Let us Plan your own Kent Self guided walking holiday
Create a Bespoke Walking Route Designed Around You and Kent’s Hidden Trails
At Boots On Adventures, we live and breathe the landscapes of Kent. Our team has spent years exploring its woodlands, coastal paths, and historic trails, uncovering hidden gems, breathtaking viewpoints, and the best local inns for a warm welcome and a good pint of ale.
If you already have an idea for your ideal self-guided walking holiday but can’t find the perfect route, we’ll design one tailored just for you. Whether you want to wander through ancient Neolithic Medway sites, follow the dramatic Saxon Shore Way from Gravesend to Hastings, or enjoy a relaxed two-day countryside break, we can make it happen.
Your journey starts with a quick, friendly call to understand what you’d like to see and experience. From there, we’ll create a personalised walking itinerary that matches your interests, pace, and schedule — turning your walking dream into a reality.
The Finer details and daily schedule
The details
Schedule
Date: January to December
Location
Car Parking: Charges not included
Route
Terrain: Dependant on your preferences
Distance: Dependant on your preferences
Walk Type: Linear or Circular – the choice is yours
We’ll Arrange Your Accommodation, Route Itinerary, and Baggage Transfers - So You Can Simply Enjoy the Walk
When you book a bespoke self-guided walking holiday with us, everything is taken care of. We’ll plan your daily routes, organise comfortable local accommodation, and handle luggage transfers between stops, leaving you free to focus on the adventure itself. Each itinerary is created using our in-depth local knowledge of Kent’s trails, villages, and coastal paths, ensuring every day offers the right mix of scenery, comfort, and discovery.
Whether you prefer cosy countryside inns or seaside guesthouses, we’ll match your accommodation style to your walking pace — so your only job is to relax and enjoy the journey.
What to knowabout the hadrians wall walk
Where will we be staying?
Accommodation Information
Accommodation will be in a mixture of handpicked hotels and B&B’s along the route.
We look to include hotels and B&B’s with breakfast included to give you the best start to your day. However due to availability at the time of booking there may be occasions where his is not possible. Alternative options will be provided should this be the case.
Facilities
Each hotel will have its own independent facilities. If you require any special requests for hotel facilities please let us know at the time of booking and we will do our best to accommodate.
Optional Extras
Option extras can be included. We will advise of these at the time of booking as each hotel is unique in what they offer.
Frequently Asked Questions About Our Bespoke Walking Holidays in Kent
Can I create my own walking route in Kent?
Absolutely. If you already have an idea of the places you’d like to explore, we can design a personalised self-guided walking route around your preferences. Whether you want to follow the coastline, explore historic villages, or walk through Kent’s ancient woodlands, our team will build a route that matches your pace, interests, and time frame.
What’s included in a bespoke self-guided walking holiday?
How long does it take to plan a custom walking holiday?
Once we’ve had a short phone call to understand what you’re looking for, we can usually provide a draft itinerary within a few days. More complex or longer routes may take a little longer, but we’ll always keep you updated throughout the process.
Do I need to be an experienced walker to enjoy a self-guided holiday?
Not at all. Our bespoke walking holidays are tailored to your ability and comfort level. Whether you’re looking for gentle coastal paths, moderate countryside routes, or challenging multi-day hikes, we’ll plan a walk that suits your experience.
Can I include specific places or landmarks in my route?
Yes — that’s exactly what makes it bespoke. You can request to visit places such as the White Cliffs of Dover, Canterbury, the Medway Valley, or even historic trails like the Saxon Shore Way. We’ll weave your chosen destinations into a cohesive, enjoyable route.
Important notes
- Please ensure you are fit enough to attend Your self guided walking holiday. Boots On Adventures are unable to accept liability if you are unable to complete the holiday due to fitness or illness.
- A 50% deposit of your holiday is required at the time of booking with the ballance due no later than 60 days prior to departure. A full copy of our terms and Conditions including our cancellation policy is available on request.
- It's worth reading our guide to improving your map reading skills before you set out.
