Weekend Getaway Itinerary – Three Perfect Days in Niagara-on-the-Lake

Prince of Wales hotel in Niagara-on-the-Lake

Consider booking a three-day getaway in Niagara-on-the-Lake, so you have time to really relax and get more familiar with some of the reasons the Niagara region is one of Canada’s most desirable destinations for elegant, event-filled escapes. Below, we have created an itinerary for your three-day weekend trip to Niagara-on-the-Lake with Vintage Hotels. However, there are nearly infinite options for what your stay with us may look like. If you want to know about one particular amenity or activity, please don’t hesitate to reach out and our Luxury Travel Team will be happy to support you to build the perfect three-day plan. 

Charcuterie board at Vintage Hotels

Day One: Arrive & Unwind

Take the easy drive into Niagara-on-the-Lake and arrive at your Vintage Hotel property. Whether you have chosen Prince of WalesPillar and Post, or Queen’s Landing, you will be welcomed by friendly and attentive staff who are eager to cultivate your ideal vacation from arrival through to departure. As part of your three-day stay, you may choose to have wine, charcuterie, or sweet treats waiting for you in your room as you ease into the freedom of time away from all your responsibilities.

Visit Our Outdoor Heated Pool Before Dinner 

Once you are settled in, why not head to our heated saltwater pool at Pillar and Post to soak away your cares? Afterward, relax and rinse off in one of our jetted tubs, then head to your room to get ready for a night of dining, fine wines and great conversation.

Visit Vintages Wine Bar or Churchill Lounge for a lovingly crafted cocktail and a delectable appetizer. Then head to dinner for your first award-winning dining experience in Niagara-on-the-Lake at one of our premier on-site restaurants: Nobel, Tiara and The Cannery. Reservations are recommended. In the mood for something different? Let one of our Luxury Travel Advisors recommend a local dining experience to perfectly satisfy your tastes.

Experience Niagara-on-the-Lake Festivals

We are proud of the vibrant community nurtured here and with this close-knit feel comes many wonderful festivals and celebrations you would be remiss to miss. Before or following your first meal with us, consider partaking in some local festivities or festivals. Whether you want to head to a concert, visit the Gardens at Pillar and Post for a food and wine event, or uncover a community group that seamlessly aligns with your interests, your evening can include countless friendly faces, different flavours and talented local and international performers. Some of our personal favourite festivals and events include the Niagara-on-the-Lake Icewine Festival takes place in January, the Niagara-on-the-Lake Summer Concert Series takes place in the summer months, and Sip & Savour in The Gardens at Pillar and Post takes place in the fall and winter – just to name a few! 

Breakfast at Vintage Hotels

Day Two: Wine, Dine & Showtime

Wake up to the smell of freshly brewed Nespresso as your breakfast in bed order arrives. Alternatively, head down for a delightful breakfast and then sip your favourite morning beverage in one of our gorgeously-appointed lounges or under an umbrella by the pool. After your slow morning, you can hop into our Vintage Hotels trolley to begin your Niagara-on-the-Lake wine tour. Visit our region’s esteemed wineries to learn more about regional viticulture, sample and purchase various wines, and pair your best glasses with some bites of our local chef’s culinary creativity.

Enjoy Farm to Table Eateries

When you return, you can either revisit your restaurant from the evening before or try one of the other upscale alternatives at our nearby properties. For example, Tiara Restaurant is Feast On®, Oceanwise Certifed, and is a Certified supporter of 100km Inc. Should you want to head into the heart of Niagara-on-the-Lake, there is also an incredible array of eateries where you will be treated to farm-to-table dishes that reflect the richness of Niagara agriculture and, of course, the unparalleled quality of our grapes.

After the curtain closes, head to Churchill Lounge in Prince of Wales – located just steps from the theatre – for a late-night cocktail and bite to eat. This lounge is famous its craft cocktails and vintage ambience. It’s the perfect place to rehash all your favourite moments from the play and your second day in Niagara-on-the-Lake.  

