Special edition podcast.
Episode 32: Holy Land auditory itinerary!
Find the written itinerary on IlluminationHebrewInsights.com
Please join us!
Shalom Friends –
This is a special podcast episode, with specific dates and times. I try to keep the podcasts timeless, but Illumination is offering something special in 2026.
Karl and I are leading our first trip to the Holy Land—so exciting! I have personally visited several times with different themes for each visit.
- One was a Jesus tour.
- Another was a Palestinian mission trip.
- A third was with Jewish friends, one who had never been.
- The next one was biblical mapping, and we were north, south, east, & west; all over the Land.
- However, my very first visit was when I was 18 months old travelling with my parents. How is that for crazy?
I must have fallen in love with the Land early on because I have such excitement to return each time.
I am going to give you a quick rundown of the trip with highlights of the special events that you won’t see on other trips.
We are intentionally keeping our group small—only 24 travelers maximum. I welcome any of you who have a heart for visiting the Land where Jesus lived to join us.
Aside from the incredible Old Testament and New Testament sites, we will secondarily be focusing on the food and wine of the land. The third 5-star trip includes incredible hotels and lovely food. We will be visiting 3 wineries so if you are not a wine drinker, please email me separately and we can accommodate you.
So now, I will speak as though you are choosing to come.
April 8th | Arrival in Tel Aviv & Israeli Dinner
Arrival is on April 8th, 2026. Please book your own flight so if needed, you can choose to use miles, your personal carrier, and your choice of booking class.
You will be transferred to the David Intercontinental Hotel, right across the road from the Mediterranean Sea in Tel Aviv.
Relax at this lovely hotel, stroll around the city or beach until our welcome dinner at Manta Ray Restaurant that evening. We will meet in the lobby and walk from our hotel, along the beach. Here you will experience your first culinary delights of Israeli food.
April 9th | Caesarea, Mt. Carmel + Winery, Megiddo & the Jezreel Valley, Hotel in Galilee
Our first touring day begins early the next morning, April 9th. Awake, pack up, and get ready for a big adventure. But first, enjoy a hearty breakfast in the hotel. All breakfasts are part of your package. Make sure you taste some delicious new foods—like halva, a sweet sesame delight. Eggplant of all sorts, and of course, Israeli hummus. Each Mediterranean community has their own renditions on Med food, so you are getting a small micro taste of Israeli style hummus, typically with less cumin and garlic.
We will begin our adventure on the Mediterranean coast north of Tel Aviv at the ruins of ancient Rome’s Judean capital, Caesarea. This Roman seaport was built by Herod the Great, I like to call him Herod the not-so-great, but he was an incredible architect and builder. This is the Herod who reigned when Jesus was born. It is here at Caesarea that Pontius Pilate resided during his Prefect period. He would travel to Jerusalem at least 3 times a year for the high Jewish holidays, the three required pilgrimage feasts, to maintain order in the then crowded city. The Apostle Paul was imprisoned here, the jail cells recently uncovered.
This is also the place where Herod Agrippa I, one of Herod the Great’s grandsons, was when he made a speech while the people were shouting that he was a god. The One True God struck him down immediately. You can read about in Acts 12. History confirms his quick demise.
We will then travel north to Mt. Carmel to see the spot where Elijah had a showdown with the prophets of Baal. We can read about this in 1 Kings 18. It is a powerful story of Elijah’s courage and obedience with God by his side, and God’s power and sovereignty proven to the pagan priests!
From this incredible biblical site, we will pop by Mt. Carmel Winery to taste our first wines of the land. Choose a bottle to take with you!
Our final stop of the day will be Megiddo. Megiddo or Megiddon in Hebrew is believed to come from the verb gadad (גָּדַד), meaning “to cut” or “to invade.” “Har” is mountain in Hebrew and the location Har Megiddon is transliterated to Armageddon as found in Revelation 16:16. Depending on how you interpret the Revelation 16 passage, the final battle of Armageddon is prophesied to come to life here.
