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Rhapsody of the Seas
Royal Caribbean
Jan 30, 2027 - Feb 6, 2027 (7 Nights)
San Juan, Puerto Rico • St. Thomas • Philipsburg, St. Maarten • St. Croix • St John's, Antigua • Roseau, Dominica • San Juan, Puerto Rico
Average Starting Price
$588pp
Jim's Onboard Credit
Norwegian Aura
Norwegian Cruise Line
Apr 8, 2028 - Apr 15, 2028 (7 Nights)
Miami • Puerto Plata, Dominican Republic • St. Thomas • Tortola • Great Stirrup Cay • Miami
Average Starting Price
$1,199pp
Jim's Onboard Credit
Star of the Seas
Royal Caribbean
Nov 28, 2027 - Dec 5, 2027 (7 Nights)
Port Canaveral (Orlando), Florida • Perfect Day Cococay • St. Thomas • Philipsburg, St. Maarten • Port Canaveral (Orlando), Florida
Average Starting Price
$1,403pp
Jim's Onboard Credit

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
Feb 21, 2027 - Feb 28, 2027 (7 Nights)
San Juan, Puerto Rico • Tortola • St. Kitts • Bridgetown, Barbados • St. Lucia • Philipsburg, St. Maarten • St. Thomas • San Juan, Puerto Rico
Average Starting Price
$1,099pp
Jim's Onboard Credit
Regal Princess
Princess Cruises
Feb 25, 2029 - Mar 11, 2029 (14 Nights)
Fort Lauderdale • Philipsburg, St. Maarten • St. Thomas • San Juan, Puerto Rico • Amber Cove, Dominican Republic • Fort Lauderdale • Relaxaway Half Moon Cay • Grand Turk • 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!

Rotterdam
Holland America Line
Dec 22, 2026 - Jan 12, 2027 (21 Nights)
Fort Lauderdale • Philipsburg, St. Maarten • St. Kitts • Roseau, Dominica • Castries, St. Lucia • St John's, Antigua • St. Thomas • Relaxaway Half Moon Cay • Fort Lauderdale • Relaxaway Half Moon Cay • Falmouth, Jamaica • George Town, Cayman Islands • Belize City • Cozumel • Key West, Florida • Fort Lauderdale
Average Starting Price
$3,689pp
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 Escape
Norwegian Cruise Line
Nov 13, 2026 - Nov 20, 2026 (7 Nights)
Port Canaveral (Orlando), Florida • Puerto Plata, Dominican Republic • St. Thomas • Tortola • Great Stirrup Cay • Port Canaveral (Orlando), Florida
Average Starting Price
$479pp
Jim's Onboard Credit
Crown Princess
Princess Cruises
Dec 28, 2028 - Jan 5, 2029 (8 Nights)
Fort Lauderdale • Amber Cove, Dominican Republic • St. Thomas • Philipsburg, St. Maarten • Tortola • Fort Lauderdale
Average Starting Price
$1,325pp
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 Meraviglia
MSC Cruises
Dec 27, 2026 - Jan 10, 2027 (14 Nights)
Miami • Grand Turk • Ocean Cay • Nassau • Miami • Philipsburg, St. Maarten • St. Kitts • St. Thomas • Amber Cove, Dominican Republic • Miami
Average Starting Price
$1,595pp
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!

Celebrity Apex
Celebrity Cruises
Nov 21, 2026 - Nov 28, 2026 (7 Nights)
Port Canaveral (Orlando), Florida • Puerto Plata, Dominican Republic • St. Thomas • Basseterre, St. Kitts and Nevis • Port Canaveral (Orlando), Florida
Average Starting Price
$1,044pp
Jim's Onboard Credit
54% OFF
Carnival Magic
Carnival Cruise Line
Dec 26, 2026 - Jan 3, 2027 (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
$758pp
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 Princess
Princess Cruises
Dec 9, 2028 - Dec 23, 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
$2,054pp
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!

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