The Best of Israel in 5 Days
The saying is, Jerusalem prays, Tel Aviv plays, and Haifa pays. It’s all worth a visit. Israel is teeming with historical sights – which is why my dad had the ancient city of Jerusalem on his bucket list for his big birthday trip. Meanwhile, Tel Aviv attracts foodies, sun worshipers, and those in search of nightlife on par with Miami and other major cosmopolitan cities. As an outsider, it has always seemed a bit intimidating to visit the Middle East, where conflict has existed for millennia, but to experience this area of the world first hand is an extraordinary experience…and once we were there, we never felt unsafe.
Israel at a Glance:
A 5 Day/5 Night Itinerary for Israel
| Day | Lodging | Activities |
| 1 | Tel Aviv | Arrive afternoon or evening Dinner and stroll in Jaffa (recommended: Onza) |
| 2 | Tel Aviv | – Explore Tel Aviv in the morning with a walking tour – Camel market food tour for an early lunch (best done on a Friday so that you can also see the Nachalat Binyamin Art Market) – Afternoon visiting other museums/sights in Tel Aviv |
| 3 | Tel Aviv | – Akko/Acre (ancient Arab-Israeli city north of Haifa) or Caesarea (Roman ruins south of Haifa), allow 1-2 hours for each. Both connect to Tel Aviv by train. – If driving, consider visiting Golan heights for the winery, coordinate Galilean cooking class for lunch, and see Sea of Galilea and surrounding sights – Late afternoon in Haifa to see the Bahai Gardens. |
| 4 | Tel Aviv or Jeruselum | Options: – Jerusalem: Mount of Olives viewpoint, museums (Tower of David, Yad Vashem holocaust museum), consider a visit to Herodium park outside Jerusalem. – Day trip to the West Bank (Bethlehem, Jericho) in the morning and afternoon in Jerusalem – Day trip to Masada & the Dead Sea (4 hours from Tel Aviv, 1 hr 45 min from Jerusalem) |
| 5 | Tel Aviv or Jeruselum | – Explore Jerusalem’s old walled city, starting with a walk on the Ramparts – Behind the scenes tour of the Western Wall (Kotel) tunnels, underground – Stroll the Jewish, Muslim and Christian quarters of Jeruselum’s old city – Walk Via Dolorosa to the Church of the Holy Sepulchre – Dinner in Ein Karem, a historical Arab village outside Jerusalem |
| 5 | Airport | Late checkout, leisure day relaxing on the beach in Tel Aviv or catching a few more sights in Jerusalem before catching red eye flight home |
Notes on our itinerary: We traveled in October 2019. We chose Tel Aviv, and specifically Jaffa (the old port) as our home base, since it would have more dining and nightlife options over Shabbat (Friday night through Saturday) and the holiday weekend (and we wanted to be near the ocean – not gonna lie). We opted to stay in one location because our time was short – we actually were only in Israel for 4 nights, not 5 (I added a 5th day to the itinerary above as I felt that 5 nights would have been more optimal). For a longer travel itinerary, it probably makes sense to divide your lodging among more than one destination. The actual content of your itinerary will vary widely, depending on whether your focus is on historical sights and ancient cities, religious sights, or to learn about the culture and people of the area. For a longer trip, there are plenty of sights in Israel to see, or consider spending a few days in Jordan. Israel is also not a far flight from many European destinations.
For Inspiration: In preparing for our trip, I found this to be a great and humorous read: How to Understand Israel in 60 Days or Less, by Sarah Glidden. (Warning: It might have jaded my view on how eager I was to drive 4 hours one way to see the Masada. It also emphasized the importance of having a tour guide in Jerusalem’s old city). Rick Steves’ TV show has two episodes viewable online for free about Israel and Palestine. TPG documented his travel to Israel on vlog in 2019, shortly before we went. If you get inspired by food, the cookbooks Jerusalem (by Ottolengi & Tamimi) and Falastin (by Tamimi & Wigley) offer delicious takes on the regional cuisine as well as stories that offer local cultural insights and perspectives.
