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Port: Philipsburg, St. Maarten×
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Seabourn Ovation
Seabourn
Dec 4, 2027 - Dec 11, 2027 (7 Nights)
Philipsburg, St. Maarten • Soper's Hole, Tortola • St. Kitts • Trois Ilets, Martinique • Bequia Island, Saint Vincent • Grenada • Bridgetown, Barbados
Average Starting Price
$4,543pp
Jim's Onboard Credit
Rhapsody of the Seas
Royal Caribbean
Feb 12, 2028 - Feb 19, 2028 (7 Nights)
San Juan, Puerto Rico • St. Thomas • Philipsburg, St. Maarten • St John's, Antigua • Basseterre, St. Kitts and Nevis • St. Croix • San Juan, Puerto Rico
Average Starting Price
$758pp
Jim's Onboard Credit
Icon of the Seas
Royal Caribbean
Feb 27, 2027 - Mar 6, 2027 (7 Nights)
Miami • Philipsburg, St. Maarten • St. Thomas • Perfect Day Cococay • Miami
Average Starting Price
$1,263pp
Jim's Onboard Credit
FREE Specialty Dining Meal
EXPLORA III
Explora Journeys
Nov 15, 2026 - Nov 29, 2026 (14 Nights)
San Juan, Puerto Rico • Road Bay, Anguilla • St John's, Antigua • St. Croix • Catalina Island, Dominican Republic • Puerto Plata, Dominican Republic • Miami • St. John • St John's, Antigua • Terre de Haut, Guadeloupe • Philipsburg, St. Maarten • San Juan, Puerto Rico
Average Starting Price
$14,035pp
Jim's Onboard Credit
Viking Sky
Viking
Dec 24, 2028 - Jan 3, 2029 (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

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
Feb 5, 2028 - Feb 12, 2028 (7 Nights)
San Juan, Puerto Rico • Oranjestad, Aruba • Willemstad, Curacao • St John's, Antigua • Philipsburg, St. Maarten • San Juan, Puerto Rico
Average Starting Price
$903pp
Jim's Onboard Credit
Star Pride
Windstar Cruises
Dec 13, 2026 - Dec 27, 2026 (14 Nights)
San Juan, Puerto Rico • St. John • Gustavia, St. Barts • Basseterre, St. Kitts and Nevis • Philipsburg, St. Maarten • Great Harbor Jost Van Dyke, British Virgin Islands • Virgin Gorda, British Virgin Islands • San Juan, Puerto Rico • Grenada • Bequia Island, Saint Vincent • Mayreau Island, Saint Vincent and the Grenadines • Deshaies, Guadeloupe • Marigot Bay, St. Martin, French West Indies • San Juan, Puerto Rico
Average Starting Price
$10,174pp
Jim's Onboard Credit
Eurodam
Holland America Line
Feb 12, 2028 - Mar 4, 2028 (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 • Cabo Rojo, Dominican Republic • Kralendijk, Bonaire • Willemstad, Curacao • Oranjestad, Aruba • Fort Lauderdale
Average Starting Price
$5,094pp
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!

Crown Princess
Princess Cruises
Jan 31, 2027 - Feb 14, 2027 (14 Nights)
San Juan, Puerto Rico • St. Thomas • Pointe-à-Pitre, Guadeloupe • Dominica • Grenada • Bridgetown, Barbados • San Juan, Puerto Rico • St. Thomas • Philipsburg, St. Maarten • St John's, Antigua • Dominica • Bridgetown, Barbados • San Juan, Puerto Rico
Average Starting Price
$1,332pp
Jim's Onboard Credit
Vision of the Seas
Royal Caribbean
Jan 24, 2027 - Jan 31, 2027 (7 Nights)
San Juan, Puerto Rico • St. Thomas • St. Croix • Philipsburg, St. Maarten • St John's, Antigua • Roseau, Dominica • San Juan, Puerto Rico
Average Starting Price
$489pp
Jim's Onboard Credit
FREE Specialty Dining Meal
Silver Shadow
Silversea
Feb 10, 2029 - Feb 17, 2029 (7 Nights)
San Juan del sur, Nicaragua • Great Harbor Jost Van Dyke, British Virgin Islands • St John's, Antigua • Les Saintes, F.W.I. • Philipsburg, St. Maarten • Gustavia, St. Barts • Charlestown, Nevis • San Juan del sur, Nicaragua
Average Starting Price
$3,900pp
Jim's Onboard Credit
Harmony of the Seas
Royal Caribbean
Nov 27, 2027 - Dec 4, 2027 (7 Nights)
Port Canaveral (Orlando), Florida • Perfect Day Cococay • St. Thomas • Philipsburg, St. Maarten • Port Canaveral (Orlando), Florida
Average Starting Price
$1,028pp
Jim's Onboard Credit
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