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Celebrity Silhouette
Celebrity Cruises
Dec 28, 2027 - Jan 8, 2028 (11 Nights)
Fort Lauderdale • Kralendijk, Bonaire • Willemstad, Curacao • Oranjestad, Aruba • St John's, Antigua • Philipsburg, St. Maarten • Fort Lauderdale
Average Starting Price
$1,569pp
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!

Celebrity Summit
Celebrity Cruises
Jan 2, 2028 - Jan 6, 2028 (4 Nights)
San Juan, Puerto Rico • Philipsburg, St. Maarten • Fort Lauderdale
Average Starting Price
$531pp
Jim's Onboard Credit
Norwegian Gem
Norwegian Cruise Line
Nov 28, 2026 - Dec 10, 2026 (12 Nights)
Tampa • San Juan, Puerto Rico • Tortola • St. Kitts • Philipsburg, St. Maarten • St. Thomas • Falmouth, Jamaica • George Town, Cayman Islands • Tampa
Average Starting Price
$909pp
Jim's Onboard Credit
Norwegian Getaway
Norwegian Cruise Line
Dec 22, 2026 - Dec 31, 2026 (9 Nights)
Port Canaveral (Orlando), Florida • Puerto Plata, Dominican Republic • San Juan, Puerto Rico • Philipsburg, St. Maarten • St. Thomas • Tortola • Great Stirrup Cay • Port Canaveral (Orlando), Florida
Average Starting Price
$1,299pp
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!

Norwegian Jewel
Norwegian Cruise Line
Dec 23, 2026 - Jan 4, 2027 (12 Nights)
Miami • Great Stirrup Cay • Cabo Rojo, Dominican Republic • Oranjestad, Aruba • Willemstad, Curacao • Philipsburg, St. Maarten • Tortola • St. Thomas • Puerto Plata, Dominican Republic • Miami
Average Starting Price
$1,599pp
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!

74% OFF
MSC Poesia
MSC Cruises
Nov 12, 2026 - Nov 22, 2026 (10 Nights)
Miami • St. Thomas • St. Kitts • Philipsburg, St. Maarten • St John's, Antigua • San Juan, Puerto Rico • Puerto Plata, Dominican Republic • Miami
Average Starting Price
$449pp
Jim's Onboard Credit
Jewel of the Seas
Royal Caribbean
Dec 7, 2026 - Dec 16, 2026 (9 Nights)
Tampa • San Juan, Puerto Rico • Philipsburg, St. Maarten • St. Thomas • Puerto Plata, Dominican Republic • Tampa
Average Starting Price
$841pp
Jim's Onboard Credit
FREE Specialty Dining Meal
Zuiderdam
Holland America Line
Mar 28, 2027 - Apr 17, 2027 (20 Nights)
Miami • Relaxaway Half Moon Cay • Cabo Rojo, Dominican Republic • Kralendijk, Bonaire • Willemstad, Curacao • Oranjestad, Aruba • Miami • Philipsburg, St. Maarten • St John's, Antigua • Castries, St. Lucia • St. Kitts • St. Thomas • Relaxaway Half Moon Cay • Miami
Average Starting Price
$3,644pp
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 Pride
Windstar Cruises
Nov 1, 2027 - Nov 15, 2027 (14 Nights)
San Juan, Puerto Rico • St. John • Basseterre, St. Kitts and Nevis • Gustavia, St. Barts • Philipsburg, St. Maarten • Great Harbor Jost Van Dyke, British Virgin Islands • Virgin Gorda, British Virgin Islands • San Juan, Puerto Rico • Grenada • Bequia Island, Saint Vincent • Mayreau Island, Saint Vincent and the Grenadines • Les Saintes, F.W.I. • Marigot Bay, St. Martin, French West Indies • San Juan, Puerto Rico
Average Starting Price
$4,224pp
Jim's Onboard Credit
31% OFF
Carnival Horizon
Carnival Cruise Line
Jan 6, 2029 - Jan 20, 2029 (14 Nights)
Galveston • Fun Day at Sea • Fun Day at Sea • Ocho Rios, Jamaica • Fun Day at Sea • St. Croix • Philipsburg, St. Maarten • St. Kitts • St. Thomas • San Juan, Puerto Rico • Amber Cove, Dominican Republic • Fun Day at Sea • Fun Day at Sea • Fun Day at Sea • Galveston
Average Starting Price
$1,335pp
Jim's Onboard Credit
Disney Destiny
Disney Cruise Line
Dec 12, 2026 - Dec 19, 2026 (7 Nights)
Fort Lauderdale • Disney Lookout Cay at Lighthouse Point, Bahamas • San Juan, Puerto Rico • Philipsburg, St. Maarten • Fort Lauderdale
Average Starting Price
$1,983pp
Jim's Onboard Credit
Oosterdam
Holland America Line
Dec 11, 2027 - Dec 22, 2027 (11 Nights)
Fort Lauderdale • Philipsburg, St. Maarten • St. Kitts • Fort-De-France, Martinique • Roseau, Dominica • St John's, Antigua • San Juan, Puerto Rico • Relaxaway Half Moon Cay • Fort Lauderdale
Average Starting Price
$2,739pp
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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