1. Home
  2. Find a cruise
  3. Little Bay, Montserrat cruises

Little Bay, Montserrat Cruises from Windstar Cruises 22 Little Bay, Montserrat cruises

Your search Clear selections

Any Destination
All Sail Months
Any Length
Little Bay, Montserrat
Any Cruise Line
Any Ship

Close

22 cruises found

Filters Save search

Sort by

Filter by

Save search

Ports

  • San Juan, Puerto Rico
  • Charlotte Amalie, St. Thomas
  • Gustavia, St. Barthelemy
  • Little Bay, Montserrat
  • Philipsburg, St. Maarten
  • Jost Van Dyke, B.V.I.
  • Spanish Town, Virgin Gorda, B.V.I.
View more ports

Ports

San Juan, Puerto Rico - Charlotte Amalie, St. Thomas - Gustavia, St. Barthelemy - Little Bay, Montserrat - Philipsburg, St. Maarten - Jost Van Dyke, B.V.I. - Spanish Town, Virgin Gorda, B.V.I. - View more ports

Star Pride XL

4.4
(36 Reviews)

2024 sail dates:

$2699*
$386/night*
Suite
View Deal
$2699* luxurycruiseconnections.com $2699* luxuryonly.com $2699* cruisesonly.com $2699* cruises.com $2699* dreamvacations.com
Loading itinerary...
Loading reviews...

Top positive review

Top critical review

Read all 36 Star Pride reviews
Partners Bonus Offers Inside Oceanview Balcony Suite
 

N/A

N/A

N/A

$2699*

See Offers

N/A

N/A

N/A

$2699*

See Offers

N/A

N/A

N/A

$2699*

See Offers

N/A

N/A

N/A

$2699*

 

N/A

N/A

N/A

$2699*

Ports

  • Bridgetown, Barbados
  • Pigeon Island, St. Lucia
  • CRUISE THE PITONS, ST. LUCIA
  • Castries, St. Lucia
  • Kingstown, St. Vincent
  • Mayreau, Grenadines
  • St. George's, Grenada
  • Bequia, Grenadines
  • Little Bay, Montserrat
  • Terre-De-Haut, Iles Des Saintes, Guadeloupe
  • Roseau, Dominica
  • Anse Mitan, Martinique
View more ports

Ports

Bridgetown, Barbados - Pigeon Island, St. Lucia - CRUISE THE PITONS, ST. LUCIA - Castries, St. Lucia - Kingstown, St. Vincent - Mayreau, Grenadines - St. George's, Grenada - Bequia, Grenadines - Little Bay, Montserrat - Terre-De-Haut, Iles Des Saintes, Guadeloupe - Roseau, Dominica - Anse Mitan, Martinique - View more ports

Wind Spirit S

4.5
(20 Reviews)

2024 sail dates:

2025 sail dates: Jan 04, Jan 18, Feb 01

$4099*
$293/night*
Oceanview
View Deal
$4099* luxurycruiseconnections.com $4099* luxuryonly.com $4099* cruisesonly.com $4099* cruises.com $4099* dreamvacations.com
Loading itinerary...
Loading reviews...

Top positive review

Top critical review

Read all 20 Wind Spirit reviews
Partners Bonus Offers Inside Oceanview Balcony Suite
 

N/A

$4099*

N/A

$9999*

See Offers

N/A

$4099*

N/A

$9999*

See Offers

N/A

$4099*

N/A

$9999*

See Offers

N/A

$4099*

N/A

$9999*

 

N/A

$4099*

N/A

$9999*

 

N/A

$4199*

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*

 

N/A

$4299*

N/A

N/A

See Offers

N/A

$4299*

N/A

N/A

See Offers

N/A

$4299*

N/A

N/A

See Offers

N/A

$4299*

N/A

N/A

 

N/A

$4299*

N/A

N/A

 

