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Emerald Princess
Princess Cruises
Nov 28, 2027 - Dec 12, 2027 (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
$1,508pp
Jim's Onboard Credit
Regal Princess
Princess Cruises
Dec 5, 2027 - Dec 19, 2027 (14 Nights)
Miami • Relaxaway Half Moon Cay • St. Thomas • Philipsburg, St. Maarten • Miami • Belize City • Roatan, Honduras • Cozumel • Celebration Key • Miami
Average Starting Price
$1,098pp
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!

Marina
Oceania Cruises
Feb 17, 2028 - Mar 5, 2028 (17 Nights)
Miami • Puerto Plata, Dominican Republic • San Juan, Puerto Rico • St. Croix • Basseterre, St. Kitts and Nevis • Gustavia, St. Barts • Philipsburg, St. Maarten • Miami • Costa Maya • Belize City • Roatan, Honduras • Cozumel • Miami
Average Starting Price
$5,449pp
Jim's Onboard Credit
46% OFF
MSC Meraviglia
MSC Cruises
Mar 27, 2027 - Apr 10, 2027 (14 Nights)
Miami • Philipsburg, St. Maarten • St. Kitts • St. Thomas • Amber Cove, Dominican Republic • Miami • Grand Turk • Ocean Cay • Nassau • Miami
Average Starting Price
$1,345pp
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!

Vision of the Seas
Royal Caribbean
Mar 21, 2027 - Mar 28, 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
$850pp
Jim's Onboard Credit
FREE Specialty Dining Meal
Island Princess
Princess Cruises
Apr 3, 2028 - Apr 19, 2028 (16 Nights)
Fort Lauderdale • St. Thomas • Philipsburg, St. Maarten • St. Kitts • St John's, Antigua • St. Lucia • Grenada • Bridgetown, Barbados • Oranjestad, Aruba • Kralendijk, Bonaire • Willemstad, Curacao • Fort Lauderdale
Average Starting Price
$1,699pp
Jim's Onboard Credit
Celebrity Constellation
Celebrity Cruises
Jan 9, 2027 - Jan 16, 2027 (7 Nights)
San Juan, Puerto Rico • St. Thomas • Philipsburg, St. Maarten • St John's, Antigua • Castries, St. Lucia • Grenada • San Juan, Puerto Rico
Average Starting Price
$716pp
Jim's Onboard Credit
Celebrity Apex
Celebrity Cruises
Dec 28, 2027 - Jan 4, 2028 (7 Nights)
Port Canaveral (Orlando), Florida • Grand Turk • San Juan, Puerto Rico • Philipsburg, St. Maarten • Port Canaveral (Orlando), Florida
Average Starting Price
$1,981pp
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!

Enchanted Princess
Princess Cruises
Dec 24, 2027 - Jan 4, 2028 (11 Nights)
Fort Lauderdale • St. Kitts • Dominica • Bridgetown, Barbados • Pointe-à-Pitre, Guadeloupe • Philipsburg, St. Maarten • San Juan, Puerto Rico • Amber Cove, Dominican Republic • Fort Lauderdale
Average Starting Price
$1,374pp
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!

38% OFF
Carnival Firenze
Carnival Cruise Line
Jan 23, 2028 - Feb 6, 2028 (14 Nights)
Port Canaveral (Orlando), Florida • Fun Day at Sea • Fun Day at Sea • St. Thomas • St John's, Antigua • Pointe-à-Pitre, Guadeloupe • Martinique • Grenada • Bridgetown, Barbados • Fun Day at Sea • Philipsburg, St. Maarten • San Juan, Puerto Rico • Fun Day at Sea • Fun Day at Sea • Port Canaveral (Orlando), Florida
Average Starting Price
$974pp
Jim's Onboard Credit
Eurodam
Holland America Line
Dec 1, 2027 - Dec 22, 2027 (21 Nights)
Fort Lauderdale • Philipsburg, St. Maarten • St John's, Antigua • Roseau, Dominica • Fort-De-France, Martinique • St. Kitts • St. Thomas • Relaxaway Half Moon Cay • Fort Lauderdale • Relaxaway Half Moon Cay • Falmouth, Jamaica • George Town, Cayman Islands • Mahogany Bay, Honduras • Belize City • Cozumel • Fort Lauderdale
Average Starting Price
$4,894pp
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!

EXPLORA III
Explora Journeys
Jan 29, 2027 - Feb 12, 2027 (14 Nights)
San Juan, Puerto Rico • Tortola • St John's, Antigua • Providenciales, Turks and Caicos Islands • Key West, Florida • Miami • Philipsburg, St. Maarten • Gustavia, St. Barts • Basseterre, St. Kitts and Nevis • St. John • San Juan, Puerto Rico
Average Starting Price
$13,000pp
Jim's Onboard Credit
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