Heading Out

Today’s the day. In about 10 minutes I will suspend my cell phone service, dismantle and box-up my computer, and catch a ride to the airport. I admit I’m a bit nervous about leaving this time, and a bit under the weather to boot, but it’s snowy here and grey, and I’m pretty confident bright sun and warm air will significantly improve both health and mood.

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Here we go!

trip map


Trip 2.0

It’s that time again. Time to pack my bag, leave my job, and catch a plane to destinations unknown.

Tomorrow is my last day of work at my day job, and Saturday is my last shift at the part-time job. Tuesday I hop aboard a one-way ticket to Guatemala City and Central America at large, but with no idea where I’ll head from there. For the first 2.5 weeks I’ll be traveling with my brother – a trip that I’ve owed him ever since he graduated high school – but once he leaves I’m on my own. No plans, no directions, no return date. I’ll be living full and traveling slow, and coming back when the money runs out or my new job prospect needs me on board. Whichever comes first.

As with my last long trip, I’ll be keeping a steady flow of pictures and updates about my journey here.

There was a time when December 10th seemed much too far away – and now it seems too soon!


On my first trip to Thailand


As of 5:00pm yesterday, I have no job to wake up for, no boss to report to, and no paychecks coming in. I’m unemployed.

As of 5:00pm yesterday, I have begun final preparations for my trip. As of 3:00pm today, Hurricane Irene is putting a damper on those plans.

Luckily, I don’t have much left to do. I’m going to spend this afternoon going through my list of things to bring and making sure I haven’t forgotten anything that will take time to get. Though if I have, it’s probably too late by now anyway. Tomorrow’s a loss due to the storm, and I’m just hoping we still have power. Monday and Tuesday I’ll wrap up loose ends, like getting toiletries, suspending my cellphone, making goodbye calls, and ensuring that I have enough American dollars to get me through Southeast Asia (they love them down there). And Wednesday morning I’m off to New York – provided New York is still there on Wednesday – and we fly out to Israel that night with a layover in Ukraine.

One chapter is closed, but another has yet to begin. I’m sitting in intermission. I’m excited, but it still hasn’t hit me that I’m leaving. And I suspect that this trip will be over before I even know it’s begun.

Travel Gear

In my previous post, I outlined some of my pre-trip expenditures to give you a sense of what I’ve been saving for and spending my money on in preparation for departure. In this post I’ll show you exactly what I bought and will be bringing with me.

Travel gear

In this picture you can see everything I’m taking – except for a pair of shorts and a watch I’m already wearing, 4 pairs of ExOfficio underwear that I’ll use before my departure, the eye mask that I forgot to take out of my toiletries bag, my iPod, and assorted toiletries (toothbrush, toothpaste, comb, ibuprofen etc). To give a little perspective, most travel forums have people recommending a 60-65L bag for long-term travel. My friend Karol is traveling with something like a 28L bag. Mine is 40L.


What’s going inside:

Bags/Clothes – REI Lookout 40 backpack, ExOfficio Nomad shorts, REI Sahara convertible pants (mostly to be used as shorts), Vasque Mindbender trail running shoes, Sanuk Yogi II sandals, Rick Steve’s clothesline, Wordlock luggage lock, Lewis N Clark cable lock, Timex Expedition watch, Sea To Summit eVent waterproof compression sack, Sea To Summit generic compression sack, Mountain Hardwear Canyon long sleeve shirt, Mountain Hardwear Canyon short sleeve shirt, Pacsafe waist wallet, REI Sahara polyester t-shirt, EMS brand polyester t-shirt, EMS Packable pack as daybag, Under Armor Heat Gear socks (3 pr)

Electronics/Gadgets – iPod, Petzl Tikka2 headlamp, GorillaPod, Sony Nex-3 camera with 18-55m and 16mm lenses + camera bag & battery charger, Belkin Mini Surge Protector, ASUS Eee PC 1015PX-PU17-BK 10.1-Inch netbook w/ 2GB upgraded RAM + charger, Case Logic VLS-110 netbook sleeve, international travel adapter, 250GB external travel hard drive

Toiletries/etc – Sea To Summit hanging toiletry bag, compass/thermometer keychain, drain stopper, carabiners (2), REI XL MultiTowel, ear plugs, travel mirror, Croakies Reax eyeglass retainers, playing cards, wallet w/ chain (attaches inside shorts pocket), silk sleep sack (gift), anti-malarial and anti-diarrhea medication, Deet bug spray, Platypus collapsible water bottle, travel tissue pack

Here’s the bag full, minus the forgotten items I noted above and with a shoe for size reference:



My goal is to fit this in the overhead compartment on planes and in the seat with me on buses. I suspect the latter is going to be rather tough to accomplish, but I figure I learn what’s really necessary as I go and I’ll be able to pare down throughout the trip.




