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020 8004 3003 
- Destinations
- Inspiration
- Our Yachts
- Our Yacht Charters
- Request a Quote
- Currency GBP
- USD
- AUD
- NZD
- GBP
- USD
Destination
Duration
Adults: 2
Amazing Sailing Holidays
with a Skipper, by Seamaster
Rated 4.9/5 by guests just like you.
Your money is ABTA and ATOL Protected
Not all Holidays are Created Equal. Here’s Why Ours are So Special
Our skippered yacht charters are a special experience. Spend a week or two on board your own private yacht skippered by an exclusive Seamaster Skipper, exploring the Mediterranean Sea. We’ll take you from island to island, where you’ll dine in traditional restaurants, and explore local villages where you’ll swim in idyllic coves, . Get involved in the sailing as much (or as little) as you want, and be as active as you want, with days filled with paddle boarding, snorkelling, and swimming. You’ll love it.
What to expect The Holiday Experience
Enjoy a wonderful holiday with a Seamaster skipper who is also your personal guide, ensuring you experience the very best of our incredible destinations.
- Gently explore a sailing area on your own yacht, blending adventure, luxury, activity, and relaxation.
- Spend your days tucked away in idyllic bays - swim, snorkel, paddleboard, explore the shore, sunbathe, relax, and lunch on fresh local produce.
- Hoist the sails and experience a quiet, relaxing way to travel with short-hop sailing legs. You can join in the sailing as much, or as little, as you like.
- Each evening, arrive in a new village to explore cobbled streets, enjoy the local vibe, and dine on authentic cuisine at a local taverna.
How it works Life Onboard
Our sailing holidays offer a safe, stress-free escape, letting you relax and soak in the many unforgettable experiences on offer.
- Think of your boat as a floating villa that moves, with bedrooms, bathrooms, kitchen andmultiple lounges, indoor and out.
- Your skipper is responsible for the sailing, ensuring a safe and comfortable environment and isa personal a guide for your trip
- The itinerary is always tailored to you. We provide inspiration and recommendations, and then help curate a bespoke route to match your personal preferences
- You’ll enjoy breakfast and lunch on board, with a larger initial shop topped up from local markets, delis, and bakeries along the way
- Evenings are spent exploring traditional villages, where you’ll typically eat out in a local taverna or restaurant
What makes our Skippered Yacht Charters Amazing
Incredible sailing holiday experiences for each and every guest. It's at the heart of everything we do.
Tailored itineraries
Quality yachts
Amazing experience
Exclusive crew
Protected and trusted
I can only describe this type of holiday as a trip of a lifetime (that you'll want to do again and again!) and I've been on a lot of holidays!
Sarah R.
2024
I would definitely recommend Seamaster - the whole booking process was both friendly and efficient.
Sandra S.
2023
I love how the skippers knew the areas like the back of their hands and recommended restaurants that we wouldn't have heard of otherwise.
Victoria B.
2022
The kids absolutely loved our sailing holiday. Swimming, exploring, sailing, and ever-changing stimulus. Just perfect.
Michael F.
2023
If you ski in winter, then should sail in summer. This holiday is a perfect summer holiday for all skiers.
Greta A.
2024
We came into this process with absolutely no knowledge whatsoever, now after one holiday we’re experts! Lol.
Leticia L.
2022
Thanks so much to Tim and his team, you made the whole experience an absolute joy.
Amanda M-J.
2021
OMG, I cried when we left the boat and our wonderful crew. The boat, the destination, but most importantly, the crew, made our holiday so special.
Jade P.
2024
The perfect holiday for a diverse and demanding teenage crew!
Eric T.
2021
Seamaster looked after us so well during the whole COVID debacle. Thank you Seamaster for saving our summer holiday!
George K.
2021
I was worried as I get a bit sea-sick but shouldn’t have. As Tim said, this was a ‘champagne sailing holiday’.
Emma H.
2023
Our boat was stunning, exactly what we needed and more. Thank you Seamaster for all your help and advice.
David D.
2024
This was our third sailing holiday, and all have been with Seamaster. They really look after us and we won’t book anywhere else!
Alex D.
2024
We had such an amazing family holiday. Eating, drinking, swimming, exploring, and plenty of sunbathing! Just what we needed.
Alice G.
2022
Thanks to Oz and Rebecca, our wonderful crew. They made our holiday that much more special with their care and attention.
Jame-Lee R.
2024
We love to help, it's kinda our thing
We're real people with proper expertise, waiting to share this with you to ensure the most incredible holiday you can imagine. Don't wait, get in touch.
How to create an Awesome Sailing holiday
1. Know Yourself
2. Choose a Destination
Search by Country or Region
Even within a country the sailing experience can differ greatly, so the goal should be to research and then target a specific region that fits your preferences. If you’re unsure on the specific region, search by holiday preference.
Search by Holiday Preference
Not sure where to sail? Then use our unique holiday preference search to follow our expert recommendations. Search family-friendly sailing holidays, off the beaten track, great nightlife and more, to compare across different destinations.
Ask a Seamaster Expert
You don’t need to do this alone. We love to curate skippered sailing holidays for our guests that ensure that you experience the best destination suited to your unique individual preferences. Get in touch for a bespoke quote!
3. Choose a Yacht
Yacht Size
Firstly, book a boat with enough cabins to fit your group and the skipper, where the skipper has their own cabin. From there, increasing the length of a boat will give you more space and comfort, so generally the bigger the better!
Yacht Age
Generally, older yachts are cheaper than newer yachts due to cosmetic wear and tear, much like buying a car. Going slightly older could get more boat for your buck, but all things being equal, book the newest boat in your budget.
Catamaran vs. Yacht
Think of cats as villas and yachts as apartments. Cats offer significant space throughout with great indoor/outdoor flow. Sailing yachts cost less than cats and offer a purer ‘sailing as an experience’ holiday, especially with the sails up.
Yacht features
Boats come with differing features and specifications, which can make a huge difference. Use our search filters to focus on the features that are important to you. Our favourites are air-con, generator, teak cockpit, BBQ, and watermaker.
Yacht Price
Our yacht search system is uniquely designed to compare yachts and help you discover incredible deals on sailing holidays. Filter the results and view the corresponding boat prices in real time.
4. Before & After Booking, We’re here for you
Enjoy our 360 degree service
We assist our guests from the first time they visit our website to the time they step back on home soil after an incredible holiday. From advising on the right holiday, to transfers, itineraries, restaurant recommendations, and provision of our incredible skippers and hosts. We do it all.
The Seamaster Yacht Selection
Why Seamaster is Your Only Choice
Excellence isn’t a choice. It’s who we are.
Tailor-Made for You
We don’t do one-size-fits-all. Every trip is crafted for you—down to the finest detail. The right yacht, the perfect destination, and an itinerary that feels effortless.
Our Guests Love Us
We’ve mastered the art of seamless family vacations. No stress, no worries—just unforgettable moments. Sit back, we’ve got you covered.
100% Safe. 100% Trustworthy.
Don’t take the risk. Book with Seamaster with free cancellation and your money is fully protected by ABTA and ATOL. You holiday, we handle the rest.
Best Price Guarantee
We are proof that a great product needn’t cost more. If you find a better price elsewhere, we’ll match it, and keep your money safe. Don’t risk your hard-earned cash.
Frequently Asked Questions
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