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By Jordan, Morocco & Israel specialist Olivia

Israel is complicated. Everywhere you go, you’ll find multi-layered history, competing religious symbolism and countless viewpoints, all of it mired deep in an ancient past but humming with a unique modern vibrance. Despite this — or, perhaps because of this — it’s a vital and exuberant country that commands your attention.

Because Israel is such an intricate mosaic of cultural, religious and historical significance, it can be hard to navigate to the places that are important to you. That’s why I strongly suggest a private guide. We’ll be sure to pair you with a guide who’s an expert in the aspects of Israel that you want to explore, whether that’s modern socio political issues, ancient Judaism or Biblical history.

Jerusalem’s Old City — the Holy Land for three great religions

You feel the weight of history pressing down on you when you visit Jerusalem. On a visit to the Old City, you might begin by admiring the exterior of the shimmering Dome of the Rock. Then, you might pass a bat mitzvah being celebrated by the Western Wall. Next, pause for a group of Christian pilgrims carrying a massive wooden cross as they walk along the Via Dolorosa ― the path that Jesus is thought to have taken to his crucifixion.

There’s so much to see in Jerusalem that I suggest you plan to spend at least two days here — one for the Old City and one for the New.

Still encircled by 16th-century walls, the Old City is the contested heart of Jerusalem, sacred to Jews, Christians and Muslims alike, who each claim one of their most holy sites in this part of the city.

My guide, Michel, began my tour in the Christian quarter at the Church of the Holy Sepulchre, thought to be built on the site of Jesus’s crucifixion as well as his empty tomb. A church has stood here since the fourth century, but the building you see today largely dates from the 12th century when Crusaders rebuilt it.

Six Christian denominations claim dominion here, an uneasy coexistence that occasionally devolves into clerical fist fights. Look for the rickety wooden ladder leaning against a window above and to the right of the entrance. It’s been there since the middle of the 1700s and the factions cannot collectively agree to take it down, turning it into a symbol of the fractious nature of the church’s history.

In the Muslim Quarter, you’ll find Temple Mount, the third-most-sacred site in all of Islam. Traditionally considered the site of Solomon’s temple, this was turned into an Islamic shrine in 691 and has been expanded into a holy complex over the centuries.

Today, non-Muslims are not allowed into the Al-Aqsa Mosque nor into the Dome of the Rock, which was built over the stone where Jews believe Abraham prepared to sacrifice his son. However, as long as your shoulders and knees are covered, you can explore the rest of the complex, which is known in Arabic as Haram esh-Sharif, the Noble Sanctuary.

The highlight of the Jewish Quarter is the Western Wall, a massive blank wall that is the most holy place in Judaism. It acts as a sort of open-air synagogue, though it’s segregated by gender. Worshipers gather here constantly to lay hands on the wall and wedge written prayers into the gaps between the enormous stones. It’s a particular treat on Friday evenings, when people from the devout to the merely curious gather to welcome Shabbat, singing, dancing and praying as the sun sets.

To fully experience Shabbat in Jerusalem, we can also arrange for you to celebrate with a local family who emigrated from the States several decades ago. You can learn what it’s like to be Jew living in Jerusalem today as you join them for a festive meal.

Jerusalem’s New City — the Dead Sea Scrolls and Mahane Yehuda

Don’t let the Old City’s history seduce you away from the sights of the New City. Here, you can visit the Israel Museum, which houses five millennia worth of items, ranging from a 9,000-year-old stone mask to contemporary works by local sculptors. The most important stop is the Shrine of the Book, a flat onion of a building created specifically to house some of Israel’s portions of the Dead Sea Scrolls.

A ten-minute drive from the museum is Yad Vashem, the World Holocaust Remembrance Center, a fraught and moving memorial to the six million Jews murdered by the Nazis. Located on a hillside overlooking the city, it includes more than 20 different museums dedicated to different aspects of the Holocaust.

You’ll see first-hand video accounts and interviews as well as personal possessions of the victims. For me, the most moving was the Hall of Names, where every victim’s name is recorded along with as much biographical detail as possible.

Mahane Yehuda Market offers a sharp contrast to the affecting experience of Yad Vashem. The lively beating heart of the New City, the market is an affirmation of the vibrancy of modern Jerusalem and the people who call it home.

Bethlehem — The Church of the Nativity

You’ll need your passport to pass through checkpoints to reach the no-longer-little town of Bethlehem. It’s located a brief half-hour drive from Jerusalem on the West Bank of the Jordan River. Boasting a skyline that bristles with minarets and church steeples, this busy, modern city is the home of the majority of Palestinian Arab Christians.

The focus of the city is the Church of the Nativity, which was built by Rome’s Emperor Constantine in 326, making it the oldest surviving church in the Holy Land. Enter by ducking down through the Door of Humility, a tiny latter-day modification intended to slow down looters. Inside, you’ll find a busy interior thick with incense and pilgrims both.

