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Where to Travel All Year Round: Top Multi-Trip Destinations for Every Season

May 09, 2025

Planning a trip can be exciting, but with so many destinations to choose from, it can also feel overwhelming. If you love to travel and explore new places, why not make it a goal to visit a different destination each season? Whether you’re travelling solo, with friends, as a couple, or with family, each season brings its own unique experiences. From the bright blooms of spring to the warm beaches of winter, there’s a perfect getaway for every time of the year.

With an annual multi-trip travel insurance policy, you can travel more, worry less, and focus on making long-lasting memories all year round. Here’s a guide to our top destinations to visit each season, helping you explore new places and enjoy a variety of experiences throughout the year.

1. Spring – Amsterdam, Netherlands

Spring is a brilliant time to visit Amsterdam, with mild weather and colourful tulip gardens in full bloom. A great way to explore the city is by renting a bike and cycling along the canals, or you can take a boat tour to enjoy the views from the water. Keukenhof Gardens, one of the world’s biggest flower gardens, is open from March to mid-May, showcasing millions of tulips in bloom. For a bit of culture, visit the Van Gogh Museum or unwind in Vondelpark, a lovely spot for a walk or picnic.

Local Traditions:


For more information on Dutch traditions and events, visit here.

2. Summer – Orlando, Florida, USA

Orlando is the ultimate summer holiday destination, packed with world-famous attractions like Walt Disney World, Universal Studios, and LEGOLAND Florida. If you need a break from the theme parks, visit one of Orlando’s water parks, such as Typhoon Lagoon, or explore the natural beauty of Wekiwa Springs State Park. Families travelling with children can save money by purchasing multi-day passes to the attractions.

Local Traditions:

For more details on family-friendly activities in Orlando, visit here.

3. Autumn – Kyoto, Japan

Autumn in Kyoto offers a lovely display of red, orange and gold leaves, making it one of Japan’s most beautiful seasons. Visit the Kinkaku-ji (Golden Pavilion), explore the Arashiyama Bamboo Grove, and stroll through the historic Gion district, known for its traditional tea houses. The city’s mild autumn weather is perfect for exploring temples and gardens.


Local Traditions:

For more information on Kyoto’s autumn traditions, visit here.

4. Winter – Phuket, Thailand

If you want to escape the winter cold, Phuket is a brilliant choice. Whether you’re looking for lively nightlife at Patong Beach or a more peaceful retreat at Kata Beach, there’s something for everyone. Explore the local markets, visit the Big Buddha, or take a boat trip to the famous Phi Phi Islands. For ethical wildlife encounters, consider a visit to the Phuket Elephant Sanctuary.

Local Traditions:

For more information on Thailand’s cultural experiences, visit here.

Multi-Trip Travel Tips:

Planning several holidays a year? Here are some tips to help make your travels smoother and more flexible:

If you plan to take multiple holidays in a year, getting an annual multi-trip travel insurance can save you money and give you peace of mind. It covers unexpected events like cancellations, lost luggage, and medical emergencies, so you can enjoy your trips without extra stress.

Make the most of your travels by choosing the right destinations and securing multi-trip travel insurance for a worry-free journey. For more information, visit here.

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