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How We Made Our Top 100 Two-Year Itinerary


How We Made Our Top 100 Two-Year Itinerary (And a few tips to help you with yours!)

Today, we are both proudly and anxiously taking off towards the first destination of our two-year itinerary – Cape Town, South Africa. Yes, a two-year itinerary. I know it sounds ridiculous, but we really do have an itinerary of 700+ days. With a goal to visit the AbsoluteVisit Top 100 Places in the World, an itinerary became less of an option and more of a necessity.

As a self-proclaimed “uber planner,” planning for such a long trip is daunting to say the least, and creating our two-year itinerary was no different. Our itinerary took us days of full-time work, even with the knowledge gained from a previous ten-month trip around the world.

I’m sitting here drinking a Peppermint Mocha (don’t judge), staring at a blank document on my MacBook, looking to answer a single question that has come up repeatedly since announcing the trip – “How did we create a two-year, 700+ day itinerary?” I am struggling to write even a single sentence. Even though I believe the task is easier than most think, it is difficult to explain. With this in mind, I will attempt to share with you how we created our itinerary and call out a few planning tips that we learned along the way.

Why plan?

First, I want to tackle the question of why we created a two-year itinerary. The answer to this is pretty simple – to accomplish our goal of seeing the AbsoluteVisit Top 100 Places in the World! But, let me add a little real world meaning to that. We are self-funded and all of our current plans only involve spending money we have made and saved over the past several years. Due to money, time is also constrained; although not directly correlated, the longer you travel, the more money you will spend. And last, but certainly not least, we wanted to ensure that we would see all of the Top 100 Places. So, there we have it, our constraints – Money, Time, and the pressures of seeing all of the Top 100 Places. These constraints are exactly why we needed a plan.

Without a plan that included both an itinerary and a budget, we knew that spending too much money in one place, would mean that our trip would be cut short, causing us to miss our chance to see some of the Top 100 Places. But, enough chit-chat for now, on with the planning!

Let’s get planning

We knew that planning this trip would take a good chunk of our time. So, we actually took an entire week off of work to plan the trip, and make significant changes to and our other websites. We planned to use two full days just to create the itinerary for the trip and a basic budget. We split our planning into two days – “Day 1, Basic Planning” – “Day 2, Detailed Planning”.

Basic planning

Our goal for the first day was to separate the trip into more manageable sections. I remember our first planning session vividly. We were sitting in Brad’s apartment with our laptops open to the AbsoluteVisit Top 100 map. As we talked through strategies on how to break up the trip, it was immediately clear that we should break up the trip by continent. We started down this path by using his wallpaper whiteboard to create a timeline of our trip. We listed out six individual legs (Antarctica was included in South America) on his whiteboard, and our first point of discussion was where should we go first? The biggest determining factor for this was weather.

Planning Tip #1 – Weather will be one of the most critical factors in your planning. Use weather averages to help guide your general planning. Use for averages and consult sites like Wikitravel for best times to visit based on events, holidays and climate.

Sometimes to get a major decision off the ground, such as where to start, all you need is a change of scenery. We grabbed a couple of red solo cups, poured some adult beverages, and went on one of many walks around Chicago’s North Pond to discuss our ordering strategy. Based on the timing of when we were planning to quit our jobs and the winter holidays, it made sense to start our trip in January. January is generally horrible to travel in the Northern Hemisphere, but ideal for much of the Southern Hemisphere. With that in mind, we automatically ruled out Europe, North America and China (yes, I know thats not a continent, but …). What that left was South America, Africa, Southeast Asia and Australia. With past trips to South America, Southeast Asia and Australia, we next went with what we wanted to experience the most – an African Safari! One mile into our “walking discussion” later, we had our starting point – Africa.

With Southeast Asia running as a second favorite on our original list, and the time of year being ideal for this region, we added on Southeast Asia to round out what we now call, “Leg 1.” As with most things, the first step was the hardest and took the longest time. After defining Leg 1, the other continents fell right into place based on time of year and our desire to see them.

