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:
- King’s Day (27th April): A lively street party with music, dancing, and everyone dressed in orange.
- Tulip Season: Explore vibrant tulip fields in full bloom, especially at Keukenhof Gardens, or take a countryside tour to see the iconic Dutch flower in its natural setting.
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:
- 4th of July Celebrations: Expect fireworks, parades, and lively celebrations across Orlando.
- Florida Summer Music Festival (June–August): Live performances and outdoor concerts for all ages.
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:
- Jidai Matsuri (22nd October): A parade celebrating Kyoto’s history with traditional costumes.
- Shichi-Go-San (15th November): A festival celebrating children’s milestones in Japan.
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:
- Loy Krathong (November–December): A festival where locals release floating lanterns onto water, making wishes for the future. The sky and waterways light up with hundreds of glowing lanterns, creating a beautiful and peaceful atmosphere.
- New Year’s Eve Celebrations (31st December): Join the fireworks and beach parties that light up the coast and welcome the new year across Phuket.
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:
- Choose annual multi-trip travel insurance: One policy covers all your trips, saving you money and hassle.
- Pack light and smart: Bring essentials that work across multiple climates to avoid overpacking.
- Book flights in advance: Especially for peak seasons, early booking can help you save.
- Plan around off-peak dates: Travelling just before or after the busiest times means better prices and fewer crowds.
- Use travel reward programmes: Collect points and get perks for future trips.
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.
