Exploring the Best Places to Travel in May: A Comprehensive Guide

May is a fantastic time to travel, offering ideal weather and thinner crowds in both the Northern and Southern Hemispheres. Whether you’re looking to explore under-the-radar cities in America, soak up the sun in Sicily, or embark on a safari in Zambia, there’s something for everyone in this diverse selection of destinations. Join us as we uncover the best places to travel in May, providing insights and recommendations for an unforgettable journey.

1. The Cyclades, Greece: Chic Island Escapes

best places to travel in may

The Cyclades, a group of Greek islands including Mykonos, Santorini, and Paros, are synonymous with effortless style and stunning landscapes. In May, the opening of the Gundari Resort on the island of Folegandros offers travelers a chance to experience luxury in a secluded setting. Additionally, the debut of the One&Only resort on Kea promises private villa accommodations with breathtaking views of the Aegean Sea. With new flight routes from major carriers and inter-island flights available, exploring the Cyclades has never been easier.

2. Holland, Michigan: Tulip Season Delight

For those unable to make it to the Netherlands for tulip season, Holland, Michigan offers a delightful alternative. This charming town celebrates its Dutch heritage with millions of tulips, old-fashioned windmills, and Germanic villages. Timing your visit to coincide with the Tulip Time Festival from May 4 to 12 allows you to immerse yourself in Dutch culture, from traditional markets to flower-themed events. Consider staying at the Castle in the Country Inn for a Victorian-style experience amidst the tulip fields.

3. Galápagos Islands, Ecuador: A Natural Wonder

best places to travel in may

The Galápagos Islands are a bucket-list destination known for their unique wildlife and pristine landscapes. May marks the beginning of the warm season, offering optimal conditions for diving and snorkeling. Cruises are the preferred way to explore the islands, with options like the environmentally conscious Silver Origin providing luxurious accommodations and immersive experiences. Whether observing giant tortoises or exploring underwater ecosystems, the Galápagos offers an unparalleled adventure.

4. Zambia: Safari Thrills

Zambia is a safari enthusiast’s paradise, with vast national parks and breathtaking natural wonders like Victoria Falls. May, marking the end of the Emerald Season, offers ideal conditions for wildlife viewing and photography. Boutique tour operator The Bushcamp Company provides intimate safari experiences in South Luangwa National Park, with renovated camps like Chindeni Bushcamp offering comfortable accommodations in the heart of the wilderness. Whether observing wildlife or marveling at natural wonders, Zambia offers an unforgettable safari experience.

5. Nantucket, Massachusetts: Coastal Charm

best places to travel in may

Nantucket, known for its coastal beauty and historic charm, is a perfect destination for May travel. With fewer crowds than in the summer months, visitors can enjoy scenic bike rides, sailing excursions, and blooming daffodil fields. The Nantucket Wine Festival, held from May 15 to 19, offers a unique opportunity to sample local wines and culinary delights. Consider staying at The Wauwinet for a luxurious retreat with stunning waterfront views and unparalleled hospitality.

6. Machu Picchu, Peru: Ancient Wonders

May marks the beginning of the dry season in Peru, making it an ideal time to visit Machu Picchu. With fewer crowds than in peak season months, visitors can explore the ancient ruins in relative tranquility. Take time to explore the colonial city of Cusco, known for its historic architecture and vibrant culture. Consider staying at boutique hotels like Inkaterra La Casona or JW Marriott El Convento Cusco for a luxurious experience in the heart of the Andes.

7. Louisville, Kentucky: Derby Days

best places to travel in may

Experience the excitement of the Kentucky Derby in Louisville, held on the first Saturday in May. Attendees can enjoy horse racing, visit the Kentucky Derby Museum, and indulge in traditional mint juleps. Boutique hotels like 21c Museum Hotel offer unique accommodations with art exhibits and locally inspired dining options. Whether cheering on the races or exploring the city’s cultural attractions, Louisville offers a memorable springtime getaway.

8. Healdsburg, California: Wine & Food Extravaganza

Healdsburg, located in California’s wine country, is a culinary paradise perfect for May travel. The Healdsburg Wine & Food Experience, held from May 16 to 19, offers a range of tastings, classes, and outdoor concerts. Boutique hotels like The Madrona provide luxurious accommodations with curated art collections and Michelin-starred dining options. Whether indulging in wine tastings or exploring scenic vineyards, Healdsburg offers a gourmet getaway for food and wine enthusiasts.

9. Sicily, Italy: Mediterranean Delights

best places to travel in may

Sicily, with its Baroque towns and Mediterranean cuisine, is an ideal destination for May travel. Explore the historic town of Noto and indulge in fresh pasta and local delicacies. Luxurious accommodations like Seven Rooms Villadorata offer ornate rooms and organic amenities for a truly indulgent experience. Whether exploring ancient ruins or relaxing by the pool, Sicily offers a blend of history, culture, and culinary delights.

10. The Hamptons, New York: Coastal Retreat

Escape to the Hamptons for a coastal retreat in May, before the summer crowds arrive. Explore cultural attractions like the Parrish Art Museum and enjoy outdoor activities like hiking and wine tasting. Wellness retreats like Shou Sugi Ban House offer zen-inspired accommodations and spa treatments for a rejuvenating experience. Whether unwinding by the beach or exploring charming villages, the Hamptons offer a tranquil escape from city life.


A wealth of travel opportunities, from island escapes in Greece to safari adventures in Zambia. Whether seeking cultural experiences, outdoor adventures, or culinary delights, these destinations provide something for every traveler. With optimal weather conditions and fewer crowds, May is the perfect time to embark on an unforgettable journey and create lasting memories around the world.

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