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Horse riding holidays in May

Horse Riding Holidays in May

May is the month that feels like a deep, contented sigh—soft sunlight, mild days, and landscapes blooming or glowing depending on where in the world your wanderlust takes you. In the Northern Hemisphere, spring is hitting her stride: wildflowers bursting, meadows humming, and long daylight hours begging for exploration.

Meanwhile, the Southern Hemisphere drapes itself in rich autumn hues—burnt oranges, warm ambers, and cool, crisp air that makes every canter feel invigorating. It’s a time when horses are feeling their best, trails are peaceful, and the world feels fresh and full of possibility.

Top Tips

  • Bring a light rain jacket—just in case. Spring and autumn sprinkles are quick and refreshing.
  • Quick-dry riding clothes are always a win. Between dew-kissed mornings and sunny afternoons, breathable fabrics keep you feeling fresh.
  • Check for local public holidays. Many countries have May celebrations that can affect travel or spark lively cultural experiences.
  • Pack a cosy layer for evenings.

Why Ride in May

Scenic Perfection

Spring blossoms in the north, autumn colour in the south—May landscapes are photo-ready, no filter required.

Golden Hours Galore

Long days mean more time riding, relaxing, and soaking up sunset views.

Peaceful Travel

Beat the crowds with smoother airports, quieter trails, and off-peak serenity.

Celebrate in the Saddle

From Mexico’s Cinco de Mayo to Spain’s equestrian festivals, May is full of ride-worthy events.

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Argentina

Corrientes

Beginner Intermediate Strong Intermediate Advanced
Next ride: 1 Jun - 7 Jun, 2026
From $3,200 USD3 nights
Exclusive to Globetrotting

Australia

The Tassie Ride

Beginner Intermediate Strong Intermediate Advanced
Next ride: 8 Mar - 12 Mar, 2027
From $2,910 AUD2 nights
Exclusive to Globetrotting

Australia

The Margaret River Ride

Beginner Intermediate Strong Intermediate Advanced
Next ride: 11 Feb - 16 Feb, 2027
From $2,395 AUD3 nights
Exclusive to Globetrotting

Australia

The Shoalhaven Ride

Intermediate Strong Intermediate Advanced
Next ride: 28 Mar - 30 Mar, 2026
From $2,500 AUD2 nights

Botswana

The Okavango Delta Ride

Intermediate Strong Intermediate Advanced
From £3,850 GBP5 nights

Botswana

The Tuli Safari

Strong Intermediate Advanced
From £3,862 GBP7 nights

Brazil

Canyons & Waterfalls

Intermediate Strong Intermediate Advanced
Next ride: 10 Mar - 16 Mar, 2026
From $4,290 USD6 nights
Exclusive to Globetrotting

England

The Cotswolds Ride

Intermediate Strong Intermediate Advanced
Next ride: 5 May - 12 May, 2026
From £3,950 GBP6 nights

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England

Dartmoor

Intermediate Strong Intermediate Advanced
Next ride: 27 Apr - 1 May, 2026
From £1,600 GBP3 nights

France

Provence Ride

Intermediate Strong Intermediate Advanced
Next ride: 4 May - 10 May, 2026
From €2,970 EUR3 nights

France

Bordeaux Wine Trail

Strong Intermediate Advanced
Next ride: 11 Apr - 18 Apr, 2027
From €2,815 EUR7 nights

Indonesia

The Sumba Ride

Beginner Intermediate Strong Intermediate Advanced
From $6,095 USD4 nights
Exclusive to Globetrotting

Ireland

Cross Country in Tipperary

Intermediate Strong Intermediate Advanced
Next ride: 27 Apr - 3 May, 2026
From €3,550 EUR6 nights

Ireland

Castle & Estate Ride

Beginner Intermediate Strong Intermediate Advanced
Next ride: 1 Mar - 6 Mar, 2026
From €2,655 EUR3 nights

What’s your riding level?

The answer might surprise you.

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Exclusive to Globetrotting

Italy

Tuscany

Beginner Intermediate Strong Intermediate Advanced
Next ride: 3 Mar - 7 Mar, 2026
From €2,090 EUR3 nights

Italy

Sicily

Strong Intermediate Advanced
Next ride: 4 Apr - 11 Apr, 2026
From €1,780 EUR7 nights

Mexico

El Rancho Ride

Beginner Intermediate Strong Intermediate
From $1,479 USD

Namibia

The Namibia Safari

Advanced
Next ride: 11 Mar - 20 Mar, 2026
From £6,600 GBP10 nights

Portugal

Lusitano Ride

Strong Intermediate Advanced
Next ride: 1 Mar - 8 Mar, 2026
From €1,820 EUR7 nights
Exclusive to Globetrotting

Scotland

The Scottish Highlands Ride

Beginner Intermediate Strong Intermediate Advanced
Next ride: 6 Apr - 12 Apr, 2026
From £4,300 GBP6 nights
Exclusive to Globetrotting

Scotland

The Scottish Borders Ride

Strong Intermediate Advanced
Next ride: 7 May - 13 May, 2026
From £3,800 GBP6 nights

South Africa

The Bushveld

Beginner Intermediate Strong Intermediate Advanced
From £1,530 GBP5 nights
Exclusive to Globetrotting

Spain

Andalusia

Intermediate Strong Intermediate Advanced
Next ride: 11 Apr - 18 Apr, 2026
From €3,520 EUR7 nights
Exclusive to Globetrotting

Spain

Costa Brava Ride

Beginner Intermediate Strong Intermediate Advanced
Next ride: 13 Apr - 19 Apr, 2026
From €2,615 EUR3 nights

Spain

Train & Trail Ride

Intermediate Strong Intermediate Advanced
From €1,225 EUR4 nights

Spain

Dressage Ride

Beginner Intermediate Strong Intermediate Advanced
From €2,235 EUR6 nights

Spain

Catalan Coast Trail

Intermediate Strong Intermediate Advanced
Next ride: 15 Mar - 22 Mar, 2026
From €2,790 EUR7 nights

USA

Shell, Wyoming

Beginner Intermediate Strong Intermediate Advanced
Next ride: 5 Apr - 11 Apr, 2026
From $4,560 USD6 nights

USA

Hobson, Montana

Beginner Intermediate
From $1,575 USD3 nights

Explore when to ride

Each month offers unique riding experiences around the globe