Tel Aviv & Jaffa
Tel Aviv is a modern, cosmopolitan hub with a secular vibe. The city has barely been in existence for a hundred years, and parts of the city are becoming gentrified – to the point of skyscrapers engulfing small older historic houses and buildings (the older historic buildings can’t be destroyed, so the skyscraper is built around it.). Street art is big in downtown Tel Aviv, and you will see murals and graffiti everywhere as a means of self expression. A stroll down the oceanfront walking path is a breath of fresh air – and a great place to people watch. Think of it as your vacation from the vacation. Come here for the beaches, and the food – Tel Aviv is the culinary highlight of Israel. Jaffa is south of Tel Aviv and is the ancient Arab port city. A stroll through Jaffa is a must, as is a visit to the Jaffa Flea Market (open daily except Saturdays and holidays). The Camel market is pure overload for all the senses, especially the taste buds. Parts of this city are being gentrified but still feel a bit gritty. We stayed at the Casa Nova Jaffa hotel and had an incredible stay; I liked the ancient stone pathways and Middle Eastern vibe of Jaffa – and sitting out on the hotel’s Instagram-worthy terrace with a glass of Israeli wine was a grand way to end a day of sightseeing. For restaurants, check out Eater for a great starting list – Abu Hassan is the hummus destination on everyone’s list (go early), and we had absolutely wonderful meals at both Onza in Jaffa and Milgo Milbar in the Rothschild district.
Caesarea & Haifa Day Trip
So many day trip options abound, it can get overwhelming! Based on the holiday weekend and my parent’s preferences (minimal driving), we opted to explore the Roman town of Caesarea in the morning, and take part in a cooking class with a Druze family midday. In the afternoon, we visited Haifa. Explore options and see what interests you. You could easily spend week exploring some of these smaller towns. The train system offers a quick way to visit Haifa and Akko/Acre if you don’t have a car or guide/driver for the day.
Jeruselum
If there is ever an international city to travel to that forces you to reflect on human history, this is the city. There are so many layers of history to unravel. To walk down the same stone roads so many feet have trodden over centuries, to take an underground tour and see the old markets that thrived during the time of Jesus, to actually put names with the physical places we have all heard about in one form or another since childhood – it’s all quite overwhelming. Jerusalem‘s history is shared deeply by so many different cultures, yet these cultures frequently remain divided. A stroll through the Christian, Arabic, and Jewish quarters of the old city is a slice into the different realities living here. A trip over to Palestine unlocks even more cultural perspectives, if one opts to peer beyond the quick five minute view of the Church of the Nativity in Bethlehem (a stop at Banksy’s Walled Off hotel offers a deep dive). Even if you don’t make it across the border into Palestine, I strongly encourage you to read and learn a little bit about of the history of this area and the constant shuffling of different people and cultures. It’s a hot mess to say the least. But after leaving, I felt very grateful to have traveled here, to immerse myself in the history – which then forced a lot of reflection about human nature.
Logistics
Good to Know:
Israel is a great fall destination. We went in October and the weather was quite warm; generally, April-June and September-October are the best times to visit weather-wise. Security is taken very seriously. We felt safe during our entire trip. Israel is NOT a budget destination – so be prepared. We saved where we could on flights and hotels, knowing meals and tour guides would be more expensive than other countries.
Pack as little as possible! our recommended packing list is here, along with our packing tips. Dress conservatively for religious sites: cover shoulders and knees, no midriffs/crop tops or cleavage, men will be asked to wear a kippah (provided) at certain sites like the Western Wall.
Get a Guide
For a short trip in particular, a guide is invaluable, particularly in Jerusalem. Whether you are here for the ancient cities and history, the religious sites, or a little of both, there is a lot to unpack here, and you will miss out on if you don’t have a local to help explain the historical significance of sights. We also thoroughly enjoyed learning about life in Israel through out guide (who actually lived in a Kibbutz!). I also suggest picking a guide early (good ones book up far in advance) and discussing your itinerary before finalizing travel dates. They can help you prioritize activities and optimize your time. We prefer a private guide so that we could go at our own pace; a small tour group can be a more affordable options. Certain days of the week are better for certain cities/attractions, so your guide can help you with planning – you will have to plan your activities around Shabbat-related closures (Tel Aviv won’t be quite as shut down as other areas of Israel) and I also recommend checking for other holidays or big events that might be occurring. I thought we were avoiding what I thought were major holidays – but did not realize until after booking our flights that we would be there during Sukkot (also known as Feast of Tabernacles). This ended up actually working to our advantage as we were able to visit Jerusalem when it was less crowded, but it also meant many things were closed on our last day in Jaffa. Find out in advance whether their are holidays, observances, or major events that might affect activities before locking in your travel dates. (We had a similar learning experience booking a trip to Jordan by buying flights first, and then months later talking to a tour guide only to find out we had booked our trip during the Arab World Summit which was in Jordan that year – and many things including all of the Dead Sea area would be shut down for security reasons…it was a trip we were forced to cancel).
