From NYC to Montreal - make the most of your road trip to Montreal

As you’ll be crossing two countries, avoid a visa blunder and make sure to check the independent visa restrictions for both the US and Canada. The US has a reputation for stricter conditions but their Visa Waiver Program is available for most Europeans who wish to stay for up to 90 days. You’ll undergo a separate visa and passport check when you make a border crossing into Canada where you will similarly require an Electronic Travel Authorisation from the Canadian government to enter. For the chillest border crossing possible, be ready to answer questions about your travel purpose and length of stay. Possession of alcohol, tobacco and firearms will be monitored, so save your trip to the liquor store until after crossing.

Bear in mind that major highway crossings tend to be busier than smaller highway and truck routes, meaning that a small detour can save you potential hours queuing in traffic. The Canadian Border Services Agency’s Twitter feed can provide up-to-date information on border waits and opening times, or check here. Those wanting to cross in style should consider investing in a NEXUS card which gives pre-approval for travellers who pay $50 for a five-year card and take an interview with US and Canadian officials at the NEXUS enrolment centre.

Don’t get caught out speeding down the freeway on the other side without first getting to grips with Canada’s metric system. You’ll see speed limits written in kilometres, not miles so check closely on your speedometer for the conversion, or otherwise, check online before heading out.

When it comes to luxury stays in New York City, a few select hotels capture the city’s unique blend of sophistication and diversity. The Greenwich Hotel in Tribeca, co-owned by Robert De Niro, is a true gem. This boutique property marries rustic elegance with cutting-edge design, offering an oasis of calm amidst the city’s buzz. The hotel’s Shibui Spa and its celebrated Italian restaurant, Locanda Verde, cater to travellers with a taste for indulgence. Moreover, Tribeca’s cobblestone streets are within easy reach of Soho’s vibrant shopping and the iconic West Village, home to the historic Stonewall Inn, a landmark of LGBTQ+ culture.

Just a short walk from the luxury boutiques of Madison Avenue and the cultural treasure trove of the Museum Mile, The Fifth Avenue Hotel epitomises Manhattan’s upscale allure. Housed in a meticulously restored Gilded Age mansion and a modern tower, this hotel fuses old-world charm with contemporary luxury. With its central location, guests are perfectly poised to explore Midtown’s dynamic energy, from the Broadway theatres to the glitzy nightlife of Hell’s Kitchen, a hub for LGBTQ+ travellers.

For those who prefer sleek modernity, Pendry Manhattan West offers a stylish retreat in the city’s newest neighbourhood, Manhattan West. With its art-filled interiors and cutting-edge amenities, the hotel is a magnet for design enthusiasts. Its proximity to the High Line and Hudson Yards, along with its curated selection of dining and entertainment options, make it an ideal base for those eager to explore New York’s evolving cultural landscape, while also being just a short cab ride away from the gay bars of Chelsea and Hell’s Kitchen.

After a hectic few days pounding the asphalt in NYC, begin the epic journey towards Montreal at any pace you choose. The direct journey will be a six to seven-hour drive northwards on I-87 North Highway. (FYI, as well as being a great destination road trip from New York, Montreal is also a 455-mile leg from Philly, 308 miles from Boston and 260 miles from Portland and Maine).

Opt for the scenic route towards Montreal and take a brief interlude at Niagara Falls. The falls are also seven hours from New York, but instead, we take the I-80 West, I-81 North or I-90 West. From there, travellers have the added option of driving to Toronto (1.5 hours via the Queen Elizabeth Way) before making their way to Montreal (5 hours via ON-401 East) and concluding in Quebec City (2.5 hours via Route Transcanadienne / Autoroute 20 East).

If a dousing at Niagara Falls is on your to-do list, pack your umbrella hat and poncho and read on. Straddling the US-Canada border, Niagara Gorge rises 160 feet covering three waterfalls where six million cubic feet of water gushes past every minute. The most powerful in the whole of North America, these falls are spectacular viewed from any angle, either side of the border. Boat rides on the US side operate daily.

Toronto’s luxury hotel scene is a testament to the city’s cosmopolitan flair and cultural vibrancy. The Hazelton Hotel, located in the heart of Yorkville, exudes an air of discreet opulence. This iconic property is renowned for its spacious rooms, bespoke service, and the critically acclaimed ONE Restaurant by celebrity chef Mark McEwan. Staying here places you amidst high-end boutiques, art galleries, and the Royal Ontario Museum, while the Church-Wellesley Village, the city’s primary gay neighbourhood, is just a quick jaunt away.

The Ritz-Carlton, Toronto offers an urban sanctuary with breathtaking views of Lake Ontario and the Toronto skyline. This hotel is celebrated for its impeccable service, luxurious spa, and TOCA, its Italian-inspired restaurant that highlights locally sourced ingredients. Located in the Entertainment District, The Ritz is within walking distance of major attractions such as the CN Tower and the Art Gallery of Ontario. The vibrant nightlife of Church-Wellesley Village is easily accessible, making it a top choice for gay travellers who appreciate both luxury and culture.