N/A

$4399*

N/A

$10299*

See Offers

N/A

$4399*

N/A

$10299*

See Offers

N/A

$4399*

N/A

$10299*

See Offers

N/A

$4399*

N/A

$10299*

 

N/A

$4399*

N/A

$10299*

Ports

  • San Juan, Puerto Rico
  • Charlotte Amalie, St. Thomas
  • Gustavia, St. Barthelemy
  • Little Bay, Montserrat
  • Roseau, Dominica
  • Pigeon Island, St. Lucia
  • St. George's, Grenada
  • Bridgetown, Barbados
  • Charlotteville, Tobago
  • Mayreau, Grenadines
  • Soufriere, St. Lucia
  • Kralendijk, Bonaire
  • Willemstad, Curacao
  • Oranjestad, Aruba
View more ports

Ports

San Juan, Puerto Rico - Charlotte Amalie, St. Thomas - Gustavia, St. Barthelemy - Little Bay, Montserrat - Roseau, Dominica - Pigeon Island, St. Lucia - St. George's, Grenada - Bridgetown, Barbados - Charlotteville, Tobago - Mayreau, Grenadines - Soufriere, St. Lucia - Kralendijk, Bonaire - Willemstad, Curacao - Oranjestad, Aruba - View more ports

Star Pride XL

4.4
(36 Reviews)

2024 sail dates:

$3999*
$286/night*
Suite
View Deal
$3999* luxurycruiseconnections.com $3999* luxuryonly.com $3999* cruisesonly.com $3999* cruises.com $3999* dreamvacations.com
Loading itinerary...
Loading reviews...

Top positive review

Top critical review

Read all 36 Star Pride reviews
Partners Bonus Offers Inside Oceanview Balcony Suite
 

N/A

N/A

N/A

$3999*

See Offers

N/A

N/A

N/A

$3999*

See Offers

N/A

N/A

N/A

$3999*

See Offers

N/A

N/A

N/A

$3999*

 

N/A

N/A

N/A

$3999*

Ports

  • Bridgetown, Barbados
  • Little Bay, Montserrat
  • Terre-De-Haut, Iles Des Saintes, Guadeloupe
  • Roseau, Dominica
  • Anse Mitan, Martinique
  • Pigeon Island, St. Lucia
  • Castries, St. Lucia
  • CRUISE THE PITONS, ST. LUCIA
  • Kingstown, St. Vincent
  • Mayreau, Grenadines
  • St. George's, Grenada
  • Bequia, Grenadines
View more ports

Ports

Bridgetown, Barbados - Little Bay, Montserrat - Terre-De-Haut, Iles Des Saintes, Guadeloupe - Roseau, Dominica - Anse Mitan, Martinique - Pigeon Island, St. Lucia - Castries, St. Lucia - CRUISE THE PITONS, ST. LUCIA - Kingstown, St. Vincent - Mayreau, Grenadines - St. George's, Grenada - Bequia, Grenadines - View more ports

Wind Spirit S

4.5
(20 Reviews)

2024 sail dates: Dec 14

2025 sail dates: Jan 11, Feb 08

$4299*
$307/night*
Oceanview
View Deal
$4299* luxurycruiseconnections.com $4299* luxuryonly.com $4299* cruisesonly.com $4299* cruises.com $4299* dreamvacations.com
Loading itinerary...
Loading reviews...

Top positive review

Top critical review

Read all 20 Wind Spirit reviews
Partners Bonus Offers Inside Oceanview Balcony Suite
 

N/A

$4599*

N/A

N/A

See Offers

N/A

$4599*

N/A

N/A

See Offers

N/A

$4599*

N/A

N/A

See Offers

N/A

$4599*

N/A

N/A

 

N/A

$4599*

N/A

N/A

 

N/A

$4399*

N/A

N/A

See Offers

N/A

$4399*

N/A

N/A

See Offers

N/A

$4399*

N/A

N/A

See Offers

N/A

$4399*

N/A

N/A

 

