Day 1 – York and the Yorkshire Dales Read Less: Day 1
York and the Yorkshire Dales
Meet your Wilderness guides at York Train Station at 11:00 am this morning and transfer to the edge of the Yorkshire Dales. Over lunch in a local pub, chat with your fellow riders and listen to a brief about the adventure ahead. Afterwards, set off on a lovely route that explores the Nidderdale Area of Outstanding Natural Beauty and ribbons its way to the village of Leyburn. Ride through Wensleydale before crossing into the Yorkshire Dales National Park and Swaledale Valley. Your destination this evening is a friendly local inn, where you can unclip and enjoy the first of many delicious dinners.
Meals Included: Lunch and Dinner
Ride Details: 37 km / 23 miles | 585 m / 1,919 ft

Day 2 – Yorkshire and the Tour de France Read Less: Day 2
Yorkshire and the Tour de France
In 2014, Yorkshire was the proud host of the Grand Départ for the Tour de France. Today’s route follows much of Stage 1 of the 2014 tour and allows you to test yourself on the amusing Anglo-French climbs of the Côte de Buttertubs (532m) and Côte de Cray (416m). The ride passes through some of England’s most picturesque scenery, typical of the Yorkshire Dales. Although one of the most challenging days of the trip, the rewards are ample. By the time the village of Malham is reached, some of the best routes found anywhere in the UK will have been ridden.
Meals Included: Breakfast, Lunch and Dinner
Ride Details: 82 km / 51 miles | 1,319 m / 4,327 ft

Day 3 – Yorkshire Dales to the Forest of Bowland Read Less: Day 3
Yorkshire Dales to the Forest of Bowland
Enjoy a relaxing start this morning after yesterday’s big ride. After a hearty breakfast, the Yorkshire Dales National Park will be left behind, crossing into Lancashire and heading to the Forest of Bowland. Lancashire is the geographic centre of Great Britain, which seems a fitting place to pedal through on your five countries tour. A late lunch will be enjoyed in the pretty village of Waddington, and from here, the journey continues south to Oswestry, close to the English and Welsh border.
Meals Included: Breakfast, Lunch and Dinner
Ride Details: 35 km / 22 miles | 425 m / 1,394 ft

Day 4 – Crossing the Border into Wales Read Less: Day 4
Crossing the Border into Wales
This morning, head west into Wales. Central and North Wales are relatively mountainous, offering great cycling opportunities. Passing through the rolling valleys of the east, the Milltir Cerrig mountain pass presents a challenge when entering Eryri (Snowdonia) National Park. However, the climb of 300 m/900 ft is steady, and the increasingly impressive views provide motivation. The descent of over 8 km/5 miles is exhilarating and leads to lunch at the beautiful Bala Lake. The second half of the day takes you through increasingly wild Welsh scenery on roads ideal for bike riding. Climbing higher into Eryri National Park, your destination awaits at the end of an amazing descent into Ffestiniog.
Meals Included: Breakfast, Lunch and Dinner
Ride Details: 76 km / 47 miles | 1,160 m / 3,806 ft

Day 5 – Eryri (Snowdonia) and Dublin Read Less: Day 5
Eryri (Snowdonia) and Dublin
The second day in Wales begins in the mountains of Eryri. In the morning, pass through many mountain villages rich in history and Welsh mythology. Continuing west, the ride’s destination is the town of Caernarfon, home to an impressive castle overlooking the Menai Straits. After a late lunch and time to explore, transfer to the Isle of Anglesey and the port of Holyhead, where the journey across the Irish Sea begins. It’s just over 2 hours by ferry to Dublin, after which you will head to your accommodation and settle in for the evening.
Meals Included: Breakfast, Lunch and Dinner
Ride Details: 51 km / 32 miles | 707 m / 2,320 ft

Day 6 – Rest Day in Dublin Read Less: Day 6
Rest Day in Dublin
After five days of pedalling, your adventure is now about halfway through. The cosmopolitan capital of Dublin provides an excellent place for a break from riding. Head out to stroll through the historic streets, relax in one of the city’s many cafés, or perhaps even check in for a massage. Very easy to explore on foot, it’s a great opportunity to enjoy the change of pace and give your hair a break from the helmet. Tonight, settle down to a relaxed dinner and maybe a pint of Guinness in the world-famous Temple Bar district.
Meals Included: Breakfast

Day 7 – The Mourne Coast Read Less: Day 7
The Mourne Coast
Feeling refreshed after a day out of the saddle, jump in with the guide this morning and travel north into Northern Ireland. Arrive in the village of Rostrevor, tucked at the foot of Slieve Martin Mountain in County Down. From here, enjoy a beautiful, salty pedal up the coast through the Mourne Area of Outstanding Natural Beauty. Take in the sweeping views across the Irish Sea, arriving at an elegant hotel in Newcastle later this afternoon with time to relax before dinner.
Meals Included: Breakfast, Lunch and Dinner
Ride Details: 43 km / 27 miles | 330 m / 1,083 ft