We now had a white-board covered with our basic itinerary, including the overall two-year itinerary broken down into six separate legs. With the basic plan in hand and six hours of different discussions behind us, it was time to kick it up a notch, and peel back the layers of the onion. Will the plan really work? Will we see all of the Top 100 Places? How would we get from country to country?

Some initial planning notes on Brad’s Whiteboard

At this point, it was time to divide and conquer. Brad took Africa and I took Southeast Asia. We poured another round of liquid courage, turned up the tunes, and used Google Docs Spreadsheets to start listing out the major questions for these regions. These questions included things like:

- Where in Africa would we start? Where is it cheapest/easiest to fly into?
- What is the best way to experience the Serengeti Migration?
- What are the visa restrictions for Myanmar?

Planning Tip #2 – Break a big problem into smaller pieces. By breaking our two-year trip into six-week segments and then week-long “trips”, we were able to narrow our focus and plan for a specific area.

After an hour or so, we traded questions and thoughts and added as much detail to our spreadsheet as possible. We next moved on to the other legs, and hundreds of trance ballads later (sometime around 4:15AM), we had wrapped up by capturing key questions and a basic itinerary for the entire trip. I had started to dig into some of the detailed questions, but I was simply exhausted. I had hundreds of questions spinning around my mind, but I finally drifted into dreams of an African Safari right on an air mattress in the middle of Brad’s living room.

It was a really long and exhausting day, but also very inspiring. Thinking through each of the places we would be visiting was surreal, but I got that tingly feeling that I was doing the right thing. We had worked all day, but we had a basic two-year itinerary covering 62 countries, and more importantly – the Top 100 Places in the World.

Connecting the dots and finalizing

Sluggish from an intense first day of planning, we made the 10 minute city walk to Starbucks just in time to get re-caffeinated for another full-day of planning. The second day’s goal was to get the itinerary in good enough condition that we could start booking the initial travel components such as flights, big tours, etc. If you are not ready to book at least part of a trip, then it is a sign that you have not planned it enough. This is always a good indicator for me.

Brad and I again divided the legs amongst ourselves and began several sessions of focused work, diving into specific regions. This time, we actually mapped out how we would traverse from place to place and estimated the number of days we would be in each place. This is the part where you will realize how important the internet is (if you haven’t already). Google will be your best friend as you use Google Maps to determine where things are, Google Search to answer your questions, and Google Docs to record your findings. Speaking of, to keep everything organized, Brad and I created a master spreadsheet which literally had every day in 2013 and 2014 as the first column. With this in place, we started filling in each place we would visit next to each day.

An Example of our Travel Itinerary in Progress
Planning Tip #3 – Take breaks and allow yourself to step back and look at the big picture. The walks we took around Chicago’s North Pond were critical to clear our minds and gave us the confidence that we were headed in the right direction.

After a first edit and a Google Spreadsheet that still had dozens of questions, sporadic gaps and some overlaps, it was time to combine our powers, and share some thoughts. This is when we would bust out our solo cups again for another walk around North Pond. These were the moments where our thoughts would gel and our worries would cease. We would often dissect the trip from top to bottom to really make sure that we were happy and confident with our current plan.

Chicago’s North Pond – A Great Place for Some Deep Thinking

An itinerary is not set in stone, can be changed, and will be changed. Honestly, there is no way around a shifting itinerary, and I would not advise it any other way – things will change – it’s a fact of life. To compensate for these unpredictable shifts, simply include a couple buffer days for every month or so of travel. This should at least give you some breathing room if you find yourself in a bind!

Planning Tip #4 – Don’t try to figure it ALL out at once. An itinerary is a living and breathing document. So, don’t stress yourself out by trying to map out every single detail. Instead, focus on the major decisions and leave some decisions to be made on the road!

