How To Build A Perfect Itinerary

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You have decided to take a trip to somewhere great, FINALLY and now need to put together an itinerary.  Should you pack your days full of activities or just leave it all to fate?

That can be a tricky question.  And the best answer of course is, IT DEPENDS!

Yes! True.

Since we do this for a living we think we have some really great tips and tricks for putting together a great itinerary.  Here are our best secrets to help you get going.

Use the old school way of working everything out on paper first.

Get a sheet out and put the dates across the top.  Please use dates instead of Monday, Tuesday, etc. because that is where you can easily make a mistake.

Put in the travel time.  Once you land at the airport and the time it will take you to travel to your location in a perfect world (meaning your flight is on time).

Never schedule something important on the day you travel because airlines can’t be trusted to get you where you need to go on time and its not worth being stressed over.  Travel days are also long and tiring in nature, so its best to plan as little as possible. We encourage our clients to get to know the block they are on and have dinner reservations somewhere that won’t fault you if you don’t make it.

That really makes the best first day: travel, close-by exploration and dinner somewhere that is ultra cool or indigenous to your location.

Each of the following days, you should have at least one activity scheduled.  If you do more than this, you will find the constant running around and trying to keep a schedule exhausting and not really vacation like.  If you have 2 activities in one day, ensure they are scheduled as far apart as possible so you don’t feel rushed.

Here is an example of what we think is a perfect itinerary of my adoptive city, Annapolis.

Day 1

Arrive at BWI and Uber to Annapolis

Check in to waterfront hotel

Walk and window shop Main Street, Maryland Ave and West Street.

Grab a drink at Stan and Joe's

Dinner at Middleton’s for a crabcakes

Day 2

Take a boat trip to the Bay Bridge

Lunch at Vida Taco

Afternoon tour of the Naval Academy

Dinner at the Chart House

Day 3

Go the First Sunday Festival

Shop the stores you saw on Day 1

Stop by the State House

Do a Ghost Tour this evening

Day 4

Stand Up Paddle boarding trip

If there is time, take the water taxi guided tour

And this would be the perfect itinerary. Plenty to do, but also time to do nothing.

Part of the charm in a vacation is just to sit down and do absolutely nothing except sip an Orange Crush (Annapolis famous).

So how do you find all these fun things to do?


There are several ways.

The first thing you should do when going to another city is to get on Facebook and do a search under events in that city with the exact dates.

Go to events on the left hand side of your page and click

Then on the right, it says find events

Pick the option that says exact dates and put them in

Once it pops up in your location, change that location back on the left side.

Once you do this- all the events in that city will populate

Another way to find fun activities is to go to Airbnb.com and type in your city and the word “experience”.  This will bring what the locals are willing to do to entertain you. I have seen everything from a hat making class to a bar crawl.  Check it out and schedule something that interests you. I really like this because you are dealing directly with the person who is doing the tour.

And the last one I am going to share with you is Viator.  Have you heard of them? They are an aggregator of thousands of excursions in every major city all over the world. Just put in the name of the city and see all the many choices you have.  Viator.com

So there you have 3 ways to find fun stuff to do in your city of choice and can fill in some time while you are visiting.  Facebook events, Airbnb Experiences and Viator.

Our best advice though is to make sure you fit in plenty of leisure and people watching time.  There is something magical about finding someone playing an instrument on the street, sitting nearby and just enjoying it.