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Rotterdam
Holland America Line
Jan 23, 2027 - Feb 13, 2027 (21 Nights)
Fort Lauderdale • Relaxaway Half Moon Cay • Falmouth, 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 • Tortola • Relaxaway Half Moon Cay • Fort Lauderdale
Average Starting Price
$4,029pp
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!

9% OFF
Crystal Symphony
Crystal Cruises
Dec 28, 2027 - Jan 11, 2028 (14 Nights)
Fort Lauderdale • George Town, Cayman Islands • Montego Bay, Jamaica • La Romana, Dominican Republic • San Juan, Puerto Rico • Gustavia, St. Barts • St John's, Antigua • St. Kitts • Tortola • Samana, Dominican Republic • Grand Turk • Fort Lauderdale
Average Starting Price
$7,030pp
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
Jan 31, 2027 - Feb 7, 2027 (7 Nights)
San Juan, Puerto Rico • Tortola • St John's, Antigua • Roseau, Dominica • St. Croix • Basseterre, St. Kitts and Nevis • San Juan, Puerto Rico
Average Starting Price
$499pp
Jim's Onboard Credit
FREE Specialty Dining Meal
15% OFF
Marina
Oceania Cruises
Feb 23, 2027 - Mar 5, 2027 (10 Nights)
Miami • San Juan, Puerto Rico • Basseterre, St. Kitts and Nevis • Philipsburg, St. Maarten • Tortola • Puerto Plata, Dominican Republic • Nassau • Miami
Average Starting Price
$3,527pp
Jim's Onboard Credit
Silver Shadow
Silversea
Dec 20, 2026 - Dec 27, 2026 (7 Nights)
San Juan, Puerto Rico • Great Harbor Jost Van Dyke, British Virgin Islands • Little Bay, Montserrat • Castries, St. Lucia • Fort-De-France, Martinique • Soper's Hole, Tortola • San Juan, Puerto Rico
Average Starting Price
$4,800pp
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!

Allura
Oceania Cruises
Feb 19, 2027 - Mar 11, 2027 (20 Nights)
San Juan, Puerto Rico • St. Thomas • Philipsburg, St. Maarten • Basseterre, St. Kitts and Nevis • St John's, Antigua • Tortola • Miami • George Town, Cayman Islands • Falmouth, Jamaica • Oranjestad, Aruba • Willemstad, Curacao • Kralendijk, Bonaire • Cabo Rojo, Dominican Republic • Nassau • Miami
Average Starting Price
$11,349pp
Jim's Onboard Credit
Norwegian Epic
Norwegian Cruise Line
Dec 10, 2027 - Dec 20, 2027 (10 Nights)
Port Canaveral (Orlando), Florida • Puerto Plata, Dominican Republic • San Juan, Puerto Rico • Tortola • St. Kitts • Philipsburg, St. Maarten • St. Thomas • Great Stirrup Cay • Port Canaveral (Orlando), Florida
Average Starting Price
$1,089pp
Jim's Onboard Credit
Vista
Oceania Cruises
Jan 7, 2029 - Jan 31, 2029 (24 Nights)
Miami • St. Thomas • Philipsburg, St. Maarten • Basseterre, St. Kitts and Nevis • Willemstad, Curacao • Oranjestad, Aruba • Cartagena, Colombia • Panama Canal, Panama • Panama City (Fuerte Amador), Panama • Panama City (Fuerte Amador), Panama • Panama City (Fuerte Amador), Panama • Panama Canal, Panama • Limon, Costa Rica • George Town, Cayman Islands • Ocho Rios, Jamaica • La Romana, Dominican Republic • Tortola • San Juan, Puerto Rico • Miami
Average Starting Price
$9,699pp
Jim's Onboard Credit
Emerald Princess
Princess Cruises
Dec 5, 2027 - Dec 19, 2027 (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 • Martinique • Dominica • Bridgetown, Barbados • San Juan, Puerto Rico
Average Starting Price
$1,483pp
Jim's Onboard Credit
Regal Princess
Princess Cruises
Dec 19, 2027 - Jan 2, 2028 (14 Nights)
Miami • Amber Cove, Dominican Republic • San Juan, Puerto Rico • Philipsburg, St. Maarten • Tortola • Miami • Celebration Key • Amber Cove, Dominican Republic • Grand Turk • Miami
Average Starting Price
$2,248pp
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!

Silver Ray
Silversea
Dec 11, 2026 - Dec 22, 2026 (11 Nights)
Miami • San Juan, Puerto Rico • St. John • St. Kitts • Gustavia, St. Barts • Deshaies, Guadeloupe • Tortola • Miami
Average Starting Price
$5,900pp
Jim's Onboard Credit
Norwegian Bliss
Norwegian Cruise Line
Dec 22, 2027 - Jan 3, 2028 (12 Nights)
Manhattan • Puerto Plata, Dominican Republic • San Juan, Puerto Rico • Tortola • St. Thomas • St. Kitts • Philipsburg, St. Maarten • Manhattan
Average Starting Price
$2,269pp
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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