There’s nothing like a girls’ weekend to recharge your soul, laugh more than you’ve laughed in ages, and remind you why your girlfriends are basically life’s greatest treasure. The Daily Drip recently curated the ultimate Toronto getaway for their Thought Leaders with the help and expertise of RNR, the custom retreat & group travel planning company I co-founded in 2021.  

Whether you’re planning a bachelorette, a milestone birthday, or just need an excuse to escape life with your besties, this is the kind of trip you’ll want to hit save.

Why Toronto you might ask? Well, our fearless leaders, Nicole Mastrangelo & Romi Wallach, are both born and raised in this epic city. They wanted their inaugural Thought Leader Weekend to feature the city that shaped them. 

Living in South Florida, we’re used to being in an epicenter of North American tourism. Toronto might not be the first destination that pops into your head, but it should be. In just a three-hour flight, you can swap palm trees for fall foliage, trade in the humidity & heat for crisp fall air, and step into one of North America’s most vibrant (yet underrated) cities. Toronto delivers it all: gourmet food, unique neighborhoods, a diverse culture, and nearby trails that make you forget you’re in Canada’s largest city. 

And for us South Florida girlies, we are always craving cozy sweaters and leaves changing colors. Am I right?  It’s the perfect blend of thrumming city energy and restorative nature - exactly what a girls’ weekend calls for.

Ready to steal our itinerary? Let’s go.

Day 1: Arrivals & a Warm Toronto Welcome

Your crew touches down in Toronto, and private transfers whisk you straight to your home base. 

For us, we chose the iconic Four Seasons Hotel Yorkville. Nestled in Yorkville, the city’s most stylish neighborhood, you’ll be steps from designer boutiques, art galleries, and some of the best restaurants in town. 

After check-in, it’s time to set the tone for the weekend with a Dinner at Quanto Basta, an upscale Italian eatery just a short walk (or rideshare) away in the historic Rosedale neighborhood. 

This charming pasta house and enoteca is proudly woman-owned by two sisters, Daniela and Julia, who carefully curate authentic menus that compliment their extensive gourmet wines from around the world, thanks to the wine bar’s state-of-the-art Enomatic serving system. 

The cozy 55-seat venue graduated from a neighborhood fan favorite to one of Toronto’s top dining choices during the COVID-19 pandemic, when Julia’s husband, former NHL all-star and Stanley Cup winner Tomas Kaberle, personally delivered take-out orders. 

What began as a family business’s desperate pivot to stay afloat during government shut-downs of nonessential services, quickly turned into a fun way to surprise and delight the community during uncertain times. As word spread and orders increased, Quanto Basta leveraged the opportunity to give back, donating a percentage of sales to Michael Garron Hospital, with Tomas matching ten times.  

For hand-made pastas, savory rustic dishes, global wine pairings, and warm atmosphere (with the potential of bumping into Tomas Kaberl!), Quanto Basta is a must on your trip to Toronto! 

Day 2: Culture, Wellness & Culinary Delights

Morning Reset

Ease into the day and enjoy breakfast at the iconic Cafe Boulud, Michelin-starred Chef Daniel Boulud’s French Brasserie- located inside the Four Seasons and renowned for its elaborate breakfast and brunch spreads!

Nicole & Romi’s “Favorite Things” Walking Tour

Nicole & Romi curated a 9-kilometer route that takes you through the best of Toronto’s neighborhoods and landmarks:

• Start in Yorkville, a chic shopping district.
  
  
• Wander into the bohemian streets of Kensington Market.
  
  
• Snap pics at Nathan Phillips Square (yes, the giant Toronto sign is mandatory).
  
  
• Graze your way through St. Lawrence Market.
  
  
• Toast with something local in the Distillery District.
  
  
• Breathe in lakeside air at the Harbourfront.
  
  
• Wrap it up near the iconic CN Tower and Rogers Centre (if you plan on riding up to the top of the tower, we highly encourage booking your tickets in advance).
  
  

It’s basically a highlight reel of the city in one loop, and the perfect way to spend your first day while racking up those 20,000 steps eating and exploring your way through Toronto!

