Tailwind Travel

04/09/2026

Hey Gen Z! Looking for your next big adventure? 🌍✈️

Let Tailwind Travel help you make it happen with exclusive savings through G Adventures.

Right now, you can save up to 25% on select worldwide trips for travel by July 31, 2026, or up to 15% if you’re planning a later getaway by October 31, 2026.

Think beyond the ordinary: hand-making noodles in Vietnam, trekking to Machu Picchu, spotting wildlife on safari in the Serengeti, or zip-lining in Costa Rica. These are the kinds of trips you’ll be talking about forever.

Not sure where to start? That’s where we come in. Tailwind Travel will help you choose the right trip, coordinate your flights, arrange transfers, and make the entire experience seamless from start to finish. No stress, just incredible travel.

Big trips and bigger memories are made easy with Tailwind Travel.

📩 Message us before the sale ends on April 30th to start planning your adventure! Terms & conditions apply.

04/08/2026

Looking for the perfect summer getaway for the kids? Let Tailwind Travel help you plan a magical escape to Walt Disney World Resort! ☀️✨

For a limited time, Disney+ Perks members can unlock exclusive summer savings on resort stays, with rooms starting from just $99 USD per night (plus tax) at Disney’s All-Star Sports Resort, along with special rates at other select Disney Resorts Collection hotels.

Whether you’re dreaming of character meet-and-greets, thrilling rides, or relaxing pool days, we’ll help you find the right resort, dates, and package to make your Disney vacation seamless and stress-free.

📅 Valid most nights from June 21 - August 15, 2026
🛏️ 2-night minimum stay required
✨ Limited availability; rooms are subject to capacity

Booking this offer requires specific steps and verification, but don’t worry - that’s where we come in. Tailwind Travel will handle all the details so you can focus on the fun.

📩 Message us for more information and to book! Terms & conditions apply.

03/27/2026

Dreaming of Ireland? 🍀 Let Tailwind Travel help you make it happen.

For a limited time, we can help you take advantage of an incredible offer with CIE Tours: round-trip airfare to Ireland starting from C$839 per person when you book a qualifying Ireland-only guided tour or a Custom Private Driver holiday.

With nearly 20 expertly crafted guided tours to choose from, or the option to design a fully customized private driver experience, we’ll help you find the perfect itinerary to explore the Emerald Isle your way.

✈️ Airfare available from Toronto, Montréal, Vancouver, Calgary, and Ottawa
📅 Travel between July 1 and December 31, 2026
⏳ Offer ends March 31, 2026

Ireland’s castles, coastlines, and charming towns are waiting. Let Tailwind Travel handle the details so you can focus on the adventure.

📩 Send us a message or contact [email protected] today to start planning your Irish getaway.

03/05/2026

🍷✨ Discover The Enticing Douro with AMA Waterways ✨🍷

Sail round-trip from Porto through Portugal’s breathtaking Douro River Valley on this unforgettable 8-day journey. From vineyard-covered hills to historic cities and world-famous Port wine, this cruise blends culture, cuisine, and stunning scenery.

Highlights include:
🍇 Mateus Palace & Gardens in Régua
🍷 Wine tastings at local quintas in Pinhão
🏛 Excursion to historic Salamanca
🌉 Exploring Porto

Cruise aboard the elegant AmaDouro and experience exceptional dining, immersive excursions, and the breathtaking beauty of Portugal’s iconic wine region.

Questions? Contact reservations@tailwindtravel for rates and more details.

02/25/2026

✈️🎉 WestJet Vacations’ Annual Birthday Sale is BACK! 🎉✈️

WestJet Vacations is turning 30, and that means it’s time to celebrate with vacation savings on 30 unforgettable sun destinations! 🌴☀️

Also enjoy instant savings of up to $450 CAD on select resorts in Mexico, the Dominican Republic, and Barbados - the perfect excuse to plan your next beach escape or even a last-minute March Break trip.

🗓️ Sale ends March 3rd
✈️ Travel window: March 1 – December 31, 2026

Terms & Conditions apply.

📩 Contact us to learn more and lock in these savings while they last!

[email protected]
https://www.tailwindtravel.ca/

02/18/2026

Looking to escape winter?

Say hello to sun and sea aboard Virgin Voyages on the Eastern Caribbean & Bimini Beach Club cruise, an adults-only getaway 🌴

📅 Best available rate: March 28 – April 4, 2026
📍 Round-trip from Miami
🌞 Visit San Juan, Puerto Rico, Puerto Plata, Dominican Republic, and unwind at Virgin’s iconic Beach Club at Bimini, Bahamas.

