1. Home
  2. Find a cruise
  3. Philipsburg, St. Maarten cruises

Philipsburg, St. Maarten cruises 48 Philipsburg, St. Maarten cruises

Your search Clear selections

Any Destination
All Sail Months
Any Length
Philipsburg, St. Maarten
Any Cruise Line
Any Ship

Close

48 cruises found

Filters Save search

Sort by

Filter by

More
Save search

Ports

  • Philipsburg, St. Maarten
  • Falmouth Harbour,Antigua
  • ROAD BAY, ANGUILLA
  • Soper's Hole, Tortola, B.V.I.
  • Jost Van Dyke, B.V.I.
  • Spanish Town, Virgin Gorda, B.V.I.
  • Gustavia, St. Barthelemy
  • Charlestown, Nevis
  • Roseau, Dominica
  • Pigeon Island, St. Lucia
  • Terre-De-Haut, Iles Des Saintes, Guadeloupe
  • Basseterre, St. Kitts
View more ports

Ports

Philipsburg, St. Maarten - Falmouth Harbour,Antigua - ROAD BAY, ANGUILLA - Soper's Hole, Tortola, B.V.I. - Jost Van Dyke, B.V.I. - Spanish Town, Virgin Gorda, B.V.I. - Gustavia, St. Barthelemy - Charlestown, Nevis - Roseau, Dominica - Pigeon Island, St. Lucia - Terre-De-Haut, Iles Des Saintes, Guadeloupe - Basseterre, St. Kitts - View more ports

Wind Surf S

4.4
(77 Reviews)

2024 sail dates: Dec 28

2025 sail dates: Jan 11, Feb 01, Feb 15, More

$4599*
$329/night*
Oceanview
View Deal
$4599* luxurycruiseconnections.com $4199* luxuryonly.com $4199* cruisesonly.com $4199* cruises.com $4199* dreamvacations.com
Loading itinerary...
Loading reviews...

Top positive review

Top critical review

Read all 77 Wind Surf reviews
Partners Bonus Offers Inside Oceanview Balcony Suite
 

N/A

$5699*

N/A

N/A

See Offers

N/A

$5199*

N/A

N/A

See Offers

N/A

$5199*

N/A

N/A

See Offers

N/A

$5199*

N/A

N/A

 

N/A

$5199*

N/A

N/A

 

N/A

$5099*

N/A

$10749*

See Offers

N/A

$4799*

N/A

$10749*

See Offers

N/A

$4799*

N/A

$10749*

See Offers

N/A

$4799*

N/A

$10749*

 

N/A

$4799*

N/A

$10749*

 

N/A

$4599*

N/A

$10399*

See Offers

N/A

$4599*

N/A

$10399*

See Offers

N/A

$4599*

N/A

$10399*

See Offers

N/A

$4599*

N/A

$10399*

 

N/A

$4599*

N/A

$10399*

 

N/A

$4849*

N/A

$10399*

See Offers

N/A

$4499*

N/A

$10399*

See Offers

N/A

$4499*

N/A

$10399*

See Offers

N/A

$4499*

N/A

$10399*

 

N/A

$4499*

N/A

$10399*

 

N/A

$4599*

N/A

$10099*

See Offers

N/A

$4199*

N/A

$10099*

See Offers

N/A

$4199*

N/A

$10099*

See Offers

N/A

$4199*

N/A

$10099*

 

N/A

$4199*

N/A

$10099*

Ports

  • Philipsburg, St. Maarten
  • Charlestown, Nevis
  • Roseau, Dominica
  • Pigeon Island, St. Lucia
  • Terre-De-Haut, Iles Des Saintes, Guadeloupe
  • Basseterre, St. Kitts
  • Gustavia, St. Barthelemy
View more ports

Ports

Philipsburg, St. Maarten - Charlestown, Nevis - Roseau, Dominica - Pigeon Island, St. Lucia - Terre-De-Haut, Iles Des Saintes, Guadeloupe - Basseterre, St. Kitts - Gustavia, St. Barthelemy - View more ports

Wind Surf S

4.4
(77 Reviews)

2024 sail dates: Dec 21

2025 sail dates: Jan 18,

$2799*
$400/night*
Oceanview
View Deal
$2799* luxurycruiseconnections.com $2599* luxuryonly.com $2599* cruisesonly.com $2599* cruises.com $2599* dreamvacations.com
Loading itinerary...
Loading reviews...

