How does a tailor-made holiday work?

It begins with a conversation, not a brochure

When you contact Expressions Holidays, you are connected with a consultant who specialises in the destination or type of holiday you have in mind. That consultant's first task is not to suggest an itinerary — it is to understand what you are looking for. Where have you been before? What worked well and what did not? What does this particular trip mean to you? Is it a milestone celebration, a long-awaited journey, a holiday that needs to work for two people with different interests?

This conversation shapes everything that follows. A client asking about a two-week holiday in Italy might leave that first call with a completely different idea of where to go than they arrived with — not because we have talked them out of their original plan, but because we have understood what they actually want from the trip and can suggest something that delivers it more fully.

Our destinations page covers over 80 regions and sub-regions across more than 20 countries. The sample itineraries you see there are starting points for a conversation, not fixed products. A client who enquires about a week in Tuscany and ends up planning ten nights split between Tuscany and Puglia has not had their request overridden — they have had access to specialist knowledge that made the holiday better.

Designing the itinerary

Once your consultant understands what you are looking for, they design an itinerary from scratch. This means choosing which specific part of a destination to base you in, selecting the hotel or hotels from a personally vetted portfolio, planning the routing if the holiday involves moving between places, arranging flights with appropriate timings and connections, and identifying any excursions, experiences or inclusions that would add value to the specific trip.

Sample itineraries on our website show you the kind of holiday we design. They illustrate routing, pacing and the level of detail involved — which properties we feature, how many nights work well in each location, which journey combinations make geographical sense. They are not packages to be booked as seen. They are illustrations of our approach, and every one of them can be amended, extended, shortened or restructured around your requirements.

The most important question we ask during itinerary design is not 'where do you want to go?' — that is the starting point. The more useful question is 'what do you want to feel at the end of this holiday?'

Hotels — a personally selected portfolio
Every hotel in our programme has been visited by a member of the Expressions Holidays team. We know which rooms are worth requesting, which properties have declined since our last visit and have consequently been removed from the programme, and which smaller, less-publicised places deserve attention precisely because they are not on every operator's list.

For a client booking a hotel holiday — a single property stay in Provence, the Maldives, Barbados or the Italian Lakes — the hotel selection is the heart of the design process. We will suggest two or three options that suit the brief, explain what distinguishes each one, and advise on board basis, room category and time of year. We do not present an undifferentiated list and ask you to choose.

Touring holidays — the journey as well as the destination
For clients who want to cover more than one area, our touring holidays are designed as coherent journeys. The routing is planned to take advantage of the best scenery and the most logical progression between places. The overnight stops are timed to give enough time in each location without the itinerary feeling rushed. If the journey involves driving, we advise on the roads worth taking and the ones to avoid. If it involves combining driving with rail, ferry or internal flights, we arrange and coordinate all of those elements.

A self-drive tour through Burgundy and the Loire Valley, a chauffeured itinerary through Andalusia, a route through the Norwegian fjords combining ferry crossings with scenic rail — these are not assembled from separate bookings. They are designed as a single, continuous experience, and the coherence of the journey is part of what we offer.

Rail holidays — complexity managed on your behalf
Our rail holidays illustrate clearly what tailor-made means in practice. Combining a flight to a gateway city, a cabin on the Venice Simplon-Orient-Express or the Glacier Express, hotel stays timed to align with departure schedules, and a return flight from a different city requires detailed knowledge of the trains, the routes and the booking systems involved. We manage all of this directly.
The train cabins, the hotel rooms, the flight connections and the transfer arrangements are all booked through us, and the result is a document that sets out the complete journey day by day, with every element confirmed. Clients travelling on prestige rail holidays often tell us that the planning process was half the pleasure — and that is because the planning was done properly.

The tailor-made process - step by step

1. The initial conversation
You contact us by telephone or email. You are connected with a consultant who specialises in your chosen destination or holiday type. They ask the right questions to understand what you are looking for, offer initial thoughts based on your brief, and establish what a successful holiday would look like for you.
There is no obligation at this stage. The conversation is the beginning of a planning process, not a sales call.

2. The itinerary proposal
Your consultant designs an itinerary and presents it to you in writing, with full details of the routing, the hotels, the flights and the inclusions. They explain the choices they have made and why — including what they have chosen not to include and for what reason.
This proposal is a starting point. Most clients amend it — adjusting the pace, swapping hotels, adding or removing elements — through a series of conversations until it reflects exactly what they want.

3. Refinement and amendment
The itinerary evolves through discussion. You might want to add a night in a second location, upgrade a room, include a private excursion, or adjust the departure dates. Your consultant advises on what is feasible, what the implications are for timing and cost, and what they would recommend based on their knowledge of the destination.
This iterative process is one of the things that distinguishes a tailor-made holiday from a booking platform. There is no algorithm making these decisions — there is a specialist applying judgment.

