How to plan the perfect travel itinerary

While it seems that travel advisers and travel agencies are almost completely a thing of the past – there is an art to crafting the perfect travel itinerary.  My husband and I fancy ourselves experts, and take turns planning our own trips.   In fact, firing up an excel document with a new location listed in the top left hand corner is a total turn-on.  It means something amazing and wonderful to look forward to is coming, and I get to plot out every last minute of it.

Planning the perfect trip varies for everyone, but hopefully I can provide you with a brief, yet effective framework for making your next trip, the BEST trip.

Lesson #1: Cram smart, or don’t cram at all

Don’t ever try to do too much.  My vacation motto is “act like you’ll never ever be coming back here” which usually means we try to cram a lot into a small amount of time, however, there is an art to the cram.  My husband and I learned a tough lesson about 8 years ago on our trip to Costa Rica.  We tried to see 4 different location in 8 days.  While this might be better accomplished in Europe, in Costa Rica where roads aren’t always the best to travel on proved a challenge.  We had bitten off more than we could chew and paid the price.  The result of cramming is that you lose time in the places you love (and of course you don’t realize you love it until you get there), and spend too much time en route, rather than on the beach, on the streets of a city, or just people watching in a cafe.  If you’re going to cram, make sure you do it in a place like an island (ex: see 5 beaches – love you St. John!), or Europe where you know transit will be easy between cities.

Lesson #2: Prioritize

Set reasonable expectations.  Unless you are spending a month in one place, you won’t be able to see everything.  Pick and choose attractions, restaurants, museums, etc. and prioritize.  While my motto is basically live like there’s no tomorrow when visiting a new place, that’s not always the case.  You may return to that location, but if not, make sure you see what’s important to you and will round out your travel.

Lesson #3: Don’t be afraid of tours

How many times on this blog (probably twice at this point) have I raved about the walking tour.  Well go on a food tour, a wine tour, any type of tour that will help you see a bunch of a new fun things.  They cover a lot of ground, and if it’s not a walking tour, they’ll manage the travel and connections, normally picking you up from your hotel.  It’s a win/win.  Sure you could see Pompeii and Vesuvius on your own, but wouldn’t it be nice to arrive at the site with your entry fare already paid for and with an awesome guide to boot?

Lesson #4: Manage connections

Getting from point A to point B is not always easy or fun, but when planning a trip, before you even book, determine if the hotel offers connections from the airport if you’re not renting a car.  Determine where the key sites are that you want to see, and if public transportation is available or if renting a car is more cost effective.  If you are relying on public transportation print the schedules before you go. While it’s so old school – having this information handy, especially with international roaming fees (I know those are being relaxed), but it’s easier to pull out a piece of paper abroad than having to manage from your phone.  Sounds crazy I know, but it’s true.

Lesson #5: You can make everyone happy

This is remarkably not as tall of an order as it seems.  After a lot of trial and error, my husband and I finally asked each other, are you a Cam or are you Mitchell?  If you’re not familiar with that great Modern Family episode, Cam pretends to be an enthusiastic on-the-go traveler who would rather be out and about than relax.  However, turns out Cam would rather lay by the pool, and who doesn’t?  I’m the Cam in this relationship and striking a balance between activities and relaxation has taken some effort, but it’s doable.  While you shouldn’t compromise on sites that are important to you, more often than not, everyone can appeased with a littl e ice cream and a lay on the beach (or maybe that’s just me).

Lesson #6: Eat smart, eat great

Ask for a free breakfast.  When booking a hotel, inquire if they offer free breakfast.  This is usually a key metric I use when book a hotel.  Will I be getting free food?  Normally, hotel breakfasts cost per person anywhere between $13-$20…for breakfast.  While it’s the most important meal of the day think about what milk, cereal, eggs, toast, or fruit costs you at home.  You probably spend $2o over the course of 2 weeks to a month on breakfast, not per day.  A free meal saves money, plain and simple.

Stock your fridge!  If your room has one (and if it doesn’t, you can call down and ask for one) – hit a local supermarket and buy some of your favorite snacks, items and booze (never poach the mini bar!).  This will go a long way to helping you stay within a reasonable budget while traveling, and can also be a fun way to pack a picnic.  What’s better than hitting up a beach or a park in a big city with a baguette, some wine, cheese, and a few meats and enjoying the afternoon sun?

Finally, food is often a large part of the travel experience (at least with me, clearly), when working with a concierge on restaurant reservations, don’t be afraid to speak up for what you really want.  The local hole in the walls are famous with locals for a reason.  They’re damn good and they’re cheap.   Where applicable, make restaurant reservations in advance of your travel as well.  There are certain destinations where famous restaurants are well known, and it can never hurt to reach out to make a reservation prior to your stay, especially if your trip is also celebrating a special occasion.

Lesson #7: Don’t be afraid to call an audible

I love to plan.  I’m a planner, and I LOVE my spreadsheets.  If you have an organized listing of all of your travel options, activities, restaurants, etc., you won’t be bummed if say mother nature gets in the way.  Things happen and that’s okay.  Hit another item on your list, and roll with it.  Once you’re on vacation there’s not much else you can do but make the best of a new and exciting situation.

Lesson #8: Do something different

It’s easy to go on vacation and not take risks or try something new, but you may be missing out on so many fun and different experiences.  For example, in Provence I decided I wanted to take a cooking class.   While many classes were incredibly expensive, my husband and I found a wonderful cooking class right in the chef’s home.  This created an intimate experience with great food and plenty of laughs.  If cooking isn’t your thing, look for different activities that will help you engage with the locals or one that just pushes you out of your comfort zone.  I never in a million years thought I’d go hot air ballooning, but sure enough it happened and created one hell of a memory.  A vacation is a time to relax, but it’s also your own personal adventure.  Come home with something other than a tan to talk about.

Lesson #9:  Use your peers!

We live in a sharing economy.  The internet has put so much power in the hands of us, the everyday consumer and traveler.  I love using sites like TripAdvisor for hotel reviews and activity suggestions, and even restaurants.  When I’m in a location and using wifi – I often times pull up Yelp! for the best restaurants nearby, and have found some amazing gems while on vacation.  When people are reviewing and being frank about their experiences, they will never ever lead you astray.  Use ’em!

Lesson #10: Don’t forget to take it all in

There are people in this world that cannot travel, either they choose not to or cannot afford it.  Every trip you take, large or small, sit back and relish the fact that you’re doing something special, new, and cool.

Add a comment below if you agree/disagree with my lessons or want to see one of our travel itineraries!


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