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

Diamant

Caribbean - Southern

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 ...

3 photos

Sail Date March 2019

Greema

1 Review Written

Caribbean Delight

Diamant

Caribbean - Southern

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 ...

3 photos

Sail Date March 2019

ruefdad

1 Review Written

Fantasy

Diamant

Caribbean - Southern

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

Diamant

Caribbean - Southern

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

IWJ Sailor

2 Reviews Written

3 Helpful Votes

Fantastic 12 days

Diamant

Caribbean - Southern

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.

Diamant

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 ...

3 photos

Sail Date January 2019

mbpharmd1

1 Review Written

2 Helpful Votes

Diamant - Diamond of the Grenadines

Diamant

Caribbean - Southern

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 ...

1 photo

Sail Date June 2018

kimmerz281

1 Review Written

No Smiles Spared!

Diamant

Caribbean - Eastern

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

inthewatersomewhere

1 Review Written

Best vacation ever!

Diamant

Caribbean - Western

My husband and I have always talked about taking a windjammer cruise and we hit the jackpot with Island Windjammers. We had planned on 2 nights in Grenada before we boarded the Diamant, but because of weather delays ...

8 photos

Sail Date January 2018

kathy glenn

1 Review Written

1 Helpful Vote

They will bend over backwards!

Diamant

Caribbean - Southern

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 ...

Sail Date August 2017

No regrets

1 Review Written

4 Helpful Votes

Magical and Idlyllic Week on Island Windjammer's Diamant

Diamant

Caribbean - Southern

Where do I start, and what wonderful things can I say that haven’t already been said by other passengers on this ship, my home for the week I was lucky enough to sail on her? After reading so many of the ...

Sail Date July 2017

enicozmo

1 Review Written

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

Diamant

Caribbean - Southern

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 ...

Sail Date July 2017

TESutko

2 Reviews Written

11 Helpful Votes

Island Windjammers - Diamant

Diamant

Caribbean - Southern

What a great time - one of the two best weeks of my life (the other was the preceding week on Island Windjammers Vela). Sailing Diamant was a last minute change as I had originally been scheduled to sail Vela on ...

Sail Date May 2017

sbl

1 Review Written

Like a dream

Diamant

Caribbean - Southern

We just came back from a 6 day cruise on Diamant. From the very first moment when Monja welcomed us in Port Louis till the last minute when we sadly had to leave Diamant it has been an incredible trip. ...

Sail Date April 2017

Allan Levine

1 Review Written

RELAXATION

Diamant

Caribbean - Eastern

Great food and service, lovely crew. LOVED our stateroom. Diamant is a goldie-locks ship: not too big not too small. ten passengers only. Highlights were swimming with the sea turtles and waking up to dawn in ...

Sail Date February 2017

vickster6834

1 Review Written

1 Helpful Vote

Best Cruise Ever!!!

Diamant

Caribbean - Southern

We wanted a cruise that was NOT with 3000 of our closest friends but that was small, intimate and personal - did we ever hit the jackpot with Island Windjammers and the Diamant! Everything from the moment we were ...

Sail Date February 2017

SailorJM

3 Reviews Written

16 Helpful Votes

The Newly Renovated Diamant: Wow!

Diamant

Caribbean - Southern

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!), ...

2 photos

Sail Date November 2016

KJR209

1 Review Written

3 Helpful Votes

Trip of a Lifetime on the Diamant

Diamant

Caribbean - Southern

Our first experience on a sailing cruise so we chose Island Windjammers because they offered a 12 night trip on a boat that appeared intimate so as not be just a number in a crowd. This trip far exceeded our ...

2 photos

Sail Date May 2016

Wendi Forster

1 Review Written

4 Helpful Votes

An Amazing Trip on the Island Windjammer Diamant

Diamant

Caribbean - Southern

The trip was everything that I imagined a tall ship cruise to be. We had incredible weather, saw some wonderful sights and incredible beaches, but the trip was made by the crew. Everyone of the crew members did ...

Sail Date April 2016

likeboats

3 Reviews Written

10 Helpful Votes

Great Trip on the Diamant

Diamant

Caribbean - Southern

My wife and I took numerous trips on the old Windjammer fleet in the 1980's and 1990's. We have chartered catamarans in the BVIs and Leeward Islands, and sail our own boat in Lake Michigan. This was our first trip ...

1 photo

Sail Date March 2016

dolphindave1

2 Reviews Written

4 Helpful Votes

Fantastic Voyage, WOW!

Diamant

Caribbean - Eastern

This was our first cruise with Island Windjammers and on the sailing schooner Diamont. It was everything we had hoped for and more! We wanted to sail, and we did. Everyday we had daytime sailing and it was just ...

Sail Date February 2016

jerryclarkpgh

1 Review Written

3 Helpful Votes

Ultimate Cruise

Diamant

Caribbean - Southern

Spent 6 nights on Island Windjammer's Diamant sailing from Grenada to several stops in the south Caribbean. We had been on quite a few large ship cruises, but this was only 11 passengers and 6 crew. Best cruise ...

12 photos

Sail Date February 2016

stobrien

1 Review Written

Our Island Windjammer Experience

Diamant

Caribbean - Eastern

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 ...

Sail Date November 2015

dmleuzzi

1 Review Written

3 Helpful Votes

Windward Islands - Diamant

Diamant

Caribbean - Southern

Very first cruise -- I am not your ordinary "lounge by the pool" type of person. I like to meet people, hear their story and build relationships. I like to go to places not normally visited and seriously dislike ...

Sail Date February 2016

Diamant Ratings

Category	Editor	Member
Cabins	3.0	4.8
Dining	3.0	5
Entertainment	2.0	4.7
Public Rooms	4.0	5
Fitness Recreation	1.0	4.8
Family	1.0	N/A
Enrichment	1.0	4.9
Service	3.0	5
Value For Money	3.0	5

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