How to Plan a Sabbatical Itinerary (That Actually Works in Real Life)

When you’re planning a sabbatical, there’s this natural temptation to go BIG. You just want to see and do it all. Make this one trip the ultimate expression of everywhere you’ve ever dreamed of going. But your sabbatical itinerary doesn’t have to impress anyone. It needs to work for you. No itinerary can truly do it all… and even though I LOVE a good sample itinerary, you can’t copy/paste your way to the ideal sabbatical.

Your goals, your budget, your timeline, your energy… they all matter for your personally imperfect sabbatical itinerary.  So how do you actually figure out where to go (and when) on a longer trip? Let me walk you through the simple (and realistic) process I used to build my own sabbatical itinerary and now take my clients through for their own planning journeys. (But yes, there is still a sample itinerary at the end!)

Start with your big-picture priorities

Before you open a single flight search engine or hop on the Instagram-inspo merry-go-round, take a step back. Ask yourself:

• What kind of travel experiences matter most to me?

• What would this journey feel incomplete without?

• Where’s a place I can’t believe I’ve never been?

Thoughtful prompts like this will help you get to the core of what YOU really want to do, not just what’s trending on social. You might realize your dream trip is focused on hiking, cultural immersion, and affordability, which could steer you toward South America rather than Australia and New Zealand. (Though there is surely plenty of hiking and culture there too, but you get what I mean right?)

You don’t need to know every detail yet. You want a rough sketch of the must haves. Let your purpose guide your path.

Map your route with logic (not just wanderlust)

Once you’ve got a sense of where those top priorities are, it’s time to get strategic.

• Note non-negotiable timing. If you’re aiming to see cherry blossoms in Japan or attend Oktoberfest in Munich, those things only happen at a certain time of year and have to dictate
• Consider weather and seasons later. Everyone wants to know the “best time to visit” but you’ll need to balance your priorities on a long trip like this.

• Smooth out your route. A free tool like Rome2Rio can help you visually connect the dots of your itinerary, so you’re not jumping back and forth all over the world. (Read more about planning transportation for your sabbatical here.)

Balance must-sees with room to breathe

I know how tempting it is to pack your itinerary with every possible bucket list item. But fast-paced travel gets exhausting fast, especially over the course of several months.

Build in:

• Longer stays in major destinations to settle in and rest

• Slow days where you just relax or settle in to your new destination or attend to an Admin Day

• Time in smaller towns or nature escapes between big cities

A good sabbatical itinerary has rhythm, not just a checklist.

Be prepared to change your sabbatical itinerary

Your sabbatical itinerary will change! You might learn about a new-to-you destination you can’t say no to, or get detoured by a safety concern in one of your destinations. You might show up somewhere and be disappointed, so you want to move on early. Or you might fall in love with a city and want to extend your stay.

I’m a big believer in balancing planning and spontaneity in travel. One of the ways you can do that is by going in with a backup plan. Have a little bucket list B-list to draw upon in case of emergency. I wound up needing a backup for my month in Istanbul when terrorist attacks rocked its airport and a military coup threatened the streets.

Example: What a year-long sabbatical itinerary could look like

If you’re looking for a starting point, here’s the rough outline of my own year-long trip:

• July: one week in Iceland, then a budget flight to the Mediterranean coast

• August: Overland through Italy and Croatia

• September: Explore the Balkans and Greek islands

• October: One-month reset in London

• November: Pit stop in India before trekking in Nepal

• December: Start the Banana Pancake Trail (Thailand & Laos)

• January: Continue through Vietnam and Cambodia

• February: Slow month in Bali

• March: Japan (chasing early cherry blossoms)

• April: Shift to South America, specifically Uruguay and Argentina

• May: Hike the Inca Trail in Peru

• June: Wrap up in Mexico, then head home early in the month

It wasn’t perfect. I skipped some places from my original sabbatical itinerary. And I added unexpected ones. But it all worked and was an amazing experience.