Explore Our Expertly Picked Yacht Charter Skippers

Horizon Yacht Charters have several experienced and friendly Yacht Charter Skippers and instructors. Some of their profiles are shown below – click on the relevant link for skippers in your preferred base. We’ve built up and refined our team of Yacht Charter Skippers over many years into a select group of truly outstanding individuals, all keen and happy to offer you first-class service during your charter experience.

Yacht Charter Skippers – Click to watch a Day in the Life of a Check-out Skipper.

Yacht Charter Skippers

Captain Cara – BVI Skipper and ASA Instructor

Hi, I’m Cara, a skipper and ASA sailing instructor for Horizon.

Originally from London, I grew up in Italy and have been coming to sail in BVI waters with Horizon Yacht Charters since I was a little girl.

I love getting people involved in sailing and fine-tuning their existing skills.  I decided to become a  yacht skipper and ASA sailing instructor because I want people to come away from their BVI sailing holidays having enjoyed the islands as much as I do.  I  have my ASA 201,203,204,205 and 214 certificates and also a Yachtmaster Offshore qualification so I bring a lot of experience to your holiday.  My approach is always safety, fun, and success!

Most of my sailing has been in the BVI but I also have sailing experience elsewhere.  I have sailed the majority of the Caribbean from the Grenadines to Puerto Rico and done yacht deliveries around the Caribbean, the coast of Spain, the UK, Gibraltar, from Annapolis to Bermuda and then Bermuda to the BVI. I’ve cruised Croatia and raced around the Solent in the UK, including competing in Cowes Week.

I can also tell you lots about everything you see under the water and I’ll enjoy showing you the best snorkelling spots and beaches.  I’m also a fully qualified personal trainer, PADI open water diver (and ski race trainer – just in case you need tips for the next ski season!).  I speak English, French and Italian fluently.

Before starting work for Horizon in the BVI, I competed for 10 years as an alpine ski racer as a member of the British National Team, reaching the World Cup level.  The switch from skiing to sailing felt natural for me as I moved from one outdoor environment to another.

My passion to be the best comes through in everything I do and I look forward to sailing with you.

Cara has been honoured as an ASA Outstanding Instructor of the Year 2022. This award honours the top 1% per cent of all active-status ASA Instructors. This well-deserved recognition highlights Cara’s exceptional teaching abilities and dedication to student success, making her an invaluable asset to our Horizon Sailing School.

This is what our clients had to say recently:

“Thanks so much Cara. Most incredible instructor, skipper & chill company. So glad to have met you.” – Sonnen, Remy, Peter and Natalie

“We are so happy we had Cara as our 24-hour captain. Her knowledge and calmness made our 1st day in the BVI great.” – The Gumbys

“Cara, this was such a perfect week – we are leaving with a huge amount of confidence and enthusiasm and I’m so truly thrilled to be able to take my kids on the trips that were so important to me” – Katie Schmid

“An incredible week sightseeing, snorkelling, and some great stops for overnight. Cara’s knowledge of sailing is tremendous, she answered all our questions, always made us feel safe, and was a great teacher.”

“Cara was awesome, she even gave us her personal cell phone number. She always responded to questions happily. A pleasure to have a board”

“Really liked the instructor, Cara Brown, as we all got on so well during our 9 days.” Robert Thompson

Read the interview with Captain Cara, ASA featured sailing instructor

Captain Dom – BVI Skipper and ASA Instructor

Hi, I’m Dom, a skipper for Horizon.

I’m from the UK but since starting working on yachts at 18 I haven’t looked back. I have spent my time on boats from South Africa to the Mediterranean and most recently, the BVI.

I am RYA Yachtmaster Ocean qualified, completing my training in the UK and in South Africa. My resume includes work on multiple superyachts in the Mediterranean, so I’m no stranger to excellent service, an Atlantic crossing, which gave me plenty of time to fine-tune my sailing skills and Captain on a 22m yacht based in Monaco which I safely navigated across France, Spain and Italy.