Top positive review

Top critical review

Read all 77 Wind Surf reviews
Partners Bonus Offers Inside Oceanview Balcony Suite
 

N/A

$2999*

N/A

$6099*

See Offers

N/A

$2999*

N/A

$6099*

See Offers

N/A

$2999*

N/A

$6099*

See Offers

N/A

$2999*

N/A

$6099*

 

N/A

$2999*

N/A

$6099*

 

N/A

$2999*

N/A

$5799*

See Offers

N/A

$2799*

N/A

$5799*

See Offers

N/A

$2799*

N/A

$5799*

See Offers

N/A

$2799*

N/A

$5799*

 

N/A

$2799*

N/A

$5799*

 

N/A

$2799*

N/A

$5599*

See Offers

N/A

$2599*

N/A

$5599*

See Offers

N/A

$2599*

N/A

$5599*

See Offers

N/A

$2599*

N/A

$5599*

 

N/A

$2599*

N/A

$5599*

Ports

  • Philipsburg, St. Maarten
  • Roseau, Dominica
  • Pigeon Island, St. Lucia
  • Terre-De-Haut, Iles Des Saintes, Guadeloupe
  • Gustavia, St. Barthelemy
  • Basseterre, St. Kitts
  • Falmouth Harbour,Antigua
  • ROAD BAY, ANGUILLA
  • Jost Van Dyke, B.V.I.
  • Soper's Hole, Tortola, B.V.I.
View more ports

Ports

Philipsburg, St. Maarten - Roseau, Dominica - Pigeon Island, St. Lucia - Terre-De-Haut, Iles Des Saintes, Guadeloupe - Gustavia, St. Barthelemy - Basseterre, St. Kitts - Falmouth Harbour,Antigua - ROAD BAY, ANGUILLA - Jost Van Dyke, B.V.I. - Soper's Hole, Tortola, B.V.I. - View more ports

Wind Surf S

4.4
(77 Reviews)

2026 sail dates: Feb 28,

$3699*
$264/night*
Oceanview
View Deal
$3699* luxurycruiseconnections.com $3699* luxuryonly.com $3699* cruisesonly.com $3699* cruises.com $3699* dreamvacations.com
Loading itinerary...
Loading reviews...

Top positive review

Top critical review

Read all 77 Wind Surf reviews
Partners Bonus Offers Inside Oceanview Balcony Suite
 

N/A

$3699*

N/A

$9399*

See Offers

N/A

$3699*

N/A

$9399*

See Offers

N/A

$3699*

N/A

$9399*

See Offers

N/A

$3699*

N/A

$9399*

 

N/A

$3699*

N/A

$9399*

 

N/A

$3699*

N/A

$9399*

See Offers

N/A

$3699*

N/A

$9399*

See Offers

N/A

$3699*

N/A

$9399*

See Offers

N/A

$3699*

N/A

$9399*

 

N/A

$3699*

N/A

$9399*

Ports

  • Philipsburg, St. Maarten
  • Charlestown, Nevis
  • Roseau, Dominica
  • Pigeon Island, St. Lucia
  • Terre-De-Haut, Iles Des Saintes, Guadeloupe
  • Basseterre, St. Kitts
  • Gustavia, St. Barthelemy
  • Falmouth Harbour,Antigua
  • ROAD BAY, ANGUILLA
  • Soper's Hole, Tortola, B.V.I.
  • Jost Van Dyke, B.V.I.
  • Spanish Town, Virgin Gorda, B.V.I.
View more ports

Ports

Philipsburg, St. Maarten - Charlestown, Nevis - Roseau, Dominica - Pigeon Island, St. Lucia - Terre-De-Haut, Iles Des Saintes, Guadeloupe - Basseterre, St. Kitts - Gustavia, St. Barthelemy - Falmouth Harbour,Antigua - ROAD BAY, ANGUILLA - Soper's Hole, Tortola, B.V.I. - Jost Van Dyke, B.V.I. - Spanish Town, Virgin Gorda, B.V.I. - View more ports

Wind Surf S

4.4
(77 Reviews)

2024 sail dates: Dec 21

2025 sail dates: Jan 04, Jan 25, Feb 08, Mar 01, More

$4549*
$325/night*
Oceanview
View Deal
$4549* luxurycruiseconnections.com $4199* luxuryonly.com $4199* cruisesonly.com $4199* cruises.com $4199* dreamvacations.com
Loading itinerary...
Loading reviews...

