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Port: Philipsburg, St. Maarten×
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Star of the Seas
Royal Caribbean
Apr 4, 2027 - Apr 11, 2027 (7 Nights)
Port Canaveral (Orlando), Florida • Perfect Day Cococay • St. Thomas • Philipsburg, St. Maarten • Port Canaveral (Orlando), Florida
Average Starting Price
$1,408pp
Jim's Onboard Credit
FREE Specialty Dining Meal

Jim's Ship Pick
This is the BEST ship I’ve EVER sailed on! It rarely felt crowded, the food was incredible, the shows were absolutely phenomenal, and there’s something for everyone!

Norwegian Prima
Norwegian Cruise Line
Jan 15, 2028 - Jan 22, 2028 (7 Nights)
San Juan, Puerto Rico • Tortola • St. Kitts • Bridgetown, Barbados • St John's, Antigua • Philipsburg, St. Maarten • St. Thomas • San Juan, Puerto Rico
Average Starting Price
$1,219pp
Jim's Onboard Credit
Viking Sea
Viking
Feb 14, 2027 - Feb 24, 2027 (10 Nights)
San Juan, Puerto Rico • St. Thomas • Basseterre, St. Kitts and Nevis • Castries, St. Lucia • Bridgetown, Barbados • Roseau, Dominica • St John's, Antigua • Philipsburg, St. Maarten • St. Croix • San Juan, Puerto Rico
Average Starting Price
$6,799pp
Jim's Onboard Credit
Star Legend
Windstar Cruises
Jan 31, 2028 - Feb 7, 2028 (7 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
Average Starting Price
$2,443pp
Jim's Onboard Credit
Hero of the Seas
Royal Caribbean
Jan 15, 2028 - Jan 22, 2028 (7 Nights)
Miami • Philipsburg, St. Maarten • St. Thomas • Perfect Day Cococay • Miami
Average Starting Price
$1,708pp
Jim's Onboard Credit
MSC Magnifica
MSC Cruises
Jan 4, 2027 - May 5, 2027 (121 Nights)
Rome (Civitavecchia), Italy • Genoa (Portofino), Italy • 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
Average Starting Price
$45,209pp
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
$1,621pp
Jim's Onboard Credit
49% OFF
MSC World Asia
MSC Cruises
Jan 16, 2028 - Jan 23, 2028 (7 Nights)
Pointe-à-Pitre, Guadeloupe • Philipsburg, St. Maarten • St John's, Antigua • St. Kitts • Roseau, Dominica • Fort-De-France, Martinique • Pointe-à-Pitre, Guadeloupe
Average Starting Price
$859pp
Jim's Onboard Credit
Rotterdam
Holland America Line
Dec 12, 2026 - Jan 2, 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. Kitts • Roseau, Dominica • Castries, St. Lucia • St John's, Antigua • St. Thomas • Relaxaway Half Moon Cay • Fort Lauderdale
Average Starting Price
$3,604pp
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 Bliss
Norwegian Cruise Line
Jan 4, 2027 - Jan 16, 2027 (12 Nights)
Manhattan • Puerto Plata, Dominican Republic • San Juan, Puerto Rico • St. Kitts • Tortola • Philipsburg, St. Maarten • St. Thomas • Manhattan
Average Starting Price
$1,619pp
Jim's Onboard Credit
Star Princess
Princess Cruises
Dec 30, 2028 - Jan 6, 2029 (7 Nights)
Fort Lauderdale • Relaxaway Half Moon Cay • St. Thomas • Philipsburg, St. Maarten • Fort Lauderdale
Average Starting Price
$1,225pp
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!

Regal Princess
Princess Cruises
Mar 20, 2027 - Mar 27, 2027 (7 Nights)
Fort Lauderdale • Relaxaway Half Moon Cay • San Juan, Puerto Rico • Philipsburg, St. Maarten • Fort Lauderdale
Average Starting Price
$669pp
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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