With a very solid 700+ day itinerary in front of us, we were beginning to gain the confidence to begin booking our first flight. The point at which you are ready to begin investing thousands of dollars into a trip is different for everyone: there is no single or right answer. You’ll have to find your own comfort zone to tell you when you are ready to book. For Brad and I, we continued to go over the first leg – over and over. Finally, in the wee hours of the morning, after reviewing the plan enough times to have it nearly memorized, we were ready to book! Pulling the trigger on the first flight was like a last second field goal to win the National Championship. Brad and I gave each other a massive high-five after booking our first flight…and then realized we had dozens of others to book!

The amount of time we put into the itinerary is difficult to truly measure, because we came into it with a lot of previous knowledge and thoughts. The best way to understand the amount of time it might take you to plan a long-term trip, is to think about the amount of time you would normally put into a one-week vacation. If that usually takes you a half-day, then you have a rough measurement of how long a two-month trip might take you (8 weeks x .5 days = 4 days to plan a two-month trip).

Planning Tip #5 – Be patient and have fun! Creating an extended travel itinerary can be frustrating with so many things to determine. But, hang in there and enjoy the ride.

At the end of it all, I honestly had a blast planning the trip. I learned a ton along the way and re-inspired myself by thinking through each of the incredible places I’d be seeing. So, let this be a time for you to reflect on what you are going to be doing and enjoy that! As they say, the journey is just as important as the destination.

Without further ado, I present to you the AbsoluteVisit Top 100 Trip Itinerary!

The AbsoluteVisit Top 100 Trip Itinerary

Full Itinerary Download – A spreadsheet containing the day-by-day itinerary of our trip.

Africa – January 9th – February 17th – 2013

View Leg 1 – Africa in a larger map
January 9th – 15th – South Africa
Cape Town, Table Mountain National Park, Great White Shark Diving

January 16th – 26th – Namibia
Fish River Canyon, Namib Desert Dunes, Etosha National Park

January 27th – 30th – Botswana
Okavango River Delta, Chobe River

January 31st – February 2nd – Zambia
Victoria Falls

February 3rd – 9th – Kenya
Samburu Game Reserve, Masai Mara National Park, Serengeti Migration

February 10th – 17th – Tanzania
Serengeti National Park, Ngorongoro Crater

Southeast Asia – February 18th – April 22nd – 2013

View Leg 1 – Southeast Asia in a larger map
February 18th – 22nd – Thailand
Grand Palace, Wat Phra Kaew, Wat Pho, Wat Arun

February 23rd – March 4th – Myanmar
Shwedagon Stupa, Bagan Temples, Mandalay Palace

March 5th – 7th – Thailand
Chiang Mai

March 8th – 15th – Laos
Luang Prabang, Vang Vieng Tubing, Pha That Luanch

March 16th – 20th – Cambodia
Angkor Wat, Angkor Temple Region

March 21st – 29th – Thailand
Koh Samui

March 30th – April 9th – Philippines
Banaue Rice Terraces, Chocolate Hills, Puerto Princessa, Taal Volcano

April 10th – 21st – Indonesia
Borobudur, Prambanan, Mt. Bromo, Bali

Europe – May 13th – August 6th – 2013

View Leg 2 – Europe in a larger map

View Leg 2 – Europe in a larger map
May 13th – 24th – Spain
Madrid, Mezquita de Cordoba, Alhambra, Barcelona

May 25th – June 13th – Italy
Pompeii, Almalfi Coast, Colosseum of Rome, St. Peters, Vatican Museum,

Trevi Fountain, Florence Cityscape, Uffizi Gallery, Florence Duomo,

Cinque Terra, Portofino, Venice Canals, St. Mark’s Square, Basilica San Marco

June 14th – 17th – Switzerland
Matterhorn, Zermatt, Zurich

June 18th – 21st – Germany
Neuschwanstein, Munich

June 22nd – 24th – Czech Republic
Prague’s Old Town

June 25th – 27th – Germany

June 28th – 30th – Netherlands

July 1st – 3rd – Belgium

July 4th – 15th – France
Louvre Museum, Eiffel Tower, Palace of Versailles, Chartres Cathedral,

