Skippered Sailing Holidays

Your pace. Your skipper. As laid back as you like.

Enjoy a different kind of beach holiday.

Wake up to a new beach view every day, where you spend your afternoons kayaking across blue lagoons, snorkelling around turquoise coral reefs and end your day sampling the best local cuisine at a different restaurant every night.

A perfect choice for families, couples and friends, skippered holidays allow you to be as carefree as you want. A holiday where you set the pace and plan your own itinerary; from a relaxed island-hopping cruise to an exhilarating blue water adventure where you can be as hands on as you like coasting in Croatia’s gentle morning breeze. Or, let your skipper take the helm, leaving you to relax and enjoy Greece's fresh, local cuisine in it's historic landmarks. It’s completely up to you.

Request a call back

Click on the link below and our Holiday Planners will contact you at your convenience

Our RYA accredited Skippers have unrivalled local knowledge and sailing expertise to ensure you get the most out of your holiday on the water.  And, hiring a skipper is easy. You have the flexibility to hire for the whole holiday, or, pay by a daily rate on top of your charter fees.

Skippers can be booked online or over the phone with our friendly Holiday Planners at the time of booking, or later, subject to availability. All you need to do is provide your skipper with their own cabin, and ensure there are food and drink provisions on board for both you and your skipper. You can choose invite your skipper to join you at meal times or enjoy quality time with your friends and family on board. We also offer provisioning services with everything you and your skipper may need, so it’s ready and waiting for your arrival at the base.

When choosing your yacht, please ensure that it is big enough to accommodate your skipper - they must have their own cabin

Our skippered holidays


Dubrovnik, Croatia

  • Gentle winds and occasional Mistrals
  • Rich history and spectacular scenery
  • Line-of-sight navigation and island hops
Flotillas Experience level 1 ICC RYA
Explore Dubrovnik, Croatia
Hvar Town, Hvar Island

Marina Agana, Croatia

  • Easy line-of-sight sailing
  • Short island hops and longer trips
  • Explore quiet islands and national parks
  • Discover Croatia's rich and two-millennia old history
Flotillas Experience level 1 ICC RYA Sailing school
Explore Marina Agana, Croatia

Athens, Greece

  • Ancient relics and ruins
  • Exciting blue water sailing
  • Catch the famous Meltemi wind
Experience level 2-3 ICC
Explore Athens, Greece

Corfu, Greece

  • Ideal for sailors of all abilities
  • Coastal sailing and open passages
  • Fine wines of Paxos and Antipaxos
Experience level 1-2 ICC
Explore Corfu, Greece
Ithaca, Greece

Lefkas Sailing Holidays

  • Easy, rewarding sailing
  • Sail the famous Heptanese Islands
  • Enjoy fantastic watersports
Flotillas Experience level 1-2 ICC Sailing school
Explore Lefkas Sailing Holidays

Sardinia, Italy

  • Excellent food and wine
  • Glamorous resorts and quiet anchorages
  • Dynamic sailing off famous Costa Smerelda
Flotillas Experience level 2 ICC RYA
Explore Sardinia, Italy
Procida, Italy

Procida, Italy

  • Perfect for experienced sailors
  • Gateway to the famous Amalfi Coast
  • Luxurious resorts, bustling towns, quiet villages
Flotillas Experience level 2 ICC RYA
Explore Procida, Italy
Aeolian Islands

Portorosa, Italy

  • Relaxed sailing with consistent winds and volcanic islands
  • Clear, warm waters ideal for snorkelling
  • Spectacular black sand beaches
  • Europe’s second largest active volcano
  • UNESCO-protected Aeolian Islands.
Flotillas Experience level 2 ICC RYA
Explore Portorosa, Italy

Antigua sailing holidays

  • Excellent wreck and reef diving
  • Blue water sailing in steady trade winds
  • A stunning beach for each day of the year
Experience level 2
Explore Antigua sailing holidays
The Bahamas

Abacos, Bahamas

  • Beautiful beaches
  • Famous wreck dive spots
  • Blissed-out year-round sailing
Experience level 2
Explore Abacos, Bahamas
Tobacco Cay Belize


  • Sheltered sailing within a barrier reef
  • Consistent coastal trade winds to exploit
  • Incredible rainforests and Mayan ruins
Experience level 3 ICC RYA
Explore Belize

British Virgin Islands

  • Visit a real-life Treasure Island
  • Steady trade winds, calm currents
  • World-famous yachting destinations
Experience level 1
Explore British Virgin Islands

Grenada sailing holidays

  • Exciting blue water sailing
  • Warm, yearlong trade winds
  • Excellent diving and snorkelling
Experience level 3
Explore Grenada sailing holidays

