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Windstar Cruise Deals

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
Transatlantic 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
Transatlantic 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 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

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 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

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
|
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, 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

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
|
Outside 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

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 $108/night to be a bargain.
$2,799*
26 nights
Transatlantic Cruise Deal
Wind Star
|
Inside Cabin
Departing
Mar 14, 2020
From Colon (Cristobal)
  • Day 1
    Colon (Cristobal)
  • Day 2
    Cruising
  • Day 3
    Cartagena (Spain)
  • Day 4
    Cruising
  • Day 5
    Cruising
  • Day 6
    Aruba
  • Day 7
    Curacao
  • Day 8
    Cruising
  • Day 9
    Cruising
  • Day 10
    Virgin Gorda
  • Day 11
    St. Barts
  • Day 12
    St. Maarten
  • Day 13
    Cruising
  • Day 14
    Cruising
  • Day 15
    Cruising
  • Day 16
    Cruising
  • Day 17
    Cruising
  • Day 18
    Cruising
  • Day 19
    Cruising
  • Day 20
    Cruising
  • Day 21
    Cruising
  • Day 22
    Cruising
  • Day 23
    Cruising
  • Day 24
    Cruising
  • Day 25
    Cruising
  • Day 26
    Cruising
  • Day 27
    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, 69% lower than the average cheap cruise. Our editors have analyzed the lowest cruise pricing and found $108/night to be a bargain.
$2,799*
26 nights
Transatlantic Cruise Deal
Wind Star
|
Outside Cabin
Departing
Mar 14, 2020
From Colon (Cristobal)
  • Day 1
    Colon (Cristobal)
  • Day 2
    Cruising
  • Day 3
    Cartagena (Spain)
  • Day 4
    Cruising
  • Day 5
    Cruising
  • Day 6
    Aruba
  • Day 7
    Curacao
  • Day 8
    Cruising
  • Day 9
    Cruising
  • Day 10
    Virgin Gorda
  • Day 11
    St. Barts
  • Day 12
    St. Maarten
  • Day 13
    Cruising
  • Day 14
    Cruising
  • Day 15
    Cruising
  • Day 16
    Cruising
  • Day 17
    Cruising
  • Day 18
    Cruising
  • Day 19
    Cruising
  • Day 20
    Cruising
  • Day 21
    Cruising
  • Day 22
    Cruising
  • Day 23
    Cruising
  • Day 24
    Cruising
  • Day 25
    Cruising
  • Day 26
    Cruising
  • Day 27
    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, 67% lower than the average cheap cruise. Our editors have analyzed the lowest cruise pricing and found $114/night to be a bargain.
$2,399*
21 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
  • Day 16
    Antigua
  • 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, 67% lower than the average cheap cruise. Our editors have analyzed the lowest cruise pricing and found $114/night to be a bargain.
$2,399*
21 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
  • Day 16
    Antigua
  • 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, 66% lower than the average cheap cruise. Our editors have analyzed the lowest cruise pricing and found $120/night to be a bargain.
$1,799*
15 nights
Transatlantic Cruise Deal
Star Legend
|
Outside Cabin
Departing
Feb 01, 2020
From San Juan
  • Day 1
    San Juan
  • Day 2
    Antigua
  • 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
    Madeira (Funchal)
  • Day 14
    Cruising
  • Day 15
    Cruising
  • Day 16
    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, 66% lower than the average cheap cruise. Our editors have analyzed the lowest cruise pricing and found $120/night to be a bargain.
$1,799*
15 nights
Transatlantic Cruise Deal
Star Legend
|
Suite
Departing
Feb 01, 2020
From San Juan
  • Day 1
    San Juan
  • Day 2
    Antigua
  • 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
    Madeira (Funchal)
  • Day 14
    Cruising
  • Day 15
    Cruising
  • Day 16
    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, 65% lower than the average cheap cruise. Our editors have analyzed the lowest cruise pricing and found $123/night to be a bargain.
$1,599*
13 nights
Transatlantic Cruise Deal
Star Pride
|
Outside Cabin
Departing
Mar 28, 2020
From San Juan
  • Day 1
    San Juan
  • 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
    Horta
  • Day 11
    Cruising
  • Day 12
    Cruising
  • Day 13
    Cruising
  • Day 14
    Lisbon

Star Pride - Windstar Cruises

Pros

Service-driven, laid-back luxury, with longer visits in lesser-known ports of call

Cons

Lacks big ship bells and whistles

Bottom Line

Great for active couples looking for romance on a sophisticated ship