Day 8 – Mourne Mountains Loop Read Less: Day 8
Mourne Mountains Loop
Today features a fantastic circular ride that takes you into the heart of the Mourne Area of Outstanding Natural Beauty. From the outset, the route climbs steadily, reaching its highest point at 1,324 ft. From here, a gradual descent takes you through a landscape of rolling heathery hills and wide open skies. After the downhill, ascend Electric Brae, or ‘Magic Hill’, where it appears the law of gravity is defied. A car without its handbrake is said to roll uphill, so be sure to stop pedalling and put the magic to the test. Having already ticked off the main climb of the day, this afternoon offers scenic, mellow riding, with a pedal along the shores of Castlewellan Lake before heading back into Newcastle.
Meals Included: Breakfast, Lunch and Dinner
Ride Details: 47 km / 29 miles | 660 m / 2,165 ft

Day 9 – Belfast Tour and Ride to Portballintrae Read Less: Day 9
Belfast Tour and Ride to Portballintrae
After breakfast, leave the mountains behind and transfer north into Belfast for a fascinating walking tour of Northern Ireland’s capital. Enjoy a morning free of cleats while exploring the bustling, vibrant city and learning more about its complex and troubled history. After lunch, travel a short distance to Broughshane for a great ride to the coast. Weave along quiet, rural lanes, stopping to see the Dark Hedges made famous by Game of Thrones. Later this afternoon, arrive in the seaside village of Portballintrae, a hidden gem home to an ancient castle, thatched cottages, and a small harbour. This evening, there is the option of riding the cycleway from the hotel down to the Giant’s Causeway, where this fascinating geological formation and World Heritage Site can be seen free from the daytime crowds.
Meals Included: Breakfast, Lunch and Dinner
Walk Details: 53 km / 33 miles | 502 m / 1,647 ft

Day 10 – The Antrim Coast and Across to Scotland Read Less: Day 10
The Antrim Coast and Across to Scotland
Today’s ride takes you into the final country of the tour, Scotland. The first part of the route follows the Antrim Coast, which many consider the finest stretch of coastline in Northern Ireland. (Some also consider it the toughest cycling road in Ireland!) Satisfying climbs are made even more enjoyable with dramatic views, as the route follows the Torr Scenic route through wild landscapes and deserted villages. A short transfer by road takes you to the port of Larne, where a 2-hour ferry to Scotland awaits. Once ashore, make your way to the final hotel in Gatehouse of Fleet.
Meals Included: Breakfast, Lunch and Dinner
Ride Details: 48 km / 30 miles | 768 m / 2,520 ft

Day 11 – The Galloway Coast Read Less: Day 11
The Galloway Coast
Dumfries and Galloway is a cycling revelation with quiet roads through beautiful scenery. The route leaves Gatehouse of Fleet this morning and winds its way across to the thriving market town of Castle Douglas, known as Scotland’s Food Town. This afternoon, you’ll pedal your way back via the beautiful Artist’s town of Kirkcudbright and along the quiet roads of the Solway Coast. With no major climbs this afternoon, cyclists should make quick progress, arriving back at the hotel by mid-afternoon, allowing some downtime before dinner.
Meals Included: Breakfast, Lunch and Dinner
Ride Details: 66 km / 41 miles | 620 m / 2,034 ft

Day 12 – Drumlanrig Castle Read Less: Day 12
Drumlanrig Castle
Your final day of riding includes pedalling along some of the region’s best biking roads, as the route heads through Galloway Forest Park beneath hills known as the ‘Range of the Awful Hand’. From here, you’ll head east through rolling farmland, passing Keir Mill, where the pedal bicycle was invented in 1839. A short distance on, cyclists will arrive at the Drumlanrig Estate, and the final km is one of the best you’ll find anywhere – a perfect boulevard leading right to the entrance of Drumlanrig Castle. Upon arrival, enjoy some celebratory drinks before returning to Gatehouse of Fleet for your final dinner.
Meals Included: Breakfast, Lunch and Dinner
Ride Details: 78 km / 48 miles | 1,070 m / 3,510 ft

Day 13 – Travel to Carlisle and Depart Read Less: Day 13
Travel to Carlisle and Depart
After a relaxed breakfast, your guide will drop you off at Carlisle Railway Station (a Grade II listed building) for 11.30 am. After saying goodbye to your guide and fellow riders, catch a train to begin your journey home ot the next stage of your adventure.
Meals Included: Breakfast

