How to Plan Your Perfect Holiday Step-by-Step

Holiday planning can feel like a full-time job—especially if you’re doing it alone. But when you break it down, it becomes a journey in itself. Whether you’re dreaming of a sandy beach in Bali or a cultural escape to Rome, having a step-by-step process makes it all easier and more enjoyable. This guide walks you through every part of holiday planning, helping you stay on track and feel in control, from your first idea to the day you return home.

And if you’d rather not do it alone, Jamie Wake Travel is here to help with every detail.

Step 1: Start With a Vision

Every great trip begins with an idea. It’s that idea that will shape your holiday planning. Think about what kind of experience you’re after. Are you picturing yourself lying by a pool, wandering through museums, zip-lining through jungles—or a mix of all three?

This step shapes everything that comes next. Take a moment to write down:

• The kind of trip you want (relaxing, adventurous, romantic, family-oriented, etc.)
• The vibe you’re looking for (luxury, budget-friendly, off the beaten path, guided)
• Your must-haves (beach, sunshine, good food, shopping, cultural sites)

Know what matters most before you look at flights.

Being clear about your holiday goals will save time and ensure that your trip matches your expectations.

Step 2: Set a Realistic Budget

When holiday planning, don’t lose sight of that your budget will influence where you can go, how long you can stay, and what type of accommodation and activities are available to you. Start by thinking in totals, then break things down into daily costs.

Ask yourself:

• How much can you spend overall?
• What are your top priorities—flights, hotels, experiences?
• What extras might come up while you’re away?

Here’s what to include in your holiday planning:

• Flights
• Accommodation
• Meals and drinks
• Travel insurance
• Transport while there
• Entry fees for sights or tours
• Shopping and souvenirs

Always budget for surprises.

Need help comparing options? Our team at Jamie Wake Travel can offer price-matched quotes from over 200 suppliers, tailored to your budget.

Step 3: Choose the Right Destination

Now that you’ve outlined your budget and goals, it’s time to pick the perfect place. Some people have a destination in mind already. Others just want sunshine, adventure, or relaxation. Either way, ask yourself these questions:

• What time of year are you travelling?
• Do you want to fly short-haul or long-haul?
• Do you prefer cities, beaches, mountains, or a combination?

Your timing can impact everything from weather to price.

For example:

• Looking for winter sun? Try the Canary Islands, Dubai, or Thailand.
• Want a cultural city break? Think Paris, Budapest, or Florence.
• After an all-inclusive beach break? Mexico, Turkey, and the Dominican Republic all shine.

Whatever you’re picturing, we can match it with offers you might not find elsewhere. Ask Jamie Wake Travel about our best options for your chosen destination.

Step 4: Pick Your Dates (and Stay Flexible)

Some people are tied to specific dates because of school holidays or work schedules. Others have more flexibility. If you fall into the second group, you’re in luck.

Travelling off-peak often means:

• Lower prices
• Fewer crowds
• Better hotel availability

Being flexible can save hundreds.

Even shifting your travel by a few days might reduce flight costs dramatically. Our team can search a wide window of dates to find the best deals for your dream holiday.

Step 5: Choose the Right Accommodation

Where you stay can make or break your experience. Think about how much time you’ll spend in the hotel or resort. Will it be your main relaxation space or just somewhere to sleep?

Here are the most common types:

• All-Inclusive Resorts – Ideal for those who want everything in one place.
• Boutique Hotels – Perfect for unique charm and personalised service.
• Apartments or Villas – Great for families or longer stays.
• City Centre Hotels – Ideal for sightseeing and public transport access.

Your base sets the tone for your whole trip.

We can provide options for every taste and budget—and because we work with hundreds of tour operators, we often have exclusive rates or upgrades available. Just ask us for today’s best offers.

Step 6: Sort Out Your Travel Documents

After all that effort you put into holiday planning, no one wants to get caught short at the airport. That’s why sorting out your paperwork early is essential.

Make sure:

• Your passport is valid for at least six months from the date of travel.
• You’ve checked whether a visa is needed.
• You have any vaccination certificates if required.

Don’t leave paperwork to the last minute.

We’re always happy to check the entry requirements for your destination. When you book with Jamie Wake Travel, we’ll help make sure nothing gets missed.

Step 7: Consider Travel Insurance

You might not want to think about what could go wrong—but travel insurance is one of the most important parts of holiday planning. It covers you in case of:

• Trip cancellation
• Delayed or missed flights
• Lost luggage
• Illness or injury abroad

Protect your holiday from the unexpected.

All tailor-made holidays with Jamie Wake Travel include Supplier Failure Insurance and Scheduled Airline Failure Insurance. It’s one more way we make sure your money is safe and your trip is protected.

