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Where to Travel by Season: A Quarter-by-Quarter Guide
- Anne Marie aka Baldgirlwilltravel
- 4 days ago
- 5 min read
One of the biggest mistakes people make when planning travel is choosing where to go without giving enough thought to when to go.
The same destination can feel completely different depending on the season. Weather, crowds, pricing, rainy seasons, mosquito activity, hurricane patterns, school holidays, and cultural calendars all matter — and ignoring them can turn a dream trip into an exhausting one.
This guide breaks travel down quarter by quarter, by continent, using seasonal realities, climate patterns, and real-world travel considerations to help you decide not just where to go — but when it actually makes sense.
January – March
Dry seasons, warm escapes, and smart long-haul travel
The first quarter of the year is one of the most strategic times to travel, especially if you’re trying to escape winter while avoiding peak crowds and inflated prices.
West Africa, particularly Ghana and Senegal, is best experienced in January — not December. December travel to Ghana is extremely popular, crowded, and expensive. Once the New Year passes and those crowds thin out, January offers warm, dry weather with a noticeably calmer energy. You’re able to move through the country more freely, find better hotel availability, and actually enjoy the experience instead of fighting through it. Senegal pairs beautifully with Ghana during this period, offering similar weather and a complementary cultural experience.
January is also an excellent time to visit Zanzibar. The weather is warm and sunny, the long rainy season hasn’t started yet, and mosquito activity is lower than it is later in the year. Timing really matters here — visiting before the rains makes the island feel relaxed and effortless rather than humid and unpredictable.
In South America, Colombia shines in February and March. Cartagena, in particular, is best visited during this window. You’ll still get warmth and sunshine, but without the intense heat that dominates summer months. Medellín remains fairly mild year-round, but this time of year offers clearer skies and more comfortable days for exploring.
Thailand is another ideal January–February destination. These months fall within the dry season, before spring rains arrive. It’s one of the easiest times to travel through the country, whether you’re exploring cities, beaches, or islands.
April – June
Europe’s shoulder season and pre-summer sweet spots
The second quarter of the year is all about catching destinations before they become overwhelmed.
April is a beautiful time to be in Southern Europe, particularly Portugal and France . Easter season brings life and tradition, but Easter week itself is expensive. Traveling just before or just after that holiday gives you a similar atmosphere without the surge pricing. You may encounter some rain — especially in Portugal — but a light raincoat and umbrella are a small price to pay for fewer crowds and more reasonable costs.
May is one of the best months to visit Greece, and Croatia. The islands begin to wake up, the weather is warm but not oppressive, and prices haven’t yet hit their summer highs. If you can travel before Memorial Day weekend, you’ll experience these destinations at their most relaxed.
In Southeast Asia, Bali is ideal in June. This marks the beginning of the dry season, bringing warm days, manageable humidity, and better travel conditions overall. June — and even July — offers a great balance between good weather and relatively lower prices compared to peak summer.
July – September
Intentional summer travel without the chaos
Summer doesn’t have to mean crowds and discomfort — it just requires smarter choices.
In the Caribbean, summer is hurricane season, but that doesn’t mean it’s off the table entirely. Early summer works well for places like Jamaica, Grenada, and Puerto Rico. As the season progresses, it’s wiser to shift toward destinations that sit outside the main hurricane belt, such as Aruba, Bonaire, Curaçao, and Trinidad & Tobago, which tend to experience far less storm activity.
If you’re set on visiting Europe in summer, skip the hottest, most crowded destinations. Ireland, Scotland, and Germany are far more enjoyable in August and early September, with less hot temperature but not as rainy and gray. You’ll get longer days and milder weather without the suffocating heat of Southern Europe.
This is also the prime time for Tanzania, particularly August and September, when the dry season makes it ideal for safaris. Wildlife viewing is at its best, and travel conditions are far more predictable.
October – December
Cultural depth, cooler weather, and meaningful travel
If you’re looking for depth rather than speed, the final quarter of the year delivers.
September, especially after Labor Day, is arguably the best time to visit Italy, France, Greece, and Portugal. Prices begin to fall, crowds thin out, and the weather is often better than in spring — warmer, sunnier, and less rainy.
Egypt is far more comfortable in October and November, when temperatures cool enough to explore without exhaustion.
In Japan, October is ideal. Typhoon season typically ends by mid-to-late September, making autumn one of the most pleasant times to visit. While cherry blossom season in spring is beautiful, it’s also extremely expensive and crowded. November and December are also excellent alternatives if you don’t mind cooler weather — just bring a coat and enjoy fewer tourists.
In the Southern Hemisphere, Australia and New Zealand enter summer between November and January. This is peak season, so prices are higher, but the weather is outstanding. If you’re willing to splurge, it’s a fantastic time to visit — especially Sydney, which offers one of the most memorable New Year’s Eve celebrations in the world.
Holiday-Specific Travel Worth Planning Around
Some experiences are best planned around specific moments.
Day of the Dead, in late October, is best experienced in Oaxaca and San Miguel de Allende, where the traditions feel deeply rooted and community-focused.
Christmas in San Miguel de Allende is also magical — festive, warm, and full of life.
For Christmas markets, cities like London, Munich, and Berlin are classic European destinations worth researching and planning for.
Final Thoughts
Timing is everything. Traveling by season isn’t about limitation — it’s about freedom, value, and choosing experiences that actually align with how you want to feel while traveling.
If you want help deciding where and when to go — or you’re ready to design a solo trip and don’t know where to start — you can learn more about my individual travel planning services on my website.
Because travel should feel good — not exhausting.
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