Gilded mosaics glitter on the walls and large pink limestone pillars line the nave, some sporting faded frescoes. Much of what you see dates from Justinian’s rule in the 6th century or the 12th-century Crusades, but you can see sections of the original, 1,700-year-old floor displayed through wooden trap doors. The busiest spot in the church is the lantern-lit Grotto of the Nativity. Here, a 14-pointed star in the floor marks the exact spot where Jesus was thought to have been born.

Tel Aviv

In Hebrew, ‘tel aviv’ means ‘hill of spring’ and the first modern Jewish city has a definite sense of new life. Breezy and bustling, its thoroughly contemporary atmosphere provides a sharp contrast to the freighted age of Jerusalem, just a 90-minute drive to the southeast.

The city invites you to spend your mornings strolling on the waterfront promenade, your afternoons browsing through chic boutiques, and your evenings eating in trendy restaurants. You’ll find Bauhaus architecture, beaches filled with scantily clad sun worshipers and surfers, and one of the region’s biggest gay communities.

The city is also home to a thriving art scene, including galleries, museums, street art and the Tel Aviv Museum of Art, which is located in an ultra-modern building that looks like an MC Escher doodle come to life. We can arrange for a privately guided tour with a graffiti artist or art expert if you’d like to explore further.

On the edge of modern Tel Aviv, you’ll find Old Jaffa, the historic base that the city grew up around. Though it was mentioned in the Bible, today the biggest draw here is the flea market, Shuk HaPishpishim. You can while away an afternoon browsing through an endless jumble of cafés, shops and stalls selling antique brass pots, vintage clothing, historical Judaica, vinyl records and discarded family photo albums.

The Negev Desert — exploring the Makhtesh Ramon

Located in the south of the country and covering more than half of its area, the Negev Desert is a vast swathe of sun-scoured hills and rocky gullies, located just a few hour’s drive from Jerusalem. The most striking feature is Makhtesh Ramon, an enormous hole in the desert that’s earned the nickname ‘Israel’s Grand Canyon’ due to its massive size. There are a myriad of ways to explore the makhtesh, including a 4x4 tour with a local expert.

Despite wearing a baseball cap to shade his face from the relentless sun, Adam has a deeply tanned face from years of leading visitors around the desert. He began my tour by piling up the soft, fine sand to demonstrate the complicated combination of geological forces that created this enormous erosion basin.

Then, he and I climbed into a sturdy Jeep to explore the area’s terrain and ecology. As we jounced over the stony crater floor, he pointed out the region’s birdlife, including yellow-faced Egyptian vulture and Barbary falcons circling on the warm updrafts near the walls.

There’s also a more extreme way to experience the desert. Whether you call it rappelling or abseiling, climbing down the side of the makhtesh is an exhilarating way to get up close and personal with the layers of geology displayed on the eroded canyon walls. I’ll admit that the first step over the rim was as exciting as it was terrifying.

The Sea of Galilee

A two-hour drive from Tel Aviv, the city of Tiberius perches on the shores of the Sea of Galilee (actually a freshwater lake). It’s not a particularly attractive place, but makes a good base for exploring the area where Jesus is thought to have spent most of his three-year ministry.

A guide is imperative for helping you gain nuanced context into the tangle of history and myth around places like Nazareth and the Mount of the Beatitudes, where Jesus delivered the Sermon on the Mount. They can also help you contend with the busloads of pilgrims who flock to the sites such as Yardenit Baptismal Site, which is popular for mass baptisms in the Jordan River.

Nearby, the Ancient Galilee Boat is much less busy than the Biblical sites. The small museum displays a boat found on the bottom of the sea in 1986 — carbon dating indicates the boat probably plied the waters at the same time as Jesus preached in the region. Exhibits also examine the process of uncovering and preserving the boat.

You can also take a guided tour of Degania Bet, located in the Kinneret Valley to the south. Just the second kibbutz in Israel, it was established in 1920 by Jewish immigrants who came to Ottoman Palestine to live in a utopian collective in an attempt to hew productive farmland out of the rocky, barren soil of the region.

Acre — An underground crusader city

An hour to the west of Tiberius, on the shores of the Mediterranean, Acre has been a major trading port for more than 5,000 years. Phoenicians, Romans, Byzantines, medieval Crusaders, Ottomans, Napoleon’s armies and the British have all left their mark on the Old City, which is still ringed in battered ramparts. Today, Acre is a predominantly Arab city and the historic core is a tangle of narrow streets where you’ll find authentic markets and a burgeoning restaurant scene.

The most impressive site here is the underground Crusader city, built when this was the last stronghold of the Europeans who came to ‘liberate’ the Holy Land. Outside the entrance, look for a collection of missiles that have been launched at the city, from massive stone spheres flung by medieval Muslim trebuchets to iron cannonballs from Napoleon’s armies.

Inside, the 12th- and 13th-century halls are enormous and echoing, built by the knights to project authority and power. The city is well-preserved, and you can visit Gothic vaulted ceilings, the knights’ dining hall and even the latrines. You can also visit the Templars’ Tunnel, thought to connect the order’s waterfront fortress with the main citadel for safely transporting gold and treasure.