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Windstar Cruise Deals

Expert Deal
The Price you found is a great deal, 78% lower than the average cheap cruise. Our editors have analyzed the lowest cruise pricing and found $76/night to be a bargain.
$1,599*
21 nights
Around the World Cruise Deal
Wind Surf
|
Outside Cabin
Departing
Nov 30, 2019
From Lisbon
  • Day 1
    Lisbon
  • Day 2
    Cruising
  • Day 3
    Cruising
  • Day 4
    Cruising
  • Day 5
    Cruising
  • Day 6
    Cruising
  • Day 7
    Cruising
  • Day 8
    Cruising
  • Day 9
    Cruising
  • Day 10
    Cruising
  • Day 11
    Cruising
  • Day 12
    Cruising
  • Day 13
    Cruising
  • Day 14
    Antigua
  • Day 15
    St. Maarten
  • Day 16
    Charlestown
  • Day 17
    Roseau
  • Day 18
    St. Lucia
  • Day 19
    Iles des Saintes
  • Day 20
    St. Barts
  • Day 21
    St. Kitts
  • Day 22
    St. Maarten

Wind Surf - Windstar Cruises

Pros

Laid-back yacht feel; unique watersports platform; fantastic deck barbecue; friendly crew

Cons

No balcony cabins; food and service hit and miss; stairwells and passageways feel tired

Bottom Line

Intimate seven-sail ship with low-key entertainment; needs improvements to dining options

Expert Deal
The Price you found is a great deal, 78% lower than the average cheap cruise. Our editors have analyzed the lowest cruise pricing and found $76/night to be a bargain.
$1,599*
21 nights
Around the World Cruise Deal
Wind Surf
|
Inside Cabin
Departing
Nov 30, 2019
From Lisbon
  • Day 1
    Lisbon
  • Day 2
    Cruising
  • Day 3
    Cruising
  • Day 4
    Cruising
  • Day 5
    Cruising
  • Day 6
    Cruising
  • Day 7
    Cruising
  • Day 8
    Cruising
  • Day 9
    Cruising
  • Day 10
    Cruising
  • Day 11
    Cruising
  • Day 12
    Cruising
  • Day 13
    Cruising
  • Day 14
    Antigua
  • Day 15
    St. Maarten
  • Day 16
    Charlestown
  • Day 17
    Roseau
  • Day 18
    St. Lucia
  • Day 19
    Iles des Saintes
  • Day 20
    St. Barts
  • Day 21
    St. Kitts
  • Day 22
    St. Maarten

Wind Surf - Windstar Cruises

Pros

Laid-back yacht feel; unique watersports platform; fantastic deck barbecue; friendly crew

Cons

No balcony cabins; food and service hit and miss; stairwells and passageways feel tired

Bottom Line

Intimate seven-sail ship with low-key entertainment; needs improvements to dining options

Price Trending
The price you found has dropped by 73% in the last 14 days.
-73%
$1,999*
was $7,299*
11 nights
Alaska Cruise Deal
Star Legend
|
Suite
Departing
Jul 29, 2019
From Seward
  • Day 1
    Seward
  • Day 2
    Kenai
  • Day 3
    Cruising
  • Day 4
    Sitka
  • Day 5
    Juneau
  • Day 6
    Haines
  • Day 7
    Tracy Arm (Cruising)
  • Day 8
    Wrangell
  • Day 9
    Cruising
  • Day 10
    Prince Rupert
  • Day 11
    Cruising
  • Day 12
    Vancouver