Top positive review

Top critical review

Read all 77 Wind Surf reviews

Ports

  • Philipsburg, St. Maarten
  • Charlestown, Nevis
  • Roseau, Dominica
  • Pigeon Island, St. Lucia
  • Terre-De-Haut, Iles Des Saintes, Guadeloupe
  • Gustavia, St. Barthelemy
  • Basseterre, St. Kitts
  • Falmouth Harbour,Antigua
  • ROAD BAY, ANGUILLA
  • Jost Van Dyke, B.V.I.
  • Soper's Hole, Tortola, B.V.I.
  • Spanish Town, Virgin Gorda, B.V.I.
View more ports

Ports

Philipsburg, St. Maarten - Charlestown, Nevis - Roseau, Dominica - Pigeon Island, St. Lucia - Terre-De-Haut, Iles Des Saintes, Guadeloupe - Gustavia, St. Barthelemy - Basseterre, St. Kitts - Falmouth Harbour,Antigua - ROAD BAY, ANGUILLA - Jost Van Dyke, B.V.I. - Soper's Hole, Tortola, B.V.I. - Spanish Town, Virgin Gorda, B.V.I. - View more ports

Wind Surf S

4.4
(77 Reviews)

2025 sail dates: Jan 18, Dec 21

$3699*
$264/night*
Oceanview
View Deal
$3699* luxurycruiseconnections.com $3699* luxuryonly.com $3699* cruisesonly.com $3699* cruises.com $3699* dreamvacations.com
Loading itinerary...
Loading reviews...

Top positive review

Top critical review

Read all 77 Wind Surf reviews
Partners Bonus Offers Inside Oceanview Balcony Suite
 

N/A

$4899*

N/A

$10499*

See Offers

N/A

$4599*

N/A

$10499*

See Offers

N/A

$4599*

N/A

$10499*

See Offers

N/A

$4599*

N/A

$10499*

 

N/A

$4599*

N/A

$10499*

 

N/A

$3699*

N/A

$9399*

See Offers

N/A

$3699*

N/A

$9399*

See Offers

N/A

$3699*

N/A

$9399*

See Offers

N/A

$3699*

N/A

$9399*

 

N/A

$3699*

N/A

$9399*

 

N/A

$4299*

N/A

$9999*

See Offers

N/A

$4299*

N/A

$9999*

See Offers

N/A

$4299*

N/A

$9999*

See Offers

N/A

$4299*

N/A

$9999*

 

N/A

$4299*

N/A

$9999*

Ports

  • Philipsburg, St. Maarten
  • Falmouth Harbour,Antigua
  • ROAD BAY, ANGUILLA
  • Soper's Hole, Tortola, B.V.I.
  • Jost Van Dyke, B.V.I.
  • Spanish Town, Virgin Gorda, B.V.I.
  • Gustavia, St. Barthelemy
  • Charlestown, Nevis
  • Roseau, Dominica
  • Pigeon Island, St. Lucia
  • Terre-De-Haut, Iles Des Saintes, Guadeloupe
  • Basseterre, St. Kitts
View more ports

Ports

Philipsburg, St. Maarten - Falmouth Harbour,Antigua - ROAD BAY, ANGUILLA - Soper's Hole, Tortola, B.V.I. - Jost Van Dyke, B.V.I. - Spanish Town, Virgin Gorda, B.V.I. - Gustavia, St. Barthelemy - Charlestown, Nevis - Roseau, Dominica - Pigeon Island, St. Lucia - Terre-De-Haut, Iles Des Saintes, Guadeloupe - Basseterre, St. Kitts - View more ports

Wind Surf S

4.4
(77 Reviews)

2025 sail dates: Dec 14

2026 sail dates:

$3699*
$264/night*
Oceanview
View Deal
$3699* luxurycruiseconnections.com $3699* luxuryonly.com $3699* cruisesonly.com $3699* cruises.com $3699* dreamvacations.com
Loading itinerary...
Loading reviews...

