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Bank Holiday Sailing Weekend on the Isles of Scilly

  • Vessel: Pettifox
  • Where: St Mary's, Isles of Scilly
  • Duration: 4 days
  • Embark: St Mary's - 27 August 2022, 11:00
  • Disembark: St Mary's - 30 August 2022, 14:00
Per person price (whole boat charter only max. 4 guests £1470)£367.50 £91.88

Meet Pettifox in the Isles of Scilly for a short break private charter experience 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 a small group 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, bedding and water, tea and coffee while onboard. Your Skipper will set you up for your day with a continental style breakfast, inclusive of breads, cereals, fruit, jams and spreads, yoghurt and perhaps a fresh pastry or two!

With five inhabited islands, Pettifox will spend the week being 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 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 take a picnic! Finished up with 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 a small group 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 making it perfect for young families wanting to learn more about life on the water. Below deck, she has four single berths with two extra child berths available on request.

Bed & Breakfast

A continental style breakfast with water, tea and coffee is included in the charter price. All other food, soft and alcoholic drinks must be provided by the guests. 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 beach BBQ! 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 island’s suppliers to be delivered and waiting for on arrival. 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 a small group of friends or family, Pettifox is our fleet’s smallest boat 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 cooking your own meals are easy 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 quarters 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


  • What COVID policies are in place for sailing with Pettifox?

    There are currently no Test & Sail policies in place for the 2022 season.

  • 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?

    No; a continental breakfast is offered by the Skipper. All other meals are to be eaten ashore at the guests expense.

  • 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.

  • Do I need to tip the crew?

    Tips are not mandatory but are welcomed by the crew!

  • Is there WIFI?

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

  • Can I charge my phone/Camera?

    When the boat is connected to shore power or the generator is on. Solar chargers can be a great alternative.

  • 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


Penzance has some long stay parking options dedicated for those visiting The Scillies. Try Scilly Parking, Isle of Scilly Travel or Isles of Scilly Parking.


Penzance train station is minutes from both Penzance Harbour and the Heliport. There are direct trains with Great Western Railway from Plymouth, Exeter St Davids, Cardiff Central and London Paddington into Penzance.


Newquay Airport requires taking either a taxi to Redruth Train Station and then the train to the end of the line at Penzance, or a taxi direct to Penzance.


Fly by helicopter with Penzance Helicopters from Eastern Green, Penzance, direct to St. Mary’s.

Or fly by fixed wing plane from Exeter, Newquay or Land’s End arriving into St. Mary’s with the Isle of Scilly Skybus.


The Scillonian III passenger ferry is operated by Isle of Scilly Travel from Penzance once a day. 


There are plenty of places to stay in Penzance. Try Chapel House Hotel, The Dock Inn or Hotel Penzance.


There are a number of places to stay on St Mary’s. Try Schooners Hotel, St Mary’s Hall Hotel or Westford House Bed & Breakfast.


There are a number of options for lunch and dinner across The Scillies, and we’d be happy to make recommendations before your holiday begins or Johnny the skipper, can help you with reservations whilst you’re there. Alternatively, you may wish to take advantage of eating onboard Pettifox for all meal times. In this case, there are a number of island stores to get stocked up for your trip, with the majority being on St Mary’s.

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