Top 10 May vacations in 2021

We’ve made a list of our top 10 May vacations to get your imagination racing. They cover everything from brushing up on your knowledge of Greek archaeology under sunny skies to leisurely cruising the Croatian waters. There’s plenty here for active travelers, whether you want to hike or bike in the mountains or search for whales or orangutans in the wilderness.

1. Cruise Southern Croatia

Meander your way through the waters of Southern Croatia on board a small ship with up to 40 passengers. There’ll be plenty of time to enjoy swimming and snorkelling from the ship, as well as heading for dry land to hike, cycle or sightsee. It’s not too hot either, with temperatures around 23°C. The biggest crowds have yet to arrive, although the winds along the coast are less predictable.

2. Explore Scotland by rail

Explore both cities and wilderness on this car-free vacation which takes you from the cities of Glasgow, Inverness and Edinburgh to rural Perthshire and even the magical Isle of Skye. The highlight is the West Highland Line, considered by many to be one of the world’s most scenic rail journeys. You’ll lay your head in locally-run hotels, where organic meals and home baked goods are often on offer.

Our top selling trip: Scotland by railway vacation
See all our trips: Scotland rail vacations
Read more: Scotland railway vacations travel guide

3. Watch whales in the Azores

The Portuguese islands of the Azores sit conveniently in the mid-Atlantic feeding grounds of the world’s largest animal: the blue whale. Whales migrate through the Atlantic waters surrounding the Azores each May, and a week-long small group tour will give you the chance to observe these giants in their natural habitat in the company an expert marine biologist, with nights spent on a sturdy catamaran as well as in a hotel on dry land.

Our top selling trip: Blue whale tour in the Azores
See all our trips: Azores vacations
Read more: Azores travel guide

Our top Best places to go on vacation in May Vacation

Amalfi Coast walking vacation, Italy

Amalfi Coast walking vacation, Italy

Walk in lemon groves and hillside villages

From US $1649 to US $2049 8 days ex flights
Small group travel:
2021: 22 May, 29 May, 5 Jun, 12 Jun, 19 Jun, 26 Jun, 3 Jul, 10 Jul, 17 Jul, 24 Jul, 31 Jul, 7 Aug, 14 Aug, 21 Aug, 28 Aug, 4 Sep, 11 Sep, 18 Sep, 25 Sep, 2 Oct, 9 Oct, 16 Oct, 23 Oct, 30 Oct, 6 Nov, 13 Nov, 20 Nov, 23 Dec, 30 Dec
2022: 12 Feb, 19 Feb, 26 Feb, 5 Mar, 12 Mar, 19 Mar, 26 Mar, 2 Apr, 9 Apr, 16 Apr, 23 Apr, 30 Apr, 7 May, 14 May, 21 May, 28 May, 4 Jun, 11 Jun, 18 Jun, 25 Jun, 2 Jul, 9 Jul, 16 Jul, 23 Jul ...
Travel Team
If you'd like to chat about Best places to go on vacation in May or need help finding a vacation to suit you we're very happy to help.

4. Hit the trails in Japan

The Nakasendo Trail is not only one of Japan’s most ancient thoroughfares, it’s also one of modern Japan’s most aesthetically pleasing walking trails, and May livens it up even more with bursts of flowers and greenery. You’ll spend a week making your way from one ancient ‘post town’ to another, with walks lasting between two and six hours, leaving plenty of time to enjoy traditional ryokan inns and minshuku guesthouses.

5. Explore the Silk Road

Spend 16 days on an incredible overland journey through Kazakhstan, Kyrgyzstan and Uzbekistan. The dramatic landscape of desert plains, undulating steppe and mountain peaks perfectly complements the ancient Silk Road cities that you’ll visit along the way. Nights are spent in local hotels, with a night on a train and in a yurt camp to increase the adventure.

Our top selling trip: Silk Road small group tour
See all our trips: Silk Road vacations
Read more: Silk Road travel guide

6. Step into the past in Greece

You’ll follow the sandal-strapped footsteps of the past around the Peloponnese’s greatest wonders, including Sparta, Tegea and Mycenae, along with a bunch of ancient history aficionados. It’s not all about historic architecture, though. There’s time for wine tasting, cycling and lying comatose on sun-kissed beaches.

Our top selling trip: Archaeology vacation in Greece
See all our trips: Greece vacations
Read more: Greece travel guide

7. Learn Spanish in Picos de Europa

This wild mountain range rising out of the Atlantic in Northern Spain is an enduringly popular choice for walking adventures, and you can throw in some language learning too. Morning Spanish lessons are followed by afternoon or early evening walks and there’s a maximum group size of six to make sure that you get lots of time to practice your new skills.

8. Cycle Croatia

Guiding yourself around Croatia by bike on either a five- or an eight-day itinerary allows you to combine the country’s fairly moderate inclines with medieval heritage, Roman ruins and old-fashioned fishing villages. You won’t be totally on your own, with transfers, local recommendations and 24/7 backup just in case you need it.

Our top selling trip: Self guided biking tour in Croatia
See all our trips: Croatia cycling vacations
Read more: Croatia cycling travel guide

9. Walk the Amalfi Coast

You might imagine the best way to see the Amalfi coast is zipping around hairpin bends in a vintage Fiat, but spend eight days getting to know the region on foot and you’ll get behind the Mediterranean glitz to discover mountain trails with dramatic views, little-visited villages and a glorious slow food scene. With cooler temperatures and fewer crowds, May is a great time to do it.

Our top selling trip: Amalfi Coast walking vacation
See all our trips: Amalfi Coast vacations
Read more: Amalfi Coast travel guide

10. Seek out orangutans in Sabah

The state of Sabah is a region that is packed with some of the most extraordinary wilderness experiences. Much of the trip will be all about Borneo’s orangutans and their habitats in the jungles around Kinabatangan River, but you’ll also explore Mount Kinabalu National Park as well as the waters around Lankayan Island, a marine park with a prolific sea turtle population.
Our top selling trip: Borneo tour: great apes and beach escapes
See all our trips: Sabah vacations
Read more: Sabah travel guide
Written by Nana Luckham
Photo credits: [Page banner: v2osk] [Croatia: Conor Rees] [Japan: OKU Japan] [Picos de Europa: Marcus Hansson] [Sabah: Chris Charles]
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