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Hero of the Seas
Royal Caribbean
Dec 30, 2027 - Jan 8, 2028 (9 Nights)
Miami • St. Thomas • Basseterre, St. Kitts and Nevis • Philipsburg, St. Maarten • San Juan, Puerto Rico • Perfect Day Cococay • Miami
Average Starting Price
$3,825pp
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!

MSC Magnifica
MSC Cruises
Jan 6, 2027 - May 7, 2027 (121 Nights)
Marseille (Provence), France • Barcelona, Spain • Gibraltar • Casablanca, Morocco • Mindelo, Cape Verde • Salvador, Brazil • Rio de Janeiro, Brazil • Rio de Janeiro, Brazil • Buenos Aires, Argentina • Buenos Aires, Argentina • Puerto Madryn, Argentina • Port Stanley, Falkland Islands • Ushuaia, Argentina • Ushuaia, Argentina • Puerto Montt, Chile • Valparaíso, Chile • Valparaíso, Chile • Hanga Roa (Rapa Nui), Chile • Bounty Bay Passage, Pitcaim • Papeete, French Polynesia • Papeete, French Polynesia • Moorea, French Polynesia • Aitutake, Aruntanga • Avatiu, Rarotonga, Cook Islands • Bay of Islands, New Zealand • Auckland, New Zealand • Tauranga, New Zealand • Christchurch, Lyttelton, New Zealand • Port Chalmers, New Zealand • Cruising Milford Sound • Hobart (Tasmania), Australia • Hobart (Tasmania), Australia • Sydney, Australia • Sydney, Australia • Noumea, New Caledonia • Luganville, Espirutu Santo • Apia, Samoa • International Dateline • Honolulu • Honolulu • Los Angeles • Cabo San Lucas • Puntarenas, Costa Rica • Balbao, Panama • Panama Canal, Panama • Panama Canal, Panama • La Romana, Dominican Republic • Tortola • Philipsburg, St. Maarten • Las Palmas (Gran Canaria), Spain • Ibiza, Spain • Naples, Italy • Rome (Civitavecchia), Italy • Genoa (Portofino), Italy • Marseille (Provence), France
Average Starting Price
$31,619pp
Jim's Onboard Credit
Rotterdam
Holland America Line
Jan 12, 2027 - Jan 23, 2027 (11 Nights)
Fort Lauderdale • Philipsburg, St. Maarten • St John's, Antigua • Roseau, Dominica • Fort-De-France, Martinique • St. Kitts • San Juan, Puerto Rico • Relaxaway Half Moon Cay • Fort Lauderdale
Average Starting Price
$2,319pp
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!

Emerald Princess
Princess Cruises
Dec 26, 2027 - Jan 9, 2028 (14 Nights)
San Juan, Puerto Rico • Tortola • St. Kitts • Dominica • Grenada • Bridgetown, Barbados • San Juan, Puerto Rico • Philipsburg, St. Maarten • St. Thomas • St John's, Antigua • St. Lucia • Bridgetown, Barbados • San Juan, Puerto Rico
Average Starting Price
$1,613pp
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!

Star Legend
Windstar Cruises
Jan 31, 2028 - Feb 14, 2028 (14 Nights)
San Juan, Puerto Rico • St. John • Gustavia, St. Barts • Philipsburg, St. Maarten • Basseterre, St. Kitts and Nevis • 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
$4,014pp
Jim's Onboard Credit
Celebrity Ascent
Celebrity Cruises
Feb 5, 2027 - Feb 15, 2027 (10 Nights)
Fort Lauderdale • Philipsburg, St. Maarten • Castries, St. Lucia • Grenada • Roseau, Dominica • St John's, Antigua • Fort Lauderdale
Average Starting Price
$8,000pp
Jim's Onboard Credit
Regal Princess
Princess Cruises
Dec 19, 2027 - Dec 27, 2027 (8 Nights)
Miami • Amber Cove, Dominican Republic • San Juan, Puerto Rico • Philipsburg, St. Maarten • Tortola • Miami
Average Starting Price
$949pp
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 Xcel
Celebrity Cruises
Dec 20, 2026 - Dec 27, 2026 (7 Nights)
Miami • Philipsburg, St. Maarten • St. Thomas • Puerto Plata, Dominican Republic • Miami
Average Starting Price
$5,828pp
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!

Disney Fantasy
Disney Cruise Line
Apr 29, 2028 - May 6, 2028 (7 Nights)
San Juan, Puerto Rico • Oranjestad, Aruba • Kralendijk, Bonaire • Willemstad, Curacao • Philipsburg, St. Maarten • San Juan, Puerto Rico
Average Starting Price
$2,296pp
Jim's Onboard Credit
Icon of the Seas
Royal Caribbean
Mar 27, 2027 - Apr 3, 2027 (7 Nights)
Miami • Philipsburg, St. Maarten • St. Thomas • Perfect Day Cococay • Miami
Average Starting Price
$1,473pp
Jim's Onboard Credit
FREE Specialty Dining Meal
Valiant Lady
Virgin Voyages
Nov 20, 2026 - Nov 28, 2026 (8 Nights)
San Juan, Puerto Rico • St. Thomas • Willemstad, Curacao • Oranjestad, Aruba • Basseterre, St. Kitts and Nevis • Philipsburg, St. Maarten • San Juan, Puerto Rico
Average Starting Price
$952pp
Jim's Onboard Credit
EXPLORA I
Explora Journeys
Dec 13, 2026 - Dec 20, 2026 (7 Nights)
Miami • St. John • St John's, Antigua • Terre de Haut, Guadeloupe • Philipsburg, St. Maarten • San Juan, Puerto Rico
Average Starting Price
$4,385pp
Jim's Onboard Credit
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