Wednesday, Aug 31 – Departure
Depart JFK Int’l airport at 7:05 PM
Arrive at the airport four hours early

Thursday, Sep 1 – Arrival & The Golan

Landing at Ben Gurion Airport at 5:10 PM
Evening: Program introductions & ice breakers
Overnight: Afik Guest House, Golan / Tel: 972-4-6761240

Friday, Sep 2 – The Golan & Galilee

Tzfat – Birthplace of Jewish mysticism
Har Merion – Nature walk
Prepare for Shabbat
Start of Shabbat – Candle lighting ceremony
Festive Shabbat dinner
Oneg Shabbat – Celebrating Shabbat
Overnight: Afik Guest House, Golan / Tel: 972-4-6761240

Saturday, Sep 3 – The Golan

Walking tour
Shabbat activity
Havdallah ceremony – Conclusion of Shabbat
Kinneret Cruise – Boat ride on the Sea of Galilee
Overnight: Afik Guest House, Golan / Tel: 972-4-6761240

Sunday, Sep 4 – The North & Tel Aviv

Nahal Jilabun – Canyon hike in the Golan
Har Bental – Observation point and former Syrian bunkers
Jordan River rafting
Depart for Tel Aviv
Overnight: Ruth Daniel Hotel, Tel Aviv / Tel: 972-3-5264526

Monday, Sep 5 – Tel Aviv & The Negev

Welcome & ice breakers with Israeli peers
Rabin Square – Memorial to Yitzhak Rabin
Independence Hall – Declaration of the modern State of Israel
Jaffa – Ancient seaport & artist colony
Tel Aviv beach – Relax along Israel’s Mediterranean Coast
Depart for Arad
Overnight: Arad Guest House, Arad / Tel: 972-2-5945599

Tuesday, Sep 6 – The Negev

Ascend Masada – Via the Roman Ramp
Masada – Ancient mountain-top fortress
Descend Masada – Via the Snake Path
Ein Bokek – Nature walk
Dead Sea – Floating at Ein Bokek Beach
Camel trekking – Travel the Negev desert in style!
Beduin hospitality
Mifgash activity with Israeli peers
Overnight: Beduin Tent, Chan Shayarot / Tel: 972-8-6535777

Wednesday, Sep 7 – The Negev

Nachal Chavarim – Canyon hike
Sde Boker – Desert outpost & grave of Ben Gurion
Depart for Jerusalem
Haas Promenade – Panoramic view of Jerusalem
Plant a tree in Israel!
Prepare for Yad Vashem
Overnight: Caeser, Jerusalem / Tel: 972-2-5005656

Thursday, Sep 8 – Jerusalem

Yad Vashem – Holocaust Memorial & Museum
Har Herzl – National Memorial
Ben Yehuda Street – Pedestrian shopping center
Evening cultural event
Overnight: Caeser, Jerusalem / Tel: 972-2-5005656

Friday, Sep 9 – Jerusalem

Jewish Quarter – Old City walking tour
Davidson Center – Interactive exhibit
The Kotel – Reflections at the Western Wall
Wrap up and depart with Israelis
Machane Yehuda – Colorful Jerusalem marketplace
Prepare for Shabbat
Start of Shabbat – Candle lighting ceremony
Festive Shabbat dinner
Oneg Shabbat – Celebrating Shabbat
Overnight: Caeser, Jerusalem / Tel: 972-2-5005656

Saturday, Sep 10 – Jerusalem

Shabbat activity
Walking tour
Wrap up session
Havdallah ceremony – Conclusion of Shabbat
Political seminar – The Situation Today in Israel
Overnight: Caeser, Jerusalem / Tel: 972-2-5005656

Sunday, Sep 11 – Departure & Arrival

Depart Accompany group to Ben Gurion airport at 8:15 AM
Arrive at JFK Int’l airport at 5:05 PM Leave airport to continue travels!

Work vs Travel (Or: Travel IS Work)

One thing I’ve learned from preparing for this trip is that I’m a heck of a lot more excited about it than I am about working. I know – shocking, right? But what may actually come as something of a surprise is that getting ready for the trip is actually a lot of work in and of itself. Different work from my day job certainly, but a good deal of work no less.

Brainstorming. First there’s the initial planning stage of the trip. You have to decide where you’re going to go, how long you can/want to go for, and how much it will cost you to do so. If time or money are a consideration (they certainly are for me), then you’re faced with having to make a lot of cuts. Sure, you can go anywhere in the world. But the flip side of this is that wherever you choose to go, you are choosing not to go everywhere else. Making cuts like this aren’t easy, and a lot of pros and cons need to be weighed. You also have to figure out how long you can set aside for the trip. What kind of obligations do you have that might require you to return home? How will an extended absence affect your career? Are you even the type of person that would enjoy being gone for months or years on end? All are variables that need to be measured and decisions that need to be weighed.