4. Booking and confirmation
Once you are satisfied with the itinerary, we confirm the bookings. Flights, hotels, transfers, train cabins, excursions and any other inclusions are all secured. You receive a confirmation document setting out every element of the trip.
Your air holiday is ATOL protected under licence number 3076, your non flight-inclusive holiday is protected with AFPS licence 6104, and you have the additional reassurance of our AITO membership, which requires members to meet independently assessed standards of financial protection and service quality.

5. The pre-departure briefing
Before you travel, your consultant provides detailed pre-departure briefing notes. These cover what to expect at each stage of the journey, recommendations for restaurants and experiences in each location that are not in the standard guides, and practical information about the destination that only comes from having been there.

6. During your holiday
Your consultant remains contactable throughout the trip. If plans need to change — you call the person who designed the itinerary and knows the booking in detail.

7. When you return
After you return, your consultant contacts you to hear how the trip went. What exceeded expectations and what could have been better becomes the foundation of the next holiday — whether that is a return to the same region, a new destination, or an evolution of what worked well this time.
Many Expressions Holidays clients have been booking with us for a decade or more. The relationship that develops over multiple trips — the accumulated knowledge of your preferences, standards and travel history — is one of the things that makes each subsequent holiday better than the last.

What kinds of holiday can be tailor-made?

The short answer is: any of the holidays on our site, and most things that are not on our site but fall within our areas of specialist knowledge. The longer answer covers the specific holiday types we design:

Hotel holidays
A luxury hotel holiday based in a single property or region — Tuscany, Provence, Mauritius, Norway, Barbados, Sri Lanka, New Zealand. The choice of hotel, the room type, the board basis, the arrival and departure transfers and any excursions are all arranged by us. The dates and duration are chosen by you.

Touring holidays
A touring holiday moving between two or more regions or properties — by self-drive car, private driver, or a combination of both. These are designed as complete journeys, with the routing, the overnight stops and the hotel selections all considered as a whole rather than as separate bookings.

Rail holidays
A rail holiday built around one or more scenic or prestige train journeys — the Venice Simplon-Orient-Express, the Glacier Express, the Bernina Express, the Al Andalus, and others. We book the train cabins directly and design the wider itinerary around the rail journey.

Honeymoons
A honeymoon is perhaps the purest expression of what tailor-made means. We design around the couple — their interests, the kind of experience they want, the destinations that resonate — and arrange the specific hotel, room and welcome details that mark it as a celebration rather than a standard stay. Many of our most requested honeymoon destinations include the Maldives, the Seychelles, Mauritius, the Caribbean, Sri Lanka and Tuscany.

Special occasion holidays
For milestone birthdays, significant anniversaries, retirements and other celebrations, the tailor-made approach allows the holiday to be designed around the occasion rather than fitted into a pre-existing product. The choice of destination, the specific property, the inclusions and the personal arrangements all reflect what the occasion calls for.

Special interest holidays
Our food and wine holidays, garden tours and cultural holidays are designed around a particular theme or interest. A wine holiday in Burgundy, a garden tour of the Loire Valley, a cultural itinerary through Sicily — these are original programmes designed by specialists who know the subject, not assembled from third-party products.

What a tailor-made holiday is not

It is worth being clear about what distinguishes a genuinely tailor-made holiday from a holiday that uses the phrase but delivers something else.
A booking platform that allows you to combine a hotel with a flight is not offering tailor-made holidays. It is offering a configurable search result. The difference is the absence of specialist knowledge, personal recommendation, accountability when things go wrong, and the continuity of a single person who knows your booking.
A travel agent who adapts a tour operator's pre-designed itinerary for your dates is not offering a tailor-made holiday in the fullest sense. The underlying product was designed by someone else, and the agent's ability to customise it is limited by what that supplier allows.
At Expressions Holidays, tailor-made means that the holiday does not exist until we design it for you. The itinerary, the hotel selection, the routing and the inclusions are all the product of a planning conversation between you and a specialist who knows the destination from personal experience. That is the distinction, and it is the reason our clients return.

Starting the conversation

If you are considering a tailor-made holiday and would like to speak to a specialist, we would be glad to hear from you. Call us on 01392 441245 Monday to Friday 9am to 5.30pm, Saturday 10am to 2pm, or email info@expressionsholidays.co.uk. You can also browse our destination pages or holiday types to start thinking about where you would like to go.

There is no obligation in an initial conversation. We would rather take the time to understand properly what you are looking for before making any suggestion.