day by day itinerary
October 2026
Day 1
Saturday
Shalom Yisrael! Welcome to Israel. Welcome HOME! Guests arrive per schedule. Once you have checked in to your hotel, enjoy the day in Tel Aviv. Even on Shabbat, many stores are open. You may visit the beautiful beaches, stroll through Old Yaffa, or visit one of the many museums.
Whatever your travel arrangements, we ask that you arrive in Tel Aviv by 5:00 pm. We are happy to help with any additional travel if you choose to arrive earlier.
Our trip officially begins as we meet together as a group for our festive welcome dinner at a local restaurant.
After dinner, take a walk on the beach promenade or maybe visit a beer garden.
Overnight: Royal Beach Hotel, Tel Aviv
Meals
Dinner
Included and optional experiences
Let's Tailgate
Welcome Dinner
Included with your pre-trip
Day 2
Sunday
Enjoy a free morning in Tel Aviv to tour or shop. Maybe a visit to Carmel Market to sample some of the amazing food, or Old Yaffa to visit art galleries, jewelry stores and more.
Around midday we will head west toward the Gaza envelope.
Our time this afternoon centers around the sobering memorials to the October 7 attack. You will spend some introspective moments at the NOVA festival site to appreciate the personal stories that pay tribute to the young men and women who lost their lives here. We will also visit the town of Sderot and its awe-inspiring memorial to its fallen.
We will return to Tel Aviv for you to enjoy a free evening to explore the city and the opportunity to dine at one of the many amazing restaurants it has to offer.
Overnight: Royal Beach Hotel, Tel Aviv
Meals
Breakfast
Day 3
Monday
Our day begins with a guided tour of the ruins of the Roman port city of Caesarea, named in honor of Augustus Caesar. When this ancient city was originally constructed, it had an artificial harbor of large concrete blocks and typical Hellenistic-Roman public buildings. An aqueduct brought water from springs located almost 10 miles (16 km) to the northeast. Caesarea served as a base during the time of King Herod the Great through the time of the Crusaders.
We will then enjoy a delicious lunch at one of the local wineries before heading up north to the Galilee. You will have the rest of the day to take advantage of all of the amenities at our resort hotel, as well as a fabulous dinner.
Overnight: Ayala Nature Reserve, Upper Galilee
Meals
Breakfast, Lunch, Dinner
Day 4
Tuesday
Our day begins with a visit to Mount Ben Tal to see sweeping panoramic views of Israel's north, as well as it's close by neighbors. This location was the site of one of Israel's battles for independence.
Then on to the mystical city of Tzfat. We will tour the city and offer plenty of time for lunch and shopping. Tzfat is home to a variety of vendors selling art, jewelry, religious items, candles, whiskey, cigars and more!
Afterward we depart for dinner at a local winery on our way to Jerusalem.
Overnight: Inbal Hotel, Jerusalem
Meals
Breakfast, Dinner
Day 5
Wednesday
After a good night's and well deserved rest, we spend the day with a walking tour of the fabulous Old City of Jerusalem. We will visit the Kotel (the Wailing Wall), the Kotel tunnel, as well as underground Jerusalem. You will have the opportunity to walk through the ancient watery route of Hezekiah's Tunnel (you'll need your bathing suit and water shoes!)
You will have time to enjoy lunch on your own at one of the many vendors.
After this full day of touring you will have the opportunity to explore Jerusalem on your own. Perhaps some shopping at Mamilla Mall, Ben Yehuda Street and the Machane Yehuda marketplace.
Overnight: Inbal Hotel Jerusalem
Meals
Breakfast
Day 6
Thursday
Today we rise early to visit and hike 1500 ft upward to the top of Masada. (A cable car is available for those who do not wish to climb). Masada is the historic mountain fortress, built by Herod the Great as a refuge. It boasts panoramic views of the Dead Sea, Jordan, and the Judean desert. While atop this wonder, we will tour its ruins and learn of the tragic story of this inhabitants.
After our decent by cable car, we will have lunch for you and then onward to the Dead Sea. Cover yourself in the mineral-rich sea mud and then float and soak in its healing waters. (You will have the opportunity to shower and change).
Our next stop with be the Ein Gedi nature preserve where you have the opportunity to hike through its paths and cool off under its waterfalls.
We then venture to Eretz B'reshit for a one-of-a-kind dinner hosted by none other than Abraham. Enjoy a camel ride to his welcoming tents followed by a delicious meal.
Then it's back to Jerusalem to enjoy a free evening to shop and dine. Thursday nights are hopping and lively at Machane Yehuda when the bars open and the market is full of both young and not so young enjoying the end of the work week!
Overnight: Inbal Hotel Jerusalem
Meals
Breakfast, Lunch, Dinner
Day 7
Friday
After breakfast we begin our day with a fully guided tour of the world-renowned Holocaust Museum, Yad Vashem, A short hike follows to Har Herzl Cemetery to visit the gravesites of Israel’s soldiers, past leaders, and of course, Theodore Herzl.
Afterward, you will have the afternoon free to eat and shop and prepare for Shabbat.
OPTIONAL ACTVITY: Those who wish to are welcome to walk to the Kotel to experience Kabbalat Shabbat.
You are all invited to a lively, festive, and delicious Shabbat dinner at our hotel.
Meals
Breakfast, Dinner
Included and optional experiences
Let's Tailgate
Kabbalat Shabbat at the Kotel and Shabbat Dinner
Included with your tour
Day 8
Saturday: Shabbat
Enjoy Shabbat in the Holy City and relax! Breakfast and lunch are at your leisure and included at our hotel.
Feel free to sleep-in, relax by the pool, have a leisurely stroll through the streets of the Old City, or attend services at one of the many synagogues throughout the city.
As Shabbat draws to a close, we will celebrate with a special Havdalah service.
Explore the city and its restaurants even more during your free evening in Jerusalem.
Overnight: Inbal Hotel Jerusalem
Meals
Breakfast, Lunch
Day 9
Sunday
After breakfast and hotel check-out, our final day begins with a visit to Rachel's Tomb to see the burial place of the matriarch Rachel. Afterward, we will participate with Pantry Packers to pack food for IDF soldiers.
From there we will visit the Gush Etzion Heritage Center for a very informative and amazing multi-media light and sound presentation, detailing the history of the region and struggles of the settlers with their unfriendly neighbors.
Finally, we head to the Gush Etzion Winery for our farewell dinner.
Then to our final destination: Ben Gurion Airport.
For guests returning home, airport transportation is included. For guests who wish to stay longer, we are happy to help make hotel and transportation arrangements for you, but these will be at your own cost.
We say l'hitraot! Goodbye for now! Come back again on another fantastic TAILGATE tour!
Meals
Breakfast, Dinner
Israel | Your Journey Begins
Uncover the wonders of Israel, from the ancient streets of Jerusalem to the beaches of Tel Aviv, to the serene beauty of the Galilee and everything in between. Imagine exploring the historic ruins of Masada, soaking in the healing waters of the Dead Sea, wandering through the spiritual alleys of Tzfat, and tasting the fruits of the land.
Notes:
The itinerary is subject to change based on current conditions. The substituted activity will be comparable.
Meals in the itinerary are kosher.
Activities and meals listed in the itinerary are included in the cost unless otherwise noted.
Alcoholic beverages are not included with meals unless indicated.
Hotel rooms are based on double occupancy. Single supplements are available for an additional cost.
Optional activities have an additional cost.
Security detail included where appropriate.
Activity Level
High 🔥
Meals
8 Breakfasts, 4 Lunches,
6 Dinners