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Five Island Sailing in the Isles of Scilly

  • Vessel: Pettifox
  • Where: Isles of Scilly
  • Duration: 4 days
  • Embark: St Mary's - 21 June 2022, 11:00
  • Disembark: St Mary's - 24 June 2022, 14:00

Meet Pettifox in the Isles of Scilly for a bed & breakfast whole boat charter exploring the beauty of the islands under sail.

Arrive in St Mary’s, the capital island of the Isles of Scilly. Pettifox will be waiting in the harbour for her guests to arrive so you won’t need to chance the sea crossing from Cornwall if that level of adventure isn’t for you!

Setting the Sails

The Isles of Scilly boasts a plethora of dramatic, rugged coastlines – steep rock faces and deep inlets caused by the continuous pounding of huge rollers coming in from the Atlantic Ocean. These stunning islands feature large stretches of deserted white sandy beaches, dramatic rocky coves, stunning seascapes, amazing archaeological sites, beautiful walks and scenery along miles of coastal and country paths and nature trails.

This sailing holiday in the Isles of Scilly is perfect for small groups of friends or family who want to use Pettifox as their exclusive sailing boat to explore this beautiful archipelago.  Your ticket price includes full use of Pettifox, her qualified Skipper to sail you around the coast, all bedding, drinking water and tea and coffee while onboard. You will also be provided with a continental style breakfast each day which includes, breads, cereal, fruit and yoghurt.

With five inhabited islands, Pettifox will be your base as you explore the magic of the Scillies. Sail around and anchor at each island as you spend the day discovering the very different personality that each has to offer.


Five Islands of Scilly

St Mary’s is the Isles of Scilly’s largest island and the gateway to the rest of the islands. Covering an area a little more than 6 square miles, it’s still not exactly bustling but with its air and sea links, it’ll to be your first port of call.

St Agnes is the southernmost and smallest populated island of the Isles of Scilly and is totally unspoilt and astonishingly peaceful. An island of extreme contrasts, with rocky outcrops on its exposed western side to serene beaches with the tranquillity of the sandbar between St. Agnes and Gugh on the other side.

Bryher is the smallest of the inhabited island on the Scillies it has some beautiful walks and scenery and just 80 people are lucky enough to call it home.  An opportunity, perhaps, to drop you off by tender to either Bar or Church Quay to let you stretch your legs and explore the island on foot – don’t forget to ask the cook for a picnic! A stop off at Hell Bay Hotel or the Fraggle Rock Pub for a light refreshment is a must

Tresco is the second largest of the islands and a subtropical gem home of the famous Abbey Garden, established in the 1830s by Augustus Smith. This horticultural paradise hosts a spectacular collection of more than 20,000 exotic plants from all corners of the world – many of which cannot be grown anywhere else in Britain.

St Martin is marked with its red and white Daymark erected in 1683. St Martins is just two miles long yet it has some of the finest beaches in the British Isles.

The choice is yours…

Your Skipper knows these islands well and can certainly point you in the right direction, take you to secret spots off the beaten track or moor up in St Mary’s while you see what the shops have to offer. Whatever you want from your Isles of Scilly sailing holiday – the choice is entirely yours!

Family Friendly

Pettifox is well suited to families or small groups of friends who are looking for a secluded sailing holiday exploring the Isles of Scilly. No experience is needed to climb aboard – Pettifox is an easy rig to sail so is perfect for young families wanting to learn more about life on the water. Below decks, she has four single berths with two extra child berths available on request.

Bed & Breakfast

A continental style breakfast with drinking water, tea & coffee is included in the charter price. All other food and canned soft/alcoholic drinks must be provided by the guest. Pettifox will act as your base for your sailing holiday and guests are welcomed to shop ashore at St Mary’s and use the boat’s galley for cooking or eat ashore on the islands – maybe even a BBQ on the beach! Johnny the Skipper can help you with your food shop once you’ve dropped your luggage at the boat, or even pre-order from some of the islands suppliers to be delivered and waiting for you when you arrive.  Alternatively, guests are welcome to bring food/drinks with them on the ferry or plane. Full details of food and drink options on the islands will be given to guests when booking.


Simply click “Enquire Now” to reserve your berth for five days whilst you sort your travel plans. No booking form or deposit is required until you are ready to book!


Guest berths: 4 Rig: Gaff Cutter

Pettifox was built on the Isles of Scilly in 1992. She was the last classic wooden boat of her kind to be built on the islands and is still sailing and exploring the Cornish coasts today. Offering guests a chance to experience life under sail in arguably one of the most beautiful sailing locations of the UK.

Perfect for small groups of family or friends, Pettifox is one of our fleet’s smallest but has been finished to a high standard, comfortably sleeping 4 guests.

Her easy rig makes her a dream to sail and the perfect boat to get involved with. Her Skipper Johnny has been sailing all his life making him the perfect guide to learning the ropes. That being said, she can be sailed single-handedly so if you simply want to sit back, relax and inhale that fresh sea air while taking in the views, that’s just fine too!

Below decks have been recently revamped to better use her space and offer guests a bijou but comfortable experience. A well-designed galley means home-cooked meals are top of the menu and you can sit back and enjoy them on her beautifully bespoke oak plank table or perhaps on deck under the stars.

Sleeping arrangements are cosy with two single bunks in the fore cabin and two single bunks set back in the saloon. Two smaller bunks can be made available for children should you wish to bring the whole family. The crew have separate sleeping corners and there is a toilet and pull out shower onboard too.

With consideration given to energy supply and consumption, she has even been set up to accommodate “off-grid” living so she can comfortably visit those remote locations with not a soul in sight.

She spends her sailing season with voyages exploring the coasts of Cornwall with a stint in the Isles of Scilly where you can fly direct to St Mary’s and meet her straight over there giving you maximum time to explore the islands!

More about Pettifox


  • Is there an age limit for children?

    We would recommend 5+ but this can be dependent on family experience so please check with the office.

  • Are all meals included?

    Yes, all meals onboard are included in the price, except on Isles of Scilly voyages where 2 meals are to be eaten ashore at the guests expense. (Breakfast, Lunch, Dinner and hot drinks) Alcohol is not included.

  • Can you cater for dietary needs?

    Yes, Vegetarian diets can be accommodated. Please let us know at the time of booking of other dietary needs.

  • What language is spoken onboard?


  • What are the sleeping arrangements?

    4 adult berths (2x fore cabin bunks, 2x saloon bunks), a further 2 child bunks can be made available as needed.

  • How many toilet/showers does she have?

    1 bathroom with a pull out shower.

  • Is there an age limit?

    Voyage dependent. Please check with the office.

  • Is there WIFI?

    No, but you should easily be able to reach 3G/4G from the shore.

  • Can I charge my phone/Camera?


  • Are bedding and towels provided?

    Bedding, yes - Towels, no

  • Are there life jackets provided?


  • Are Waterproofs provided?

    No, please bring your own.

  • Do I need sailing experience?

    No, absolutely not! Just a lust for adventure and a want to get actively involved.

  • Will I be sea sick?

    Everyone reacts differently but we recommend if you are at all worried to take some medication 24 hours before departure.


From: St Mary's

To: St Mary's

Getting There:

Unlike our other Isles of Scilly voyages, Pettifox will be ready and waiting for you on the island of St Mary’s. You’ll need to get either the Scillonian from Penzance or the Skybus from Newquay Airport.

Click here for the Scillonian

Click here for the Skybus

Both deliver directly to St Mary’s so you will either need to walk around the harbour or get a short taxi ride from the airport.

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