Star Legend - Windstar Cruises

Pros

Upscale, destination-driven yacht that visits off-the-beaten-path ports of call

Cons

Without sails, it lacks some of the panache of Windstar's original iconic ships

Bottom Line

Ideal for active couples seeking a romantic, small ship atmosphere

Expert Deal
The Price you found is a great deal, 73% lower than the average cheap cruise. Our editors have analyzed the lowest cruise pricing and found $96/night to be a bargain.
$2,399*
25 nights
Around the World Cruise Deal
Wind Star
|
Outside Cabin
Departing
Nov 12, 2019
From Lisbon
  • Day 1
    Lisbon
  • Day 2
    Cruising
  • Day 3
    Cruising
  • Day 4
    Cruising
  • Day 5
    Cruising
  • Day 6
    Cruising
  • Day 7
    Cruising
  • Day 8
    Cruising
  • Day 9
    Cruising
  • Day 10
    Cruising
  • Day 11
    Cruising
  • Day 12
    Cruising
  • Day 13
    Cruising
  • Day 14
    Cruising
  • Day 15
    St. Maarten
  • Day 16
    St. Barts
  • Day 17
    Virgin Gorda
  • Day 18
    Cruising
  • Day 19
    Cruising
  • Day 20
    Bonaire
  • Day 21
    Curacao
  • Day 22
    Aruba
  • Day 23
    Cruising
  • Day 24
    Cartagena (Spain)
  • Day 25
    Cruising
  • Day 26
    Colon (Cristobal)

Wind Star - Windstar Cruises

Pros

Romantic four-mast sailing ship with exceptional service.

Cons

Lack of daytime activities and nighttime entertainment.

Bottom Line

Perfect for adventurous travelers and sailing enthusiasts who prefer to go off the beaten path.

Expert Deal
The Price you found is a great deal, 73% lower than the average cheap cruise. Our editors have analyzed the lowest cruise pricing and found $96/night to be a bargain.
$2,399*
25 nights
Around the World Cruise Deal
Wind Star
|
Inside Cabin
Departing
Nov 12, 2019
From Lisbon
  • Day 1
    Lisbon
  • Day 2
    Cruising
  • Day 3
    Cruising
  • Day 4
    Cruising
  • Day 5
    Cruising
  • Day 6
    Cruising
  • Day 7
    Cruising
  • Day 8
    Cruising
  • Day 9
    Cruising
  • Day 10
    Cruising
  • Day 11
    Cruising
  • Day 12
    Cruising
  • Day 13
    Cruising
  • Day 14
    Cruising
  • Day 15
    St. Maarten
  • Day 16
    St. Barts
  • Day 17
    Virgin Gorda
  • Day 18
    Cruising
  • Day 19
    Cruising
  • Day 20
    Bonaire
  • Day 21
    Curacao
  • Day 22
    Aruba
  • Day 23
    Cruising
  • Day 24
    Cartagena (Spain)
  • Day 25
    Cruising
  • Day 26
    Colon (Cristobal)

Wind Star - Windstar Cruises

Pros

Romantic four-mast sailing ship with exceptional service.

Cons

Lack of daytime activities and nighttime entertainment.

Bottom Line

Perfect for adventurous travelers and sailing enthusiasts who prefer to go off the beaten path.

Expert Deal
The Price you found is a great deal, 71% lower than the average cheap cruise. Our editors have analyzed the lowest cruise pricing and found $100/night to be a bargain.
$1,399*
14 nights
Transatlantic Cruise Deal
Wind Surf
|
Inside Cabin
Departing
Nov 30, 2019
From Lisbon
  • Day 1
    Lisbon
  • Day 2
    Cruising
  • Day 3
    Cruising
  • Day 4
    Cruising
  • Day 5
    Cruising
  • Day 6
    Cruising
  • Day 7
    Cruising
  • Day 8
    Cruising
  • Day 9
    Cruising
  • Day 10
    Cruising
  • Day 11
    Cruising
  • Day 12
    Cruising
  • Day 13
    Cruising
  • Day 14
    Antigua
  • Day 15
    St. Maarten

Wind Surf - Windstar Cruises

Pros

Laid-back yacht feel; unique watersports platform; fantastic deck barbecue; friendly crew

Cons

No balcony cabins; food and service hit and miss; stairwells and passageways feel tired

Bottom Line

Intimate seven-sail ship with low-key entertainment; needs improvements to dining options