Budgeting. Traveling isn’t free, and long-term travel in particular takes a monumental amount of dedication for most people to save up for. Not only does it require months or even years of sacrifice, cutbacks, prioritizing, and self-restraint, but there’s no way to know how much you even need! From flights to housing, food to fun, there’s simply no way to accurately calculate just how much money you’ll need for your time on the road. In my case, I spent hours drawing up a painstakingly detailed Excel sheet. I outlined my anticipated costs pre-trip (backpack, clothes, computer, camera, vaccines, visas, flights, etc), during-trip (food, housing, activities, travel, etc), and post-trip (rent, food, getting to and from job interviews, etc). I then took it a step further and created high, medium, and low-cost estimates for all non-fixed items on my list (travel gear, flights, cost-per-day on the ground, etc). This provided me with a large margin of error for my savings vs expenditures by giving me low targets to aim for when shopping, but high targets for my savings. Finally, I mapped out my income from the time I started saving through until the time I expected to leave, and made sure that the amount I planned to save from each paycheck would allow me to hit my High target by the time I left.

Market research and analysis. Sure, you could walk into REI and buy the first backpack, sleeping bag, first aid kit, wicking shirts, diving watch and guidebooks you see. But for most people this is not only financially untenable, but foolish for practicality. Those of us with limited funds – and in the case of those trying to travel light, limited space – end up spending a good deal of time on product research, cost/benefit analysis, and dialogue with other travelers in an effort to find products that best suit our needs while staying within our budgets. Not only do you want to make sure your investments are the best you can make, you also want to make sure you’re not investing in things you don’t need. Not planning on going anywhere near the ocean? You probably don’t need that diving watch. Traveling through Northern Africa during the middle of summer? A sleep sack is probably a better investment than a full sleeping bag. Choosing the right gear, and avoiding the temptation of unnecessary ‘stuff’ is of course no small feat, as anyone who’s ever seen the WALLS of just backpacks or hiking shoes at an EMS can attest. These decisions can be tough with so many options – the last thing any traveler wants is that feeling of regret half way through their trip when they realize they should have bought the other _____. Research and analysis is key.

Finally, I’ve found it necessary to approach the trip with a good deal of Communication and diplomacy. Necessary for any long-term travel is telling those you care about that you’re leaving. For some people this is easier said than done. While the best reactions are support and enthusiasm from your loved ones, there may be those who, out of jealousy, differing views of what’s “prudent”, or simple concern for your safety, are less than thrilled about your decision. Whether it’s parents, coworkers, or significant others, the tact needed for breaking the news and bearing the possible consequences (especially if you’ve still got months to go before you actually leave) is of no small import. It’s key to be solid in your decision while being understanding of the concerns of others.

For me, this trip is shaping up to be a once-in-a-lifetime chance to step outside of my world, outside of myself, and to see and experience the world from a totally new perspective. I’m going on this trip because I think it will be more fun than work, because I think it will be differently rewarding than work, and because I know the memories I gain will be worth more than any physical goods my paychecks can buy. I’m going on this trip to relax, to unwind, to force myself to take things day by day and situation by situation. But I know that by going on this trip I’m also testing myself. That I’m putting effort into my decisions and into my actions. That I’m investing in what I’m doing, and that it’s taking a good deal of work of its own. But I know that this is one job I won’t regret.


There’s now less than 1 month until I leave. We just moved into our new apartment, so things have been kind of hectic. I still have a few more things I need to get for my trip, most notably a netbook.

Since most of my trip to Israel will be organized, I’ve started researching Egypt to get a sense of how it works and what the must-see sites are. After Birthright I plan to visit Jordan and get my Egypt visa, but not really spent much more time in Israel itself.
Approximate travel breakdown:

8/30 – Bus from Boston to NYC.
8/31 – NYC to Israel
8/31 – 9/11 – Birthright trip
9/11 – ~9/17 – Visit Elinor in Israel, Petra in Jordan, and acquire Egyptian visa.
~9/18 – Cross from Eilat into Cairo to meet up with Karol.
10/9 – Flight from Cairo to BKK or Kuala Lumpur (need to decide on this soon)
10/20 – Cait arrives 🙂
10/20 – 10/28 – Tour Thailand
10/29 – Thailand to Angkor Wat
10/30 – 11/3 – Angkor Wat
11/4 – Return to BKK
11/5 – Cait leaves 😦
11/5 – 12/18 – Explore Southeast Asia. No itinerary yet
12/19 – Fly home

Just 3.5 weeks left at work. We’re starting to interview possible replacements today, with the goal that I’ll have at least a week to train them before I leave. Between the move, work, finalizing trip details, my father visiting, my grandparents visiting, and all the regular summer activities, August is shaping up to be an exceptionally busy month.

Bring it on!