Plan A Year of Dream Holidays: Top Multi-Trip Destinations for Every Season

May 09, 2025

If you love to relax and unwind in new destinations, why not set a goal to visit a new destination every season? With longer days and warmer weather, May is the perfect time to start planning your next peaceful holiday.

Whether it’s a city break to Amsterdam or a relaxing retreat to Dubai, you can experience the world at a slower pace, one season at a time. With an annual multi-trip policy, you can travel more, worry less, and focus on making long-lasting memories throughout the year.

Here’s a guide to give ideas of 4 of our top destinations to visit for each season, helping you explore new places along with useful multi-trip travel tips to help you make the most of your travel experiences throughout the year.

1. Spring – Amsterdam, Netherlands

Spring is the perfect time to visit Amsterdam, as the city comes to life with blooming flowers, mild weather, and relaxed outdoor spaces. Wander through Keukenhof Gardens to see fields of colourful tulips or rent a bike to explore the scenic canals. The Van Gogh Museum offers a cultural escape, while Amsterdam’s cafés provide a cosy spot to relax with a coffee by the water. The city’s lively atmosphere makes it a great place to embrace the new season.

Local Traditions:

• King’s Day (27th April): A national celebration where the streets turn orange with music, dancing, and festivities.
• 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 – Diani Beach, Kenya

For those looking for a tropical escape, Kenya’s Diani Beach is an excellent summer destination. The white sandy beaches and warm Indian Ocean waters make it a great place to relax. Spend your days sunbathing, exploring coral reefs, or taking a boat tour to spot dolphins. If you’re up for an adventure, go on a safari in one of Kenya’s nearby national parks, where you can see elephants, lions, and giraffes in their natural habitat. In the evenings, enjoy fresh seafood while watching the sunset over the ocean.

Local Traditions:

• Beachside Relaxation: Spend your days sunbathing, swimming, or enjoying a beachfront massage as the ocean breeze rolls in.
• Summer Tides Festival (early July): This laid-back beach festival features live music, cultural performances, and local food – perfect for soaking up the atmosphere without the crowds.

For more information on Kenya’s amazing beach and safari destinations, visit here.

3. Autumn – Rome, Italy

Autumn is a fantastic time to visit Rome, as the summer heat fades and the city becomes more comfortable to explore. Visit iconic landmarks such as the Colosseum, the Vatican Museums, and the Sistine Chapel without the peak-season crowds. Strolling through the historic streets, you’ll find cosy cafés serving freshly brewed espresso and traditional Italian dishes. Rome’s lively squares, markets, and rich history make it an ideal destination for a cultural experience.

Local Traditions:

• Autumn Wine Festivals: A time to celebrate the grape harvest with wine tastings and traditional food. Highlights include Vendemmiata Romana and Sagra dell’Uva di Marino, featuring local wine, food, and festive traditions.
• All Saints’ Day (1st November): A religious holiday where families visit cemeteries to honour loved ones.

To explore more of Italy’s culture, click here.

4. Winter – Dubai, UAE

When the cold weather arrives, Dubai offers a warm and luxurious escape. Relax on Jumeirah Beach, shop in the world-famous Dubai Mall, or take in the views from the top of the Burj Khalifa. A desert safari is a must, offering camel rides, dune bashing, and traditional entertainment under the stars. Dubai’s winter months also bring exciting events, making it a great place to unwind while still enjoying a vibrant city atmosphere. Whether you prefer relaxing in luxury or exploring vibrant city life, Dubai is perfect for a winter holiday.

Local Traditions:

• Dubai Shopping Festival (December–January): A city-wide event filled with shopping discounts, concerts, and fireworks.
• National Day (2nd December): A celebration of the UAE’s heritage with parades, performances, and cultural events.

For more details about Dubai’s winter attractions and events, visit here.

Multi-Trip Travel Tips:

Planning several holidays a year? Here are some tailored tips to help make your travels smoother, more flexible, and filled with relaxation and luxury:

• Choose annual multi-trip travel insurance: One policy covers all your trips, saving you money and hassle while ensuring peace of mind.
• Pack light and smart: Bring essentials that work across multiple climates to avoid overpacking and ensure you travel with ease and comfort.
• Book flights in advance: Especially for peak seasons, early booking can help you save money and secure those premium travel experiences.
• Plan around off-peak dates: Travelling just before or after the busiest times not only ensures better prices, but also fewer crowds, allowing for a more relaxed experience.
• Use travel reward programmes: Collect points and enjoy exclusive perks for future trips, adding extra luxury to your travel experience.

Why wait for just one trip a year when you can explore new destinations every season? Whether you prefer relaxing on a beach, exploring a historic city, or discovering new cultures, planning trips throughout the year ensures a variety of unforgettable experiences.

And remember, while you plan for unforgettable trips, make sure you’re also prepared for the unexpected. With an annual multi-trip travel insurance, you can travel more often without the worry. For more information about our annual multi-trip travel insurance, visit here.