Dinner in Yorkville

After freshening up, it’s time for an elegant dinner back in Yorkville. 

We chose Kasa Moto, which nails contemporary Japanese. 

The chic, two-story contemporary Japanese restaurant and lounge is located in Yorkville, just steps from the Four Seasons. Known for its upscale, minimalist interior and lush, tropical-themed rooftop terrace, Kasa Moto offers izakaya-style dining paired with city views and perfect vibes. 

The atmosphere transforms from a vibrant daytime patio lunch spot to an electric supper club with a late night bustling party scene- an ideal choice that checks off all the must-haves for a memorable night with the girls!

Day 3: Nature & Nurture

Scenic Morning Nature Walk

Did you know that Toronto is known as the “city within a park”? 

Toronto might be a bustling city, but its countless green spaces and “parkettes” are dreamy (especially in fall). Enjoy the crisp fall air with a nature walk through some of the city’s iconic ravines, lined by forests, rivers, + creeks.

We took the group for a walk on the Beltline Trail (about 3.5 km at a relaxed pace). 

Expect leafy tunnels, ravine views, and those famous wooden bridges that beg for group photos. It’s the perfect setting for a reflective group discussion - or simply catching up one-on-one. Some of our deepest conversations happen when we’re moving and walking, so this activity really helps set you up for success in diving deeper in your relationships with each other. 

Casual Exploration

Nothing takes the relaxation out of travel like over scheduling. 

Carve out free time for an agenda-free day where you can have some me-time or check off something you want to see or do in Toronto, like touring the Royal Ontario Museum, shopping at the Eaton Centre, or exploring the historic Casa Loma.

However you choose to spend your time, embrace the possibility and spontaneity of casual exploration!

Afternoon Spa Bliss at the Four Seasons

A spa experience is always the crown jewel of a truly restorative girls weekend. And the spa experience at the Four Seasons Day Spa did not disappoint. 

The Four Seasons Toronto Day Spa is the largest city spa in the global Four Seasons portfolio, boasting a huge 30,000-square-foot luxury facility with floor-to-ceiling windows providing city views from the relaxation areas alongside an array of holistic wellness treatments including an indoor pool, a Wellness & Bio Bar with bio-hacking services, a fitness center, and a salon.

From massages and facials, to the steam room and sauna, the Spa Team at the Four Seasons can handle all your strategic scheduling so your group will feel like you have the spa almost entirely to yourselves. This is the perfect way to end the day- and what girls trips are truly made for.

Dinner & Girls’ Night Out

All this relaxation will energize you for taking on Toronto’s downtown nightlife scene!  

For dinner, we chose Oretta, where the food and cocktails are as Instagrammable as the décor. This vibrant and modern restaurant is known for its stylish interior design featuring historic Italian architecture with a modern twist, including soaring arches, gold-trimmed chairs, and colorful imported tile flooring. 

With 3 locations to choose throughout the city, we chose their newest landmark property on Front Street, featuring over 8,000 square feet of indoor and outdoor space in the heart of Toronto’s vibrant nightlife scene. From dancing, to bar hopping, downtown Toronto can take the night wherever you want it to go!

Day 4: Farewell Brunch & Goodbyes

On your final morning, check out of the hotel and make your way to Manita in Rosedale, a hybrid cafe, grocery, and bar most known for its brunch, sandwiches, and cozy atmosphere. An ideal setting for a laid-back, trendy farewell meal, you and the girls can toast to a weekend well-spent, share your favorite moments, and (probably) start plotting your next girls’ getaway before the last mimosa is poured!

Private transfers return you to the airport, and just like that - you’re on your way home, bags a little heavier from shopping, and hearts definitely fuller from the intentional time carved out for each other and yourselves.

Steal this itinerary and make it your own. Whether you follow it to a tee or just use it for inspiration, Toronto is a destination worth exploring, especially when you’ve got your best girlfriends by your side!

Thank you to our friends at the Four Season’s Toronto, Quanto Basta, Kasa Moto, and Oretta, for providing an unforgettable experience!