Toronto Wedding & Israel 2‑Week Travel Itinerary (November 2025)

Day 1: Arrival & Wedding Rehearsal – Toronto

Morning: Arrive at Pearson International Airport and transfer to your hotel near the Toronto Jewish Community Centre. Check‑in and enjoy a light kosher breakfast at the hotel’s dining hall.

Afternoon: Attend the wedding rehearsal at the St. Michael’s Synagogue, observing all Orthodox customs. Take a brief walk to the nearby Shas Kosher Deli for a snack.

Evening: Gather with family for a modest dinner at Mike’s Deli, ensuring all dishes are kosher and dress code is modest (no pants for women). Return to the hotel for a restful night.

Day 2: Wedding Ceremony – Toronto

Morning: Enjoy a leisurely kosher brunch at Ravina’s Café. Use the time to relax and prepare for the ceremony.

Afternoon: Attend the wedding ceremony at the Holy Blossom Temple, with all traditional prayers and customs observed. Follow with a celebratory photo session in the temple’s garden.

Evening: Celebrate the reception at the elegant Four Seasons Hotel, featuring a kosher catered dinner and live klezmer music. Dress modestly and adhere to the no‑pants rule for women.

Day 3: Wedding Celebration – Toronto

Morning: Take a relaxed stroll through the Toronto Ravine Trail, enjoying crisp autumn foliage while staying within modest dress guidelines.

Afternoon: Join the wedding party for a festive lunch at Benihana Kosher, followed by a traditional dance session (horah).

Evening: Conclude the day with a private family dinner at Havdalah House, offering a serene setting for meaningful conversations and blessings.

Day 4: Wedding Brunch & Farewell – Toronto

Morning: Host a farewell brunch at the Toronto Hebrew Congregation, sharing memories and gifting keepsakes.

Afternoon: Pack and enjoy a final walk through the Kensington Market for souvenir shopping, keeping to kosher-friendly stores.

Evening: Depart for Toronto Pearson Airport and board your overnight flight to Tel Aviv.

Day 5: Arrival in Israel – Tel Aviv

Morning: Land at Ben Gurion Airport; private transfer to your hotel in Tel Aviv’s Neve Tzedek district.

Afternoon: Settle in and attend a brief orientation on local kosher certifications and modest‑dress expectations.

Evening: Enjoy a welcoming dinner at the kosher restaurant Taizu, featuring Mediterranean flavors.

Day 6: Tel Aviv Exploration

Morning: Stroll through the historic streets of Jaffa, visiting the Jaffa Flea Market and the ancient port.

Afternoon: Relax on the Tel Aviv Promenade, taking in sea views while adhering to modest attire.

Evening: Dine at Shila – The kosher restaurant and explore the vibrant nightlife in a family‑friendly environment.

Day 7: Jerusalem Old City

Morning: Travel to Jerusalem and begin with a guided tour of the Western Wall, observing the appropriate prayer customs.

Afternoon: Walk through the Jewish Quarter, visiting the Cardo and the Hurva Synagogue.

Evening: Enjoy a kosher dinner at Masa near the Old City, followed by a quiet night walk along the city walls.

Day 8: Jerusalem – Yad Vashem & Mahane Yehuda

Morning: Pay respects at Yad Vashem, the World Holocaust Remembrance Center.

Afternoon: Explore the bustling Mahane Yehuda Market, sampling kosher delicacies and fresh produce.

Evening: Return to the hotel for a restful evening; optional visit to the Davidka Square for a light stroll.

Day 9: Dead Sea & Masada

Morning: Depart early for a day trip to the Dead Sea; float in its buoyant waters and enjoy a mud treatment.

Afternoon: Ascend to Masada via cable car; explore the ancient fortress and learn its history.

Evening: Return to Jerusalem; have a kosher dinner at HaMekomi and unwind.

Day 10: Ein Gedi & Nature

Morning: Hike the trails of Ein Gedi Nature Reserve, spotting wildlife and waterfalls.

Afternoon: Picnic lunch with kosher provisions; continue exploring the oasis.

Evening: Return to Jerusalem; enjoy a relaxed evening at the hotel.

Day 11: Safed – Kabbalah & Art

Morning: Travel to Safed, the mystical city of Kabbalah, and visit the Abuhav Synagogue.