Step 8: Plan Your Itinerary

This is where things get exciting. With your destination chosen and flights booked, you can now decide how to spend your days. The key? Keep a balance between must-see sights and unplanned time.

Ask yourself:

• What are the top 3 things I want to do?
• How much time should I allow for rest?
• Do I want to book tours in advance?

Mix planned activities with freedom to explore.

For city breaks, we can book skip-the-line entry to popular attractions. For beach holidays, we can arrange boat trips, spa days, or dinner reservations in advance.

Step 9: Think About How You’ll Get Around

Getting around might mean a hire car, train pass, or simple public transport. It depends on where you’re going—and what you’re planning to do.

Options include:

• Airport Transfers – Easy, stress-free, and often cheaper than a taxi.
• Car Hire – Ideal for exploring rural areas or combining locations.
• Rail Passes – Perfect for multi-city holidays in Europe or Japan.
• Ride-Hailing Apps – Widely available in cities worldwide.

Plan transport early to avoid stress on arrival.

Let us know what kind of travel you’re comfortable with. We’ll recommend the best option for your destination.

Step 10: Pack Smart

Packing shouldn’t be a chore. The secret? Less is more. Think about your destination, weather, and activities.

Start with a list:

• Comfortable walking shoes
• Clothing for your chosen climate
• Swimwear and sunscreen
• Plug adapters
• Any prescription medications

Don’t forget your travel documents and insurance details.

We also recommend printing out copies of your itinerary, booking confirmations, and emergency contacts.

Step 11: Check Local Customs and Laws

It’s always a good idea to brush up on cultural dos and don’ts, especially when travelling somewhere new. What’s polite in the UK might be rude elsewhere.

Respecting local norms makes travel smoother.

We’ll point out any major cultural considerations or legal restrictions when helping you plan.

Step 12: Know You’re Protected

When you book with Jamie Wake Travel, your money is fully protected. Here’s what you get:

• ATOL Protection – All flight-inclusive packages are covered.
• PTS Membership – All payments are securely held in a client trust account until your holiday is complete.
• Supplier Failure Insurance – If any supplier collapses, you’re still covered.
• Scheduled Airline Failure Insurance – Even if an airline ceases trading, your money is safe.

With us, you’re in safe hands from start to finish.

This is the difference between booking with an experienced travel agency and doing it all yourself online. Our support doesn’t stop once you’ve paid—we’re here every step of the way.

Jamie Says:

“Holiday planning isn’t about picking something off the shelf. It’s about creating a trip that feels completely yours—down to the last detail. That’s what we do every day at Jamie Wake Travel.”

Step 13: Ask About Exclusive Offers

We often have access to special offers you won’t find online. That includes:

• Room upgrades
• Free nights
• Resort credits
• Early booking discounts
• Late deals

Here are a few example destinations to consider:

Hotel: Iberostar Grand Bávaro, Dominican Republic
A luxurious adults-only resort with beachfront elegance, fine dining, and butler service.
Ask Jamie Wake Travel about current Dominican Republic offers.

Hotel: Domes Noruz Chania, Crete
A modern, stylish resort for adults with beautiful sea views and spa treatments.
Ask Jamie Wake Travel about exclusive offers for Greece.

Hotel: The Pavilions Bali
Private villas, outdoor bathrooms, and a calm tropical setting.
We have amazing rates—just ask about our Bali offers.

Even if we don’t have an offer listed, we can usually find something great. Just ask when you enquire.

Step 14: Add the Finishing Touches

The last details can take your holiday from good to unforgettable. Think about extras like:

• Airport lounge passes
• Spa bookings
• Private airport transfers
• Champagne in your room
• Birthday or anniversary surprises

Little luxuries make big memories.

We can add those finishing touches for you, making the whole experience feel effortless and personalised.

Step 15: Get Excited—You’re Ready to Go!

With everything booked and planned, all that’s left is to look forward to the journey. Count down the days, share your excitement with friends, and start dreaming about your destination.

You’ve earned this.

And remember, if anything comes up before you fly, Jamie Wake Travel is just a phone call away.

Your Next Step: Talk to Jamie Wake Travel

Holiday planning doesn’t have to be stressful or overwhelming. With our help, it becomes something to enjoy—just like the holiday itself.

We tailor every trip to your wishes and take care of the hard work behind the scenes. You’ll benefit from expert advice, exclusive supplier access, and full financial protection every step of the way.

Call us now on 01495 400005
Or fill in our Holiday Enquiry Form

Let’s plan a holiday you’ll never forget—because with Jamie Wake Travel, your perfect trip is just one conversation away.