I have a range of skills from yacht maintenance to water sports and I pride myself on always giving guests a great experience in all aspects of their trip. Here are just some of his many reviews:

  1. “Fantastic time! Our skipper, Dom, was absolutely the best!” – Wade Barker

“Dom was awesome! Very knowledgeable and helpful. Explained everything in an easy-to-understand way.” – Patrick Whattey

“Captain Dom is the greatest! As is all the staff at Horizon. We had to alter our dates last minute due to a death in the family and everyone was very sympathetic and accommodating. Even prior to that incident, the whole Horizon family made our trip a breeze (no pun intended) and ensured that we had everything we needed as first-timers. Highly recommend this company.” – Nathan McElmurry

Captain Orlagh – BVI Skipper and ASA Instructor

Hi, I’m Orlagh originally from Ireland and I’m a skipper for Horizon Yacht Charters.

I have been a charter skipper since 2019 mainly based in the Mediterranean and returning back to my all-time favourite sailing destination the BVI this season. I like to have everyone involved on board with safety always being first, so if you want to learn the ropes, or just chill and relax, I got you!

I love being in the water so I’ll definitely be taking you to some of the best snorkelling spots and beaches, I’m a rescue PADI diver also so if you are interested in marine life or diving, we can go to some of the best sites.

Before starting work as a skipper, I spent five years living in the middle east as an air hostess catering for people in premium cabins, my experience in the airline industry really reflects in this role to ensure your needs and expectations are met throughout our time together.

I will also be joining the team of ASA instructors at Horizon Sailing School this season. I’m certified to teach ASA 101, 103 and 104. I’m looking forward to sharing my passion for sailing with you and getting more people certified to begin their own sailing adventures!


Recent Review:

“We’re having a great time. Our captain Orlagh was tremendous. I wanted to mention to you that she was absolutely wonderful knowledgeable, and an excellent guide and teacher. Thank you again I just wanted to make sure that we let you know that we have the highest recommendations for our captain Orlagh!! Wonderful!!”
Susan Herreid.

Captain Ciarán – BVI Skipper

Hi, I’m Ciarán, a Skipper with Horizon Yacht Charters. I’m from Ireland but have had the privilege of sailing in lots of amazing places around the world.

I studied Outdoor Adventure Management in college and became an instructor in outdoor sports such as kayaking, windsurfing, dinghy sailing and mountaineering. It’s always been a passion of mine to instruct people and share my knowledge of the outdoors.

I originally learned how to sail in Ireland and have gone on to work and sail in San Francisco, the BVIs, South Africa, Greece and the Canary Islands.

I love working on Yachts and use every opportunity I can to get in the water and to explore. I hope to give my guests as many opportunities as possible to do the same and to check out some really cool places.

“Thank you so so much for an amazing week. Not only have you been a top skipper/ DJ/ Tour guide/ dinner recommender, but you’ve been a top bloke to have with us for all the fun. We’ve loved getting to know you and hopefully we cross paths again”

“We couldn’t have asked for a better skipper! Thanks for making our tour so fun and interesting. Your skills and knowledge are beyond! We had the best time with you”

Captain Chris Simpson – BVI Skipper and ASA Instructor

Hi, I am Chris, a Skipper and Instructor for Horizon. I am more than excited and feel very privileged to be going back to my roots and my #1 vocational passion that I left in my late 20s, to pursue other avenues in the marine industry, as Operation Manager for a 50-boat charter company here in the BVI and, then later, as co-owner and Senior Yacht Broker for BVI Yacht Sales.

I first arrived in the BVI in 1985, as an instructor for Steve Colgate’s Offshore Sailing School, fell in love with the territory and was lucky enough to be able to come back here again in 1990, where I have happily lived and worked for the last 28 years with my American wife.

My passion for sailing and, then much later, teaching sailing, started when my sailing-crazy parents put me in a dinghy at the age of one! Long family summer sailing trips then became the norm, and by my late teens, I had logged thousands of offshore sailing miles. Circumstances then conspired to have my training for my RYA Yachtmaster certificate (USCG 100 Ton equivalent) and, a year later, becoming a Yachtmaster Instructor. My teacher was exceptional and infinitely inspiring, she not only instructed me to the highest standards but also noticed my aptitude for instructing my classmates. She encouraged me to get into sailing instruction which I then happily pursued for the next 8 years of my life, 4 of those as the Principal and Chief Instructor of my own sailing school.

