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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
Azamara Quest
Azamara
Oct 28, 2027 - Nov 6, 2027 (9 Nights)
New York, New York • Hamilton, Bermuda • Hamilton, Bermuda • Hamilton, Bermuda • Philipsburg, St. Maarten • Tortola • San Juan, Puerto Rico
Average Starting Price
$2,089pp
Jim's Onboard Credit
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!

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
$1,219pp
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!

71% 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
$498pp
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
$961pp
Jim's Onboard Credit
FREE Specialty Dining Meal
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
Majestic Princess
Princess Cruises
Nov 19, 2026 - Dec 7, 2026 (18 Nights)
Fort Lauderdale • Philipsburg, St. Maarten • St. Lucia • Bridgetown, Barbados • Fortaleza, Brazil • Rio de Janeiro, Brazil • Montevideo, Uruguay • Buenos Aires, Argentina • Buenos Aires, Argentina
Average Starting Price
$1,780pp
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
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
Oasis of the Seas
Royal Caribbean
Dec 28, 2026 - Jan 4, 2027 (7 Nights)
Fort Lauderdale • Perfect Day Cococay • St. Thomas • Philipsburg, St. Maarten • Fort Lauderdale
Average Starting Price
$1,698pp
Jim's Onboard Credit
FREE Specialty Dining Meal

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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