9 tips for traveling without an itinerary

The most flexible way to travel

I’ve traveled extensively for many years – both for business and for pleasure. One thing I know to be true is that traveling for pleasure without an overly structured day to day travel itinerary is liberating! Having an open plan gives you the ultimate freedom in choosing whether to stay or go. In every case where I’ve traveled this way it’s been an overall great experience to not be tethered to a rigid plan.

Recently my partner and I went to Europe for 15 days. We had a departure date and city and a return date and city and everything else in between was undecided. NOT kidding. Even the day before we left we knew only that we would be flying from Denver to Barcelona and we knew that we would return 15 days later from Rome. Other than that we had no idea what was going to transpire in the space in between. You know what it was gloriously unrushed and flexible and full of fun twists and turns that we could not have expected with an overly planned itinerary.

How to approach travel without a plan

Having roughed out our mutual punch list of places we wanted to see we agreed on Barcelona-Venice-Tuscany-Amalfi-Rome. From there we decided the day of our departure from Denver to book a hotel for two nights in our first location, Barcelona. We packed one small roller bag each and we were underway. We found it was easy to book our trip a day or two at a time in advance of our next destination. Access to the internet was readily available everywhere and we had no issues getting online. Last minute flights, hotels, cars, and trains were readily available and we often found bargain last minute deals.

An open itinerary allowed us to stay longer in places like Tuscany where we fell in love with the slower pace, scenery and the quaint town we were staying in. Of course there will be hiccups when you travel this way. One misstep was being met by a closed Hertz office near the train station in southern Italy. Was this in the small print when we booked? We don’t think so though unsure what exactly happened since it was noon on a Saturday. The manager at our hotel tried to help us solve our car rental challenge by arranging a meet up with his friend “Luigi” and after walking several blocks and waiting for Luigi in front of his barred up place of business for 45 minutes we gave up on him. Instead we roamed around the train station neighborhood to find an Avis office open and thankfully we were underway within an hour.

TIPS for traveling without an itinerary

1. RELAX When I’ve approached travel without a structured plan and itinerary I’ve experienced freedom and liberation in not being boxed into a day to day itinerary. Keep a come as it may attitude. You have to leave your type A personality at home and takes things as they come.
2. Do some RESEARCH so you have a rough idea of what destinations/sights are of interest. Look online, glance through guidebooks, talk to friends for their insights and then create an outline with musts versus nice to experiences. Rick Steves also has a free app for download that offers tips and suggestions for numerous destinations. Also don’t be shy about asking the locals for their recommendations this has served us well.
3. Have a ROUGH OUTLINE and book a departure and a return airport while leaving everything open in between. For instance, we knew we wanted to see to see Spain and Italy so booked a ticket from from Denver to Barcelona and from Rome to Denver 15 days later. In between those locations we knew there were several MUST locations like Venice and yet there were some nice-to-see locations like Florence. We structured our trip around the musts and stayed flexible on the nice to see locations.
4. Book 1 to 2 days in advance of your next stay. This gives you the satisfaction of knowing you’re set up for the next couple of days and the flexibility to either stay or move on if you choose.
5. Pack light. Only pack a bag that can be a carry-on. Full stop. Less is more. I prefer a roller versus a backpack because it’s more comfortable. Up to you. You will be surprised at how few clothing items you really need and that 90% of the time you will be able to buy things you are ‘missing’ from your bag as well as sink wash items OR do laundry. We packed for 7 days and at day 7 found a laundromat next to our hotel in Tuscany. Ninety minutes later we had clean clothes for the next 7 days. Packing light gives you the freedom to move more seamlessly on sidewalks, stairs, airports, trains, etc. There are myriad packing lists, tips and products to buy on the web depending on where you are going and what time of the year. Highly recommend searching for lists or YouTube. AS example: YouTube Packing Video.
6. Pack electronics. It’s critical to have access to the internet to travel with an open plan. Must have phone, laptop or tablet for WIFI access AND highly recommend having International cell coverage for access to maps and access to the internet anytime anywhere. All major carriers offer international plans so contact your provider BEFORE you travel to get coverage. I have a $40 unlimited plan through ATT for Europe. Check with your cell carrier to be sure of the usage limits and whether you need to turn roaming on and off to save costs. Finally, carry the appropriate international adapters in your bag and if you forget just ask the front desk. Often they will have a stash they are happy to share or an adapter they will require a deposit for.
7. KNOW where the best deals are available. I regularly use two travel websites: Kayak and Trivago as they are my favorites although I also book directly with airlines, hotels, car companies and have walked into hotels as a ‘drop in’ occasionally.
8. Rent a car. Where possible, rent a car. You’ll see more and having a vehicle gives a lot of flexibility to get off the beaten path. On this particular trip we saw the Amalfi Coast. This highway ranks in the top 20 of all scenic roads in the world. Thankful we could experience that by renting a car. One bit of advice check with your insurance company on coverage overseas and specific to the countries traveling to. Sometimes just to be safe we spend the extra money and buy full coverage through the car company knowing we will be more than adequately covered. This decision largely depends on where we are. Another transportation tip is to not be shy about using public transport we often use the underground, taxi’s, hop on hop off buses and of course the train system in Europe in this case was a very good experience. We took the high speed train from Venice to Florence in business class and it was fabulous. Clean, comfortable, leather seats and a smooth, quiet ride made for an easy trip.
9. Modify as you go. Not everything will go perfectly however rolling with it and letting things go will make an enormous difference. You’ll find the locals have insightful recommendations and asking for advice has served us well. An open itinerary gives you FLEXIBILITY to see unplanned sights, to stay longer in places you love (either a location or a hotel for instance) or leave early if you’re disappointed.

Parting thoughts

To be fair there is one downside to traveling this way and that is we had to honker down every couple of days and book our upcoming plans. On at least one occasion it was very late at night and I would have preferred to have been sleeping rather than surfing the web, however, overall it was WELL worth it and having done this now for multiple international trips this will continue to be the way we travel.

Have you every traveled without a plan?  Or are you considering traveling without one?  If so I’d love to hear about your concerns or your experience!

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