Chambord Chateau, Mont St. Michel

July 16th – 18th – England
British Museum, London

July 19th – 23rd – Ireland
Dublin, Cliffs of Moher

July 24th – 28th – Norway

July 29th – August 6th – Russia
Hermitage Museum, Church of Spilled Blood, The Kremlin, St. Basil’s Cathedral

China-Nepal-India – August 25th – December 5th – 2013

View Leg 3 – China/Nepal/India in a larger map

View Leg 3 – China/Nepal/India in a larger map
August 25th – October 13th – China
Lijiang, Yangtze River Cruise, Wulingyuan, Li River, Hong Kong,

Shanghai Skyline, The Bund, Forbidden City, Tiananmen Square,

Temple of Heaven, Great Wall of China, Terracotta Warriors,

Potala Palaca, Tibet

October 14th – November 4th – Nepal
Kathmandu, Mt. Everest

November 5th – December 5th – India
Ladakh, Kashmir Valley, Golden Temple, Taj Mahal, Tiger Safari,

Golden Triangle, Kerala Backwaters, Kanchipuram, Meenakshi Temple

Antarctica/South America – January 3rd – March 27th – 2014

View Leg 4 – Antarctica/South America in a larger map

View Leg 4 – Antarctica/South America in a larger map
January 3rd – 15th – Antarctica
Drake Passage, Antarctic Penninsula

January 15th – 23rd – Chile
Torres del Paine

January 24th – February 2nd – Argentina
Perito Moreno Glacier, Mt. Fitz Roy, Buenos Aires

February 3rd – 5th – Uruguay

January 6th – 9th – Argentina
Iguazu Falls

January 10th – 11th – Paraguay

January 12th – 18th – Brazil
Rio de Janeiro Cityview, Cristo, Sugarloaf, Pantanal

January 19th – 25th – Bolivia
Santa Cruz, Salar de Uyuni, La Paz

January 26th – February 12th – Peru
Cusco, Machu Picchu, Lima, Amazon Rainforest

February 13th – 22nd – Ecuador
Galapagos Islands, Quito

February 23rd – 26th – Easter Island
Easter Island

North/Central America – May 1st – August 22nd – 2014

View Leg 5 – North/Central America in a larger map

View Leg 5 – North/Central America in a larger map
May 1st – June 3rd – United States
Moab Desert, Bryce Canyon, Grand Canyon, Las Vegas,

Pacific Coast Highway, Golden Gate Bridge, Yosemite NP,

Grand Teton NP, Yellowstone NP, Glacier NP

June 4th – 15th – Canada
Banff NP, Jasper NP, Yukon

June 16th – July 1st – United States
Glacier Bay NP, Seward, New York City Skyline, Denali NP,

The Metropolitan Museum,

July 2nd – 7th – Venezuela
Caracas, Angel Falls

July 8th – 17th – Colombia
Bogota, Cartagena, Cali, Medellin

July 18th – 21st – Panama
Panama City, Bocas del Toro

July 22nd – 26th – Costa Rica
San Jose, Jaco, Miguel Antonio NP,

July 27th – 31st – Nicaragua

August 1st – 4th – Honduras
Tegucigalpa, Bay Islands

August 5th – 6th – El Salvador
San Salvador, Lake Coatepeque

August 7th – 10th – Guatemala
Tikal, Santa Cruz

August 11th – 15th – Belize
Belize City

August 16th – 22nd – Mexico
Chichen Itza, Teotihuacan

Middle East and Oceania – September 21st – December 15th – 2014

View Leg 6 – Middle East & Oceania in a larger map

View Leg 6 – Middle East & Oceania in a larger map
September 21st – 29th – Morocco
Fez Markets, Sahara Desert, Marrakesh

September 30th – October 7th – Greece
Santorini, Acropolis, Delphi

October 8th – 10th – Croatia

October 11th – 17th – Turkey
Hagia Sophia, Blue Mosque, Topkapi Palace, Cappadocia

