New Chat

Download App

Ask me about your trip!

There are no messages for this conversation.

Free AI trip planner

5-Day Toronto and Windsor Adventure

5-Day Toronto and Windsor Adventure Itinerary

Last updated: 2024 Jun 14

City Icons and Culinary Delights

Morning
Start your Toronto adventure with a sumptuous breakfast at The Black Hoof, known for its innovative dishes. Afterward, visit the iconic CN Tower to enjoy panoramic views of the city.
Afternoon
For lunch, head to Kinka Izakaya for authentic Japanese cuisine. Spend your afternoon exploring the fascinating exhibits at the Royal Ontario Museum (ROM) and immerse yourself in history and culture.
Evening
Dine at Bar Isabel, offering a vibrant atmosphere and Spanish-inspired dishes. End your evening with a leisurely walk at the Entertainment District, where you can catch a live performance or simply enjoy the lively ambiance.
Bedtime
Find amazing hotels in Toronto.

Waterfront Wonders and Island Escape

Morning
Enjoy a delightful breakfast at Terroni, known for its rustic Italian fare. Then, take a stroll along the serene Toronto Harbour and admire the beautiful waterfront.
Afternoon
Have lunch at Miku Toronto, famous for its aburi sushi, and then take a ferry to the Toronto Islands. Spend the afternoon exploring the islands, renting a bike, or simply relaxing by the water.
Evening
Indulge in a fine dining experience at Canoe Restaurant and Bar, located on the 54th floor with breathtaking views of the city. After dinner, take a romantic walk at the Sugar Beach and enjoy the city lights.
Bedtime
Find amazing hotels in Toronto.

Cultural Gems and Distillery Delights

Morning
Start your day with a hearty breakfast at Lee Restaurant, known for its modern Asian cuisine. Then, visit the historic Distillery Historic District and explore the charming shops and galleries.
Afternoon
Enjoy a guided Toronto 3–Hour Secret Food Tour to discover hidden culinary gems and local favorites. Savor a variety of dishes and learn about the city's food scene.
Evening
Dine at Byblos Toronto, offering a sophisticated atmosphere and Eastern Mediterranean dishes. Afterward, catch a performance at the Elgin and Winter Garden Theatres, a historic and stunning venue.
Bedtime
Find amazing hotels in Toronto.

Windsor Waterfront and Casino Excursion

Morning
Begin your day with a delightful breakfast at Scaramouche Restaurant Pasta Bar & Grill, known for its elegant ambiance and Italian cuisine. After breakfast, take a walk along the beautiful Windsor Riverfront and enjoy the scenic views of the Detroit River.
Afternoon
For lunch, head to Sukhothai and indulge in authentic Thai flavors. Afterward, try your luck at the Caesars Windsor Casino, where you can enjoy a variety of gaming options and entertainment.
Evening
Dine at The City Grill, a stylish restaurant offering a diverse menu and a vibrant atmosphere. After dinner, take a leisurely stroll through the Olde Walkerville Neighborhood, known for its historic charm and unique shops.
Bedtime
Find amazing hotels in Windsor, Ontario, Canada.

Toronto Sports and Evening Elegance

Morning
Start your day with a classic breakfast at Richmond Station, a popular spot known for its farm-to-table fare. Afterward, visit the Hockey Hall of Fame to immerse yourself in the history of the sport.
Afternoon
Enjoy a casual lunch at La Carnita, famous for its vibrant atmosphere and delicious tacos. Spend your afternoon shopping and exploring the shops at Yorkville Village, a high-end retail destination.
Evening
For a memorable evening, dine at Alo Restaurant, one of the city's most acclaimed fine dining establishments. Afterward, enjoy a live performance at the Royal Alexandra Theatre, one of the oldest and most famous theatres in North America.
Bedtime
Find amazing hotels in Toronto.

Top Toronto Travel Videos

kayakFind the right stay during your trip.
Got a question about your trip?