United Kingdom · August


The perfect combination of Bucket List sailing and sights, with the opportunity for some real adventure sailing including a long passage



Sail Scotland in 2023! Join us on our Scottish Isles Sailing Adventure, departing Oban for 10 days and explore some of Scotland’s most iconic islands by yacht with Jim Dobie. We think this is the perfect combination of bucket List sailing and sightseeing. Real, hands-on sailing including a long passage to visit the UNESCO heritage site at St Kilda and through the Pentland Firth. We will combine some night sailing as well as some evenings, at anchor, allowing us to enjoy time ashore in the sleepy harbour villages along the coast. Jim Dobie is a hugely experienced Skipper and RYA Yachtmaster Examiner meaning you can use the trip to brush up on sailing skills, with plenty of time for one to one mentoring, or simply enjoy being part of the voyage. With a maximum of six crew aboard our comfortable yacht, you will have space to relax and plenty of opportunity to adapt the itineary to the groups wishes.


Comfortable Yacht

Comfortable Yacht

a large , comfortable and practical cockpit she has an uncluttered layout with high quality teak finishes in the cockpit. The twin wheels allow a choice of comfortable helming positions and easy viewing when berthing. She’s comfortable and beautifully kitted out with 8 berths, so there’ll be plenty of space on board. She’s perfect for long trips. You’ll have your own berth.

Highly experienced Skipper

Highly experienced Skipper

Jim Dobie will be your Skipper for the duration of the trip. A hugely experienced Skipper and RYA Yachtmaster Examiner who has sailed almost every ocean of the world. Jim is a well-respected training skipper and examiner, known for his patience and ability to share his passion for ocean sailing with those around him.

Scenic, Adventurous Sailing

Scenic, Adventurous Sailing

Our trip starts (and ends) in Oban, Scotland. We plan to visit Tobomory, Skye (or Col) and St Kilda as well as Fingals cave. Fabulous sailing with incredible destinations!


Jim Dobie

Jim Dobie

A hugely experienced Skipper and RYA Yachtmaster Examiner who has sailed almost every ocean of the world, leading expeditions to some of the remotest places including the Galapagos, Cook Islands, French Polynesia and Tasmania. Jim is experienced, not only on, but also under water, as a Scuba Diving Instructor delivering expeditions to the Great Barrier Reef, Oceania and Asia.

Jim has a long history of successful race campaigns including  skipper for the 09-10 Clipper Round the World Yacht Race, competed in five Sydney to Hobart races, two Fastnet races, Round Britain and Ireland Race and many other offshore race events 


This is a rough guide to our itinerary - the actual route will depend on the weather and preferences of the crew




Day 1 - Thursday

Join us at 1pm for a welcome on board. Meet your fellow crew and your skipper, Jim Dobie. 

Once you're introduced to your cabin, we will complete a full safety brief and yacht orientation.

Dinnner will either be on board, or if preferred, we can head into Oban where there are plenty of restaurants to chose from.


Day 2 - Friday

We depart Oban and will route towards Tobermory under sail. This is a nice 23 nautical mile trip and perfect to ease into the adventure ahead.

You will become comfortable with handling the yacht under Jim's expert supervision with plenty of time to ask questions and practice or learn your sailing skills.


Day 3 - Saturday

After breakfast, either on board or ashore, we will have time to explore this charming village. We will set sail late afternoon, heading towards Rum and then on to either the isle of Skye or Coll. This is around 80miles of sailing which will put us into harbour late in the evening.


Day 4 - Sunday

After a morning exploring the Isle of Skye, we will depart and head through sound of Harris  - a narrow channel between the isle of Harris and the national scenic area of Uist. The sound is the main sea passage through the Hebridean archipelago and the various reefs and islets make this a great exercise in passage planning. Depending on the crews wishes we may sail overnight towards St Kilda.


Day 5 - Monday

Weather permitting, we will continue our sail towards Saint Kilda, the isolated archipelago of volcanic islands that lie 40 miles to the west of the main archipelago chain. With the highest sea cliffs in Britain, St Kilda is the most important sea bird breeding station in north west Europe. Sailing to St Kilda is a truly magnificent experience with wildlife and the glorious isolation of the North Atlantic all around us.


