Travel Tips

How to Plan Your Next Trip Like a Pro

Updated March 23, 2023

Ready to plan your next trip to Europe or Great Britain?

Let’s agree the internet is a great source for ideas, but it can make it harder to choose. There’s literally thousands of options, hundreds of travel sites and dozens of travel apps to choose from!

When I started thinking about a trip to Europe last year I ran into a roadblock. In the US, travel agencies have gone the way of the independent book store. Unlike the UK and Europe, you won’t find a high street travel agency ready to help you book your dream trip. In fact after Googling my fingers off, I couldn’t come up with one local agency in Denver CO besides AAA. Now AAA is handy if you have a flat tire and need a tow but they’re not European travel experts.

The other option I turned to was Costco; who advertise package travel to Europe, Central and South America, Hawaii and Caribbean. I had difficulty finding what I had in mind – a rail based trip from London to Italy – so gave up and went back to searching online.

Spouse, Partner or Fiance UK Visa

I eventually realized two weeks wasn’t enough time to take a train from London to Italy – unless that’s all I wanted to do.

The compromise was staying in London as a base, making a quick hop over to Paris on the Eurostar instead and squeezing in an overnight to Edinburgh. Italy was put on the back burner, for now.

Perhaps you’ve experienced similar frustration when you’ve tried to put together a bespoke trip for yourself or your family?

In the UK, many travel agencies offer inclusive packages with rail, cruises and flights to choose from. Lots of options.

With that in mind I grabbed The Times on a spring trip to the UK, and found an ad for Riviera Travel that led me to the perfect Italian lakes trip I’d been dreaming about. Experiencing a destination I’d dreamed about for years was priceless.

Don’t give up. Keep searching for the type of travel experience you’re dreaming about. Here’s my takeaway tips.

8 Tips on How to Plan Your Next Trip

1. WHERE do you want to go?

It may be obvious but if your bucket list is long, choose the destination that’s lighting a fire in you right now, a place you can’t wait to cross off that list. We stayed in London for two weeks with an overnight to Edinburgh and a three day trip to Paris. Ticked a few boxes.

2. HOW LONG do you want your trip to be?

I’d make it a two week minimum if you’re traveling from the US to Europe. It takes a day or two to get over jet lag, and by the time you’re really starting to enjoy yourself, it will feel like time to pack up and go home. If you have more time by all means take it. It may let you squeeze in some extra stops.

3. Consider a tour

Could you use some help? On our first trip to Italy, I really wanted to sit back and let someone else organize everything so I didn’t have to worry about the details. Booking a trip with an tour company might make sense for you too. Another plus, tour travel can run cheaper because they can bundle and get deals you can’t.

4. WHERE will you stay?

Personally I like to know where I’m sleeping each night because I prefer having a “home” base and travel from there if possible. On a road trip this is harder to do but if you can it’s so much more relaxing. (Do you hate to pack and unpack as much as I do?) So I book all nights away ahead of time.


Figure out what you’re comfortable spending. Your biggest expense is likely to be accommodation. Next big expense is hiring a car. In fact this cost has gone UP in recent years. In the UK and Europe, public transportation and taxis are reasonable and available and less stressful than driving. Airfares are most affordable off season as are hotels. Find out when is “low” season is to book a bargain.

6. PLAN your “must sees”

To enjoy those fully, be ruthless and eliminate any “maybe” stops. Really think about what’s most important to you especially if time is precious. Don’t feel you have to see it ALL. I guarantee you I won’t miss seeing the Mona Lisa in person. But if you’re a super fan then by all means, go!

7. BLOCK out each day of your trip.

Give yourself some wiggle room. Often. But use your calendar to put in any events, travel or sightseeing you plan to do that day so you can stay organized and on top of your trip. I highly endorse using an app like Tripit. It’s awesome. You forward all your travel detail emails to Tripit, and it creates a day by day chronological list of where you’ll be and how  you’ll get there.


How did we do without one? Keep track of emails , use Google maps to navigate, have access to Tripit for trip details including flights and rental cars. Boarding passes go in Apple Wallet. Use the airline app to check for flight delays. Consider upgrading if you don’t have a smartphone. With the right app you can also call home at no cost. It’s one piece of technology I don’t leave home without.

The key to planning your next getaway trip successfully is have most of the details covered before you leave. Then you can relax and enjoy your travel experiences without worrying too much about the details. Planning everything ahead of time doesn’t mean you can’t be spontaneous! But I prefer doing my planning at home with strong Wifi and plenty of time to sort out changes or hiccups.

Where are you dreaming of going? Use this road trip planner to keep all your details in one place.

About Author

With over 30 years in a creative role in advertising and publishing, and a lifetime of journeys between the US and UK, I've created Hipoverfifty for you. I hope my journey and perspective will guide you on yours.