🔥 Book before February 26th & score these perks:
💸 80% off the second sailor
🍹 Up to $250 in free drinks per cabin

Plus, enjoy Virgin’s Always Included Luxury:
✔️ 20+ world-class restaurants
✔️ Shows, entertainment & fitness classes
✔️ Wi-Fi, tips & basic drinks — all included

💬 Message us or email [email protected] to lock in this deal before it sails away!

02/12/2026

✨ Enchanting Danube: 8-Day Boutique River Cruise with Uniworld ✨

One of Uniworld’s most iconic itineraries, this 8-day sailing from Budapest to Passau captures the very best of Central Europe. Discover legendary capitals, cruise through the breathtaking Wachau Valley, and experience a region celebrated for its history, music, and diverse culinary traditions.

🌍 Ideal for curious travellers, first-time river cruisers, and families alike!

💸 Limited-time savings:
✔️ Save 10–30% on select 2026 and 2027 departures when you book by February 28th, 2026.
✈️ Save even more on flights when you arrange the rest of your trip with Tailwind Travel—we’ll coordinate your cruise, flights, and any extras for a seamless experience.

📩 Thinking about a European river cruise? Email us today at [email protected] to lock in these savings and start planning your Danube adventure!

02/09/2026

🚨 JUST IN!

Air Canada has halted flights to Cuba after authorities announced the island will run out of jet fuel by tomorrow, February 10th. This crisis comes amid U.S. President Trump’s threats to impose tariffs on any country that ships oil to Cuba, and after oil shipments were halted from two of the island’s biggest suppliers: Venezuela and now Mexico.

Situations like this are exactly why booking with a travel agent matters. When the unexpected happens, Expedia and online booking sites can’t help, but we can.

✨ 24/7 white-glove service
✨ We advocate for you when plans change

If your travel is affected, Tailwind Travel is here for you, any time of day.

To book your next hassle-free trip, contact us anytime at [email protected].

02/09/2026

With the Olympics shining a global spotlight on Milan, there’s never been a better time to explore this incredible city 🇮🇹✨

From world-class fashion and history to vibrant neighbourhoods and unforgettable food, Milan is so much more than a quick stop.

If you’re thinking about starting your next Italy adventure, you’re in great hands. One of our leisure agents, Gabriella, lived in Milan for several years and knows the city inside and out!

Ready to plan your Italian getaway? Contact us at [email protected], and we can connect you with Gabriella. Let us help you build the perfect trip, starting in Milan ✈️

02/03/2026

We’ll be sharing just as much travel inspo, tips, and updates on our Instagram, ✈️🌍

Follow us so you don’t miss a thing — from dreamy destinations to special offers and behind-the-scenes moments.

02/02/2026

We wouldn’t be here without you, and we really mean that.

Thank you to all our wonderful clients who have trusted Tailwind Travel with your travel plans over the years. Your loyalty and support allow us to keep doing what we love every single day.

As we head into the second month of 2026, we’re excited to share that we’re putting a bigger spotlight on leisure travel this year. We’ve grown our team of leisure travel specialists, each with unique backgrounds and expertise. No matter the trip you’re dreaming of, there’s a perfect-fit planner here for you ✈️🌍

Think sunny all-inclusives, European adventures, cruises, Disney trips, and milestone getaways across South America and Asia-Pacific, too.

You deserve a vacation that’s easy to plan and incredible to experience, and we’d love to help make it happen.

Let’s start planning:
📩 [email protected]

12/19/2025

Heads up, golf lovers: luxury train operator La Dolce Vita Orient Express is offering an Italian golf-themed trip in 2026!

Called Italian Swing, this three-day itinerary will merge the "heritage of luxury train travel with the prestige of some of the country's most celebrated golf courses," according to a statement the company gave to Travel and Leisure.

The trip will kickstart with a welcome reception in a private lounge at Rome's Ostiense station. Accompanied by a professional golfer, travellers will first be brought to the Marco Simone Golf & Country Club outside Rome - host of the 2023 Ryder Cup - before embarking to Puglia and Tuscany to play at the following golf courses:

San Domenico Golf Club in Fasano - host of the PGA Challenge Tour finals

The Club at Castiglion Del Bosco - Italy's only private members' club, and one of Europe's finest golf and wine experiences

Argentario Golf Club - considered a PGA National Italy Golf Course since 2019

Offering deluxe cabins and suites alongside food cooked by three Michelin-starred Chef Heinz Beck, prices start at EUR 12,360 per person 🤯.

Do you know anyone who might be interested? If so, share this post with them and have them reach out to us at [email protected]. The luxury starts with having an expert agent plan everything from start to finish - and we can provide just that.

Est. 2013, our leisure travel agents bring 20+ years of experience, specializing in Mexico & Caribbean vacations, all-inclusive resorts, Disney trips, cruises, and Europe & Asia-Pacific travel. We are your first stop for stress-free getaways.