To now have the opportunity to go back to my true vocational passion of sailing instruction is tremendous, it’s what I thrive on and so I really look forward to sailing with you. I also love to windsurf, stand-up paddle and snorkel, so I look forward to sharing my knowledge of those pastimes should you have an interest, as well as showing you the many special places that I have discovered over the majority of my life spent in the waters of the beautiful BVI.

This is what one of our clients had to say recently: “First time charting a boat and Horizon Yacht Charters delivered. From initial reservation to check out was thoroughly explained and easy to deal with. Everyone we met was helpful and friendly. The boat we chartered was clean and trouble-free for the entire week we used it. My wife and I also completed our ASA 103 and 104 with an instructor provided by HYC. Our skipper was Chris Simpson and the knowledge and confidence he possesses made the difference.

Chris’ training focus is on safety, doing things the right way and having a thorough understanding of the water. While I am still a novice skipper I feel as if I know more than a lot of the skippers that I watched during the week. If you follow his instruction you too will be a better skipper. No shortcuts and you will ensure a safe happy trip for you and your family.

If you want an instructor or just a skipper ask for Chris. You will not be disappointed.

I will recommend this charter company to my friends and family – We will be back”. Patrick Anglim – January 13th 2020.


Skippers and instructors Greg Allen

Yacht Charter Skippers: Greg Allen – St Vincent Skipper

The sea has been Greg’s passion for all his life and consequently, his chosen career.  He is extremely well qualified with his RYA Commercially Endorsed Yachtmaster and is very experienced.  Greg has worked on dive boats, as the captain of a large private yacht, and as the owner/skipper of a sports fishing tour business in St Vincent (he also worked on the set of the Pirates of the Caribbean films, as a location scout and as the Director’s boat)  In recent years, he has worked as a freelance skipper and as a delivery skipper.  He is also a PADI-qualified dive instructor and a keen fisherman.  He considers of prime importance the comfort and safety of his crew and guests alike and the immaculate condition and maintenance of whatever boat he captains. He is a relaxed, convivial captain who will make you feel at home.

“Greg is an excellent sailor/skipper! His knowledge and explanations were fantastic” ~ Kaczmarek

Skippers and instructors Brian Mascoll

Brian Mascoll – St Vincent Skipper and ASA Instructor

Brian Mascoll is an ASA-certified instructor qualified to teach courses from the basic keelboat sailing course (ASA101) through to the Bareboat cruising course (ASA104) and the Catamaran cruising course (ASA 114). From St.Vincent and the Grenadines,  Brian grew up in a small fishing village. Being so close to the waterfront, he would spend most of his free time at the beach, snorkelling and spearfishing and being around boats with his older brother and dad.  He also got involved with helping the local fishermen, and this is where he developed his love of the ocean. Brian became one of the youngest divemasters in the region and then ventured on to achieve his sailing certifications and to work as a professional skipper.  Never stopping, Brian then went on to achieve his ASA instructor qualifications and now works for us as either a skipper or ASA instructor.

“Just wanted to drop you a quick note on the trip. It was FABULOUS!! We had a fantastic time!! The boat was wonderful and Brian, our captain, was wonderful! We plan on doing another one in the future.” ~ Scrobola

Skippers and instructors Laura Hadaway

Laura Hadaway – St Vincent Charter Chef

Laura was born and raised in St. Vincent and the Grenadines, 30-something years ago (she has stopped counting) Cooking and the sea were both an integral part of her early life.

Growing up with fresh local cuisine at her disposal, she has learned to prepare food from the greatest cooks around, her grandmother and mother. As she has grown and sampled, dabbled and researched cuisines, it comes as an enjoyable ongoing learning experience for her. Sailing also runs through her blood; her grandfather captained schooners sailing in the Caribbean which explains her continuing love of sailing.

She has attained jobs as a cook or crew on charter yachts since 2004, mainly the Caribbean chain from the BVI to Grenada, not only for the experience and to build her portfolio, but just for the sheer love of doing it. Her easy-going, pleasant, witty disposition, combined with her attention to detail are just some of the attributes that continue to make her guests feel comfortable, relaxed and appreciative of their time spent with her.

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