1. Home
  2. Find a cruise
  3. ROAD BAY, ANGUILLA cruises

ROAD BAY, ANGUILLA cruises 75 ROAD BAY, ANGUILLA cruises

Your search Clear selections

Any Destination
All Sail Months
Any Length
ROAD BAY, ANGUILLA
Any Cruise Line
Any Ship

Close

75 cruises found

Filters Save search

Sort by

Filter by

Save search

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
  • 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 - Basseterre, St. Kitts - Gustavia, St. Barthelemy - 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
(78 Reviews)

2024 sail dates: Dec 21

2025 sail dates: Jan 04, Feb 08,

$5569*
$398/night*
Oceanview
View Deal
$5569* luxurycruiseconnections.com $5501* luxuryonly.com $5501* dreamvacations.com
Loading itinerary...
Loading reviews...

Top positive review

Top critical review

Read all 78 Wind Surf reviews
Partners Bonus Offers Inside Oceanview Balcony Suite
 

N/A

$7519*

N/A

N/A

 

N/A

$5719*

N/A

N/A

See Offers

N/A

$5651*

N/A

N/A

 

N/A

$5651*

N/A

N/A

 

N/A

$5609*

N/A

N/A

See Offers

N/A

$5541*

N/A

N/A

 

N/A

$5541*

N/A

N/A

 

N/A

$5569*

N/A

$11519*

See Offers

N/A

$5501*

N/A

$11451*

 

N/A

$5501*

N/A

$11451*

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
(78 Reviews)

2025 sail dates: Jan 18, Dec 21

$3819*
$273/night*
Oceanview
View Deal
$3819* luxurycruiseconnections.com $3819* luxuryonly.com $3819* dreamvacations.com
Loading itinerary...
Loading reviews...

Top positive review

Top critical review

Read all 78 Wind Surf reviews
Partners Bonus Offers Inside Oceanview Balcony Suite
 

N/A

$6019*

N/A

$11419*

See Offers

N/A

$6019*

N/A

$11419*

 

N/A

$6019*

N/A

$11419*

 

N/A

$3819*

N/A

$9519*

See Offers

N/A

$3819*

N/A

$9519*

 

N/A

$3819*

N/A

$9519*

 

N/A

$4419*

N/A

$10119*

See Offers

N/A

$4419*

N/A

$10119*

 

N/A

$4419*

N/A

$10119*

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
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 - View more ports

Wind Surf S

4.4
(78 Reviews)

2025 sail dates: Feb 01

2026 sail dates:

$2610*
$373/night*
Oceanview
View Deal
$2610* luxurycruiseconnections.com $2846* luxuryonly.com $2846* dreamvacations.com
Loading itinerary...
Loading reviews...

Top positive review

Top critical review

Read all 78 Wind Surf reviews
Partners Bonus Offers Inside Oceanview Balcony Suite
 

N/A

$3667*

N/A

$6267*

See Offers

N/A

$3667*

N/A

$6267*

 

N/A

$3667*

N/A

$6267*

 

N/A

$2610*

N/A

$5510*

See Offers

N/A

$2846*

N/A

$5746*

 

N/A

$2846*

N/A

$5746*

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
(78 Reviews)

2024 sail dates: Dec 28

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

$5519*
$394/night*
Oceanview
View Deal
$5519* luxurycruiseconnections.com $5467* luxuryonly.com $5467* dreamvacations.com
Loading itinerary...
Loading reviews...

Top positive review

Top critical review

Read all 78 Wind Surf reviews
Partners Bonus Offers Inside Oceanview Balcony Suite
 

N/A

$6419*

N/A

N/A

 

N/A

$5719*

N/A

N/A

See Offers

N/A

$5667*

N/A

N/A

 

N/A

$5667*

N/A

N/A

 

N/A

$5819*

N/A

N/A

See Offers

N/A

$5767*

N/A

N/A

 

N/A

$5767*

N/A

N/A

 

N/A

$5719*

N/A

$11519*

See Offers

N/A

$5667*

N/A

$11467*

 

N/A

$5667*

N/A

$11467*

 

N/A

$5519*

N/A

$11019*

See Offers

N/A

$5467*

N/A

$10967*

 

N/A

$5467*

N/A

$10967*

Ports

  • Philipsburg, St. Maarten
  • 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.
  • Gustavia, St. Barthelemy
View more ports

Ports

Philipsburg, St. Maarten - 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. - Gustavia, St. Barthelemy - View more ports

Wind Surf S

4.4
(78 Reviews)

2024 sail dates: Dec 28

2025 sail dates: Jan 11, Jan 25, Mar 01, Mar 08, Mar 22, Dec 28 More

$2467*
$352/night*
Oceanview
View Deal
$2467* luxurycruiseconnections.com $2519* luxuryonly.com $2519* dreamvacations.com
Loading itinerary...
Loading reviews...

Top positive review

Top critical review

Read all 78 Wind Surf reviews
Partners Bonus Offers Inside Oceanview Balcony Suite
 

N/A

$4167*

N/A

N/A

See Offers

N/A

$4167*

N/A

N/A

 

N/A

$4167*

N/A

N/A

 

N/A

$2626*

N/A

N/A

See Offers

N/A

$2626*

N/A

N/A

 

N/A

$2626*

N/A

N/A

 

N/A

$2956*

N/A

$6267*

See Offers

N/A

$2956*

N/A

$6267*

 

N/A

$2956*

N/A

$6267*

 

N/A

$3367*

N/A

$6267*

See Offers

N/A

$3367*

N/A

$6267*

 

N/A

$3367*

N/A

$6267*

 

N/A

$3517*

N/A

$6167*

See Offers

N/A

$3517*

N/A

$6167*

 

N/A

$3517*

N/A

$6167*

 

N/A

$3267*

N/A

$6167*

See Offers

N/A

$3267*

N/A

$6167*

 

N/A

$3267*

N/A

$6167*

 

N/A

$2467*

N/A

$5367*

See Offers

N/A

$2519*

N/A

$5419*

 

N/A

$2519*

N/A

$5419*

 

N/A

$2767*

N/A

$5767*

See Offers

N/A

$2767*

N/A

$5767*

 

N/A

$2767*

N/A

$5767*

 

N/A

$2767*

N/A

$5667*

See Offers

N/A

$2767*

N/A

$5667*

 

N/A

$2767*

N/A

$5667*

 

N/A

$2467*

N/A

$5367*

See Offers

N/A

$2519*

N/A

$5419*

 

N/A

$2519*

N/A

$5419*

 

N/A

$2467*

N/A

$5367*

See Offers

N/A

$2494*

N/A

$5394*

 

N/A

$2494*

N/A

$5394*

71 - 75 of 75

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