Be Entertained at the SHAW Festival

We highly recommend you pair your winery visits and elegant dining experience with a SHAW Festival performance. Nearly year-round, the SHAW Festival plays host to the incredible talent of its actors, directors and musical connoisseurs. From knuckle-whitening dramas through to laugh out loud comedies, the SHAW Theatre is home to spectacular spectacle that theatre lovers and those just getting their dramatic toes wet will love.

A couple enjoying tea at The Drawing Room

Day Three: Revitalize & Visit the Past

Another easy morning with Vintage Hotels can be set at whichever pace best suits your preferences. On your third day, you can make it all about revitalization and visiting our heritage downtown core and surrounding historical monuments. But first things first, don’t forget about a delicious multicourse breakfast or a light and ceremonious Afternoon Tea in the Drawing Room at Prince of Wales.

Experience Our Award-Winning Spas

During your three-day getaway in Niagara-on-the-Lake, we would love the opportunity to welcome you into one of our award-winning spas. Choose either Secret Garden Spa at Prince of Wales or 100 Fountain Spa at Pillar and Post. Within each of these pristine, high-end spas, you will be able to choose from a robust menu of signature spa services, massage therapy, and aesthetic treatments that will leave you feeling refreshed and your best. Our staff are as passionate about wellness as they are well-educated and certified in their fields of expertise. More than that, our products are absolutely top of the line, and they reflect our dedication to a natural, results-oriented approach to beauty and wellness.  

Visit Galleries and Shops in the Heart of Niagara-on-the-Lake

After you leave your chosen spa feeling immaculate and rejuvenated on your third day in Niagara-on-the-Lake, you can head to the heart of town to visit art galleries, boutique shops and the beautiful park at the centre of our beautiful historic community. If you are searching for more learning experiences that will take you back to the very beginning of our wonderful country, consider going to the Fort George National Historic Site, the Laura Secord Homestead or Queenston Heights Park. These are just a few of the historical landmarks our visiting history buffs love to visit.  

Couple on the walking through the woods in Niagara-on-the-Lake
Picnic Tables in a field surrounded by forest by a Vintage Hotels property in Niagara-on-the-Lake.

Complete your third day in Niagara-on-the-Lake with a walk along anyone of our region’s gorgeous trails, which will take you along the Niagara Escarpment. Or walk along the harbourfront to take in the serene sounds of undulating waves and the chirping of the birds. We can imagine all this walking down memory lane may leave you parched or peckish, so we invite you back to whichever Vintage Hotel property calls to you for a delicious lunch and accompanying cocktail.

The dining room at the Cannery Restaurant.
Local, savory steak from Cannery Restaurant at the Pillar & Post in Niagara-on-the-Lake

Choose from from a selection of fantastic local dining establishments, such as Tiara Restaurant where you can experience renowned Sunday brunch or delicious lunch on a wonderful patio. Or, consider Cannery Restaurant, where you can have one of the best steak dinners in all of Niagara. The Vintages Lounge Bar offers upscale pub favourites such as cauliflower wings that are not to be missed, mouth-watering crab cakes and our famous Pillar Burger.

A couple relaxing by the pool
A couple enjoying a charcuterie board

After that, you may just decide to stay one more night as you extend your indulgent relaxation with more fine dining, dips in the pool, lounging in your suite with a cheese plate or reading in our oversized tubs. Otherwise, if you must depart, you have a short drive back home where you can enjoy the remainder of your evening looking through photos from your Niagara-on-the-Lake trip and reflecting on your favourite moments with us.

Plan your Ideal Itinerary in Niagara-on-the-Lake 

Does all this sound like the perfect way to spend three days? If so, join Vintage Hotels in Niagara-on-the-Lake and create your ideal itinerary. You deserve more than one day away, so let’s curate an escape that actually feels like sufficient time to yourself and your passion for upscale relaxation. 

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