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Port: Philipsburg, St. Maarten×
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46% OFF
MSC World Asia
MSC Cruises
Apr 22, 2028 - May 5, 2028 (13 Nights)
Fort-De-France, Martinique • Pointe-à-Pitre, Guadeloupe • Philipsburg, St. Maarten • St John's, Antigua • Santa Cruz de Tenerife, Spain • Barcelona, Spain
Average Starting Price
$824pp
Jim's Onboard Credit
Wind Surf
Windstar Cruises
Mar 13, 2027 - Mar 20, 2027 (7 Nights)
Philipsburg, St. Maarten • Falmouth (English Harbour), Antigua & Barbuda • 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
$3,288pp
Jim's Onboard Credit
Seabourn Ovation
Seabourn
Feb 5, 2028 - Feb 19, 2028 (14 Nights)
Philipsburg, St. Maarten • Soper's Hole, Tortola • St. Kitts • Trois Ilets, Martinique • Bequia Island, Saint Vincent • Grenada • 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
$10,008pp
Jim's Onboard Credit
Regal Princess
Princess Cruises
Jan 22, 2029 - Feb 5, 2029 (14 Nights)
Fort Lauderdale • Relaxaway Half Moon Cay • Grand Turk • Amber Cove, Dominican Republic • Fort Lauderdale • Philipsburg, St. Maarten • St. Thomas • San Juan, Puerto Rico • Amber Cove, Dominican Republic • Fort Lauderdale
Average Starting Price
$1,874pp
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!

Rhapsody of the Seas
Royal Caribbean
Dec 26, 2026 - Jan 2, 2027 (7 Nights)
San Juan, Puerto Rico • Tortola • Philipsburg, St. Maarten • St John's, Antigua • Basseterre, St. Kitts and Nevis • St. Thomas • San Juan, Puerto Rico
Average Starting Price
$1,258pp
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!

49% OFF
MSC Opera
MSC Cruises
Jun 10, 2027 - Jun 24, 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
$1,758pp
Jim's Onboard Credit
Crown Princess
Princess Cruises
Feb 26, 2027 - Mar 5, 2027 (7 Nights)
Bridgetown, Barbados • San Juan, Puerto Rico • Philipsburg, St. Maarten • Martinique • Dominica • Grenada • Bridgetown, Barbados
Average Starting Price
$1,559pp
Jim's Onboard Credit
30% OFF
MSC World Europa
MSC Cruises
Dec 5, 2026 - Dec 12, 2026 (7 Nights)
Fort-De-France, Martinique • Pointe-à-Pitre, Guadeloupe • St John's, Antigua • Philipsburg, St. Maarten • St. Kitts • Roseau, Dominica • Fort-De-France, Martinique
Average Starting Price
$929pp
Jim's Onboard Credit
48% OFF
MSC World Asia
MSC Cruises
Apr 22, 2028 - May 7, 2028 (15 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 • Genoa (Portofino), Italy
Average Starting Price
$959pp
Jim's Onboard Credit
Norwegian Prima
Norwegian Cruise Line
Nov 15, 2026 - Nov 22, 2026 (7 Nights)
San Juan, Puerto Rico • Tortola • St John's, Antigua • Bridgetown, Barbados • St. Kitts • Philipsburg, St. Maarten • St. Thomas • San Juan, Puerto Rico
Average Starting Price
$1,229pp
Jim's Onboard Credit
Wind Surf
Windstar Cruises
Mar 6, 2027 - Mar 13, 2027 (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
$2,817pp
Jim's Onboard Credit
Seabourn Ovation
Seabourn
Feb 19, 2028 - Mar 4, 2028 (14 Nights)
Philipsburg, St. Maarten • Soper's Hole, Tortola • St. Kitts • Trois Ilets, Martinique • Bequia Island, Saint Vincent • Grenada • 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
$9,708pp
Jim's Onboard Credit
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