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Road Cycling

The Five Countries Tour

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Trip Dates & Prices

All payments taken in local currency GBP

Trip Dates for 2025	Availability	Status	Price	Book
4th May - 16th May 2025	12 place(s) left	Available	£4,995	Book Now
15th Jun - 27th Jun 2025	12 place(s) left	Available	£4,995	Book Now
3rd Aug - 15th Aug 2025	12 place(s) left	Available	£4,995	Book Now

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Make This Trip Private

Fancy this trip just for your group? Get together with family and friends spend quality time exploring wild places. A private trip allows you to benefit from all the features of the group departure, including hand-picked accommodation and expert local guides but with the advantage of the flexibility to tailor the days to your group. Make the trip more or less challenging depending on your experience or choose to add in some optional extras like castle or distillery visits depending on your interests. The price of a private trip will depend on the number of travellers in your group. Let us know your preferred departure date and we'll take care of the rest.

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Road Cycling

The Five Countries Tour

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Trip Details

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Accommodation Read More

This trip features some of the best hotel and guest house accommodation and food in the British Isles and Ireland. We use a variety of accommodations such as country inns, guesthouses and small hotels, all hand-picked by us. Accommodation is in a choice of double or twin rooms with ensuite facilities.

Single Rooms

There is no supplement charged to solo travellers, however, you will be required to share a room with another person of the same sex. If you request a double room for single occupancy, a supplement of £950.00 is charged.

Due to the nature of the accommodations we use, single supplements are limited and are allocated on a first come first served basis.

Meals Read More

Breakfast is provided each morning at your accommodation. Lunch each day will be either a wilderness picnic or taken at a local cafe/restaurant. Drinks and snacks are provided throughout the day as you require. Most evening meals are included and on this itinerary and we have the flexibility to take evening meals either in the hotel or in local restaurants. Based upon our knowledge and experience, we will visit the best places to eat along the route. Included dinners are two courses as standard.

Day 6 is a rest day and breakfast only is provided that day. Your guide will be on hand for lunch and dinner suggestions.

On this trip, we generally eat dinner as a group however if you would like to make alternative arrangements, you are free to do so. Your guide will have an evening off during this trip where they do not eat with the group. They will recommend options for dinner that evening and will help you make any necessary reservations.

Inclusions Read More

12 days professional guiding with a lead guide, plus assistant guide/support driver.
11 nights accommodation in 3 star and 4 star hotels/inns/guest houses on a B&B basis.
Most meals as stated in the itinerary.
Vehicle transport throughout including ride support and luggage transfers.
Ferry and private boat transport as required.
Entrance and admission fees as stated in the itinerary.
Ride snacks, home-baking and drinks and some Wilderness extras.

Grading Read More

Blue Graded 4-6

Blue graded trips are suitable for people with a good level of bike fitness, who regularly enjoy cycling and may have joined a multi-day cycle holiday before.

Distances each day will be between 35 – 45 miles, cycling at around 12/13mph. Each day will be rolling and hilly terrain and there will be notable climbs most days. Some of these will be more testing and some riders may opt to push or ride in the support vehicle. Some climbs are also followed by exciting descents. We will be in the saddle for 5 – 7 hours each day plus the odd longer day. There is also time each day for breaks and lunches, plus some visits to sites of interest.

Travel - Arrival and Departure Read More

You will be met by your guide at 11:00am on Day 1 at York Railway Station. The meeting place will be at the bottom of the stairs, under the gold clock (on the ATM side).

We will finish at Carlisle Railway Station for 11:30am on Day 13.

Advice on travel to York and from Carlisle is available on our website under Recommended Travel.

Bike Hire / Bring Your Own Bike Read More

Bike Hire

We have an excellent fleet of bikes available to hire – including road bikes and E-bikes.
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Bring Your Own Bike

You are also more than welcome to bring your own bike.

If you choose to do so, please ensure it’s in excellent working condition and has been recently serviced – either by you or by a reputable bike shop.

In addition, please bring the following:

Multi-tool, including a chain tool
Mini pump and/or CO2 canisters
Two spare tubes and a puncture repair kit

Because we will need to load your bike onto one of our trailers, please ensure that:

Your rear wheel is clear of any obstructions; including lights, mudguard or panniers
Your tyres are no wider than 45mm

Due to the nature of our trips, we are unfortunately unable to carry bike boxes or bags with us, so please make prior arrangements if necessary.

If you have any questions at all, don’t hesitate to get in touch. Our friendly and knowledgable sales team are always delighted to answer any queries you may have.

