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Port: Philipsburg, St. Maarten×
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55% OFF
Margaritaville at Sea Beachcomber
Margaritaville at Sea
Apr 24, 2027 - May 1, 2027 (7 Nights)
Miami • Philipsburg, St. Maarten • San Juan, Puerto Rico • Puerto Plata, Dominican Republic • Miami
Average Starting Price
$529pp
Jim's Onboard Credit
Norwegian Prima
Norwegian Cruise Line
Jan 8, 2028 - Jan 15, 2028 (7 Nights)
San Juan, Puerto Rico • Tortola • St. Kitts • Bridgetown, Barbados • St. Lucia • Philipsburg, St. Maarten • St. Thomas • San Juan, Puerto Rico
Average Starting Price
$1,219pp
Jim's Onboard Credit
49% OFF
MSC World Asia
MSC Cruises
Dec 19, 2027 - Dec 26, 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
$1,499pp
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!

Viking Sea
Viking
Feb 6, 2028 - Feb 16, 2028 (10 Nights)
San Juan, Puerto Rico • St. Thomas • Basseterre, St. Kitts and Nevis • Castries, St. Lucia • Bridgetown, Barbados • Roseau, Dominica • St John's, Antigua • Philipsburg, St. Maarten • St. Croix • San Juan, Puerto Rico
Average Starting Price
$4,299pp
Jim's Onboard Credit
Celebrity Ascent
Celebrity Cruises
Feb 15, 2027 - Feb 26, 2027 (11 Nights)
Fort Lauderdale • Philipsburg, St. Maarten • St John's, Antigua • Castries, St. Lucia • Bridgetown, Barbados • Roseau, Dominica • Basseterre, St. Kitts and Nevis • Fort Lauderdale
Average Starting Price
$1,914pp
Jim's Onboard Credit
Star Legend
Windstar Cruises
Jan 24, 2028 - Feb 7, 2028 (14 Nights)
San Juan, Puerto Rico • Grenada • Bequia Island, Saint Vincent • Mayreau Island, Saint Vincent and the Grenadines • Les Saintes, F.W.I. • Marigot Bay, St. Martin, French West Indies • San Juan, Puerto Rico • St. John • Gustavia, St. Barts • Philipsburg, St. Maarten • Basseterre, St. Kitts and Nevis • Great Harbor Jost Van Dyke, British Virgin Islands • Virgin Gorda, British Virgin Islands • San Juan, Puerto Rico
Average Starting Price
$4,014pp
Jim's Onboard Credit
Viking Sky
Viking
Feb 17, 2028 - Feb 27, 2028 (10 Nights)
San Juan, Puerto Rico • St. Thomas • Basseterre, St. Kitts and Nevis • Castries, St. Lucia • Bridgetown, Barbados • Roseau, Dominica • St John's, Antigua • Philipsburg, St. Maarten • St. Croix • San Juan, Puerto Rico
Average Starting Price
$4,499pp
Jim's Onboard Credit
Emerald Princess
Princess Cruises
Dec 12, 2027 - Dec 26, 2027 (14 Nights)
San Juan, Puerto Rico • Tortola • St. Kitts • Martinique • Dominica • Bridgetown, Barbados • San Juan, Puerto Rico • St. Thomas • Philipsburg, St. Maarten • St John's, Antigua • St. Lucia • Bridgetown, Barbados • San Juan, Puerto Rico
Average Starting Price
$1,458pp
Jim's Onboard Credit
Icon of the Seas
Royal Caribbean
Apr 10, 2027 - Apr 17, 2027 (7 Nights)
Miami • Philipsburg, St. Maarten • St. Thomas • Perfect Day Cococay • Miami
Average Starting Price
$1,303pp
Jim's Onboard Credit
FREE Specialty Dining Meal
Rotterdam
Holland America Line
Jan 12, 2027 - Feb 2, 2027 (21 Nights)
Fort Lauderdale • Philipsburg, St. Maarten • St John's, Antigua • Roseau, Dominica • Fort-De-France, Martinique • St. Kitts • San Juan, Puerto Rico • Relaxaway Half Moon Cay • Fort Lauderdale • Relaxaway Half Moon Cay • Falmouth, Jamaica • George Town, Cayman Islands • Mahogany Bay, Honduras • Belize City • Cozumel • Fort Lauderdale
Average Starting Price
$3,939pp
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!

33% OFF
Carnival Magic
Carnival Cruise Line
Dec 26, 2027 - Jan 3, 2028 (8 Nights)
Miami • Relaxaway Half Moon Cay • Fun Day at Sea • San Juan, Puerto Rico • Philipsburg, St. Maarten • St. Thomas • Fun Day at Sea • Fun Day at Sea • Miami
Average Starting Price
$1,155pp
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!

Celebrity Xcel
Celebrity Cruises
Jan 10, 2027 - Jan 17, 2027 (7 Nights)
Miami • Philipsburg, St. Maarten • St. Thomas • Puerto Plata, Dominican Republic • Miami
Average Starting Price
$898pp
Jim's Onboard Credit
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