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Port: Philipsburg, St. Maarten×
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Star of the Seas
Royal Caribbean
Jan 10, 2027 - Jan 17, 2027 (7 Nights)
Port Canaveral (Orlando), Florida • Perfect Day Cococay • St. Thomas • Philipsburg, St. Maarten • Port Canaveral (Orlando), Florida
Average Starting Price
$1,453pp
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!

67% OFF
MSC Meraviglia
MSC Cruises
Dec 19, 2026 - Dec 27, 2026 (8 Nights)
Miami • Philipsburg, St. Maarten • St. Kitts • St. Thomas • Amber Cove, Dominican Republic • Miami
Average Starting Price
$598pp
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!

Enchanted Princess
Princess Cruises
Mar 6, 2029 - Mar 17, 2029 (11 Nights)
Fort Lauderdale • Amber Cove, Dominican Republic • San Juan, Puerto Rico • St. Kitts • St. Lucia • Bridgetown, Barbados • St John's, Antigua • Philipsburg, St. Maarten • Fort Lauderdale
Average Starting Price
$1,500pp
Jim's Onboard Credit
48% OFF
MSC Opera
MSC Cruises
Aug 19, 2027 - Sep 2, 2027 (14 Nights)
Bridgetown, Barbados • Fort-De-France, Martinique • Pointe-à-Pitre, Guadeloupe • Tortola • La Romana, Dominican Republic • Catalina Island, Dominican Republic • Virgin Gorda, British Virgin Islands • Philipsburg, St. Maarten • Fort-De-France, Martinique • St John's, Antigua • La Romana, Dominican Republic • Catalina Island, Dominican Republic • Bridgetown, Barbados
Average Starting Price
$1,908pp
Jim's Onboard Credit
49% OFF
MSC World Asia
MSC Cruises
Mar 26, 2028 - Apr 2, 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
$1,049pp
Jim's Onboard Credit
Norwegian Prima
Norwegian Cruise Line
Jan 10, 2027 - Jan 17, 2027 (7 Nights)
San Juan, Puerto Rico • Tortola • Philipsburg, St. Maarten • Bridgetown, Barbados • St. Lucia • St. Kitts • St. Thomas • San Juan, Puerto Rico
Average Starting Price
$899pp
Jim's Onboard Credit
Grandeur of the Seas
Royal Caribbean
Nov 27, 2027 - Dec 4, 2027 (7 Nights)
San Juan, Puerto Rico • St. Thomas • Philipsburg, St. Maarten • Castries, St. Lucia • Willemstad, Curacao • Colon, Panama
Average Starting Price
$660pp
Jim's Onboard Credit
56% OFF
MSC World Europa
MSC Cruises
Nov 18, 2026 - Dec 6, 2026 (18 Nights)
Barcelona, Spain • Arrecife (Lanzarote), Spain • Santa Cruz de Tenerife, Spain • Philipsburg, St. Maarten • St. Kitts • Kingstown, Saint Vincent Island, Saint Vincent • Bridgetown, Barbados • Grenada • Fort-De-France, Martinique • Pointe-à-Pitre, Guadeloupe
Average Starting Price
$729pp
Jim's Onboard Credit
Wind Surf
Windstar Cruises
Jan 9, 2028 - Jan 16, 2028 (7 Nights)
Philipsburg, St. Maarten • Charlestown, Nevis • Roseau, Dominica • Mayreau Island, Saint Vincent and the Grenadines • Les Saintes, F.W.I. • Basseterre, St. Kitts and Nevis • Gustavia, St. Barts • Philipsburg, St. Maarten
Average Starting Price
$2,642pp
Jim's Onboard Credit
Seabourn Ovation
Seabourn
Jan 29, 2028 - Feb 5, 2028 (7 Nights)
Bridgetown, Barbados • Castries, St. Lucia • Little Bay, Montserrat • St John's, Antigua • St. Kitts • Great Harbor Jost Van Dyke, British Virgin Islands • Philipsburg, St. Maarten
Average Starting Price
$5,668pp
Jim's Onboard Credit
Regal Princess
Princess Cruises
Dec 26, 2026 - Jan 9, 2027 (14 Nights)
Fort Lauderdale • Amber Cove, Dominican Republic • San Juan, Puerto Rico • Philipsburg, St. Maarten • Grand Turk • Fort Lauderdale • Celebration Key • Grand Turk • Nassau • Fort Lauderdale
Average Starting Price
$1,229pp
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!

Rhapsody of the Seas
Royal Caribbean
Jan 9, 2027 - Jan 16, 2027 (7 Nights)
San Juan, Puerto Rico • St. Croix • Philipsburg, St. Maarten • St John's, Antigua • Fort-De-France, Martinique • Basseterre, St. Kitts and Nevis • San Juan, Puerto Rico
Average Starting Price
$548pp
Jim's Onboard Credit
FREE Specialty Dining Meal
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