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Port: Philipsburg, St. Maarten×
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Regal Princess
Princess Cruises
Mar 20, 2027 - Apr 3, 2027 (14 Nights)
Fort Lauderdale • Relaxaway Half Moon Cay • San Juan, Puerto Rico • Philipsburg, St. Maarten • Fort Lauderdale • Belize City • Roatan, Honduras • Cozumel • Cozumel • Fort Lauderdale
Average Starting Price
$1,258pp
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!

Harmony of the Seas
Royal Caribbean
Apr 17, 2027 - Apr 24, 2027 (7 Nights)
Port Canaveral (Orlando), Florida • Philipsburg, St. Maarten • San Juan, Puerto Rico • Perfect Day Cococay • Port Canaveral (Orlando), Florida
Average Starting Price
$915pp
Jim's Onboard Credit
CBT Exclusive
$$$ Savings
FREE Specialty Dining Meal
Silver Spirit
Silversea
Feb 5, 2028 - Feb 17, 2028 (12 Nights)
Bridgetown, Barbados • Canouan, Saint Vincent and the Grenadines • Fort-De-France, Martinique • Gustavia, St. Barts • Philipsburg, St. Maarten • Oranjestad, Aruba • Willemstad, Curacao • Kralendijk, Bonaire • Grenada • Castries, St. Lucia • Bridgetown, Barbados
Average Starting Price
$5,000pp
Jim's Onboard Credit
Disney Fantasy
Disney Cruise Line
May 13, 2028 - May 19, 2028 (6 Nights)
San Juan, Puerto Rico • Philipsburg, St. Maarten • St. Thomas • Disney Lookout Cay at Lighthouse Point, Bahamas • Disney Castaway Cay, Bahamas • Port Canaveral (Orlando), Florida
Average Starting Price
$1,612pp
Jim's Onboard Credit
Star Princess
Princess Cruises
Feb 10, 2029 - Feb 17, 2029 (7 Nights)
Fort Lauderdale • Relaxaway Half Moon Cay • St. Thomas • Philipsburg, St. Maarten • Fort Lauderdale
Average Starting Price
$1,025pp
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!

Caribbean Princess
Princess Cruises
Jan 14, 2029 - Jan 28, 2029 (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
$1,714pp
Jim's Onboard Credit
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
$1,032pp
Jim's Onboard Credit
MSC Seaview
MSC Cruises
Nov 17, 2026 - Dec 4, 2026 (17 Nights)
Barcelona, Spain • Las Palmas (Gran Canaria), Spain • Philipsburg, St. Maarten • St. Kitts • Dominica • Bridgetown, Barbados • Saint George • Kingstown, Saint Vincent Island, Saint Vincent • Fort-De-France, Martinique
Average Starting Price
$1,798pp
Jim's Onboard Credit
EXPLORA I
Explora Journeys
Dec 5, 2026 - Dec 20, 2026 (15 Nights)
Miami • Cozumel • Costa Maya • Santo Tomas de Castilla, Guatemala • Belize City • Roatan, Honduras • Miami • St. John • St John's, Antigua • Terre de Haut, Guadeloupe • Philipsburg, St. Maarten • San Juan, Puerto Rico
Average Starting Price
$7,115pp
Jim's Onboard Credit
46% OFF
MSC Meraviglia
MSC Cruises
Mar 13, 2027 - Mar 27, 2027 (14 Nights)
Miami • Philipsburg, St. Maarten • St John's, Antigua • St. Thomas • Nassau • Miami • Grand Turk • Ocean Cay • Nassau • Miami
Average Starting Price
$1,345pp
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!

Wind Surf
Windstar Cruises
Nov 5, 2027 - Nov 20, 2027 (15 Nights)
Lisbon, Portugal • Funchal, Portugal • Great Harbor Jost Van Dyke, British Virgin Islands • Philipsburg, St. Maarten
Average Starting Price
$2,580pp
Jim's Onboard Credit
49% OFF
MSC Opera
MSC Cruises
May 13, 2027 - May 27, 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
$1,748pp
Jim's Onboard Credit
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