Trip Reviews

Rated 4.94 out of 5 based on 34 review(s) of Road Cycling – The Five Countries Tour

Every client receives a feedback survey when they return from their guided, self guided or tailor made holiday with us. Once completed the review is published on our website just as soon as our database updates. The little touches and details are important to us and where issues are raised we make positive changes to our trips to improve your experience.

That’s why we read each of our client’s reviews and although we don’t respond to all of them, if it’s glowing feedback then we get the satisfaction of helping to make your holidays truly memorable.

Joanne St-Coeur

Reviewed on 10/06/2024

Age: 50 - 60
Country: Canada
Trip Date: 19/05/2024
Trips Taken: 2

The Bottom Line

The Bottom Line

Excellent adventure. Many thanks

Andre Michaud

Reviewed on 10/06/2024

Age: 50 - 60
Country: Canada
Trip Date: 19/05/2024
Trips Taken: 1

The Bottom Line

Pre-Trip Service

Pre-trip, there was always someone with a quick email response to my inquiries. Since I was booking from Canada, my chosen communication tool was email and Wilderness Scotland never left me hanging.

Trip Comments

Best tour/trip I’ve been on by far. Chosen routes made for amazing views, discoveries and provided us with promised chalenges. Our guides Simon and Ben made the trip even better by preparing us everyday and educating us on historical and current facts as we visited several countries . I appreciated that we spent more time on the countryside and in nature. Thank you for such an experience.

Accommodation & Food

Excellent during most nights with one exception. The Seren Hotel needs improvement at a few aspects of their hospitality offer. I understand that they have given employees with special needs opportunities but when a group of 14 shows up for breakfast and you are not ready and you forgot to order supplies for your guests, that is not a employee issue but a management issue. Also, since we happened to ride on several wet and windy days, we were all expecting to use the towel warmers to dry our clothes. I complained to a few hotels that the one in our room was not working and was told several times to try different options which most often failed. I eventually discovered that the on switch was located at reception and employees were advised to shutdown system at 10 pm in most hotels. But we always figured a way, we managed

Your Guide

SIMON & BEN WERE MORE THAN EXCELLENT…. THEY MADE OUR TRIP ( and I was not paid to say this) They said they had never worked together before and they made sure not to show it. They worked their A$&### off for us. Some of us were very demanding and they just pushed forward. Their support on the ride was always welcomed , be it van support for our breaks or encouragement on the ride. Their operation was clockwork, from the morning debrief , the ride support and hotel transfers. These two superb gentlemen provided us with as much info that they could for the day’s ride but also facts about the countries we were visiting. I would definitely hope that I would have them as my partners on my next tour with you. They were able in such a short period of time, to make us feel special as if we were part of their family.

The Bottom Line

Our Adventure was one of the most exiting vacations we´ve had in a long time. I would recommend the Five Countries Tour in a heartbeat. Our guides provided us with top notch assistance and the chosen daily rides were just superb. Accommodations and meals were better than expected when you consider that we were riding on the country side. I got to ride amongst some of the nicest country roads in in five countries over 13 days…it was a blast. Finally if you have doubts about your abilities, try the E-Bike.

Judith Pyle

Reviewed on 07/06/2024

Age: 70 - 80
Country: United States
Trip Date: 19/05/2024
Trips Taken: 1

The Bottom Line

The Bottom Line

For me this was an adventure of a lifetime. It was phenomenal from all aspects. Seeing all of the beautiful sights and experiencing the different cultures was awesome. I loved having time on ferries or boats that took us past different coasts and the beautiful scenery to get us to a new destination.

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Wilderness Scotland

The Five Countries Tour

Trip Overview

Day by DayItinerary

Day 1

York and the Yorkshire Dales

Day 2

Yorkshire and the Tour de France

Day 3

Yorkshire Dales to the Forest of Bowland

Day 4

Crossing the Border into Wales

Day 5

Eryri (Snowdonia) and Dublin

Day 6

Rest Day in Dublin

Day 7

The Mourne Coast

Day 8

Mourne Mountains Loop

Day 9

Belfast Tour and Ride to Portballintrae

Day 10

The Antrim Coast and Across to Scotland

Day 11

The Galloway Coast

Day 12

Drumlanrig Castle

Day 13

Travel to Carlisle and Depart

Trip Dates & Prices

Make This Trip Private

Trip Details

Single Rooms

Blue Graded 4-6

Bike Hire

Bring Your Own Bike

Speak to an Expert

Chris Page

Meet Your Guide

Difficulty Grades Explained

Blue Graded 4-6

Trip Reviews

Your Guide

The Bottom Line

Pre-Trip Service

Trip Comments

Accommodation & Food

Your Guide

The Bottom Line

Pre-Trip Service

Trip Comments

Accommodation & Food

Your Guide

The Bottom Line

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