Expert Deal
The Price you found is a great deal, 71% lower than the average cheap cruise. Our editors have analyzed the lowest cruise pricing and found $100/night to be a bargain.
$1,399*
14 nights
Transatlantic Cruise Deal
Wind Surf
|
Outside Cabin
Departing
Nov 30, 2019
From Lisbon
  • Day 1
    Lisbon
  • Day 2
    Cruising
  • Day 3
    Cruising
  • Day 4
    Cruising
  • Day 5
    Cruising
  • Day 6
    Cruising
  • Day 7
    Cruising
  • Day 8
    Cruising
  • Day 9
    Cruising
  • Day 10
    Cruising
  • Day 11
    Cruising
  • Day 12
    Cruising
  • Day 13
    Cruising
  • Day 14
    Antigua
  • Day 15
    St. Maarten

Wind Surf - Windstar Cruises

Pros

Laid-back yacht feel; unique watersports platform; fantastic deck barbecue; friendly crew

Cons

No balcony cabins; food and service hit and miss; stairwells and passageways feel tired

Bottom Line

Intimate seven-sail ship with low-key entertainment; needs improvements to dining options

Expert Deal
The Price you found is a great deal, 71% lower than the average cheap cruise. Our editors have analyzed the lowest cruise pricing and found $100/night to be a bargain.
$1,499*
15 nights
Transatlantic Cruise Deal
Wind Star
|
Inside Cabin
Departing
Mar 25, 2020
From St. Maarten
  • Day 1
    St. Maarten
  • Day 2
    Cruising
  • Day 3
    Cruising
  • Day 4
    Cruising
  • Day 5
    Cruising
  • Day 6
    Cruising
  • Day 7
    Cruising
  • Day 8
    Cruising
  • Day 9
    Cruising
  • Day 10
    Cruising
  • Day 11
    Cruising
  • Day 12
    Cruising
  • Day 13
    Cruising
  • Day 14
    Cruising
  • Day 15
    Cruising
  • Day 16
    Lisbon

Wind Star - Windstar Cruises

Pros

Romantic four-mast sailing ship with exceptional service.

Cons

Lack of daytime activities and nighttime entertainment.

Bottom Line

Perfect for adventurous travelers and sailing enthusiasts who prefer to go off the beaten path.

Expert Deal
The Price you found is a great deal, 71% lower than the average cheap cruise. Our editors have analyzed the lowest cruise pricing and found $100/night to be a bargain.
$1,499*
15 nights
Transatlantic Cruise Deal
Wind Star
|
Outside Cabin
Departing
Mar 25, 2020
From St. Maarten
  • Day 1
    St. Maarten
  • Day 2
    Cruising
  • Day 3
    Cruising
  • Day 4
    Cruising
  • Day 5
    Cruising
  • Day 6
    Cruising
  • Day 7
    Cruising
  • Day 8
    Cruising
  • Day 9
    Cruising
  • Day 10
    Cruising
  • Day 11
    Cruising
  • Day 12
    Cruising
  • Day 13
    Cruising
  • Day 14
    Cruising
  • Day 15
    Cruising
  • Day 16
    Lisbon

Wind Star - Windstar Cruises

Pros

Romantic four-mast sailing ship with exceptional service.

Cons

Lack of daytime activities and nighttime entertainment.

Bottom Line

Perfect for adventurous travelers and sailing enthusiasts who prefer to go off the beaten path.

Expert Deal
The Price you found is a great deal, 71% lower than the average cheap cruise. Our editors have analyzed the lowest cruise pricing and found $100/night to be a bargain.
$1,499*
15 nights
Transatlantic Cruise Deal
Star Breeze
|
Suite
Departing
Feb 28, 2020
From Lisbon
  • Day 1
    Lisbon
  • Day 2
    Cruising
  • Day 3
    Cruising
  • Day 4
    Cruising
  • Day 5
    Cruising
  • Day 6
    Cruising
  • Day 7
    Cruising
  • Day 8
    Cruising
  • Day 9
    Cruising
  • Day 10
    Cruising
  • Day 11
    Cruising
  • Day 12
    Cruising
  • Day 13
    Cruising
  • Day 14
    Cruising
  • Day 15
    Cruising
  • Day 16
    Miami

