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Port: Philipsburg, St. Maarten×
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Eurodam
Holland America Line
Dec 1, 2027 - Dec 22, 2027 (21 Nights)
Fort Lauderdale • Philipsburg, St. Maarten • St John's, Antigua • Roseau, Dominica • Fort-De-France, Martinique • St. Kitts • St. Thomas • 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
$4,894pp
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
Nov 26, 2028 - Dec 10, 2028 (14 Nights)
San Juan, Puerto Rico • St. Thomas • Philipsburg, St. Maarten • St John's, Antigua • St. Lucia • Bridgetown, Barbados • San Juan, Puerto Rico • St. Thomas • St. Kitts • Martinique • Grenada • Bridgetown, Barbados • San Juan, Puerto Rico
Average Starting Price
$1,604pp
Jim's Onboard Credit
EXPLORA III
Explora Journeys
Jan 29, 2027 - Feb 12, 2027 (14 Nights)
San Juan, Puerto Rico • Tortola • St John's, Antigua • Providenciales, Turks and Caicos Islands • Key West, Florida • Miami • Philipsburg, St. Maarten • Gustavia, St. Barts • Basseterre, St. Kitts and Nevis • St. John • San Juan, Puerto Rico
Average Starting Price
$12,675pp
Jim's Onboard Credit
Coral Princess
Princess Cruises
Dec 26, 2026 - Jan 6, 2027 (11 Nights)
Fort Lauderdale • St. Thomas • St. Kitts • Martinique • Bridgetown, Barbados • St. Lucia • Philipsburg, St. Maarten • Fort Lauderdale
Average Starting Price
$969pp
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!

Scarlet Lady
Virgin Voyages
Dec 18, 2027 - Dec 26, 2027 (8 Nights)
San Juan, Puerto Rico • Philipsburg, St. Maarten • St John's, Antigua • Roseau, Dominica • Oranjestad, Aruba • Willemstad, Curacao • San Juan, Puerto Rico
Average Starting Price
$1,192pp
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!

Allura
Oceania Cruises
Jan 27, 2027 - Feb 5, 2027 (9 Nights)
Miami • St. Thomas • Philipsburg, St. Maarten • Basseterre, St. Kitts and Nevis • Tortola • Miami
Average Starting Price
$5,799pp
Jim's Onboard Credit
Rhapsody of the Seas
Royal Caribbean
Mar 6, 2027 - Mar 16, 2027 (10 Nights)
San Juan, Puerto Rico • Tortola • Philipsburg, St. Maarten • St John's, Antigua • Bridgetown, Barbados • Castries, St. Lucia • Roseau, Dominica • St. Croix • Miami
Average Starting Price
$1,078pp
Jim's Onboard Credit
FREE Specialty Dining Meal
49% OFF
MSC Opera
MSC Cruises
Oct 15, 2027 - Oct 22, 2027 (7 Nights)
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
Average Starting Price
$739pp
Jim's Onboard Credit
Grandeur of the Seas
Royal Caribbean
Sep 25, 2027 - Oct 2, 2027 (7 Nights)
San Juan, Puerto Rico • Tortola • Philipsburg, St. Maarten • St John's, Antigua • Basseterre, St. Kitts and Nevis • St. Croix • San Juan, Puerto Rico
Average Starting Price
$606pp
Jim's Onboard Credit
Norwegian Bliss
Norwegian Cruise Line
Mar 1, 2027 - Mar 13, 2027 (12 Nights)
Manhattan • Puerto Plata, Dominican Republic • San Juan, Puerto Rico • St. Kitts • Tortola • Philipsburg, St. Maarten • St. Thomas • Manhattan
Average Starting Price
$1,859pp
Jim's Onboard Credit
Crown Princess
Princess Cruises
Feb 28, 2027 - Mar 14, 2027 (14 Nights)
San Juan, Puerto Rico • Philipsburg, St. Maarten • Martinique • Dominica • Grenada • 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
$1,296pp
Jim's Onboard Credit
29% OFF
Seven Seas Prestige
Regent Seven Seas Cruises
Dec 20, 2028 - Dec 30, 2028 (10 Nights)
Miami • Puerto Plata, Dominican Republic • San Juan, Puerto Rico • St. Thomas • Philipsburg, St. Maarten • Gustavia, St. Barts • Tortola • Miami
Average Starting Price
$7,399pp
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!

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