Travel Advisor 101: When Should You Actually Go?

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When Should You Actually Go? A Quick Guide to Timing Your Dream Trip

In 10 Seconds

Every destination has a best season, an okay season, and a season you probably want to skip. Here’s a quick reference for eleven popular spots, plus why “best time to visit” isn’t quite as simple as one column in a chart, because the right time for you depends on what kind of trip you’re actually after.

You’ll Learn

The best, okay, and worst windows to visit eleven popular destinations
Why “worst time to visit” doesn’t always mean “skip it entirely”
How the right timing can shift depending on what you want out of the trip
Why a chart like this gets you most of the way there, and where the rest comes from

Best Times to Visit

• Mexico: November to April – Enjoy pleasant temperatures and minimal rainfall.

• The Caribbean: December to April – Experience warm, dry weather ideal for beach activities.

• Hawaiian Islands: April to June, September to November – Mild weather and fewer tourists.

• Bora Bora: November and April – Pleasant temperatures and fewer crowds.

• The Maldives: November to April – Dry season with clear skies and calm seas.

• Fiji: May to October – Cooler temperatures and less humidity.

• Thailand: November to February – Cooler, dry season perfect for sightseeing.

• Southern Italy and Greece: April to June, September to October – Mild weather and fewer tourists.

• Africa (e.g., South Africa): May to September – Ideal for wildlife viewing during the dry season.

• Ireland & Scotland: May to September – Warmer temperatures and longer days.

• London & France: June to August – Warm weather and vibrant city life.

Okay Times to Visit

• Mexico: May and October – Shoulder seasons with occasional rain.

• The Caribbean: May to June – Start of the rainy season but still enjoyable.

• Hawaiian Islands: December to March – Cooler temperatures and higher chances of rain.

• Bora Bora: May to October – Peak tourist season with higher prices.

• The Maldives: May to October – Wet season with occasional storms.

• Fiji: November to April – Warmer temperatures with higher humidity.

• Thailand: March to May – Hot season with higher temperatures.

• Southern Italy and Greece: July and August – Hotter temperatures and more tourists.

• Africa: November to April – Wet season in many regions.

• Ireland & Scotland: April and October – Cooler temperatures with possible rain.

• London & France: April to May, September to October – Mild weather with occasional rain.

Worst Times to Visit

• Mexico: June to September – Hurricane season with high humidity.

• The Caribbean: July to November – Hurricane season with potential storms.

• Hawaiian Islands: June to August – Peak tourist season with higher prices.

• Bora Bora: December to March – Wet season with increased rainfall.

• The Maldives: June to August – Monsoon season with rough seas.

• Fiji: January to March – Cyclone season with heavy rains.

• Thailand: June to October – Monsoon season with heavy rainfall.

• Southern Italy and Greece: December to February – Cooler temperatures and off-season closures.

• Africa: March to May – Heavy rains in East Africa can hinder wildlife viewing.

• Ireland & Scotland: November to February – Cold, wet, and shorter daylight hours.

• London & France: November to February – Cold and damp conditions.

Jani’s Tip 📆: “Worst time to visit” doesn’t always mean “don’t go.” It usually means higher risk of rain, lower prices, and thinner crowds. Some of my favorite client trips have been booked in a so-called worst window on purpose, because they wanted the deal and didn’t mind gambling a little on weather. Just go in with your eyes open about what you’re trading for that lower rate.

Why This Chart Gets You Most of the Way, Not All the Way

A chart like this is a genuinely useful starting point, and I still pull one up myself when a client asks about timing. But “best time to visit” can shift depending on what you actually want from the trip.

Chasing a specific festival, event, or shoulder season deal can flip the calendar entirely. Hurricane season in the Caribbean, for example, isn’t a flat no if you’re watching the forecast and have flexibility, some of the best resort pricing of the year shows up in exactly those months. Wildlife viewing windows in Africa can vary by region and by what animals you’re hoping to see, not just the general rainy or dry season. And a “best” window for one traveler chasing empty beaches is someone else’s nightmare if they were hoping for a lively, crowded, event-filled trip instead.

This is where a chart hands off to a conversation. The dates get you close. The specifics of your actual trip, and what you’re hoping to get out of it, are what get you the rest of the way there.

One Last Thing… ☕

Timing matters, but it’s only one piece of planning a trip that actually delivers what you’re picturing in your head. If you’ve got a destination in mind and want to talk through when to actually book it, that’s exactly the kind of conversation I love having.

Let’s start planning and figure out the timing that’s right for your trip, not just the general guideline.

One page at a time, we’re building a smarter way to travel. ❤️

XOXO, Jani ~ Personal Travel Advisor | Take Time To Travel, LLC

Updated August 2026. These are general guidelines, and specific conditions vary year to year. Always check local climate and weather forecasts closer to your travel dates.

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