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Celebrity Apex
Celebrity Cruises
Mar 18, 2028 - Mar 25, 2028 (7 Nights)
Port Canaveral (Orlando), Florida • Puerto Plata, Dominican Republic • St. Thomas • Philipsburg, St. Maarten • Port Canaveral (Orlando), Florida
Average Starting Price
$1,112pp
Jim's Onboard Credit
Norwegian Prima
Norwegian Cruise Line
Feb 28, 2027 - Mar 7, 2027 (7 Nights)
San Juan, Puerto Rico • Tortola • Roseau, Dominica • Bridgetown, Barbados • Philipsburg, St. Maarten • St. Thomas • San Juan, Puerto Rico
Average Starting Price
$1,099pp
Jim's Onboard Credit
Viking Sea
Viking
Feb 26, 2028 - Mar 10, 2028 (13 Nights)
San Juan, Puerto Rico • Philipsburg, St. Maarten • Sail the Atlantic Ocean • Sail the Atlantic Ocean • Sail the Atlantic Ocean • Sail the Atlantic Ocean • Sail the Atlantic Ocean • Sail the Atlantic Ocean • Funchal, Portugal • Sail the Atlantic Ocean • Cadiz, Spain • Sail the Strait of Gibraltar • Valencia, Spain • Barcelona, Spain
Average Starting Price
$3,299pp
Jim's Onboard Credit
Star of the Seas
Royal Caribbean
Dec 12, 2027 - Dec 19, 2027 (7 Nights)
Port Canaveral (Orlando), Florida • Perfect Day Cococay • St. Thomas • Philipsburg, St. Maarten • Port Canaveral (Orlando), Florida
Average Starting Price
$1,589pp
Jim's Onboard Credit

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!

29% OFF
Seven Seas Grandeur
Regent Seven Seas Cruises
Feb 7, 2029 - Feb 17, 2029 (10 Nights)
Bridgetown, Barbados • Castries, St. Lucia • Fort-De-France, Martinique • Roseau, Dominica • Pointe-à-Pitre, Guadeloupe • Gustavia, St. Barts • Philipsburg, St. Maarten • Tortola • Miami
Average Starting Price
$7,299pp
Jim's Onboard Credit
Star Legend
Windstar Cruises
Feb 14, 2028 - Feb 21, 2028 (7 Nights)
San Juan, Puerto Rico • St. John • Philipsburg, St. Maarten • Gustavia, St. Barts • 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
MSC Magnifica
MSC Cruises
Jan 7, 2027 - May 8, 2027 (121 Nights)
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 • Tarragona, Spain
Average Starting Price
$30,439pp
Jim's Onboard Credit
29% OFF
MSC World Europa
MSC Cruises
Feb 23, 2027 - Mar 9, 2027 (14 Nights)
Bridgetown, Barbados • Kingstown, Saint Vincent Island, Saint Vincent • Grenada • Fort-De-France, Martinique • Pointe-à-Pitre, Guadeloupe • St John's, Antigua • Philipsburg, St. Maarten • St. Kitts • Roseau, Dominica • Fort-De-France, Martinique • Pointe-à-Pitre, Guadeloupe • Castries, St. Lucia • Bridgetown, Barbados
Average Starting Price
$1,918pp
Jim's Onboard Credit
Hero of the Seas
Royal Caribbean
Jan 29, 2028 - Feb 5, 2028 (7 Nights)
Miami • Philipsburg, St. Maarten • St. Thomas • Perfect Day Cococay • Miami
Average Starting Price
$1,477pp
Jim's Onboard Credit
Rotterdam
Holland America Line
Dec 22, 2026 - Jan 12, 2027 (21 Nights)
Fort Lauderdale • Philipsburg, St. Maarten • St. Kitts • Roseau, Dominica • Castries, St. Lucia • St John's, Antigua • St. Thomas • Relaxaway Half Moon Cay • Fort Lauderdale • Relaxaway Half Moon Cay • Falmouth, Jamaica • George Town, Cayman Islands • Belize City • Cozumel • Key West, Florida • Fort Lauderdale
Average Starting Price
$3,689pp
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!

49% OFF
MSC World Asia
MSC Cruises
Jan 30, 2028 - Feb 6, 2028 (7 Nights)
Pointe-à-Pitre, Guadeloupe • St John's, Antigua • Philipsburg, St. Maarten • St. Kitts • Roseau, Dominica • Fort-De-France, Martinique • Pointe-à-Pitre, Guadeloupe
Average Starting Price
$889pp
Jim's Onboard Credit
Star Princess
Princess Cruises
Jan 20, 2029 - Jan 27, 2029 (7 Nights)
Fort Lauderdale • Relaxaway Half Moon Cay • St. Thomas • Philipsburg, St. Maarten • Fort Lauderdale
Average Starting Price
$925pp
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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