Day 6 - Tuesday

From St Kilda, we will sail to the isle of Iona, probably sailing overnight to arrive in the morning. We will then anchor in the Iona sound which will permit us to go ashore and spend a day visiting the ancient abbey and exploring this symbolic centre of Scottish Christianity.


Day 7 - Wednesday

Departing Iona in the morning, we will sail towards the uninhabited island of Staffa, famous for the mighty sea cave known as Fingal's Cave. The natural basalt columns give the cave a unique atmosphere and it is famous for its acoustics - however, the sea state is often rough in this area meaning we may not venture too close! 


Day 8 - Thursday

Flexible day - we always leave space in the itinerary for weather or other amends to the plan - don't worry, you will be doing something lovely!


Day 9 - Friday

From Fingals cave, we will sail back towards Oban - a wonderful passage that will give us plenty of ocean mileage under sail. We will arrive in Oban towards the late afternoon, just in time for dinner ashore and to share experiences of a wonderful adventure. 


Day 10 - Saturday

After a final breakfast on board, it will be time to say our goodbyes.

What's Included

What's Included

All food and drink (non-alcoholic) on board

Safety equipment including life-jackets.

All mooring and port entry fees for the boat.

• Hands on sailing, watch keeping, helming and opportunity to fully immerse in life on board.

Overnight accommodation onboard, your own bunk and bedding

• Waterproof Clothing available to hire

• Travel to and from Oban

• Meals Ashore

• Entrance fees to visitor centres or distilleries

• Sailing & Travel Insurance

You'll Be Staying Here

Big Blue

Big Blue

Big Blue is a Beneteau Oceanis 523. Spacious, comfortable and well equipped she is a powerful but easily handled yacht. 

In Big Blue we cover the ground quickly which leaves more time for exploring ashore or sailing further. `Big Blue` is very well equipped for offshore sailing and carries a paddle board and inflatable kayak for exploring the anchorages you will visit.

We have 4 sleeping cabins, one is for the Skipper and the others consist of 1 large double and 2 smaller double cabins. All three can be converted into twin cabins -  the bunks can be divided by lee cloths if preferred. 

 All cabins are en-suite. Bedding is provided. On board comfort is a priority - the layout offers privacy and there are heating outlets in all cabins.


We design the trips for a wide range of experience which that means that even if you’ve not sailed, our experienced Skippers will ensure you have a fantastic time

The longer legs will suit “mile builders” who already have some sailing qualifications, and we can spend time supporting you with everything from helming to sail trimming or passage planning as you wish!

Before you join, we’ll ask you about your previous sailing experience and what you want to get out of the trip. That way, we’ll tailor the tour to your specific needs

The group size is kept very small on our trips which gives you a real ‘masterclass’ with our highly experienced Skippers However, that means each place is valuable and we need full groups

We ask for a 10% deposit to secure your berth, with the balance being due 6 weeks before departure

If you cancel your place over 6 weeks out, we’ll retain the deposit, but no other fees will be due

If you cancel 6 weeks or less, the full price will be payable

We’ll share with you a kit-list which will be adapted to the trip you’re taking

A good sleeping bag and some decent deck shoes (or sailing boots) are the main things to organise, otherwise it’s layers of clothing adapted to the conditions you’re likely to encounter

Bring a camera – if you want to bring a drone, let us know beforehand and bear in mind drones tend not to be waterproof and are carried / used at your own risk!

We want everyone to get the most out of their time on board – so we’ll work around your wants

However, our trips are designed for you to take an active role – that means, for example, we’ll take turns in cooking (all the menus are planned already and step by step instructions given, so you don’t need to be a masterchef!)

You can get tips and instruction on all aspects of sailing from our Skippers and get as involved as you want, grinding, trimming, helming and learning – on the other hand, there’s also plenty of time to relax and just take in the beautiful Ocean scenery. It’s your trip!

We aim to do some night sailing (sailing under the stars is amazing!) so we will run a watch system.


August 18 - 27 2024

FROM$2,955.62 /pp $3,940.82 /pp

August 16 - 25 2025

FROM$3,940.82 /pp


United Kingdom · August · 9 nights

$3,940.82 /pp