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Port: Philipsburg, St. Maarten×
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Seabourn Ovation
Seabourn
Feb 13, 2027 - Feb 27, 2027 (14 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 • Soper's Hole, Tortola • St. Kitts • Trois Ilets, Martinique • Bequia Island, Saint Vincent • Grenada • Bridgetown, Barbados
Average Starting Price
$10,518pp
Jim's Onboard Credit
52% OFF
MSC Opera
MSC Cruises
May 17, 2027 - May 24, 2027 (7 Nights)
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
Average Starting Price
$702pp
Jim's Onboard Credit
Emerald Princess
Princess Cruises
Feb 11, 2028 - Feb 18, 2028 (7 Nights)
Bridgetown, Barbados • San Juan, Puerto Rico • St. Thomas • Philipsburg, St. Maarten • Dominica • St. Lucia • Bridgetown, Barbados
Average Starting Price
$1,479pp
Jim's Onboard Credit
28% OFF
MSC World Europa
MSC Cruises
Dec 6, 2026 - Dec 13, 2026 (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
$996pp
Jim's Onboard Credit
46% OFF
MSC World Asia
MSC Cruises
Apr 23, 2028 - May 6, 2028 (13 Nights)
Pointe-à-Pitre, Guadeloupe • Philipsburg, St. Maarten • St John's, Antigua • Santa Cruz de Tenerife, Spain • Barcelona, Spain • Marseille (Provence), France
Average Starting Price
$824pp
Jim's Onboard Credit
Wind Surf
Windstar Cruises
Feb 6, 2028 - Feb 13, 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
Regal Princess
Princess Cruises
Feb 19, 2029 - Mar 5, 2029 (14 Nights)
Fort Lauderdale • Relaxaway Half Moon Cay • Amber Cove, Dominican Republic • Grand Turk • Fort Lauderdale • Philipsburg, St. Maarten • St. Thomas • San Juan, Puerto Rico • Amber Cove, Dominican Republic • Fort Lauderdale
Average Starting Price
$1,974pp
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!

Seabourn Ovation
Seabourn
Feb 26, 2028 - Mar 4, 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
$5,368pp
Jim's Onboard Credit
46% OFF
MSC Opera
MSC Cruises
Jun 14, 2027 - Jun 28, 2027 (14 Nights)
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 • Fort-De-France, Martinique • Pointe-à-Pitre, Guadeloupe • Tortola • La Romana, Dominican Republic
Average Starting Price
$3,607pp
Jim's Onboard Credit
Emerald Princess
Princess Cruises
Feb 25, 2028 - Mar 3, 2028 (7 Nights)
Bridgetown, Barbados • San Juan, Puerto Rico • St. Thomas • Philipsburg, St. Maarten • St John's, Antigua • St. Lucia • Bridgetown, Barbados
Average Starting Price
$1,829pp
Jim's Onboard Credit
49% OFF
MSC World Asia
MSC Cruises
Apr 22, 2028 - May 6, 2028 (14 Nights)
Fort-De-France, Martinique • Pointe-à-Pitre, Guadeloupe • Philipsburg, St. Maarten • St John's, Antigua • Santa Cruz de Tenerife, Spain • Barcelona, Spain • Marseille (Provence), France
Average Starting Price
$898pp
Jim's Onboard Credit
Wind Surf
Windstar Cruises
Feb 6, 2028 - Feb 20, 2028 (14 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 • St John's, Antigua • Road Bay, Anguilla • Soper's Hole, Tortola • Great Harbor Jost Van Dyke, British Virgin Islands • Great Harbor Jost Van Dyke, British Virgin Islands • Virgin Gorda, British Virgin Islands • Gustavia, St. Barts • Philipsburg, St. Maarten
Average Starting Price
$4,460pp
Jim's Onboard Credit
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