How to build a muli-stop vacation: Think of the big picture

The trips I plan often involve multiple stops and destinations. These types of vacations require a lot of planning, coordination, and attention to detail.

Are you considering a multi-stop adventure? Because I do this day in and day out, I consider myself to be well-versed in all the considerations of building a multi-stop itinerary. Over the next few weeks, I’d love to lay out the key points to think about so it can be a successful one.

STEP 1: Think of the Big Picture

There are so many benefits of choosing to fit in a number of stops during one trip, but you have to think about how they all fit together. In the same way you enjoy a scintillating movie, or a great book, your vacation needs to be laid out in a way that makes sense and leaves you feeling satisfied at the end. Make sure your story is swelling and ebbing in the right places by giving it a beginning, middle, and an end.


how to go on a multi destination vacation

The first part of your trip is all about getting acclimated. You are likely fighting a bit of jet lag and arriving in a new destination that will take a little bit of adjustment before you settle in. Ease into your vacation and don’t try and hit the ground at a full sprint. Make time in your schedule for spontaneous naps and a chance to roam and discover your surroundings. I love a great walking tour (bonus points if it involves food), that gives you a sense of the lay of the land and points of interest you know you’ll want to come back to. 


Pack your your biggest adventures here. This portion of your trip is when the plot of your book thickens. Your days can be action-packed and it’s possible to enjoy some late urban nights, because jet lag isn’t forcing you to bed by 9pm. This is when you go hiking in the Cinque Terre, zip line through the canopied forests in Monteverde, or catch a late night Flamenco show before you try out your own dance moves at a club in Barcelona.


With the end in sight, it’s important that your pace slows. You don’t want to go home feeling like you need a vacation from your vacation. There is a sense of revitalization and rejuvenation that comes from traveling, but we have to create the space for that to happen. Think of ending your adventure in a way that speaks to your soul. That could be calm ocean waves, the beautiful countryside, or wherever allows you to just be. 

How to create a multi-stop itinerary

When I create itineraries for clients, I’m always thinking of the big picture. I want to make sure your vacation gives you what you desire, in a way that makes sense and allows you to come home feeling like you accomplished everything you desired. If you are interested in my help creating the right multi-stop vacation for you, I’d love to hear from you. Let me know what you have in mind HERE.