Skippered Yacht Charter

Your Skipper. Your pace.

Enjoy a skippered sailing vacation where a professional captain takes the helm leaving you to completely sit back and relax away from the helm. Whether you're new to sailing or an expert looking for a chance to relax, a skippered vacation allows you to decide how you spend your sailing days.

You can decide to hire a Skipper for a day or two, or for your entire charter vacation.  Our friendly, professionally qualified and experienced Skippers are available at any of our destinations sharing expert local knowledge and sailing expertise aboard one of our world-class yachts. 

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Skippered Charters: Frequently asked questions

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 fulfill a number of different roles and should be considered if you don’t have a sailing certificate or if it’s been a few years since you were at the helm.

A Skipper is also a good option if you want to first mate or only Captain part of your adventure.

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 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. 

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 should be agreed upon with discretion before you book your charter.

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

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 remember to buy enough to accommodate your Skipper.

If you’re planning to provision when you arrive, then we suggest you speak to your Skipper when you meet to find out what he or she likes and dislikes and any dietary restrictions.

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 with 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. 

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 vacation is not impeded in any way.

How much value does a Skipper add?

Our skippers will help you benefit from the best places to moor up, eat out and the best times to visit certain places. They are fully qualified, commercially endorsed and are experienced sailors with extensive local knowledge to share with you. They can teach you 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 vacations?

Yes – if you’re new to sailing, want someone else to take care of maneuvering your yacht, or simply want a helping hand or regional expert aboard, then you can hire a Skipper to join you on a 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 888 350 3568 for more information

Our skippered vacations


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

  • 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

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, Greece

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

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

Amalfi Coast, Procida

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

Portorosa, Italy

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


  • 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
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

The British Virgin Islands

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

Grenada yacht charter

  • Exciting blue water sailing
  • Warm, yearlong trade winds
  • Excellent diving and snorkeling
Experience level 3
Explore Grenada yacht charter

St. Martin yacht charter

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

St. Lucia yacht charter

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

Mahé, Seychelles

  • Remote, largely unexplored islands
  • Strong winds ideal for experienced sailors
  • Good diving, snorkeling and sport fishing
Experience level 3 ICC RYA
Explore Mahé, Seychelles
Sunsail Tahiti view pier catamaran


  • Year-round trade winds
  • Excellent fishing, kayaking and snorkelling
  • Dozens of remote, exotic islands to explore
Experience level 2 ICC RYA
Explore Tahiti


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


  • Ancient fishing villages
  • Exotic beauty and idyllic islands
  • World-class diving and snorkeling
Experience level 2
Explore Thailand