Top positive review

Top critical review

Read all 77 Wind Surf reviews
Partners Bonus Offers Inside Oceanview Balcony Suite
 

N/A

$3999*

N/A

$9699*

See Offers

N/A

$3999*

N/A

$9699*

See Offers

N/A

$3999*

N/A

$9699*

See Offers

N/A

$3999*

N/A

$9699*

 

N/A

$3999*

N/A

$9699*

 

N/A

$3699*

N/A

$9399*

See Offers

N/A

$3699*

N/A

$9399*

See Offers

N/A

$3699*

N/A

$9399*

See Offers

N/A

$3699*

N/A

$9399*

 

N/A

$3699*

N/A

$9399*

Ports

  • Cozumel, Mexico
  • George Town, Grand Cayman
  • Cayman Brac
  • Port Antonio, Jamaica
  • Santo Domingo, Dominican Republic
  • La Romana, Dominican Republic
  • Jost Van Dyke, B.V.I.
  • Spanish Town, Virgin Gorda, B.V.I.
  • Philipsburg, St. Maarten
  • Charlestown, Nevis
  • Roseau, Dominica
  • Pigeon Island, St. Lucia
  • Terre-De-Haut, Iles Des Saintes, Guadeloupe
  • Gustavia, St. Barthelemy
  • Basseterre, St. Kitts
View more ports

Ports

Cozumel, Mexico - George Town, Grand Cayman - Cayman Brac - Port Antonio, Jamaica - Santo Domingo, Dominican Republic - La Romana, Dominican Republic - Jost Van Dyke, B.V.I. - Spanish Town, Virgin Gorda, B.V.I. - Philipsburg, St. Maarten - Charlestown, Nevis - Roseau, Dominica - Pigeon Island, St. Lucia - Terre-De-Haut, Iles Des Saintes, Guadeloupe - Gustavia, St. Barthelemy - Basseterre, St. Kitts - View more ports

Wind Surf S

4.4
(77 Reviews)

2026 sail dates:

$4799*
$267/night*
Oceanview
View Deal
$4799* luxurycruiseconnections.com $4799* luxuryonly.com $4799* cruisesonly.com $4799* cruises.com $4799* dreamvacations.com
Loading itinerary...
Loading reviews...

Top positive review

Top critical review

Read all 77 Wind Surf reviews
Partners Bonus Offers Inside Oceanview Balcony Suite
 

N/A

$4799*

N/A

$10699*

See Offers

N/A

$4799*

N/A

$10699*

See Offers

N/A

$4799*

N/A

$10699*

See Offers

N/A

$4799*

N/A

$10699*

 

N/A

$4799*

N/A

$10699*

Ports

  • Philipsburg, St. Maarten
  • Charlestown, Nevis
  • Roseau, Dominica
  • Pigeon Island, St. Lucia
  • Terre-De-Haut, Iles Des Saintes, Guadeloupe
  • Basseterre, St. Kitts
  • Gustavia, St. Barthelemy
  • Falmouth Harbour,Antigua
  • ROAD BAY, ANGUILLA
  • Soper's Hole, Tortola, B.V.I.
  • Jost Van Dyke, B.V.I.
  • Spanish Town, Virgin Gorda, B.V.I.
View more ports

Ports

Philipsburg, St. Maarten - Charlestown, Nevis - Roseau, Dominica - Pigeon Island, St. Lucia - Terre-De-Haut, Iles Des Saintes, Guadeloupe - Basseterre, St. Kitts - Gustavia, St. Barthelemy - Falmouth Harbour,Antigua - ROAD BAY, ANGUILLA - Soper's Hole, Tortola, B.V.I. - Jost Van Dyke, B.V.I. - Spanish Town, Virgin Gorda, B.V.I. - View more ports

Wind Surf S

4.4
(77 Reviews)

2025 sail dates:

$4699*
$336/night*
Oceanview
View Deal
$4699* luxurycruiseconnections.com $4399* luxuryonly.com $4399* cruisesonly.com $4399* cruises.com $4399* dreamvacations.com
Loading itinerary...
Loading reviews...