St. Martin sailing holidays

  • Blue water and coastal sailing
  • World-class diving and snorkelling
  • Glamorous resorts and laid-back beaches
Experience level 2-3
Explore St. Martin sailing holidays
St. Lucia

St. Lucia Sailing Holidays

  • Year-round trade winds
  • Unique, delicious local cuisine
  • Stunning mountainous, rainforest isle
Experience level 3
Explore St. Lucia Sailing Holidays

Mahé, Seychelles

  • Remote, largely unexplored islands
  • Stable, stronger winds ideal for experienced sailors
  • Good diving, snorkelling and sport fishing
Experience level 3 ICC RYA
Explore Mahé, Seychelles

Vavau, Tonga

  • Exotic, colourful marine life
  • Excellent diving, snorkelling and fishing
  • Blue water sailing, remote island hopping
Experience level 2
Explore Vavau, Tonga

Skippered Charters: Questions answered and myths busted

Our skippers can be added to any of our bareboat or flotilla charters for your entire trip or just a day two, whichever suits you.

 Skippers can come in handy and fulfil a number of different roles and should be considered if you don’t have a sailing certificate or if it’s been a good few years since you were at the helm.

You may have a first mate who just prefers sunbathing to getting fenders ready or has to much on their hands keeping the children occupied.

A skipper can also benefit you if you have been hoisting your own sails for decades and just want a little help and support with some of the more physical aspects of keeping a yacht moving under sail.

Below are some commonly asked questions about the finer details that come up when considering a skipper and the answers to help you decide what’s right for you.

Will the skipper always be in charge to the yacht, can I do any sailing?

Our skippers will be officially in charge of taking care of handling the yacht. Though depending on your level of sailing experience you can do as much or as little as you like, including taking the helm, so long as the skipper feels it is safe to do so. Please note that skippers will take pride in the presentation of the yacht but they are not cooks, cleaners or maids.

Where will the skipper sleep?

Skippers must generally be allocated a stern cabin to themselves for the duration of your charter, though occasionally the bow can be agreed upon. Anything outside of this normal arrangement may be agreed upon with discretion before you book your charter but please assume your skipper will need a cabin in the stern.

What/ how do we feed our skipper?

That’s entirely up to you. If you’re planning to pre-order all of your food online then remembers to buy enough to accommodate the skipper.

If you’re planning to provision when you arrive then speak to your skipper when you meet them to find out what they like or don’t like and can or can’t eat.

You may invite your skipper to dinner and they may accept or choose to stay aboard. If there is no food aboard and you do not want your skipper to come with you then you can give them ‘pocket money’ so that they can pop in to their favourite local haunt. They’ll only ever be a phone call away should you need them.

What does the skipper do in the evening?

Again, that’s entirely up to you as every group is different and interacts with with people in different ways. Rest assured our skippers are professionals who are comfortable at meeting new people and adept at reading different social situations.

If you invite your skipper to be part of the fun in the evening they may accept or choose to stay on the yacht and wait for your return. You may find that your skipper is an early riser who bunks down early after a long day’s sailing.

Do we have to tip our skipper?

We do recommend and it is customary that you tip your skipper. A guideline amount would be 15-20% of your skipper fee, though as this could encompass quite a range, we leave it at your discretion and ask that you offer the gratuity you think your skipper deserves. We’re sure they’ll add immense value to your charter experience.

Will the skipper speak English?

Our skippers are of mixed nationalities, but all of them will speak English to a level that will mean your holiday is not impeded in any way, and the vast majority will speak excellent English and generally be excellent communicators.

You could have a French national skippering you out in St Martin or find a proud Lancastrian at the helm in Athens. You may find a native Virgin Islander taking you under his wing in Tortola, but all of them will speak English to a more than acceptable level.

How much value does a skipper add?

A fully qualified, commercially endorsed and experienced sailor, with tonnes of local knowledge to share with you. Our skippers will help you benefit from the best places to moor up, eat out and the best times to visit certain places. They can teach you new things about sailing, help you rediscover confidence at the helm, provide an extra pair of hands and handle the heavy lifting for you.

Can we have a skipper for flotilla holidays?

Yes – if you’re new to sailing, want someone else to take care of manoeuvring your yacht, or simply want a helping hand or regional expert aboard, then you can hire a skipper to join you on the flotilla. If you’re travelling alone or as a pair, and don’t need the whole yacht to yourselves, you can even charter by the cabin to join a flotilla with a skipper and crew of up to 8 others. Click here or call 03303321503 for more information