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Port: Philipsburg, St. Maarten×
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Emerald Princess
Princess Cruises
Dec 19, 2027 - Jan 2, 2028 (14 Nights)
San Juan, Puerto Rico • St. Thomas • Philipsburg, St. Maarten • St John's, Antigua • St. Lucia • Bridgetown, Barbados • San Juan, Puerto Rico • Tortola • St. Kitts • Dominica • Grenada • 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!

Regal Princess
Princess Cruises
Dec 12, 2027 - Dec 27, 2027 (15 Nights)
Miami • Belize City • Roatan, Honduras • Cozumel • Celebration Key • Miami • Amber Cove, Dominican Republic • San Juan, Puerto Rico • Philipsburg, St. Maarten • Tortola • Miami
Average Starting Price
$1,403pp
Jim's Onboard Credit
Disney Fantasy
Disney Cruise Line
Apr 23, 2028 - Apr 29, 2028 (6 Nights)
Fort Lauderdale • Disney Castaway Cay, Bahamas • Disney Lookout Cay at Lighthouse Point, Bahamas • St. Thomas • Philipsburg, St. Maarten • San Juan, Puerto Rico
Average Starting Price
$1,649pp
Jim's Onboard Credit
Celebrity Eclipse
Celebrity Cruises
Jan 8, 2027 - Jan 17, 2027 (9 Nights)
Fort Lauderdale • St John's, Antigua • Roseau, Dominica • Fort-De-France, Martinique • Philipsburg, St. Maarten • Fort Lauderdale
Average Starting Price
$1,388pp
Jim's Onboard Credit
Star Princess
Princess Cruises
Feb 3, 2029 - Feb 17, 2029 (14 Nights)
Fort Lauderdale • Belize City • Roatan, Honduras • Cozumel • Celebration Key • Fort Lauderdale • Relaxaway Half Moon Cay • St. Thomas • Philipsburg, St. Maarten • Fort Lauderdale
Average Starting Price
$2,154pp
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!

48% OFF
MSC Seashore
MSC Cruises
Jan 29, 2028 - Feb 12, 2028 (14 Nights)
Miami • Philipsburg, St. Maarten • St. Kitts • St. Thomas • Puerto Plata, Dominican Republic • Miami • Ocean Cay • Grand Turk • Nassau • Miami
Average Starting Price
$1,257pp
Jim's Onboard Credit

Luke's Port Pick
Grand Turk has it all - stunning ship views, a pool, great snorkeling, and crystal-clear water! This port will always be my favorite!

Caribbean Princess
Princess Cruises
Nov 26, 2028 - Dec 1, 2028 (5 Nights)
San Juan, Puerto Rico • St. Thomas • Philipsburg, St. Maarten • St John's, Antigua • St. Lucia • Bridgetown, Barbados
Average Starting Price
$628pp
Jim's Onboard Credit
Valiant Lady
Virgin Voyages
Nov 28, 2026 - Dec 5, 2026 (7 Nights)
San Juan, Puerto Rico • St. Thomas • Tortola • Basseterre, St. Kitts and Nevis • St John's, Antigua • Philipsburg, St. Maarten • San Juan, Puerto Rico
Average Starting Price
$763pp
Jim's Onboard Credit
Silver Ray
Silversea
Feb 26, 2027 - Mar 10, 2027 (12 Nights)
Bridgetown, Barbados • Bequia Island, Saint Vincent • Grenada • Fort-De-France, Martinique • Deshaies, Guadeloupe • Soufrier Bay, St. Lucia • St. Kitts • Philipsburg, St. Maarten • Gustavia, St. Barts • Road Bay, Anguilla • Miami
Average Starting Price
$6,500pp
Jim's Onboard Credit
MSC Magnifica
MSC Cruises
Mar 16, 2027 - May 5, 2027 (50 Nights)
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
$11,649pp
Jim's Onboard Credit
Allure of the Seas
Royal Caribbean
Nov 22, 2026 - Nov 29, 2026 (7 Nights)
Miami • Philipsburg, St. Maarten • St. Thomas • Puerto Plata, Dominican Republic • Miami
Average Starting Price
$529pp
Jim's Onboard Credit
46% OFF
MSC Meraviglia
MSC Cruises
Mar 7, 2027 - Mar 21, 2027 (14 Nights)
Miami • Grand Turk • Ocean Cay • Nassau • Miami • Philipsburg, St. Maarten • St John's, Antigua • St. Thomas • Nassau • Miami
Average Starting Price
$1,265pp
Jim's Onboard Credit

Luke's Port Pick
Grand Turk has it all - stunning ship views, a pool, great snorkeling, and crystal-clear water! This port will always be my favorite!

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