Plan A Year Full of Adventure: Top Multi-Trip Destinations for Every Season
If you love to travel and explore, why settle for just one holiday a year when you can explore a new destination every season? Whether you’re chasing the spring sunshine, summer adventures, autumn colours, or winter warmth, there’s always an adventure waiting for you.
Travelling several times a year doesn’t have to be expensive or complicated. With annual multi-trip travel insurance, you can save time and money by covering all your trips under one policy. No need to book separate insurance for every trip, just focus on exploring, making memories, and enjoying every season to the fullest.
This guide will help you plan the perfect travel year, with top destinations to visit in spring, summer, autumn, and winter. Whether you love outdoor adventures, cultural experiences, or beach escapes, these destinations offer something special - whenever you choose to go. You’ll also find some helpful multi-trip travel tips to make planning easier and travelling smoother throughout the year.
1. Spring: Portugal
Spring is an amazing time to visit Portugal, with its mild weather and amazing surroundings. Whether you’re into outdoor activities, historical sites, or scenic coastlines, Portugal has something for every type of traveller.
The Azores offer amazing volcanic hikes with crater lakes. Head to Ericeira for world-class surfing in a relaxed coastal town. For climbing enthusiasts, the Algarve’s rugged cliffs offer exciting challenges along the sea. Hikers can enjoy the dramatic views along the Rota Vicentina trail, and if you love history, the fairytale town of Sintra provides scenic forest walks and magnificent palaces.
Local Traditions:
- Easter Celebrations (March/April) - Experience colourful processions and religious festivals take place across Portugal.
- Festa das Cruzes (May) - Join the historic festival in Barcelos with vibrant parades, performances, and traditional decorations.
For more information on Portugal's local festivals and activities, visit here.
2. Summer: Costa Rica
Costa Rica is the ultimate summer destination for adventure lovers. Known for its rainforests, beaches, and incredible wildlife, this country is perfect for outdoor activities.
Surfing at Tamarindo Beach is a must, with gentle waves for beginners and stronger swells for experienced surfers. Hiking through dense rainforest to the top of Arenal Volcano rewards you with breath-taking views of the landscape. For wildlife spotting, Manuel Antonio National Park is perfect - you’re likely to see sloths, monkeys, and colourful birds during your trek.
Local Traditions:
- Annexation of Guanacaste (25th July) - Celebrated with music, dancing, and parades.
- Virgen de Los Angeles Day (2nd August) - Join thousands of people walk to the Basilica of Cartago in a famous pilgrimage.
For more information on Costa Rica, visit here.
3. Autumn: Kyoto, Japan
Autumn transforms Kyoto into a beautiful landscape of red and gold leaves, making it perfect for peaceful exploration and cultural experiences.
The Kiyomizu-dera Temple offers incredible autumn views, while Fushimi Inari Shrine’s red torii gates provide a unique hiking experience. Take part in a traditional Japanese tea ceremony for a moment of calm and culture, and consider hopping on the Shinkansen (bullet train) for an exciting day trip to Tokyo.
Local Traditions:
- Jidai Matsuri (22nd October) - A historic parade with people dressed in traditional Japanese clothing.
- Kurama Fire Festival (22nd October) - Experience the giant torches light up the mountain village of Kurama.
To explore more of Kyoto’s cultural heritage, visit here.
4. Winter: Phuket, Thailand
When winter arrives, Phuket is the perfect place for sunshine and adventure. Relax on the golden sands of Patong Beach or hop on a boat to explore the nearby Phi Phi Islands. Make time to visit the island’s iconic Big Buddha, where you’ll be rewarded with panoramic views. Discover authentic Thai culture by wandering through the night markets and tasting delicious street food, and don’t miss a boat tour around Phang Nga Bay with its towering limestone cliffs and hidden caves.
Local Traditions:
- Loy Krathong Festival (November) - Floating lotus-shaped boats with candles on the water to bring good fortune.
- Old Phuket Festival (February) - Celebrate Phuket’s rich heritage with traditional music, colourful parades, local food, and street performances in the historic Old Town.
For more information about activities and events in Phuket, 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 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 travel confidently, no matter where the year takes you.
For more information about our annual multi-trip travel insurance, visit here.
