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Eurodam
Holland America Line
Nov 21, 2027 - Dec 12, 2027 (21 Nights)
Fort Lauderdale • Relaxaway Half Moon Cay • Ocho Rios, Jamaica • George Town, Cayman Islands • Mahogany Bay, Honduras • Belize City • Cozumel • 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
Average Starting Price
$5,094pp
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
Dec 18, 2027 - Dec 28, 2027 (10 Nights)
Port Canaveral (Orlando), Florida • Philipsburg, St. Maarten • Castries, St. Lucia • St John's, Antigua • St. Thomas • Grand Turk • Port Canaveral (Orlando), Florida
Average Starting Price
$1,991pp
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!

Crown Princess
Princess Cruises
Mar 21, 2027 - Mar 28, 2027 (7 Nights)
San Juan, Puerto Rico • St. Thomas • Philipsburg, St. Maarten • St John's, Antigua • St. Lucia • Bridgetown, Barbados • San Juan, Puerto Rico
Average Starting Price
$784pp
Jim's Onboard Credit
Sirena
Oceania Cruises
Nov 6, 2027 - Nov 21, 2027 (15 Nights)
New York, New York • Tortola • St John's, Antigua • Basseterre, St. Kitts and Nevis • Kralendijk, Bonaire • Willemstad, Curacao • Oranjestad, Aruba • Ocho Rios, Jamaica • George Town, Cayman Islands • Miami
Average Starting Price
$4,149pp
Jim's Onboard Credit
Celebrity Silhouette
Celebrity Cruises
Dec 19, 2027 - Dec 28, 2027 (9 Nights)
Fort Lauderdale • St. Thomas • St John's, Antigua • Philipsburg, St. Maarten • Basseterre, St. Kitts and Nevis • Fort Lauderdale
Average Starting Price
$1,017pp
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!

Scarlet Lady
Virgin Voyages
Nov 20, 2027 - Nov 27, 2027 (7 Nights)
San Juan, Puerto Rico • Oranjestad, Aruba • Willemstad, Curacao • St John's, Antigua • Philipsburg, St. Maarten • San Juan, Puerto Rico
Average Starting Price
$973pp
Jim's Onboard Credit
Celebrity Constellation
Celebrity Cruises
Mar 20, 2027 - Mar 27, 2027 (7 Nights)
San Juan, Puerto Rico • St. Thomas • St John's, Antigua • Roseau, Dominica • Castries, St. Lucia • Bridgetown, Barbados • San Juan, Puerto Rico
Average Starting Price
$714pp
Jim's Onboard Credit
41% OFF
MSC Meraviglia
MSC Cruises
Mar 13, 2027 - Mar 21, 2027 (8 Nights)
Miami • Philipsburg, St. Maarten • St John's, Antigua • St. Thomas • Nassau • Miami
Average Starting Price
$778pp
Jim's Onboard Credit
Rotterdam
Holland America Line
Mar 16, 2027 - Mar 27, 2027 (11 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
Average Starting Price
$2,219pp
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!

Valiant Lady
Virgin Voyages
Mar 13, 2027 - Mar 19, 2027 (6 Nights)
San Juan, Puerto Rico • Tortola • Basseterre, St. Kitts and Nevis • St John's, Antigua • Castries, St. Lucia • San Juan, Puerto Rico
Average Starting Price
$894pp
Jim's Onboard Credit
Norwegian Dawn
Norwegian Cruise Line
Jan 2, 2028 - Jan 14, 2028 (12 Nights)
Jacksonville • Great Stirrup Cay • Grand Bahama Island • Puerto Plata, Dominican Republic • Samana, Dominican Republic • Tortola • St John's, Antigua • Philipsburg, St. Maarten • San Juan, Puerto Rico • Jacksonville
Average Starting Price
$1,299pp
Jim's Onboard Credit
Silver Nova
Silversea
Dec 29, 2027 - Jan 9, 2028 (11 Nights)
Miami • Key West, Florida • St. Thomas • Soper's Hole, Tortola • Gustavia, St. Barts • St John's, Antigua • St. John • Miami
Average Starting Price
$6,800pp
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!

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