Star Breeze - Windstar Cruises

Pros

Small-ship cruising, port-intensive itineraries

Cons

Limited entertainment and enrichment activities

Bottom Line

Terrific upscale yet casual cruise line for active travelers

Expert Deal
The Price you found is a great deal, 71% lower than the average cheap cruise. Our editors have analyzed the lowest cruise pricing and found $100/night to be a bargain.
$1,499*
15 nights
Transatlantic Cruise Deal
Star Breeze
|
Inside Cabin
Departing
Feb 28, 2020
From Lisbon
  • Day 1
    Lisbon
  • Day 2
    Cruising
  • Day 3
    Cruising
  • Day 4
    Cruising
  • Day 5
    Cruising
  • Day 6
    Cruising
  • Day 7
    Cruising
  • Day 8
    Cruising
  • Day 9
    Cruising
  • Day 10
    Cruising
  • Day 11
    Cruising
  • Day 12
    Cruising
  • Day 13
    Cruising
  • Day 14
    Cruising
  • Day 15
    Cruising
  • Day 16
    Miami

Star Breeze - Windstar Cruises

Pros

Small-ship cruising, port-intensive itineraries

Cons

Limited entertainment and enrichment activities

Bottom Line

Terrific upscale yet casual cruise line for active travelers

Expert Deal
The Price you found is a great deal, 71% lower than the average cheap cruise. Our editors have analyzed the lowest cruise pricing and found $100/night to be a bargain.
$1,499*
15 nights
Transatlantic Cruise Deal
Star Breeze
|
Outside Cabin
Departing
Feb 28, 2020
From Lisbon
  • Day 1
    Lisbon
  • Day 2
    Cruising
  • Day 3
    Cruising
  • Day 4
    Cruising
  • Day 5
    Cruising
  • Day 6
    Cruising
  • Day 7
    Cruising
  • Day 8
    Cruising
  • Day 9
    Cruising
  • Day 10
    Cruising
  • Day 11
    Cruising
  • Day 12
    Cruising
  • Day 13
    Cruising
  • Day 14
    Cruising
  • Day 15
    Cruising
  • Day 16
    Miami

Star Breeze - Windstar Cruises

Pros

Small-ship cruising, port-intensive itineraries

Cons

Limited entertainment and enrichment activities

Bottom Line

Terrific upscale yet casual cruise line for active travelers

Expert Deal
The Price you found is a great deal, 71% lower than the average cheap cruise. Our editors have analyzed the lowest cruise pricing and found $100/night to be a bargain.
$2,199*
22 nights
Around the World Cruise Deal
Star Legend
|
Suite
Departing
Jan 25, 2020
From San Juan
  • Day 1
    San Juan
  • Day 2
    Island of Mozambique
  • Day 3
    St. Maarten
  • Day 4
    Little Bay
  • Day 5
    St. Barts
  • Day 6
    Jost Van Dyke
  • Day 7
    Virgin Gorda
  • Day 8
    San Juan
  • Day 9
    Antigua
  • Day 10
    Cruising
  • Day 11
    Cruising
  • Day 12
    Cruising
  • Day 13
    Cruising
  • Day 14
    Cruising
  • Day 15
    Cruising
  • Day 16
    Cruising
  • Day 17
    Cruising
  • Day 18
    Cruising
  • Day 19
    Cruising
  • Day 20
    Madeira (Funchal)
  • Day 21
    Cruising
  • Day 22
    Cruising
  • Day 23
    Lisbon

