How to Plan the Perfect Multi-Destination Trip

Once a group has managed to secure a budget and a few days off to spend traveling, they want to use them to the fullest. This is why multi-destination trips remain popular with’s clients and partners

Business representatives may fill the trips up with client meetings. Students and K-12 groups try to absorb as many sights and experiences as possible. Tour groups rarely limit themselves to the walking distance from the accommodation — instead they use charter buses to pick best-of-the-best experiences and attractions. Non-profits visit multiple destinations to get the most out of their fundraising run.

With all the perks of an extended itinerary, planning a route with multiple stops might still look intimidating. For that reason, has created a user-friendly tool to support trip planners.

Booking or a multi-destination trip from zero to booked includes just three steps: 1. Build your trip; 2. Review prices; 3. Check out.

The first step is a one-page dashboard with an intuitive layout and helpful auto-fill. Adding even a complicated itinerary can be done in a few clicks,.

Play with it as much as you want, and click the “view prices” button. You will see how changes impact your spending — instantly. You can always return to editing your itinerary.

Once you are satisfied with the itinerary and costs, “check out” to book your trip. Booking early helps to secure the best prices: earlier booking typically yields savings. You can still change your itinerary up to seven days prior to the trip.

Tips for Booking a Multi-Destination Trip

Multiplying your destinations means multiplying the fun. But it can also get overwhelming and frustrating if you do not know what to do. Preparation is your best friend! Here are some tips to ensure that your trip runs smoothly:

  • Plan your entire itinerary out ahead of time.
  • Start by choosing one place you absolutely have to get to (i.e., Toronto or Miami) and plan the rest from there. has published several guides about each major city’s most relevant attractions: try using them as your sample itineraries.
  • Keep your schedule realistic. Trying to jam too much into a little time might prevent your group from being able to savor each experience.
  • Leave time for the unexpected. Your bus is guaranteed to be where you expect it to, but the rest of the world — including your mind! — is prone to changes. Thick fog falling on the day of the boat trip, or a private event booking out the entire attraction happen. Have alternative options prepared.
  • Plan not only what to see, but also where to eat. Everyone needs to “refuel,” and authentic food can be a big part of your immersion into the local culture.
  • Err on the side of caution when you account for the group’s fitness level. Aching feet are not a desirable memory to make.
  • Make sure your sleeping arrangements are sufficient, and your transportation modes are comfortable. Lack of sleep and unreliable transportation can leave the group too exhausted to appreciate whatever sights you came to see.
  • Consider local weather trends and wildlife cycles: some destinations are impacted by seasonality more than others.
  • Check publication dates of your guide books: imagine arriving at a place of your interest only to find it was replaced with a parking lot five years ago.
  • Create a single document with your full itinerary and share it with your entire group.
  • Group Tours have advantages that individual travelers do not. Contract the attractions on your list and ask if they offer special group discounts.
  • Make sure you explain the logic behind the itinerary choices with the group. When every group member understands why you chose to visit three shops instead of five, they get “on board” with your choices easier.
  • And last but not least, don’t forget to have a great trip!

Ready to plan your multi-destination trip? takes it easy to make plans no matter where you’re going