Getting your passport stamped in both Israel and Cuba can present problems for you entering other countries.

Israel:

There are a number of Arab nations that do not recognize the Israeli state, and will deny you entry if you have an Israeli stamp in your passport: Lebanon, Syria, Yemen, Iran, Libya, Kuwait and Sudan. The UAE, Saudi Arabia, Oman, and Qatar have, in the past, given trouble as well,  but have no hard fast rules about it, so these days it’s unlikely you’ll have trouble with an Israeli stamp there.

When you’re entering Israel by air, it’s possible (and even likely) that you can get through Israeli airports without getting your passport stamped. However, if you are traveling into or out of the country by land, it’s often illegal for border officials not to stamp your passports.

Remember, these procedures and protocols are in a constant state of flux as political situations evolve and ebb (ie, countries reversing their longstanding policies with no special notification or reason). The easiest thing to do if you plan on touring the region would be simply to visit Israel last. That way you can feel comfortable if you happen to incur an Israeli stamp. And don’t forget, you will still be denied entry into one of the aforementioned countries as long as the stamp remains in your passport, even if your visit to Israel was on a trip long before.

Double check with embassies, consulates and/or visa services before you leave to make sure you have your ducks in a row.

Here are 2 comments from AirTreks customers that have more insight on the issue:

“The problem with going overland to Israel, if if Israel doesn’t stamp your passport, is that the countries you enter from will stamp it. And the Middle Eastern countries on the banned list know these border crossings. So, for example, if you enter Israel from Taba, Egypt, you will have an exit stamp from Taba. And from Taba, there is nowhere to “enter” other than Israel. So although you have no entry stamp from Israel, you are still possibly (even likely) denied entry to a country like Syria that examines every page on your passport closely. Overland is possible, but it is NOT certain to work, even if you talk Israeli officials into not stamping.”  ~ Michael Hodson

“Anyone traveling through the region on business should check with their embassies. If they visit Israel and anti-Israeli states frequently they may find they qualify for a second (legal) passport for business purposes. This will depend on your nationality and what rules your own country has but I do know people who’ve done it.”  ~ Mosh

“When I entered by land from Jordan two years ago I was actually asked by the official at the desk if I wanted a stamp or not. As my passport was almost full and heading for replacement I got one for souvenir purposes, but I think the alternative was a stamp on a piece of paper which was stapled into the passport.” ~ Anonymous

Cuba:

Due to the US embargo, it’s illegal for citizens of the US to visit Cuba, and for US travel agencies to sell tickets to Cuba or to give advice on traveling there. As you might imagine, AirTreks strongly opposes the law and have done our best to promote freedom of travel, lobbying against this and similar laws and providing information to would-be travelers (of course within the limits of the law as the US government currently interprets it).  At AirTreks, we know that where there’s a will there’s a way and many US passport holders do visit Cuba every year by traveling through Mexico or Canada. If you’re not a US citizen, you may not even have realized there were issues getting to Cuba.

Even if you’re not a US passport holder, having a Cuban stamp in your passport can present problems entering the US. Make sure that you don’t have any Cuban markings in your passport or on your luggage, and don’t attempt to bring any detectable Cuban goods through the US. You also shouldn’t volunteer to US authorities that you have been to Cuba.

However, the US government has, in general, only sought legal sanctions against those who either (1) are caught with obviously Cuban goods (mainly cigars, rum, books and printed matter, and audio or video recordings) on re-entry to the USA and/or (2) call attention to themselves by publicly defying the law as an act of civil disobedience.

It is possible to avoid having Israeli or Cuban stamps in your passport by presenting a separate piece of paper for customs officials to stamp that’s not actually a part of your passport. This isn’t always allowed, but if you make a point of asking clearly and politely each time you present your passport (before you hand it over to officials), we’ve had travelers tell us that this is a way to avoid potential issues down the road if you’re planning to visit these countries. If you go this route, make sure that you keep the paper with the stamp with your passport at all times throughout your stay in either of these countries (you will probably have difficulty leaving without it), and that you remove it as soon as you leave and before showing your passport to officials in any other country.