Star Legend - Windstar Cruises

Pros

Upscale, destination-driven yacht that visits off-the-beaten-path ports of call

Cons

Without sails, it lacks some of the panache of Windstar's original iconic ships

Bottom Line

Ideal for active couples seeking a romantic, small ship atmosphere

Expert Deal
The Price you found is a great deal, 71% lower than the average cheap cruise. Our editors have analyzed the lowest cruise pricing and found $100/night to be a bargain.
$2,199*
22 nights
Around the World Cruise Deal
Star Legend
|
Outside Cabin
Departing
Jan 25, 2020
From San Juan
  • Day 1
    San Juan
  • Day 2
    Island of Mozambique
  • Day 3
    St. Maarten
  • Day 4
    Little Bay
  • Day 5
    St. Barts
  • Day 6
    Jost Van Dyke
  • Day 7
    Virgin Gorda
  • Day 8
    San Juan
  • Day 9
    Antigua
  • Day 10
    Cruising
  • Day 11
    Cruising
  • Day 12
    Cruising
  • Day 13
    Cruising
  • Day 14
    Cruising
  • Day 15
    Cruising
  • Day 16
    Cruising
  • Day 17
    Cruising
  • Day 18
    Cruising
  • Day 19
    Cruising
  • Day 20
    Madeira (Funchal)
  • Day 21
    Cruising
  • Day 22
    Cruising
  • Day 23
    Lisbon

Star Legend - Windstar Cruises

Pros

Upscale, destination-driven yacht that visits off-the-beaten-path ports of call

Cons

Without sails, it lacks some of the panache of Windstar's original iconic ships

Bottom Line

Ideal for active couples seeking a romantic, small ship atmosphere

Price Trending
The price you found has dropped by 71% in the last 14 days.
-71%
$2,199*
was $7,499*
20 nights
Around the World Cruise Deal
Star Pride
|
Suite
Departing
Mar 21, 2020
From San Juan
  • Day 1
    San Juan
  • Day 2
    St. Maarten
  • Day 3
    Iles des Saintes
  • Day 4
    Bequia
  • Day 5
    Grenada
  • Day 6
    St. Lucia
  • Day 7
    Cruising
  • Day 8
    San Juan
  • Day 9
    Cruising
  • Day 10
    Cruising
  • Day 11
    Cruising
  • Day 12
    Cruising
  • Day 13
    Cruising
  • Day 14
    Cruising
  • Day 15
    Cruising
  • Day 16
    Cruising
  • Day 17
    Horta
  • Day 18
    Cruising
  • Day 19
    Cruising
  • Day 20
    Cruising
  • Day 21
    Lisbon

Star Pride - Windstar Cruises

Pros

Spacious suites and bathrooms, James Beard-influenced cuisine

Cons

Ship decor appears dated in cabins and public areas; limited entertainment

Bottom Line

Intimate feel and upscale details make Star Pride a nice choice for port-intensive cruises

Expert Deal
The Price you found is a great deal, 70% lower than the average cheap cruise. Our editors have analyzed the lowest cruise pricing and found $105/night to be a bargain.
$2,199*
21 nights
Around the World Cruise Deal
Star Pride
|
Outside Cabin
Departing
Nov 28, 2020
From Lisbon
  • Day 1
    Lisbon
  • Day 2
    Cruising
  • Day 3
    Cruising
  • Day 4
    Cruising
  • Day 5
    Cruising
  • Day 6
    Cruising
  • Day 7
    Cruising
  • Day 8
    Cruising
  • Day 9
    Cruising
  • Day 10
    Cruising
  • Day 11
    Cruising
  • Day 12
    Cruising
  • Day 13
    Cruising
  • Day 14
    Cruising
  • Day 15
    San Juan
  • Day 16
    Island of Mozambique
  • Day 17
    St. Maarten
  • Day 18
    Little Bay
  • Day 19
    St. Barts
  • Day 20
    Jost Van Dyke
  • Day 21
    Virgin Gorda
  • Day 22
    San Juan

Star Pride - Windstar Cruises

Pros

Spacious suites and bathrooms, James Beard-influenced cuisine

Cons

Ship decor appears dated in cabins and public areas; limited entertainment

Bottom Line

Intimate feel and upscale details make Star Pride a nice choice for port-intensive cruises

Expert Deal
The Price you found is a great deal, 70% lower than the average cheap cruise. Our editors have analyzed the lowest cruise pricing and found $105/night to be a bargain.
$2,199*
21 nights
Around the World Cruise Deal
Star Pride
|
Inside Cabin
Departing
Nov 28, 2020
From Lisbon
  • Day 1
    Lisbon
  • Day 2
    Cruising
  • Day 3
    Cruising
  • Day 4
    Cruising
  • Day 5
    Cruising
  • Day 6
    Cruising
  • Day 7
    Cruising
  • Day 8
    Cruising
  • Day 9
    Cruising
  • Day 10
    Cruising
  • Day 11
    Cruising
  • Day 12
    Cruising
  • Day 13
    Cruising
  • Day 14
    Cruising
  • Day 15
    San Juan
  • Day 16
    Island of Mozambique
  • Day 17
    St. Maarten
  • Day 18
    Little Bay
  • Day 19
    St. Barts
  • Day 20
    Jost Van Dyke
  • Day 21
    Virgin Gorda
  • Day 22
    San Juan

