Island Windjammers Cruise Reviews

As someone who is very uncomfortable in large crowds, I knew a cruise on a large liner was not ever going to be my cup of tea. On the other hand, sailing with a total of 23 passengers and 10 crew sounded like just ...

1 photo

Sail Date February 2020

Rowan813

4 Reviews Written

8 Helpful Votes

Another great week

This was our third trip on Island Windjammers, second out of Grenada and first on Vela. We already loved the islands and Windjammer style. Vela was new to us. We were in love with Sagitta, but Vela was as similar as ...

Sail Date October 2019

dpq695

1 Review Written

1 Helpful Vote

The boat was great and so is the company!

Caribbean - Western

My wife (32) and I (31) chose this cruise to go on our honeymoon. My dad and stepmom had gone on the old barefoot windjammer's and I always thought the trip sounded incredible. This company did not disappoint! The ...

5 photos

Sail Date March 2019

SailawayMary1

1 Review Written

Personal touch makes a sailing vacation first class

Smaller sailboat, personal attention, only 9 passengers, great food, beautiful beaches. That’s why I just took my 3rd trip on an Island Windjammer boat. I’ve tried all 3 sailboats in their fleet and each one has ...

Sail Date March 2019

Greema

1 Review Written

Caribbean Delight

This was my first time sailing. A friend encouraged me to go and vowed that once I sailed on the Diamant I would be back. She was right. I cannot wait to go again. I cannot say enough lovely things about this ...

Sail Date March 2019

ruefdad

1 Review Written

1 Helpful Vote

Fantasy

We chose the Island Windjammer's Diamant for the 3rd time in 5 years as we can't find anything better! It's all about relaxing for us and just unwinding from the hustle of job and home-life. The crew of this boat ...

Sail Date March 2019

Ruefmom

1 Review Written

Great Escape

Island Windjammers continues to deliver! We just took our 4th trip with them and had a fabulous time. With an intimate five cabins, plus crew, this is the way to see the Caribbean up close and personal. The ...

Sail Date March 2019

5Stringer

2 Reviews Written

7 Helpful Votes

Bucket List Trip!

Caribbean - All

Island Windjammer had been on my bucket list for quite a few years, and we finally had the opportunity to join the Vela and cruise the windward islands from St. Lucia. Admittedly, we have cruised the mega ships ...

Sail Date January 2019

IWJ Sailor

2 Reviews Written

3 Helpful Votes

Fantastic 12 days

This was one of the greatest sails we have ever had. Twelve days of being pampered and taken care of and sailing south bound from St Lucia and ending in Grenada. The crew consisted of Captain, Engineer, Chef, ...

Sail Date January 2019

Candace McManus

1 Review Written

1 Helpful Vote

The most amazing adventure I have ever been on.

Caribbean - Western

I have been home for 3 days but my heart is still on the beautiful Windjammer Diamant. I will never ever forget this amazing trip from St. Lucia to Granada. I could have never imagined how very well I would be ...

Sail Date January 2019

VBP

1 Review Written

3 Helpful Votes

A wonderful ship and an excellent crew

Caribbean - All

We chose this cruise because of the ship and the destinations. Vela is a very beautiful, three masted tall-ship. She takes a maximum of 26 passengers with a crew of 10. We had very personal service from the ...

Sail Date January 2019

Barnacle Tim

1 Review Written

8 Helpful Votes

Unforgettable Barefoot Sail

It has been a many-decades long dream of mine to sail the Caribbean. I never quite got around to it when I was young enough to captain my own sailboat. As we are all aware, such fantasies are rarely matched by the ...

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Sail Date August 2018

cdkeppel

1 Review Written

1 Helpful Vote

A casual cruise with crew that made you feel at home.

A casual cruise experience with a small crew and passenger count. Our ship was 24 passenger with 9 crew. All the crew was very interactive with the passengers and made you feel completely comfortable. The food ...

2 photos

Sail Date July 2018

Spanky0800

1 Review Written

4 Helpful Votes

A Great Experience!

Caribbean - All

This week's holiday began in St Lucia and Rodney Bay where I would meet up with the ship, cruise mates and crew of Vela of Island Windjammer. I had the opportunity to spend a day and night in the Rodney Bay area ...

Sail Date June 2018

mbpharmd1

1 Review Written

2 Helpful Votes

Diamant - Diamond of the Grenadines

This was our third trip on the Diamant and our first with our two 14 year old girls. We have had nothing but unbelievable trips with Island Windjammers but we were a bit nervous with our girls since there isn’t a ...

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Sail Date June 2018

LillianMC

2 Reviews Written

4 Helpful Votes

Our 40th Anniversary on Sagitta

Although it's been a year+ since we cruised on Sagitta, reading these reviews is bringing back many great memories. We decided to splurge and do something extra special for our 40th anniversary. Neither one of us ...

Sail Date March 2017

Hutchie52

1 Review Written

1 Helpful Vote

Wonderful ship, amazing staff, new friends!

Caribbean - Western

For my 60th birthday I decided I would go on a trip I had always wanted to try - I decided one week before that birthday and the support staff of IW could not have been more helpful. The trip itself was just ...

4 photos

Sail Date May 2018

kimmerz281

1 Review Written

No Smiles Spared!

Our 10th anniversary was coming up. We didn't want to sit on a beach because we live near one. We didn't want to visit a floating city either, but we wanted to see the Caribbean. I remember the Barefoot Cruise ...

7 photos

Sail Date April 2018

BAKES1

1 Review Written

An adventure I will never forget

We chose the cruise because of the more intimate nature of a smaller ship. The Vela is a beautiful sailing ship and is approximately 156 feet long. We were able to access ports that larger ships could not. Chef ...

2 photos

Sail Date April 2018

kpb468

1 Review Written

3 Helpful Votes

I forgot I had a job and didn't know what day it was... Best Vacation EVER

I have only great things to say about my 1st experience with Island Windjammers and I will certainly be back! I have not stopped smiling since I have been home. I have been to many different places and on many ...

5 photos

Sail Date April 2018

SailorBee

1 Review Written

One of my all time favourite vacations

I've been on larger cruise ships and I've also chartered monohulls and catamarans with friends in the Caribbean, Croatia and Thailand. I love sailing on smaller ships and knew for my 50th Birthday I wanted a sun, ...

Sail Date February 2018

hcarruth

2 Reviews Written

28 Helpful Votes

Excellent experience from beginning to end.

This was my fourth experience over two years with Island Windjammers, though this was my first trip on Sagitta. My previous trips were on the Vela. I found the overall experience very similar. Common to all my ...

Sail Date February 2018

dolphindave1

2 Reviews Written

4 Helpful Votes

Another fantastic voyage!

This was our 4th cruise on Island Windjammers. We absolutely loved them all and plan to do another next year. We've done 2 on the "Diamant" and now 2 on the "Vela". This review is posted for the "Vela" northern ...

Sail Date February 2018

CanuckSailors

1 Review Written

3 Helpful Votes

Trip of a Lifetime!

As the Medical Officers on Amazing Grace of the previous Windjammer Barefoot Cruises fleet 20 years ago, my husband and I were able to visit all of the tall ships of that fleet as well as many of the islands visited ...

Sail Date January 2018

micheler56

2 Reviews Written

4 Helpful Votes

Best way to see the Islands and enjoy great company