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Crown Princess
Princess Cruises
Jan 3, 2027 - Jan 17, 2027 (14 Nights)
San Juan, Puerto Rico • St. Thomas • 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
$1,606pp
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!

Harmony of the Seas
Royal Caribbean
Jan 22, 2028 - Jan 29, 2028 (7 Nights)
Port Canaveral (Orlando), Florida • Perfect Day Cococay • St. Thomas • Philipsburg, St. Maarten • Port Canaveral (Orlando), Florida
Average Starting Price
$918pp
Jim's Onboard Credit
Star of the Seas
Royal Caribbean
Jan 23, 2028 - Jan 30, 2028 (7 Nights)
Port Canaveral (Orlando), Florida • Perfect Day Cococay • St. Thomas • Philipsburg, St. Maarten • Port Canaveral (Orlando), Florida
Average Starting Price
$1,236pp
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
Mar 4, 2028 - Mar 11, 2028 (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
$1,239pp
Jim's Onboard Credit
Icon of the Seas
Royal Caribbean
Dec 19, 2026 - Dec 26, 2026 (7 Nights)
Miami • Philipsburg, St. Maarten • St. Thomas • Perfect Day Cococay • Miami
Average Starting Price
$1,600pp
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!

49% OFF
MSC Opera
MSC Cruises
Aug 5, 2027 - Aug 19, 2027 (14 Nights)
Bridgetown, Barbados • Fort-De-France, Martinique • Pointe-à-Pitre, Guadeloupe • Tortola • La Romana, Dominican Republic • Catalina Island, Dominican Republic • Virgin Gorda, British Virgin Islands • Philipsburg, St. Maarten • Fort-De-France, Martinique • St John's, Antigua • La Romana, Dominican Republic • Catalina Island, Dominican Republic • Bridgetown, Barbados
Average Starting Price
$1,998pp
Jim's Onboard Credit
Grandeur of the Seas
Royal Caribbean
Oct 9, 2027 - Oct 16, 2027 (7 Nights)
San Juan, Puerto Rico • Tortola • Philipsburg, St. Maarten • St John's, Antigua • Basseterre, St. Kitts and Nevis • St. Croix • San Juan, Puerto Rico
Average Starting Price
$670pp
Jim's Onboard Credit
Emerald Princess
Princess Cruises
Jan 30, 2028 - Feb 13, 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
$1,323pp
Jim's Onboard Credit
Azamara Quest
Azamara
Nov 28, 2027 - Dec 12, 2027 (14 Nights)
Bridgetown, Barbados • Castries, St. Lucia • Roseau, Dominica • Basseterre, St. Kitts and Nevis • Charlestown, Nevis • Philipsburg, St. Maarten • St. Thomas • San Juan, Puerto Rico • Virgin Gorda, British Virgin Islands • St John's, Antigua • St. Pierre • Port Elizabeth (Bequia), Saint Vincent and the Grenadines • Grenada • Scarborough (Tobago), Trinidad and Tobago • Bridgetown, Barbados
Average Starting Price
$3,199pp
Jim's Onboard Credit
Regal Princess
Princess Cruises
Feb 6, 2028 - Feb 20, 2028 (14 Nights)
Miami • Relaxaway Half Moon Cay • St. Thomas • Philipsburg, St. Maarten • Miami • Belize City • Roatan, Honduras • Cozumel • Celebration Key • Miami
Average Starting Price
$1,484pp
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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