A landmark of sophisticated elegance, Park Hyatt Toronto recently emerged from a comprehensive renovation that has further cemented its status as one of the city’s premier addresses. Situated at the crossroads of culture and style in Yorkville, this hotel offers a rooftop lounge with panoramic views, making it a perfect spot to unwind after a day of exploring. With its close proximity to the LGBTQ+ scene in Church-Wellesley Village and the nearby ROM and Bata Shoe Museum, Park Hyatt is ideal for those who seek both luxury and a deep dive into Toronto’s rich cultural offerings.

Whether you’ve come straight from the border or taken a sojourn in Toronto, Montreal will feel like a whole world away. Distinctly Canadian yet licked with French heritage, Montreal features European-style avenues side by side with chaotic Chinatown alleyways and, of course, an internationally contending Gay Village. The second-largest city in Canada, Montreal is also the world’s second-largest French-speaking city, although – unlike Paris – English is widely spoken.

Either way, brush up on your Français and you won’t regret it. A little effort goes a long way and a few words in French can quickly make you a local friend or two. As for dating, old school Montrealians still seem to prefer face-to-face flirtation in bars, nightclubs and bathhouses over hook-up apps. Discover more of Montreal with our full-length Montreal travel guide.

Montreal’s vibrant blend of European charm and North American energy is reflected in its selection of luxurious hotels. The Ritz-Carlton, Montreal is a grand dame of the city, offering timeless elegance and world-class service. Located in the Golden Square Mile, the hotel is near the Montreal Museum of Fine Arts and the city’s upscale shopping district. Its Maison Boulud restaurant is a culinary highlight, offering French cuisine with a modern twist. The Ritz’s rich history and refined atmosphere make it a favourite among discerning gay travellers.

For those who appreciate a mix of history and modernity, Le Mount Stephen is a standout choice. This hotel is set within a beautifully restored 19th-century mansion, complemented by a sleek, glass-walled tower that houses the rooms. Located in the heart of the Golden Square Mile, Le Mount Stephen is close to Montreal’s best dining, shopping, and cultural attractions. Its luxurious spa and sophisticated dining options, coupled with its proximity to the vibrant Gay Village, make it an ideal choice for those who seek both elegance and inclusivity.

The Four Seasons Hotel Montreal is the epitome of contemporary luxury, offering an unparalleled experience in the city’s downtown core. Its chic design, coupled with a world-class spa and the acclaimed MARCUS restaurant, makes it a destination in itself. The hotel is directly connected to Holt Renfrew Ogilvy, catering to fashion-forward guests, and is just a short distance from the Gay Village, making it an excellent base for exploring the city’s diverse cultural landscape.

Take your sweet time on the next leg which will take you from Montreal to Quebec City through rural Canada at its most mesmerising, dotted as it is with quaint towns, local wineries and boutique districts. More slow-paced than its opposing urban ends, Quebec province allows visitors to return to nature, rekindling an appreciation for the simple things such as moseying through forests, indulging in farm-to-table fare and exploring the provincial sites of a gone-by era alongside a friendly diverse community.

The wider Quebec province encompasses the majority of Canada’s northeast, flanking Ontario in the west and rugged Newfoundland in the east. Feel free to venture further north for hiking excursions and picturesque drives, but for now, we stick to the more populated areas, following the St Lawrence River east to where Quebec City sits spoiled with stunning backdrops including Montmorency Falls, the Jacques-Cartier National Park and a variety of idyllic isles just moments from the centre.

Quebec City’s historic charm and European flair are best experienced from some of its most luxurious hotels. Fairmont Le Chateau Frontenac, perched high above the St. Lawrence River, is an iconic symbol of the city’s heritage. This grand hotel, often considered the most photographed in the world, combines historic elegance with modern comforts. Its prime location within Old Quebec means that guests are just steps away from the city’s cobbled streets, quaint shops, and rich cultural landmarks, making it an exceptional choice for travellers who appreciate a blend of history, culture, and luxury.

For a more intimate yet equally luxurious experience, Auberge Saint-Antoine offers a unique stay in the heart of the Old Port. This boutique hotel is set in a collection of historic buildings, and its interiors are a fascinating blend of contemporary design and historical artefacts. The hotel’s restaurant, Chez Muffy, serves farm-to-table cuisine in a cosy, chic setting. With its proximity to the Musée de la Civilisation and the charming Petit Champlain district, Auberge Saint-Antoine appeals to travellers seeking a culturally immersive stay.

For those who prefer a modern twist on luxury, Monsieur Jean – Hôtel Particulier offers a fresh and artistic approach to hospitality. Located just outside the walls of Old Quebec, this hotel combines avant-garde design with playful touches, creating an atmosphere that is both stylish and welcoming. The property’s central location makes it easy to explore the city’s historic sites, while its proximity to the lively St. Roch district offers a glimpse into Quebec City’s contemporary culture, making it a perfect choice for the modern, discerning gay traveller.