October 18th – 21st – Syria
Damascus Old City

October 22nd – 24th – Lebanon

October 25th – 30th – Jordan
Petra, Wadi Rum

October 31st – November 2nd – Israel
Jerusalem Old City, Tel Aviv

November 3rd – 10th – Egypt
Pyramids of Giza, Egyptian Museum, Karnak, Luxor Temple

November 11th – 13th – UAE
Burj Khalifa, Burj al Arab

November 14th – November 28th – Australia
Sydney Opera House, Great Barrier Reef, Ayers Rock, Great Ocean Road

November 29th – December 6th – New Zealand
Auckland, Tongariro Alpine Crossing

December 7th – December 15th – French Polynesia
Tahiti, Bora Bora
Full Itinerary Download – A spreadsheet containing the day-by-day itinerary of our trip.

How can we help YOU?

Well, that’s it. I know it may still seem daunting, and frankly, it is. But, if you break down your trip into small pieces, take some basic factors into consideration, and have fun with it, I know you can figure it out! In fact, I guarantee it. If you ever run into an issue or just need someone to talk through your “itinerary,” we’re here for you. We love to help others plan their trips – how can we help YOU?

Frequently Asked Questions

We know there will be lots of questions so don’t hesitate to ask. You can learn more about the trip and see the answers to frequently asked questions, go here.

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The Top 100 Places in the World
1 Great Wall of China
2 Pyramids of Egypt
3 Machu Picchu
4 Serengeti Migration
5 Galapagos Islands
6 Grand Canyon
7 Angkor Temples
8 Antarctica Cruise
9 Taj Mahal
10 Iguazu Falls
11 Amazon Rain Forest
12 Great Barrier Reef
13 Bora Bora
14 Victoria Falls
15 Bagan
16 Petra
17 Potala Palace
18 Karnak
19 Mt Everest
20 Cappadocia
21 St Peters Basilica
22 Fjords of Norway
23 Jerusalem Old City
24 Burj Khalifa
25 Borobudur
26 Forbidden City
27 Kashmir Valley
28 Li River Cruise
29 Ladakh
30 Alhambra
31 Louvre Museum
32 Perito Moreno Glac.
33 Banaue Terraces
34 Colosseum of Rome
35 Easter Island
36 Venice Canals/Alleys
37 Kathmandu Valley
38 Wat Phra Kaew
39 Yellowstone NP
40 Pompeii
41 Rio Panoramic View
42 Palace of Versailles
43 Dubrovnik
44 Golden Temple
45 St. Basils Cathedral
46 Vatican Museum
47 Florence Cityscape
48 Acropolis
49 Amalfi Coast Drive
50 Kremlin
51 Hong Kong View
52 TerraCotta Warriors
53 Mezquita Cordoba
54 Chichen Itza
55 Damascus Old City
56 Shwedagon Stupa
57 Sahara Desert
58 Mont St Michel
59 St. Marks Square
60 Egyptian Museum
61 Hagia Sophia
62 Angel Falls
63 Delphi
64 Teotihuacan
65 Baalbek
66 Banff NP
67 Santorini
68 Matterhorn
69 New York Skyline
70 Neuschwanstein
71 Chartres Cathedral
72 British Museum
73 Prague Old Town
74 Burj al Arab
75 Yangtze River Cruise
76 Yosemite NP
77 Hermitage Museum
78 Torres del Paine
79 Chambord Chateau
80 Lijiang
81 Portofino
82 Great Ocean Road
83 Tongariro Alpine
84 Las Vegas Strip
85 Tikal
86 Topkapi Palace
87 Sydney Opera House
88 Eiffel Tower
89 Luxor Temple
90 Kerala Backwaters
91 Golden Gate Bridge
92 Cinque Terre
93 Metropolitan Mus
94 Uffizi Gallery
95 Ayers Rock
96 Cliffs of Moher
97 Pacific Coast Hwy
98 Shanghai Skyline
99 Glacier Bay NP
100 Wulingyuan
Cappadocia  Cappadocia, Turkey
Top 100 by Name Top 100 on a Map
Top 100 by Country Top 100 by Continent