Basseterre, St. Kitts and Nevis • Port Canaveral (Orlando), Florida
Average Starting Price
$1,356pp
Jim's Onboard Credit
Viking Sky
Viking
Jan 13, 2029 - Feb 3, 2029 (21 Nights)
San Juan, Puerto Rico • Sail the Caribbean Sea • Bridgetown, Barbados • Sail the Atlantic Ocean • Iles du Salut (Ile Royale), French Guiana • Sail the Atlantic Ocean • Sail the Mouth of the Amazon River • Santarem, Brazil • Parintins, Brazil • Manaus, Brazil • Manaus, Brazil • Sail the Amazon River • Sail the Amazon River • Belem, Brazil • Sail the Atlantic Ocean • Sail the Atlantic Ocean • Scarborough (Tobago), Trinidad and Tobago • Castries, St. Lucia • St John's, Antigua • St. Thomas • San Juan, Puerto Rico
Average Starting Price
$12,299pp
Jim's Onboard Credit
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