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Port: Philipsburg, St. Maarten×
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27% OFF
Seven Seas Grandeur
Regent Seven Seas Cruises
Feb 24, 2028 - Mar 5, 2028 (10 Nights)
Bridgetown, Barbados • Castries, St. Lucia • Fort-De-France, Martinique • Roseau, Dominica • Pointe-à-Pitre, Guadeloupe • Gustavia, St. Barts • Philipsburg, St. Maarten • Tortola • Miami
Average Starting Price
$6,849pp
Jim's Onboard Credit
Viking Sky
Viking
Dec 4, 2028 - Dec 14, 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
$3,799pp
Jim's Onboard Credit
Viking Vesta
Viking
Dec 8, 2028 - Dec 21, 2028 (13 Nights)
Barcelona, Spain • Sail the Mediterranean Sea • Sail the Atlantic Ocean • Funchal, Portugal • Sail the Atlantic Ocean • Sail the Atlantic Ocean • Sail the Atlantic Ocean • Sail the Atlantic Ocean • Sail the Atlantic Ocean • Sail the Atlantic Ocean • Philipsburg, St. Maarten • Sail the Caribbean Sea • Sail the Caribbean Sea • Fort Lauderdale
Average Starting Price
$2,999pp
Jim's Onboard Credit
Eurodam
Holland America Line
Feb 27, 2027 - Mar 9, 2027 (10 Nights)
Fort Lauderdale • Relaxaway Half Moon Cay • San Juan, Puerto Rico • Tortola • Philipsburg, St. Maarten • St John's, Antigua • St. Kitts • Fort Lauderdale
Average Starting Price
$1,989pp
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!

Harmony of the Seas
Royal Caribbean
Dec 23, 2027 - Dec 30, 2027 (7 Nights)
Port Canaveral (Orlando), Florida • Perfect Day Cococay • St. Thomas • Philipsburg, St. Maarten • Port Canaveral (Orlando), Florida
Average Starting Price
$1,420pp
Jim's Onboard Credit
CBT Exclusive
$$$ Savings

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!

Vision of the Seas
Royal Caribbean
Feb 14, 2027 - Feb 21, 2027 (7 Nights)
San Juan, Puerto Rico • Tortola • St John's, Antigua • Philipsburg, St. Maarten • St. Croix • Basseterre, St. Kitts and Nevis • San Juan, Puerto Rico
Average Starting Price
$548pp
Jim's Onboard Credit
FREE Specialty Dining Meal
29% OFF
MSC World Europa
MSC Cruises
Mar 23, 2027 - Apr 6, 2027 (14 Nights)
Bridgetown, Barbados • Grenada • Kingstown, Saint Vincent Island, Saint Vincent • Fort-De-France, Martinique • Pointe-à-Pitre, Guadeloupe • Philipsburg, St. Maarten • St John's, Antigua • St. Kitts • Roseau, Dominica • Fort-De-France, Martinique • Pointe-à-Pitre, Guadeloupe • Castries, St. Lucia • Bridgetown, Barbados
Average Starting Price
$1,918pp
Jim's Onboard Credit
Crown Princess
Princess Cruises
Feb 14, 2027 - Feb 28, 2027 (14 Nights)
San Juan, Puerto Rico • St. Thomas • St. Kitts • 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
$1,428pp
Jim's Onboard Credit
Star Pride
Windstar Cruises
Jan 10, 2027 - Jan 17, 2027 (7 Nights)
San Juan, Puerto Rico • St. John • Basseterre, St. Kitts and Nevis • Gustavia, St. Barts • Philipsburg, St. Maarten • Great Harbor Jost Van Dyke, British Virgin Islands • Virgin Gorda, British Virgin Islands • San Juan, Puerto Rico
Average Starting Price
$4,403pp
Jim's Onboard Credit
Celebrity Apex
Celebrity Cruises
Mar 4, 2028 - Mar 11, 2028 (7 Nights)
Port Canaveral (Orlando), Florida • Puerto Plata, Dominican Republic • St. Thomas • Philipsburg, St. Maarten • Port Canaveral (Orlando), Florida
Average Starting Price
$1,162pp
Jim's Onboard Credit
Silver Shadow
Silversea
Dec 16, 2028 - Dec 23, 2028 (7 Nights)
San Juan del sur, Nicaragua • Virgin Gorda, British Virgin Islands • St John's, Antigua • Les Saintes, F.W.I. • Philipsburg, St. Maarten • Charlestown, Nevis • Gustavia, St. Barts • San Juan del sur, Nicaragua
Average Starting Price
$3,700pp
Jim's Onboard Credit
36% OFF
Carnival Firenze
Carnival Cruise Line
Apr 2, 2028 - Apr 16, 2028 (14 Nights)
Port Canaveral (Orlando), Florida • Fun Day at Sea • Amber Cove, Dominican Republic • Fun Day at Sea • Oranjestad, Aruba • Willemstad, Curacao • Fun Day at Sea • St. Lucia • Bridgetown, Barbados • Martinique • Philipsburg, St. Maarten • St. Thomas • Fun Day at Sea • Fun Day at Sea • Port Canaveral (Orlando), Florida
Average Starting Price
$1,054pp
Jim's Onboard Credit
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