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Island Windjammers Family Cruises Cruise Reviews

Island Windjammers
Departure Port

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Cruise type

Romantic Cruises


Family Cruises


First-Time Cruisers


Group and Theme Cruises


Senior Cruises


18 Island Windjammers Family Cruises Cruise Reviews

cdkeppel avatar


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 ...
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2 photos

Sail Date July 2018

kpb468 avatar


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 ...
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Sail Date April 2018

ryansetssail avatar


1 Review Written

4 Helpful Votes

Amazing Relaxed Sail with Intimate Setting

We had an amazing time aboard the Vela! My wife and I traveled down to Saint Lucia the day before and stayed in the quaint town of Marigot Bay, where Vela was located. We met the crew the day of the sail and I knew ...
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Sail Date January 2018

kathy glenn avatar

kathy glenn

1 Review Written

1 Helpful Vote

They will bend over backwards!

We won our first Cruise on Diamant in an auction. 7 years later we took our college age children on the cruise. I cannot express how amazing it is to work with these people in setting up a cruise. They answer ...
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Sail Date August 2017

enicozmo avatar


1 Review Written

The best way to sail! Amazing islands and lovely crew!

Fantastic crew performance. Absolutely stellar captain. He was funny and entertaining, as well as professional/knowledgable. None could be better.World class crew, that caters to your every need.The owner cabin was ...
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Sail Date July 2017

LAnnab avatar


1 Review Written

5 Helpful Votes

Sail Away!

I love tall masted ships and always have. Four years ago, I was so lucky to find a company that continued the tradition of simple but comfortable sailing in the Caribbean. Island Windjammer has 3 wonderful ships ...
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Sail Date June 2017

DPJ46 avatar


1 Review Written

1 Helpful Vote

Another Fantastic Island Windjammers Sagitta Cruise

As usual, an excellent sailing experience aboard the Sagitta, with a great itinerary and a comfortable mix of sailing and island visits. It is so nice to be able to work with a crew who are as professional, ...
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Sail Date January 2017

staledale avatar


1 Review Written

1 Helpful Vote

Great relaxing week & great staff

Family of 4 traveling with two teens. Looking into long-term sailing and just getting our feet wet in the sailboat world. This cruise was extremely relaxing with enjoyable ports of call and a stellar staff. With ...
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Sail Date December 2016

AndrewSchoening avatar


1 Review Written

1 Helpful Vote

We would do it again!

I have been interested in a windjammer cruise for years and finally convinced my family. After looking at several options we chose Island Windjammers, and could not have enjoyed our trip more. I should say that the ...
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Sail Date June 2015

SailorJM avatar


3 Reviews Written

16 Helpful Votes

The Newly Renovated Diamant: Wow!

My husband and I have sailed on Island Windjammers’ tall ship Diamant 3x before, and love her. First, let me say we much prefer cruising on tall ships, with their intimate atmosphere (no crowds, no lines!), ...
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Sail Date November 2016

daffydoc avatar


1 Review Written

4 Helpful Votes

Casual relaxation with continual pampering!

My husband and I traveled on Windjammer Barefoot cruises in the 1990's and 2000's, and loved the casual atmosphere, amazing Caribbean scenery, and the thrill of sailing on a tall ship. We've been watching Island ...
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Sail Date October 2016

lucygoosey1971 avatar


1 Review Written

13 Helpful Votes

Amazing, Unique Sailing Experience

My 9 year old son and I had a fabulous experience aboard the Vela in the British Virgin Islands. We are "adventure travelers" and were looking for something a bit outside the norm. We prefer small, personalized, ...
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Sail Date June 2016

stobrien avatar


1 Review Written

Our Island Windjammer Experience

We were greeted by the staff with smiles and open arms. My boyfriend and I were one of six couples. We are both 26 and the ages ranged up into the 60's. This was our first cruise of this style. We had read several ...
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Sail Date November 2015

luckydux avatar


1 Review Written

25 Helpful Votes

Feeling the Vela Vibes

This was our second trip with an Island Windjammers ship. In December 2014 we enjoyed our time on the Sagitta so much that we signed up for a January 2016 week on the Vela without hesitation. The Vela has been ...
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Sail Date January 2016

19turkeys avatar


1 Review Written

4 Helpful Votes

Better Than the Old Windjammer Barefoot Company

My wife & I sailed The Mandalay in 1990 and had a wonderful experience. I decided that, since her death, I needed to add another sail to my bucket list. Through Internet research I found Island Windjammers, and they ...
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Sail Date November 2015

VRMullins avatar


1 Review Written

3 Helpful Votes

2 Amazing Vacations with Island Windjammers

This was my 2nd Island Windjammer Cruise and I enjoyed it just as much as the first one although the experiences were different. Both captains and the crew were outstanding! My recent cruise was on Sagitta which is ...
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Sail Date December 2015

RkyMtCCRN avatar


1 Review Written

Island Windjammer Trip Report – S/V Diamant – The Grenadines

Friday, 06Aug2010: Travel Day (RDU-MIA-SJU-GND): Finally time to head to the Caribbean again to sail on a Tall Ship!! Traveled to Grenada (all day 6am to 9:03pm) and was met by the Island Windjammers driver at the ...
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Sail Date August 2010

jumprope avatar


1 Review Written

1 Helpful Vote

Awesome trip, especially for our grandsons, ages 13, 14, 15 16, 17.

This was perfect for our family. The grandsons were totally all about using the rope swing off the side of the ship, paddle boarding, snorkeling, kayaking, night time swimming with the underwater lights, visiting ...
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Sail Date June 2018

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