Star Pride - Windstar Cruises

Pros

Spacious suites and bathrooms, James Beard-influenced cuisine

Cons

Ship decor appears dated in cabins and public areas; limited entertainment

Bottom Line

Intimate feel and upscale details make Star Pride a nice choice for port-intensive cruises

Expert Deal
The Price you found is a great deal, 69% lower than the average cheap cruise. Our editors have analyzed the lowest cruise pricing and found $107/night to be a bargain.
$1,499*
14 nights
Transatlantic Cruise Deal
Wind Star
|
Outside Cabin
Departing
Nov 04, 2020
From Lisbon
  • Day 1
    Lisbon
  • Day 2
    Cruising
  • Day 3
    Cruising
  • Day 4
    Cruising
  • Day 5
    Cruising
  • Day 6
    Cruising
  • Day 7
    Cruising
  • Day 8
    Cruising
  • Day 9
    Cruising
  • Day 10
    Cruising
  • Day 11
    Cruising
  • Day 12
    Cruising
  • Day 13
    Cruising
  • Day 14
    Cruising
  • Day 15
    St. Maarten

Wind Star - Windstar Cruises

Pros

Romantic four-mast sailing ship with exceptional service.

Cons

Lack of daytime activities and nighttime entertainment.

Bottom Line

Perfect for adventurous travelers and sailing enthusiasts who prefer to go off the beaten path.

Expert Deal
The Price you found is a great deal, 69% lower than the average cheap cruise. Our editors have analyzed the lowest cruise pricing and found $107/night to be a bargain.
$1,499*
14 nights
Transatlantic Cruise Deal
Wind Star
|
Inside Cabin
Departing
Nov 04, 2020
From Lisbon
  • Day 1
    Lisbon
  • Day 2
    Cruising
  • Day 3
    Cruising
  • Day 4
    Cruising
  • Day 5
    Cruising
  • Day 6
    Cruising
  • Day 7
    Cruising
  • Day 8
    Cruising
  • Day 9
    Cruising
  • Day 10
    Cruising
  • Day 11
    Cruising
  • Day 12
    Cruising
  • Day 13
    Cruising
  • Day 14
    Cruising
  • Day 15
    St. Maarten

Wind Star - Windstar Cruises

Pros

Romantic four-mast sailing ship with exceptional service.

Cons

Lack of daytime activities and nighttime entertainment.

Bottom Line

Perfect for adventurous travelers and sailing enthusiasts who prefer to go off the beaten path.

Expert Deal
The Price you found is a great deal, 69% lower than the average cheap cruise. Our editors have analyzed the lowest cruise pricing and found $107/night to be a bargain.
$1,499*
14 nights
Transatlantic Cruise Deal
Wind Surf
|
Inside Cabin
Departing
Apr 04, 2020
From St. Maarten
  • Day 1
    St. Maarten
  • Day 2
    Cruising
  • Day 3
    Cruising
  • Day 4
    Cruising
  • Day 5
    Cruising
  • Day 6
    Cruising
  • Day 7
    Cruising
  • Day 8
    Cruising
  • Day 9
    Cruising
  • Day 10
    Cruising
  • Day 11
    Ponta Delgada
  • Day 12
    Cruising
  • Day 13
    Cruising
  • Day 14
    Cruising
  • Day 15
    Lisbon

Wind Surf - Windstar Cruises

Pros

Laid-back yacht feel; unique watersports platform; fantastic deck barbecue; friendly crew

Cons

No balcony cabins; food and service hit and miss; stairwells and passageways feel tired

Bottom Line

Intimate seven-sail ship with low-key entertainment; needs improvements to dining options