Transportation in Israel:
Flying into TLV: No matter where you stay in Israel, all international flights arrive at the Ben Gurion International Airport in Tel Aviv (TLV), which is really in between Tel Aviv (20 minutes) and Jerusalem (45 minutes). Prior to boarding your flight to Israel, you will be called up for a brief interview where they ask a few questions about the purpose of your travel – it was not intimidating, but is certainly different from boarding most international flights! Pay extra for the VIP service on both arrival and departure in Tel Aviv to avoid the notoriously hours-long immigration/customs lines (it was $50 each at the time of our travel to add it to our tour, and well worth the cost to save hours of hassle). We zipped through passport control and were outside the airport within a few minutes.
Booking a ticket for free on points and miles: we booked through United for our trip, nonstop from TLV-SFO (85,000 miles round trip in economy), but a cheaper points redemption for Star Alliance flights is available through ANA’s Mileage Club for 65,000 miles round trip (transfer from American Express). Flying Blue (Air France/KLM’s rewards program) had a sweet spot in their award chart for a one way economy seat for only 27,000 miles, and you can transfer to Flying Blue from Chase Ultimate Rewards and American Express, or credit Delta flights to Flying Blue. A challenge with Flying Blue in my experience has been availability – you must book far in advance, close to when seats are released for those dates. A round trip flight through American Airlines will cost ~70,000 miles and SAAver award flights need to be booked far in advance; American did not offer direct flights from the US at the time of our travel but is planning on adding several direct flights to TLV in 2021. If using United, I strongly recommend looking into United’s Excursionist perk, which might allow you to tack on another destination or two within Europe or the Middle East for the same number of points. If adding on Jordan, consider flying into Tel Aviv and out of Amman – or vise versa.
Driving: For most of our trip, we had a tour guide who drove us, but in Tel Aviv we did rely on ride shares to see a few sights and to get to dinner – Gett/GetTaxi was the most widely used ride share app at the time of our travel and was as easy to use as Uber. Renting a car is NOT advisable in Tel Aviv or Jerusalem – parking is non-existent and a major headache, and the traffic in Tel Aviv can get unbearable. However, renting a car is a feasible way to explore the Dead Sea and Masada, as well as sites in Northern Israel; driving across the border to the West Bank is a bit more logistically complicated and wouldn’t be my cup of tea.
Trains: Israel has good public transportation including a train system, and during our trip in 2019, the high speed line between Tel Aviv, Ben Gurion Airport, and Jerusalem was just opening, cutting transportation time between Tel Aviv and Jerusalem to just 32 minutes. View the map of the train system here. Be sure to check for holiday-related closures.
Hotels & Lodging
We opted to stay in Jaffa/Tel Aviv as it is more secular with fewer closures on Shabbat and on holidays. In Jerusalem (and in Kosher hotels elsewhere in Israel), know that on Shabbat, hotels will only offer instant coffee and cold foods – you will have to seek out a non-Kosher hotel or cafe if you want real coffee! Finding a way to cover lodging with points and miles can be a great way to save money on your stay in Israel. One option we utilize is to book through Chase Ultimate Rewards, which allows you to book at any number of small Israeli-owned hotels at a redemption rate of 1.6 cents per mile with the Chase Sapphire Reserve card. This will give you the most options by far. For booking on points through a hotel chain, the W Jaffa would be my pick for ambiance, and runs 50,000 to 60,000 points per night; it is the only large chain hotel in Jaffa. For a beach view, there are a number of options through Marriott including the Sheraton Tel Aviv, as well as the Hilton Tel Aviv and the Intercontinental David Tel Aviv. I recommend staying in a walkable area so you have some dining options at hand for the end of a long day of touring. In Jerusalem, options are limited and include the Waldorf Astoria Jerusalem (bookable through Hilton), the Crown Plaza Jerusalem (IGH), and TRYP Wyndham Jerusalem Bat Sheva (Wyndham). If none of the above strategies work, another consideration is to book through Hotels.com where you can get a free night’s stay after 10 nights booked (essentially 10% back). This is what we did for our stay at Casa Nova Jaffa – our stay was absolutely lovely, and we were able to utilize a free night certificate and a gift card to cut the cost a bit. Always, always book refundable rooms given that you never quite know what might change in this politically volatile area (not to mention with the pandemic!).
Speaking of the Pandemic: At the time of this post, Tel Aviv has its borders shut down to most of the world (Ben Gurion Airport/TLV is currently closed). However, Israel is outpacing the world in vaccination rates and I suspect they will be back open for tourism in some capacity by late 2021. Given that travel to this area takes some advance planning, aiming for a trip in 2022 seems very feasible (Fall of 2021 might be possible for those with an optimistic mindset). At the time of this writing, all the mentioned hotels remain open, and given that the major sites and attractions have been around for centuries if not millennia, I suspect they will still be there awaiting guests once the pandemic dust settles.