But this Har or Mount resides above the Jezreel Valley, “Jezreel” meaning “God sows” in Hebrew. This beautiful and peaceful valley’s name will become abundantly clear as you look over fields of produce like a patchwork quilt over the land. Further, this Jezreel Valley, in antiquity, connected the Via Maris, which was a travelers road going north/south along the Mediterranean Sea from Egypt to Lebanon & beyond, but if one needed to cut across to Jordan, or Syria (I am using modern day country names), one would cut through this valley and spill out to Magdala on the south side of the Sea of Galilee. You would travel along the lake until the north and continue north and east.
But by now, after our very active day, we will be tired, maybe dusty and sweaty. We will proceed to Galilee, and our David’s Harp Hotel on the north side of the lake. Dinner will be at this new hotel at your leisure. You will relax and reflect and enjoy the views looking over the Lake.
April 10th | Mount of Beautides, Tabgha, Capernaum, Sunset Boatride on Galilee
Start your day with a beautiful view of the Sea of Galilee from the top of Mt. Arbel. We will be able to see the ranges surrounding the Lake, which explains why fast and hard squalls could blow in, deadly to boaters in Jesus’ time. The disciples were caught and terrified in two of these squalls!
We will also be able to see the Golan Heights, Mt Hermon and the only ski site in the Land. The views will take your breath away.
From here, we will journey down to the Mt. of Beautides where Jesus delivered the Sermon on the Mount. You will learn some interesting facts as we stand on top of the mount, but see the bay where realistically Jesus stood in and taught up, rather on the top and taught down. Mind blower, right? Biblical accuracy is our goal!
Lunch this day will be an exclusive activity from a private food truck near the Beatitudes.
After our picnic, we will visit Peter’s Primacy, or Tabgha, where Peter was reinstated (3 times) by Jesus after the resurrection. From here we will go to Jesus’ adult hometown, Capernaum, where the original foundation of the only synagogue in the town still stands as Jesus cast a demon out of a man. See Mark 1. Peter’s Mother-in-law’s home is here as well, where Jesus healed her fever, and she immediately got up and began serving them! What a mother-in-law!
For our final activity of the day, we will enjoy another exclusive experience – a private sunset boat ride on the serene waters of the Sea of Galilee. We will appreciate locally sourced wine and appetizers from the Golan Heights as each of you reflect on the waters where Jesus walked. Take this in while the sun sets.
Back to the hotel for dinner and a good relax. Our next day will be exciting and busy again!
April 11th | Hike in the Dan Nature Reserve, Jordan River, Caesarea Philippi, Winery in the Golan Heights Region, Kursi, travel to hotel in The Holy City of Jerusalem
Arise, pack your bags, breakfast, and head to the van. We will head further north for a hike in Northern Israel in the Dan Nature Reserve. We will walk along the headwaters of the Jordan River. This impressive archeological site has remains of ancient Canaanite and Israelite cities. Visit the very spot where Israel fell into idolatry under King Jeroboam. This is also the territory of the Dan tribe of Israel, but not the land that God had given them. They were given land in the SW of Israel, but chose not to drive out the Philistines, but rather packed their ancient bags and moved up north. This was in direct disobedience to God’s commands to clear the land for their people.
Right next door we will visit Caesarea Philippi. This important site in Jesus’ ministry is where Peter declared Jesus the Messiah, the One True God. Jesus then gave the disciples their marching orders: “Upon this Rock, I will build My Church, and the gates of hell will not prevail against it.” Read Matthew 16 and Mark 8.
After our walk and hike (per CO standards, it is all a walk) we will pause to visit a winery in the Golan Heights region. We will tour the vineyards and enjoy lunch there with locally sourced food.
Last, on our way south to Jerusalem, will stop by Kursi on the east side of the Sea of Galilee. Kursi is the believed site where Jesus cast out a legion of demons and sent them into swine. These swine ran down a hill and jumped over a cliff. Please read Matthew 8, Mark 5, and Luke 8.