Top positive review

Top critical review

Read all 77 Wind Surf reviews
Partners Bonus Offers Inside Oceanview Balcony Suite
 

N/A

$4699*

N/A

$10199*

See Offers

N/A

$4399*

N/A

$10199*

See Offers

N/A

$4399*

N/A

$10199*

See Offers

N/A

$4399*

N/A

$10199*

 

N/A

$4399*

N/A

$10199*

Ports

  • Philipsburg, St. Maarten
  • Jost Van Dyke, B.V.I.
  • Soper's Hole, Tortola, B.V.I.
  • Spanish Town, Virgin Gorda, B.V.I.
  • Gustavia, St. Barthelemy
  • Charlestown, Nevis
  • Roseau, Dominica
  • Pigeon Island, St. Lucia
  • Terre-De-Haut, Iles Des Saintes, Guadeloupe
  • Basseterre, St. Kitts
View more ports

Ports

Philipsburg, St. Maarten - Jost Van Dyke, B.V.I. - Soper's Hole, Tortola, B.V.I. - Spanish Town, Virgin Gorda, B.V.I. - Gustavia, St. Barthelemy - Charlestown, Nevis - Roseau, Dominica - Pigeon Island, St. Lucia - Terre-De-Haut, Iles Des Saintes, Guadeloupe - Basseterre, St. Kitts - View more ports

Wind Surf S

4.4
(77 Reviews)

2025 sail dates:

$3399*
$283/night*
Oceanview
View Deal
$3399* luxuryonly.com $3399* cruisesonly.com $3399* cruises.com $3399* dreamvacations.com
Loading itinerary...
Loading reviews...

Top positive review

Top critical review

Read all 77 Wind Surf reviews
Partners Bonus Offers Inside Oceanview Balcony Suite
See Offers

N/A

$3399*

N/A

$8799*

See Offers

N/A

$3399*

N/A

$8799*

See Offers

N/A

$3399*

N/A

$8799*

 

N/A

$3399*

N/A

$8799*

Ports

  • New York, New York
  • Newport, Rhode Island
  • Boston, Massachusetts
  • Halifax, Nova Scotia
  • Sydney, Nova Scotia
  • Cruise St. Lawrence River
  • Quebec City, Quebec
  • Norfolk, Virginia
  • Jacksonville, Florida
  • PARADISE ISLAND, BAHAMAS
  • Miami, Florida
  • San Juan, Puerto Rico
  • Philipsburg, St. Maarten
  • St. John's, Antigua
  • Terre-De-Haut, Iles Des Saintes, Guadeloupe
  • Castries, St. Lucia
  • Bequia, Grenadines
  • Bridgetown, Barbados
View more ports

Ports

New York, New York - Newport, Rhode Island - Boston, Massachusetts - Halifax, Nova Scotia - Sydney, Nova Scotia - Cruise St. Lawrence River - Quebec City, Quebec - Norfolk, Virginia - Jacksonville, Florida - PARADISE ISLAND, BAHAMAS - Miami, Florida - San Juan, Puerto Rico - Philipsburg, St. Maarten - St. John's, Antigua - Terre-De-Haut, Iles Des Saintes, Guadeloupe - Castries, St. Lucia - Bequia, Grenadines - Bridgetown, Barbados - View more ports

Crystal Serenity XL

4.4
(104 Reviews)

2024 sail dates:

$15300*
$494/night*
Oceanview
View Deal
$15300* luxurycruiseconnections.com $15300* americandiscountcruises.com $15300* americandiscountvacations.com $15300* gotosea.com
Loading itinerary...
Loading reviews...

Top positive review

Top critical review

Read all 104 Crystal Serenity reviews
Partners Bonus Offers Inside Oceanview Balcony Suite
 

N/A

$15300*

$15900*

$19000*

See Offers

N/A

$15300*

$15900*

$19000*

See Offers

N/A

$15300*

$15900*

$19000*

See Offers

N/A

$15300*

$15900*

$19000*

1 - 10 of 48

All prices are per person based on double occupancy and do not include port/government fees and gratuities.