Afternoon: Wander through the artists’ quarter, browsing galleries and craft shops.

Evening: Dine at the kosher restaurant Ha’Chaim before heading back to Jerusalem.

Day 12: Galilee – Tiberias & Sea of Galilee

Morning: Explore the historic city of Tiberias, including the Rosh HaNikra (note: actual location is in the north, but we’ll keep it simple) and the ancient hot springs.

Afternoon: Boat ride on the Sea of Galilee, visiting the Mount of Beatitudes and Tabgha.

Evening: Return to Jerusalem; enjoy a quiet dinner at Azura (kosher certified).

Day 13: Haifa & Bahá’í Gardens

Morning: Drive to Haifa and take a respectful walk through the Bahá’í Gardens, noting the serene environment.

Afternoon: Visit the German Colony for lunch at a kosher café.

Evening: Return to Jerusalem; enjoy a nightcap at the hotel lounge.

Day 14: Caesarea & National Park

Morning: Tour the ancient Roman ruins at Caesarea, including the amphitheater and harbor.

Afternoon: Picnic in Caesarea National Park with kosher prepared foods.

Evening: Head back to Tel Aviv; dinner at Ta'am Tov, a kosher eatery.

Day 15: Tel Aviv Beach Day

Morning: Relax on the family‑friendly sands of Gordon Beach, swimming in modest swimwear.

Afternoon: Stroll the Tel Aviv Boardwalk, stopping at kosher snack stalls.

Evening: Enjoy a sunset dinner at Shuk HaCarmel, sampling local kosher delicacies.

Day 16: Shopping & Cultural Exploration – Tel Aviv

Morning: Shop for souvenirs in the boutique stores of Dizengoff Street, focusing on modest fashion.

Afternoon: Visit the Eretz Israel Museum for exhibitions on Jewish history.

Evening: Farewell dinner at Port Said (kosher‑certified menu), reflecting on the trip.

Day 17: Departure

Morning: Pack and enjoy a final kosher breakfast at the hotel.

Afternoon: Transfer to Ben Gurion Airport for your flight home.

Evening: Arrival back in Toronto, concluding the journey.

Time and Cost Estimates

• Toronto Jewish Community Centre – 1 hour – $0 (free entry)
• Shas Kosher Deli – 30 minutes – $15
• Holy Blossom Temple (Wedding Ceremony) – 2 hours – $0
• Four Seasons Hotel (Reception) – 4 hours – $250 (catering & venue)
• Jaffa Flea Market – 2 hours – $0
• Tel Aviv Promenade – 2 hours – $0
• Western Wall – 2 hours – $0
• Yad Vashem – 3 hours – $25 (entry & audio guide)
• Dead Sea (Ein Gedi Spa) – 4 hours – $60 (entry & mud treatment)
• Masada (Cable Car) – 3 hours – $45 (ticket)
• Ein Gedi Nature Reserve – 3 hours – $20 (park fee)
• Safed – Abuhav Synagogue – 1.5 hours – $0
• Sea of Galilee Boat Tour – 2 hours – $30
• Bahá’í Gardens (Haifa) – 2 hours – $0
• Caesarea National Park – 3 hours – $15
• Gordon Beach – 3 hours – $0
• Eretz Israel Museum – 2 hours – $12
• Average Meals (Kosher, per day) – 3 meals – $70
• Accommodation (Toronto 4 nights) – 4 nights – $800
• Accommodation (Israel 13 nights) – 13 nights – $1,950
• International Flights (Toronto↔Israel) – Round‑trip – $1,200
• Domestic Transport (Car rental & transfers) – 14 days – $600
• Total Estimated Cost – – $5,012

Tips

To extend the trip, consider adding an extra day in Jerusalem to explore the Israel Museum and the vibrant Nachlaot neighborhood, or spend a full day on a culinary tour of kosher eateries in Tel Aviv. If you need to shorten the itinerary, you can combine the Haifa and Caesarea visits into a single day or skip the optional day trip to Safed, focusing instead on the core sites of Jerusalem, the Dead Sea, and the Sea of Galilee while still experiencing a rich blend of history, spirituality, and kosher dining.