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Port: Philipsburg, St. Maarten×
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Regal Princess
Princess Cruises
Dec 3, 2028 - Dec 11, 2028 (8 Nights)
Fort Lauderdale • Philipsburg, St. Maarten • St. Thomas • San Juan, Puerto Rico • Amber Cove, Dominican Republic • Fort Lauderdale
Average Starting Price
$825pp
Jim's Onboard Credit
Rhapsody of the Seas
Royal Caribbean
Dec 19, 2026 - Dec 26, 2026 (7 Nights)
San Juan, Puerto Rico • St. Thomas • St. Croix • Philipsburg, St. Maarten • St John's, Antigua • Roseau, Dominica • San Juan, Puerto Rico
Average Starting Price
$1,172pp
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!

43% OFF
MSC Opera
MSC Cruises
Oct 4, 2027 - Oct 11, 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
$747pp
Jim's Onboard Credit
Crown Princess
Princess Cruises
Feb 19, 2027 - Feb 26, 2027 (7 Nights)
Bridgetown, Barbados • San Juan, Puerto Rico • St. Thomas • Philipsburg, St. Maarten • St John's, Antigua • St. Lucia • Bridgetown, Barbados
Average Starting Price
$1,669pp
Jim's Onboard Credit
Emerald Princess
Princess Cruises
Dec 3, 2027 - Dec 10, 2027 (7 Nights)
Bridgetown, Barbados • San Juan, Puerto Rico • St. Thomas • Philipsburg, St. Maarten • St John's, Antigua • St. Lucia • Bridgetown, Barbados
Average Starting Price
$1,924pp
Jim's Onboard Credit
24% OFF
MSC World Europa
MSC Cruises
Jan 3, 2027 - Jan 10, 2027 (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
$1,392pp
Jim's Onboard Credit
Norwegian Prima
Norwegian Cruise Line
Dec 20, 2026 - Dec 27, 2026 (7 Nights)
San Juan, Puerto Rico • Oranjestad, Aruba • Philipsburg, St. Maarten • St. Thomas • Tortola • San Juan, Puerto Rico
Average Starting Price
$939pp
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!

47% OFF
MSC World Asia
MSC Cruises
Apr 22, 2028 - May 8, 2028 (16 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 • Naples, Italy
Average Starting Price
$1,019pp
Jim's Onboard Credit
Wind Surf
Windstar Cruises
Jan 30, 2028 - Feb 13, 2028 (14 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 • 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
$4,040pp
Jim's Onboard Credit
Regal Princess
Princess Cruises
Dec 28, 2028 - Jan 8, 2029 (11 Nights)
Fort Lauderdale • Philipsburg, St. Maarten • St John's, Antigua • Dominica • Bridgetown, Barbados • St. Kitts • St. Thomas • Fort Lauderdale
Average Starting Price
$2,150pp
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!

Seabourn Ovation
Seabourn
Feb 26, 2028 - Mar 11, 2028 (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
$9,608pp
Jim's Onboard Credit
44% OFF
MSC Opera
MSC Cruises
Aug 23, 2027 - Aug 30, 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
$892pp
Jim's Onboard Credit
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