From here, we will travel to Jerusalem, The Holy City. From any direction, we travel up to Jerusalem as it sits on a hill, higher in elevation. In fact, the peak of this hill is Mount Moriah (more on that in a moment).
As we travel, we will read the Psalms of Ascent, Psalms 120-134. These are the Psalms that Jewish Pilgrims would recite as they travelled up to the Holy City. Per God’s command, 3 of the 7 Feasts of the LORD were pilgrimage holidays: Pesach, which we call Passover, Shavuot, which the church calls Pentecost (meaning 50th), and Sukkot in the fall.
(Please listen to my 7 Feasts podcasts for incredible Jewish information with Messianic fulfillment and future fulfillment regarding these God instilled festivals!)
We arrive in the Holy City and check into our Mamilla Hotel. Our hotel is an incredible location, one block from the Old City. Relax and enjoy dinner at the hotel. Early morning tomorrow!
April 12th | Mount of Olives, Garden of Gethsemane, Zion Gate, Upper Room, Church of The Holy Sepulcher
Rise and breakfast! We are starting the day at the Mt. of Olives. We cross the Kidron Valley to the east of the Old city. The Mount of Olives is the highest of the three ridges surrounding Jerusalem, and from here, Jesus wept over the city. Jesus also was standing on this mountain when He ascended to Heaven. Many believe He will return here at His second coming and the mountain will split in half.
As we walk down Palm Sunday Road, we will stop at the Garden of Gethsemane. It is here we will take time to reflect at the site where Jesus prayed and agonized before His arrest. Continue walking across the Kidron Valley, into the Old City to visit the Upper Room, the traditional site where Jesus shared his final meal with his disciples. We will visit other Jerusalem sites as well, such as the Church of The Holy Sepulcher.
Dinner tonight is at the hotel but should you choose to walk back into the Old City, that is where you will find me!
April 13th | Temple Mount, Western Wall, Southern Steps, City of David, Desert Dinner
After breakfast-ing this morning, we will walk to the Temple Mount. The Temple Mount is the culmination location on Mt. Moriah, where Abraham was prepared to sacrifice his son Isaac. It is also the site where David bought the threshing floor for the future temple. Islam’s Dome of the Rock and al-Aqsa Mosque are presently on the site, but many believe it will be gone one day when Jesus returns.
One of my favorite parts of the temple mount is the Southern Steps. Jesus taught here the last week of his earthly life. This is also the site of Peter’s famous sermon in Acts where 3,000 people came to know Jesus, as the Holy Spirit was released and birthed the body of believers, the Church, on Pentecost.
For those not worried about getting feet wet, we will walk south to tour the City of David then walk through Hezekiah’s Tunnel. This tunnel was dug under the order of King Hezekiah to keep the water source of the Gihon Spring inside Jerusalem as Assyria came to besiege Jerusalem. Read 2 Kings 20 and 2 Chronicles 32.
We will end the day with a wonderful outdoor dinner in the desert. This unforgettable evening will include special dishes from a sought-after private chef.
April 14th | Masada, En Gedi, Qumran, En Gedi, Dead Sea, Dinner at Mona’s
After breakfast, we will start the day at Masada, Herod the Great’s desert home. This is also the fortress where a handful of Jewish Zealots last stood against Rome after the Fall of Jerusalem in 70 AD. Remains of the Roman camps are still there as is part of the ramp built to crash into this fortress. Rather than becoming Roman slaves, the Jewish refugees committed mass suicide.
The next desert site we will visit is Qumran. The location where the Dead Sea Scrolls were found. This miraculous find confirmed the legitimacy of the Scriptures that we read today.
Following, we will tour En Gedi, where Ruth and Naomi walked up the rugged mountain to Bethlehem. Boaz would marry this Moabite, who became a follower of the God of Israel and Jesus’ ancestor. This site has a spectacular waterfall and caves where David hid from King Saul, as recorded in 1 Samuel 23.