N/A

$4399*

N/A

N/A

 

N/A

$4299*

N/A

$10199*

See Offers

N/A

$4299*

N/A

$10199*

See Offers

N/A

$4299*

N/A

$10199*

See Offers

N/A

$4299*

N/A

$10199*

 

N/A

$4299*

N/A

$10199*

 

N/A

$4399*

N/A

N/A

See Offers

N/A

$4399*

N/A

N/A

See Offers

N/A

$4399*

N/A

N/A

See Offers

N/A

$4399*

N/A

N/A

 

N/A

$4399*

N/A

N/A

Ports

  • Bridgetown, Barbados
  • Little Bay, Montserrat
  • Terre-De-Haut, Iles Des Saintes, Guadeloupe
  • Roseau, Dominica
  • Anse Mitan, Martinique
  • Pigeon Island, St. Lucia
View more ports

Ports

Bridgetown, Barbados - Little Bay, Montserrat - Terre-De-Haut, Iles Des Saintes, Guadeloupe - Roseau, Dominica - Anse Mitan, Martinique - Pigeon Island, St. Lucia - View more ports

Wind Spirit S

4.5
(20 Reviews)

2024 sail dates:

2025 sail dates: Jan 11, Jan 25, Feb 08

$2499*
$357/night*
Oceanview
View Deal
$2499* luxurycruiseconnections.com $2499* luxuryonly.com $2499* cruisesonly.com $2499* cruises.com $2499* dreamvacations.com
Loading itinerary...
Loading reviews...

Top positive review

Top critical review

Read all 20 Wind Spirit reviews

Ports

  • Philipsburg, St. Maarten
  • Little Bay, Montserrat
  • Roseau, Dominica
  • Castries, St. Lucia
  • Mayreau, Grenadines
  • St. George's, Grenada
  • Bequia, Grenadines
  • Anse Mitan, Martinique
  • Terre-De-Haut, Iles Des Saintes, Guadeloupe
  • Gustavia, St. Barthelemy
  • Jost Van Dyke, B.V.I.
  • Soper's Hole, Tortola, B.V.I.
  • Spanish Town, Virgin Gorda, B.V.I.
  • ROAD BAY, ANGUILLA
  • Falmouth Harbour,Antigua
View more ports

Ports

Philipsburg, St. Maarten - Little Bay, Montserrat - Roseau, Dominica - Castries, St. Lucia - Mayreau, Grenadines - St. George's, Grenada - Bequia, Grenadines - Anse Mitan, Martinique - Terre-De-Haut, Iles Des Saintes, Guadeloupe - Gustavia, St. Barthelemy - Jost Van Dyke, B.V.I. - Soper's Hole, Tortola, B.V.I. - Spanish Town, Virgin Gorda, B.V.I. - ROAD BAY, ANGUILLA - Falmouth Harbour,Antigua - View more ports

Wind Spirit S

4.5
(20 Reviews)

2026 sail dates:

$4799*
$282/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 20 Wind Spirit reviews
Partners Bonus Offers Inside Oceanview Balcony Suite
 

N/A

$4799*

N/A

$11699*

See Offers

N/A

$4799*

N/A

$11699*

See Offers

N/A

$4799*

N/A

$11699*

See Offers

N/A

$4799*

N/A

$11699*

 

N/A

$4799*

N/A

$11699*

Ports

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

Ports

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

Wind Spirit S

4.5
(20 Reviews)

2026 sail dates:

$6099*
$290/night*
Oceanview
View Deal
$6099* luxurycruiseconnections.com $6099* luxuryonly.com $6099* cruisesonly.com $6099* cruises.com $6099* dreamvacations.com
Loading itinerary...
Loading reviews...

