Where to Travel in May: 10 Destinations Worth Booking Now

May is that sweet spot in the travel calendar when everything feels just right. Spring is in full swing, summer crowds have not quite arrived, and destinations around the world are at their most inviting. If you are thinking about a trip, these are the places worth booking now.

Scotland

May is one of the best times to experience Scotland, with green landscapes, blooming wildflowers, and clear conditions across most of the country.

It is ideal for exploring the Isle of Skye, spotting wildlife along the coast, or visiting during the early Highland Games season before summer crowds arrive.

Croatia

Warm days and manageable temperatures make this an ideal time to experience Croatia before peak season begins. Coastal cities, national parks, and island landscapes are easier to explore without crowds, while local events like Split’s St. Domnius festival add a layer of culture to the experience.

Italy

Across both cities and countryside, May brings warm, steady weather and fewer crowds, making it one of the most enjoyable times to visit.

Gardens are in peak bloom during the Month of the Rose, while festivals like Assisi’s Calendimaggio and Venice’s Festa della Sensa add cultural depth and seasonal tradition.

Portugal

Sunshine, mild temperatures, and fewer crowds make May an ideal time to explore Portugal. Coastal cities like Lisbon and Porto are vibrant without feeling crowded, while the Douro Valley and Algarve offer scenic landscapes, blooming countryside, and excellent conditions for walking, wine tasting, and relaxed coastal travel.