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Port: Philipsburg, St. Maarten×
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Volendam
Holland America Line
Dec 11, 2027 - Jan 4, 2028 (24 Nights)
Fort Lauderdale • Relaxaway Half Moon Cay • Willemstad, Curacao • Cartagena, Colombia • Enter Panama Canal at Cristobal • Cruising Panama Canal And Gatun Lake • Gatun Lake, Panama • Cruising Gatun Lake And Panama Canal • Panama Canal, Panama • Colon, Panama • Limon, Costa Rica • George Town, Cayman Islands • Fort Lauderdale • Relaxaway Half Moon Cay • Philipsburg, St. Maarten • Fort-De-France, Martinique • Bridgetown, Barbados • Scarborough (Tobago), Trinidad and Tobago • Castries, St. Lucia • Basseterre, St. Kitts and Nevis • Fort Lauderdale
Average Starting Price
$6,189pp
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!

Majestic Princess
Princess Cruises
Nov 19, 2026 - Dec 22, 2026 (33 Nights)
Fort Lauderdale • Philipsburg, St. Maarten • St. Lucia • Bridgetown, Barbados • Fortaleza, Brazil • Rio de Janeiro, Brazil • Montevideo, Uruguay • Buenos Aires, Argentina • Buenos Aires, Argentina • Buenos Aires, Argentina • Montevideo, Uruguay • Puerto Madryn, Argentina • Falkland Islands • Cape Horn, Chile • Ushuaia, Argentina • Beagle Channel, Argentina • Punta Arenas, Chile • Puerto Montt, Chile • Valparaíso, Chile
Average Starting Price
$3,671pp
Jim's Onboard Credit
Oasis of the Seas
Royal Caribbean
Dec 28, 2026 - Jan 4, 2027 (7 Nights)
Fort Lauderdale • Perfect Day Cococay • St. Thomas • Philipsburg, St. Maarten • Fort Lauderdale
Average Starting Price
$1,598pp
Jim's Onboard Credit
FREE Specialty Dining Meal

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!

Celebrity Ascent
Celebrity Cruises
Apr 9, 2027 - Apr 19, 2027 (10 Nights)
Fort Lauderdale • Philipsburg, St. Maarten • Castries, St. Lucia • Grenada • Bridgetown, Barbados • St John's, Antigua • Fort Lauderdale
Average Starting Price
$1,596pp
Jim's Onboard Credit
Hero of the Seas
Royal Caribbean
Sep 11, 2027 - Sep 18, 2027 (7 Nights)
Miami • Philipsburg, St. Maarten • St. Thomas • Perfect Day Cococay • Miami
Average Starting Price
$1,605pp
Jim's Onboard Credit
Sirena
Oceania Cruises
Nov 21, 2027 - Dec 22, 2027 (31 Nights)
Miami • Cozumel • Santo Tomas de Castilla, Guatemala • Harvest Caye, Belize • Costa Maya • Miami • Oranjestad, Aruba • Willemstad, Curacao • Kralendijk, Bonaire • Grenada • Castries, St. Lucia • Pointe-à-Pitre, Guadeloupe • Philipsburg, St. Maarten • Miami • Nassau • Puerto Plata, Dominican Republic • San Juan, Puerto Rico • Basseterre, St. Kitts and Nevis • St. Thomas • St John's, Antigua • Gustavia, St. Barts • Tortola • Miami
Average Starting Price
$8,649pp
Jim's Onboard Credit
Sun Princess
Princess Cruises
Dec 18, 2027 - Dec 28, 2027 (10 Nights)
Fort Lauderdale • Amber Cove, Dominican Republic • San Juan, Puerto Rico • St. Kitts • Martinique • Philipsburg, St. Maarten • Celebration Key • Fort Lauderdale
Average Starting Price
$1,224pp
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!

Valiant Lady
Virgin Voyages
Mar 6, 2027 - Mar 13, 2027 (7 Nights)
San Juan, Puerto Rico • Philipsburg, St. Maarten • Bridgetown, Barbados • Castries, St. Lucia • St John's, Antigua • Tortola • San Juan, Puerto Rico
Average Starting Price
$1,113pp
Jim's Onboard Credit
Celebrity Constellation
Celebrity Cruises
Mar 6, 2027 - Mar 13, 2027 (7 Nights)
San Juan, Puerto Rico • St. Thomas • Philipsburg, St. Maarten • St John's, Antigua • Castries, St. Lucia • Bridgetown, Barbados • San Juan, Puerto Rico
Average Starting Price
$843pp
Jim's Onboard Credit
Viking Sea
Viking
Dec 7, 2027 - Dec 17, 2027 (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
EXPLORA I
Explora Journeys
Mar 8, 2027 - Mar 24, 2027 (16 Nights)
Miami • San Juan, Puerto Rico • Philipsburg, St. Maarten • Funchal, Portugal • Cadiz, Spain • Malaga, Spain • Barcelona, Spain
Average Starting Price
$7,620pp
Jim's Onboard Credit
Celebrity Eclipse
Celebrity Cruises
Jan 17, 2028 - Jan 29, 2028 (12 Nights)
Fort Lauderdale • Oranjestad, Aruba • Willemstad, Curacao • Kralendijk, Bonaire • Philipsburg, St. Maarten • Castries, St. Lucia • St John's, Antigua • Fort Lauderdale
Average Starting Price
$1,685pp
Jim's Onboard Credit
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