Top positive review

Top critical review

Read all 20 Wind Spirit reviews
Partners Bonus Offers Inside Oceanview Balcony Suite
 

N/A

$6099*

N/A

$15999*

See Offers

N/A

$6099*

N/A

$15999*

See Offers

N/A

$6099*

N/A

$15999*

See Offers

N/A

$6099*

N/A

$15999*

 

N/A

$6099*

N/A

$15999*

Ports

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

Ports

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

Wind Spirit S

4.5
(20 Reviews)

2026 sail dates:

$3999*
$286/night*
Oceanview
View Deal
$3999* luxurycruiseconnections.com $3999* luxuryonly.com $3999* cruisesonly.com $3999* cruises.com $3999* dreamvacations.com
Loading itinerary...
Loading reviews...

Top positive review

Top critical review

Read all 20 Wind Spirit reviews
Partners Bonus Offers Inside Oceanview Balcony Suite
 

N/A

$3999*

N/A

$10899*

See Offers

N/A

$3999*

N/A

$10899*

See Offers

N/A

$3999*

N/A

$10899*

See Offers

N/A

$3999*

N/A

$10899*

 

N/A

$3999*

N/A

$10899*

Ports

  • Philipsburg, St. Maarten
  • Basseterre, St. Kitts
  • Gustavia, St. Barthelemy
  • Little Bay, Montserrat
  • Terre-De-Haut, Iles Des Saintes, Guadeloupe
  • Roseau, Dominica
  • Pigeon Island, St. Lucia
  • Bridgetown, Barbados
  • Anse Mitan, Martinique
View more ports

Ports

Philipsburg, St. Maarten - Basseterre, St. Kitts - Gustavia, St. Barthelemy - Little Bay, Montserrat - Terre-De-Haut, Iles Des Saintes, Guadeloupe - Roseau, Dominica - Pigeon Island, St. Lucia - Bridgetown, Barbados - Anse Mitan, Martinique - View more ports

Wind Spirit S

4.5
(20 Reviews)

2026 sail dates:

$3999*
$286/night*
Oceanview
View Deal
$3999* luxurycruiseconnections.com $3999* luxuryonly.com $3999* cruisesonly.com $3999* cruises.com $3999* dreamvacations.com
Loading itinerary...
Loading reviews...

Top positive review

Top critical review

Read all 20 Wind Spirit reviews
Partners Bonus Offers Inside Oceanview Balcony Suite
 

N/A

$3999*

N/A

$10399*

See Offers

N/A

$3999*

N/A

$10399*

See Offers

N/A

$3999*

N/A

$10399*

See Offers

N/A

$3999*

N/A

$10399*

 

N/A

$3999*

N/A

$10399*

Ports

  • Philipsburg, St. Maarten
  • Basseterre, St. Kitts
  • Gustavia, St. Barthelemy
  • Little Bay, Montserrat
  • Terre-De-Haut, Iles Des Saintes, Guadeloupe
  • Roseau, Dominica
  • Pigeon Island, St. Lucia
  • Bridgetown, Barbados
View more ports

Ports

Philipsburg, St. Maarten - Basseterre, St. Kitts - Gustavia, St. Barthelemy - Little Bay, Montserrat - Terre-De-Haut, Iles Des Saintes, Guadeloupe - Roseau, Dominica - Pigeon Island, St. Lucia - Bridgetown, Barbados - View more ports

Wind Spirit S

4.5
(20 Reviews)

2026 sail dates:

$2399*
$343/night*
Oceanview
View Deal
$2399* luxurycruiseconnections.com $2399* luxuryonly.com $2399* cruisesonly.com $2399* cruises.com $2399* dreamvacations.com
Loading itinerary...
Loading reviews...

Top positive review

Top critical review

Read all 20 Wind Spirit reviews
Partners Bonus Offers Inside Oceanview Balcony Suite
 

N/A

$2399*

N/A

$5899*

See Offers

N/A

$2399*

N/A

$5899*

See Offers

N/A

$2399*

N/A

$5899*

See Offers

N/A

$2399*

N/A

$5899*

 

N/A

$2399*

N/A

$5899*

11 - 20 of 22

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