We will take time this day to float in the Dead Sea as well. The Dead Sea is the lowest elevation and the lowest body of water on the surface of Earth. It contains 10 times the amount of salt as the oceans. Make sure you don’t have any cuts on your body!
Back to the hotel to shower and clean up.
We will conclude the day at an artist’s home, Mona’s restaurant.
You should sleep well this night!
April 15th | Bethlehem, Garden Tomb, Yad Vashem, Gush Etzion Winery
After breakfast, we will start the day at Bethlehem and tour the Church of Nativity and Shepherds Fields. This city was not only the home of Ruth and David, but the precious town where Jesus was born.
Next, we will hop into the bus and tour the lush Garden Tomb, one of the traditional sites where many believe Jesus was buried and resurrected. Many folks who come to the Holy Land remember the Garden Tomb as one of the most special spots on the entire trip. One site nearby is also the possible site of Golgotha.
Finally, we will conclude the day at the Gush Etzion Winery and Restaurant. Sip on fantastic Israeli wines and incredible eats.
April 16th | Israel Museum, Jerusalem free day, Farewell Dinner at Eucalyptus Restaurant
Start the day with a tour of the Israel Museum. It is a must-see museum while in the Holy Land. This incredible place houses many Jewish artifacts including the Dead Sea Scrolls.
Enjoy the rest of the afternoon exploring Jerusalem with a free day. Shop or return to your favorite site! This is your time to enjoy the amenities at the hotel shop in Jerusalem. I have several favorite shops and am happy to help you spend your money!
Finally, we will conclude the Israel part of the trip with a special Farewell Dinner at Eucalyptus Restaurant. We will use this as a time to remember the incredible tour that you just embarked on.
Fly home on a red eye UNLESS you choose the fabulous 2-day Petra extension.
April 17th | Travel to Eilat
Petra Pilgrims will spend an extra night at the Mamilla Hotel.
We will begin the day early with a drive from Jerusalem to Eilat, which is seated on the Red Sea.
We will enjoy lunch on the way down to Eilat while taking in the breathtaking views of the Zin Wilderness, areas where the Israelites wandered for 40 years.
We cross the Southern Border into Jordan.
Finally, we conclude the day by driving to the famous archaeological site of Petra.
We will arrive at the Old Village Resort in Petra in time for settling in and dinner.
April 18th | City of Petra, Wadi Rum, Southern Crossing, Red Eye Home
After a delicious Jordanian breakfast, we will start the day early with a visit to the iconic city of Petra, where you’ll walk through the rose-colored carvings that have captivated travelers for centuries. This magnificent rock-carved city was the home of the ancient Arab people, the Nabateans, believed to be ancestors of Ishmael’s eldest son. They were great merchants and controlled the incense & spice trade.
From here, we will set out on a 2-hour 4×4 ride through the stunning desert landscape of Wadi Rum. Wadi Rum is the filming location of movies such as Star Wars, The Martian, and Dune. This area would also have been part of the desert wanderings of the Israelites, before they crossed the Jordan River into the Holy Land.
Much later in the day, we will cross the southern border from Jordan into Israel, making our way to Eilat, Israel. Finally, we will catch an evening flight from Eilat to Tel Aviv.
Plan your Red-Eye flight home to the USA.
There it is, friends. Every time I go over the itinerary, I get so excited!
Please join us! You can find this itinerary on the Illuminationhebrewinsights.com website.
There is also a link to read about Karl and I, plus a button to sign up.
The Holy Land is lovingly dubbed as the Fifth Gospel.
I encourage travelers to bring a favorite Bible and highlighter. Highlight all of the biblical sites we visit and as you read your bible in the future, you will trigger a beautiful memory that will make your Bible come alive.
Questions?
Please email me at IlluminationHebrewInsights@gmail.com.
Looking forward to meeting many of you!
Shalom, friends— and as always, pray for peace in the Land.
**Heather!
©2025 Heather M R Olsen, Illumination: Hebrew Insights. All rights reserved.
