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 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.

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.

Are You A Good Candidate for Surprise Travel?

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Hey, my fellow wanderers!

Have you been thinking about Surprise! Trips lately and how much fun it would be? If not, that is OK too. It is definitely not for everyone. But how do you know if you would like it or not? Here are some traits that we think are great to have in order to enjoy the unknown.

1..Can you give up control just for a long weekend? There are some people on this earth who think this is the worst thing that could happen to them, and they would not be a good fit for us. We love busy people who make a million decisions and just need to give their mind a rest while we fill in the blanks. Have you ever suffered decision fatigue? If you have, then you know exactly what I am talking about. Some days the thought of trying to figure out what we are going to eat for dinner is just too much because we have already had a LONG DAY making a million little decisions. One vacation where you don’t need to decide all the details would be like a dream come true for you. And so exhilarating!

2. Do you enjoy surprises? Most of us love a surprise every now and then especially when they are pleasant and not like a surprise bill that is due right now or surprise visit from a family member you are not crazy about. Surprise! Trips give you something to look forward to as in, you know you are leaving town, just not sure where yet. And you won’t be flying by the seat of your pants only because we give you just enough information so you won’t be caught without. And we always say, if you forget something or just didn’t bring it, buy it. Just buy it!

3. Do you like to explore new places? We think exploring new places really slows time and helps you savor life. Do you ever feel like days, weeks, months pass really quickly? They do when you do the same things every day. Get up, go to work, come home, start over the next day. When you see and experience new things, time really does slow down as you savor the new locations, foods, people, and culture. If you are one of those people who can’t believe its almost 2019 or how fast this month flew by, then Surprise! Trips are right up your alley.

No one ever says, remember last Tuesday when you went to work? NO! We don’t. But I remember when I went to the coast with a couple of friends for St. Patrick’s Day weekend and we all wore costumes and went to the local parade. In fact, we will remember that for years to come.

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4. Are adventures important to you? You don’t need to go far for an adventure- in fact, you can find them in your own town if you are willing to look. But if you want to do something epic and really memorable that you will recall for your entire life, it’s great to get outside of your element and maybe even comfort zone. Pick your favorite people to have an adventure with because let's face it, not everyone is cut out for exploring the unknown. You will have stories to tell your grandchildren.

5. What are you waiting for? When the laundry is calling your name and your To-Do list is a mile long, the fun you love to have is easy to put off. We are all busy but make certain things a priority. It behooves you to make your bucket list Surprise! Trip a priority also. Pick a long weekend 3-6 months from now and MAKE IT HAPPEN. Be one of those people!

Oh, the stories you are going to collect! And talk about and share forever...

Go fill out the Questionnaire HERE

Came hang out with me on Facebook HERE

How Much Does the Hotel Matter?

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Have you ever heard someone say, “I don’t care about my room, it’s just a place to sleep?”

Or something along that line? I hear it all the time and couldn’t disagree more. Since when is sleep underrated?

I have stayed in 100’s of nights in hotel around the country and world. I’ve been in some really good one and really crappy ones. And I can tell you with 100% certainty that your hotel matters, A LOT!

Here is a list of things that matter (at least to me).

Location: When your hotel is located in the heart of the city or directly in heart of ‘old town’ or even in the castle wall like the one I stayed in in Seville, Spain it gives you direct access to all the action and that is something that can’t be done with a typical budget hotel. I like to walk right out the door and BE in the place where I can see and do without a lot of transportation modes.

It saves time and adds a lot of character to your vacation. It is more expensive than staying outside of the city, but in the end, worth it.

I have seen on a couple of occasions where travelers realize they are too far away from where everything is and want to change their hotel reservation. So much easier to do it right the first time.

Bed Quality: I know of a couple who rented a hotel for a fun weekend trip away and ended up sleeping in the chair in the room because the bed quality was horrid. Can you imagine? Not sleeping well is enough to ruin your entire trip. I will admit, there was one time I was staying with friends and I thought their bed was going to kill me! The following day, I asked my husband to just relax in the local park and let me sleep for ½ hour. I was slowing everyone else down and felt fairly miserable. Beds are so important and some hotels do a better job than others.

Extra Amenities: Who doesn’t love eating breakfast in bed? Room service is only available in hotels that typically have restaurants. This also means the hotel has a bar. This makes the hotel a destination within itself. If for some reason, you could not leave your hotel because you were sick or something else is going on, I need to be stuck at a hotel where I can eat and drink. Don’t you agree? And hey, getting toast crumbs in a bed that is not your own is best!

Some other factors that could improve your hotel stay:

Swimming pools



Business Centers

Lobby where you can meet with others


View from your room

So, we know (I KNOW from personal experience) that hotels can make or break your precious vacation time. There are too many important pieces that can get messed up. It’s important to put as much money as you can towards your accommodations because in the end, it is where you sleep and that is important!

PS. My biggest pet peeve about a hotel is if it has popcorn ceilings-- if it does. I’m out!=)

What do love or dislike about hotels? Come and tell me on my FB Page LETS WANDER TRAVEL