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Port: Philipsburg, St. Maarten×
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31% OFF
MSC World Europa
MSC Cruises
Jan 16, 2027 - Jan 23, 2027 (7 Nights)
Fort-De-France, Martinique • Pointe-à-Pitre, Guadeloupe • Philipsburg, St. Maarten • St John's, Antigua • St. Kitts • Roseau, Dominica • Fort-De-France, Martinique
Average Starting Price
$863pp
Jim's Onboard Credit
Wind Surf
Windstar Cruises
Jan 3, 2028 - Jan 16, 2028 (13 Nights)
Philipsburg, St. Maarten • Road Bay, Anguilla • Gustavia, St. Barts • Great Harbor Jost Van Dyke, British Virgin Islands • Virgin Gorda, British Virgin Islands • Soper's Hole, Tortola • 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
$4,280pp
Jim's Onboard Credit
Star of the Seas
Royal Caribbean
Mar 5, 2028 - Mar 12, 2028 (7 Nights)
Port Canaveral (Orlando), Florida • Perfect Day Cococay • St. Thomas • Philipsburg, St. Maarten • Port Canaveral (Orlando), Florida
Average Starting Price
$1,788pp
Jim's Onboard Credit

Jim's Ship Pick
This is the BEST ship I’ve EVER sailed on! It rarely felt crowded, the food was incredible, the shows were absolutely phenomenal, and there’s something for everyone!

Seabourn Ovation
Seabourn
Mar 13, 2027 - Mar 27, 2027 (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
$10,918pp
Jim's Onboard Credit
Harmony of the Seas
Royal Caribbean
Apr 1, 2028 - Apr 8, 2028 (7 Nights)
Port Canaveral (Orlando), Florida • Perfect Day Cococay • St. Thomas • Philipsburg, St. Maarten • Port Canaveral (Orlando), Florida
Average Starting Price
$959pp
Jim's Onboard Credit
Rhapsody of the Seas
Royal Caribbean
Jan 23, 2027 - Jan 30, 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
$568pp
Jim's Onboard Credit
FREE Specialty Dining Meal
Azamara Quest
Azamara
Feb 16, 2028 - Mar 22, 2028 (35 Nights)
Buenos Aires, Argentina • Montevideo, Uruguay • Rio Grande Do Sul, Brazil • Porto Belo, Brazil • Sao Francisco do Sul, Brazil • Paranagua, brazil • Santos (Sao Paulo), Brazil • Ilhabela, Brazil • Paraty, Brazil • Rio de Janeiro, Brazil • Rio de Janeiro, Brazil • Rio de Janeiro, Brazil • Salvador da Bahia, Brazil • Salvador da Bahia, Brazil • Natal, Brazil • Belem, Brazil • Iles du Salut (Ile Royale), French Guiana • Scarborough (Tobago), Trinidad and Tobago • Bridgetown, Barbados • Grenada • Castries, St. Lucia • St. Pierre • Roseau, Dominica • Philipsburg, St. Maarten • Tortola • Miami
Average Starting Price
$14,819pp
Jim's Onboard Credit
74% OFF
MSC Meraviglia
MSC Cruises
Nov 21, 2026 - Nov 29, 2026 (8 Nights)
Miami • Philipsburg, St. Maarten • St. Kitts • St. Thomas • Amber Cove, Dominican Republic • Miami
Average Starting Price
$483pp
Jim's Onboard Credit
Enchanted Princess
Princess Cruises
Dec 13, 2028 - Dec 23, 2028 (10 Nights)
Fort Lauderdale • Amber Cove, Dominican Republic • San Juan, Puerto Rico • St. Kitts • St John's, Antigua • Martinique • Philipsburg, St. Maarten • Fort Lauderdale
Average Starting Price
$1,300pp
Jim's Onboard Credit
Crown Princess
Princess Cruises
Dec 27, 2026 - Jan 10, 2027 (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 • Dominica • Grenada • Bridgetown, Barbados • San Juan, Puerto Rico
Average Starting Price
$1,938pp
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!

Star Princess
Princess Cruises
Mar 3, 2029 - Mar 10, 2029 (7 Nights)
Fort Lauderdale • Relaxaway Half Moon Cay • St. Thomas • Philipsburg, St. Maarten • Fort Lauderdale
Average Starting Price
$1,025pp
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!

Scarlet Lady
Virgin Voyages
Apr 15, 2028 - Apr 22, 2028 (7 Nights)
San Juan, Puerto Rico • St. Thomas • Basseterre, St. Kitts and Nevis • Castries, St. Lucia • St John's, Antigua • Philipsburg, St. Maarten • San Juan, Puerto Rico
Average Starting Price
$1,043pp
Jim's Onboard Credit
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