Pride holidays are more than just trips; they’re powerful celebrations of identity, community, and love. Whether you are a seasoned traveller who schedules trips around global pride events or you’re thinking about attending your first, May offers some incredible options. At Wide Awake Holidays, we believe that “gay friendly” is not always friendly enough. As a gay-owned travel company, we tailor every journey to your needs with genuine care and understanding.
If you are wondering where to start planning your next pride holiday, we have gathered some of the best LGBT+ pride events happening in May. Get ready to celebrate, explore, and connect.
Why Plan Your Pride Holidays in May?
May is a wonderful month to travel. The weather starts warming up across Europe and North America, crowds are lighter than peak summer, and flight prices are still relatively low. Plus, there’s an exciting range of pride events happening worldwide.
Travelling for pride holidays also offers a unique chance to be part of local LGBT+ communities, enjoy parades, and attend cultural events that celebrate diversity and inclusion. It’s an unforgettable way to combine a getaway with meaningful experiences.
Best Pride Holidays in May 2025
Miami Beach Pride (United States)
Miami Beach Pride kicks off May with a sun-soaked celebration that stretches across ten days. From drag brunches and pool parties to the main parade, it’s a vibrant affair you will never forget.
Highlights:
- The legendary Pride Parade along Ocean Drive
- Pride Festival with live music and food trucks
- Nighttime dance parties hosted by international DJs
Offer Available: Ask us about special Miami Beach Pride hotel packages at premium resorts.
How Gay Friendly is Miami?
- Homosexuality has been legal since 1973.
- Same-sex marriage has been recognised since 2015.
- Anti-discrimination protections are in place statewide.
- Employment protections exist through both federal and state law.
- Equal age of consent applies.
- Public opinion in Miami is broadly supportive, making it a very safe and welcoming city.
Maspalomas Pride (Gran Canaria, Spain)
One of Europe’s most beloved pride holidays, Maspalomas Pride is a spectacular beachside celebration. Held in Playa del Ingles, it combines pool parties, boat cruises, and a joyful parade through the Yumbo Centre.
Highlights:
- Pool parties and drag shows
- Pride Walk and Freedom Parade
- Internationally famous DJs and performers
Offer Available:Â Contact us for exclusive Maspalomas Pride hotel deals.
How Gay Friendly is Gran Canaria?
- Homosexuality was decriminalised in 1979.
- Same-sex marriage has been legal since 2005.
- Anti-discrimination laws are enforced nationwide.
- LGBT+ staff have strong employment protections.
- Equal age of consent is in place.
- Gran Canaria, particularly Maspalomas, has a long-standing and open LGBT+ culture.
Jamie says: “Gran Canaria holds a special place in our hearts. There’s an incredible sense of freedom here that makes every pride holiday unforgettable.”
Tokyo Rainbow Pride (Japan)
Tokyo Rainbow Pride is a colourful and deeply inspiring event. Japan’s pride scene is growing rapidly, and May is a fantastic time to visit when spring is still in full bloom.
Highlights:
- Parade through Yoyogi Park
- Rainbow Pride Festival with performances and talks
- LGBT+ film screenings and art exhibitions
Offer Available: We have fantastic Tokyo hotel deals available during pride week. Ask us for more details.
How Gay Friendly is Tokyo?
- Homosexuality has never been illegal in Japan.
- Same-sex marriage is not legally recognised yet, but some local governments offer partnership certificates.
- National anti-discrimination laws are limited, but Tokyo has enacted its own ordinances.
- Employment protections exist through some city-specific policies.
- Equal age of consent applies.
- Public opinion is becoming more supportive, especially among younger generations.
Brussels Pride (Belgium)
Brussels Pride is a lively celebration that kicks off the European pride season. The city becomes a canvas for rainbow colours, love, and activism.
Highlights:
- Pride Parade through the streets of Brussels
- Rainbow Village in Sainte-Catherine district
- Concerts, drag shows, and cultural exhibitions
Offer Available: Save with our pride holiday packages that include central Brussels hotels.
How Gay Friendly is Brussels?
- Homosexuality was decriminalised in 1795.
- Same-sex marriage was legalised in 2003.
- Strong anti-discrimination protections are enforced.
- LGBT employees are protected under employment law.
- Equal age of consent applies.
- Brussels is widely considered one of the most inclusive cities in Europe.
Havana Pride (Cuba)
Havana Pride, also known as the Cuban Day Against Homophobia and Transphobia, is a vibrant and politically significant event.
Highlights:
- Marches led by prominent Cuban LGBT+ activists
- Educational workshops and cultural activities
- Open-air concerts celebrating diversity
Offer Available: Speak to us about hand-picked hotels in Havana during pride week.
How Gay Friendly is Havana?
- Homosexuality was decriminalised in 1979.
- Same-sex marriage became legal in 2022.
- Anti-discrimination laws exist but can be inconsistently enforced.
- Employment protections for LGBT+ individuals are recognised.
- Equal age of consent applies.
- Public opinion is steadily improving, especially among the youth.
What to Expect on Pride Holidays
Every pride celebration is unique. Some focus heavily on activism, while others are more about partying and community-building. When choosing your pride holidays, consider:
- Size of the event:Â Smaller prides can feel more intimate.
- Type of activities:Â Some events are parade-focused; others are festival-heavy.
- Local LGBT+ scene:Â Look into what bars, clubs, and social events are available year-round.
- Safety:Â Even in gay-friendly cities, it’s smart to stay aware.
Packing Tips for Pride Holidays
- Lightweight clothing for warm climates
- Comfortable shoes for parades and walking
- Sunscreen and hats
- Pride flags, accessories, and outfits
- A portable charger for your phone
- Travel insurance that covers event cancellation
Are you wondering if it’s better to pack multiple pride outfits or buy locally? Local shopping not only supports the community but also gives you great souvenirs.
How Wide Awake Holidays Makes Pride Holidays Easy
Planning a pride trip on your own can feel overwhelming. Where should you stay? Which events are a must? How can you make sure you are safe and comfortable?
That’s where we come in.
At Wide Awake Holidays, we understand the importance of feeling truly welcome and celebrated, not just tolerated. We are part of the LGBT+ community ourselves, so we know what matters to you. With over 200 suppliers, exclusive deals, and fully protected travel arrangements, we take the guesswork out of your holiday planning.
When you book with us, you get:
- A tailored pride holiday designed around your interests
- Hand-picked, LGBT-welcoming hotels
- VIP access to select pride events
- 24/7 support before and during your trip
- Complete financial protection through Protected Trust Services
Many travellers who book their first pride holidays with us come back year after year. That’s the best sign of a great travel experience.
Final Thoughts: Where Will Your Pride Holidays Take You?
Pride holidays in May offer a dazzling array of options, from the sunny beaches of Gran Canaria to the buzzing streets of Brussels. Whether you dream of dancing at Maspalomas Pride, exploring Tokyo’s growing LGBT+ scene, or standing proud in Havana, May is the perfect month to make it happen.
Let Wide Awake Holidays help you craft the pride holiday you’ve always dreamed of — safe, joyful, and completely yours.
Ready to plan your perfect pride holiday? Call us today on 01495 400947 to speak to a travel expert, or use our easy holiday enquiry form on the website. Your next adventure is only a call or click away.
