You can make the most of your precious annual leave by turning your next holiday into a life-changing island-hopping adventure – and it doesn’t have to break the bank. All you need is the Skyscanner multi-city tool and your bucket list.
1. Greece: Athens > Mykonos > Santorini
Fly cheap to Athens’ international airport for the perfect starting point to your Greek odyssey. Some 6,000 islands are scattered across the Aegean and Ionian Seas, with the Greek Archipelago taking up 7,500km of white-sand coastline. Spend a night in the ancient capital at Hotel Thissio, overlooking the Acropolis, before hopping over to Mykonos using Skyscanner’s ferry booking tool.
Perhaps Greece’s most famous island, Mykonos is a haven of whitewashed villas, fine seafood dining, and vast nightclubs that attract international DJ talent. Hole up at Makis Place, a three-star hotel offering harbour views, an inviting pool, and a free shuttle from the nearby ferry port.
From there, it takes 2-3 hours by ferry to get to Santorini. This beautiful island is famed for its pretty blue-and-white houses that cling to rugged volcanic cliffs overlooking the Aegean Sea. Take your time exploring its sandy coves from Santorini Mesotopos, which has a pool, hot tub, and easy access to the nearby Santo Winery (thank us later).
2. The Caribbean: Punta Cana > San Juan > Anguilla
The Caribbean is an island-hopper’s paradise, where high mountains meet white-sand beaches, reggae rhythms, and reefs. If you’re island-hopping in the Caribbean, it’s cheapest to fly to Punta Cana first, at the easternmost tip of the Dominican Republic. Here you can unwind at an all-inclusive resort after the long-haul journey. We like the palm-fringed Natura Park Beach & Spa Eco Resort, built entirely from organic materials and situated between a lagoon and the sea.
From there, it’s less than an hour’s flight to San Juan. The capital of Puerto Rico, it’s rich with colonial architecture and palm tree-lined beaches. Isla Verde is lined with resorts but aim for Condado to mingle with the island’s fashion set. The Best Western Plus Condado Palm Inn & Suites is a good-value and well-positioned spot for all of the above.
Lastly, hop over to The Valley, where Anguilla’s main airport, government buildings, and shops are found. While this isn’t a shoestring destination, Paradise Cove Resort(a short drive west of the airport) is both affordable and beautifully placed in tropical gardens with ocean views – a great starting point for days spent snorkelling, kayaking, and rum sampling.Fly to Punta Cana from £370Search hotels in Punta Cana
3. Thailand: Krabi > Ko Samui > Phuket
On the west coast of southern Thailand is your ideal starting point for Thai island-hopping: Krabi. This rocky, mangrove-dense province has access to more than 100 nearby islands. A key transport hub, Krabi Town is chock-full of backpacker hostels and travel agencies. You’ll also find bustling restaurants, nightlife, and cosy guesthouses: try the dirt-cheap but super-comfortable Baan Andaman Hotel.
Less than an hour’s flight away is the inviting Ko Samui. The island is famed for its gentle lapping waves, hammocks strung from coconut trees, scorching-hot local curries and sunset cocktails. Bhundhari Chaweng Beach Resort Koh Samui is at the lower end of busy Chaweng Beach, bringing some welcome peace and quiet, as well as a beautiful swimming pool.
Round off your trip in mountainous Phuket, with its main resort town, Patong, packed with lively nightclubs and bars. Make sure you leave plenty of time to explore the island’s breathtaking beaches. Avista Hideaway Phuket Patong is near the surprisingly unspoilt Freedom Beach, while remaining close to the party action.
4. Hawaii: Honolulu > Maui > Hilo
Island life comes into its own in Hawaii: it’s all about living outside in harmony with nature, surrounded by the deep-blue Pacific Ocean. Start your Hawaii island-hopping adventure in the capital Honolulu, the birthplace of surfing and a water sports hotspot. Stay in the Waikiki district, where you’re only a block away from the ocean but still get to soak up the laid-back city vibe. We like the clean and simple Royal Grove Waikiki.
An hour away on the plane is the neighbouring island of Maui, whose airport is based in urban centre Kahului. Watch the surfers at Kanaha Beach before heading to Napili – a sought-after spot known for its sunsets, sea turtles, and snorkelling. Make the beach-front Mahina Surfyour base and hike, swim, and mountain-bike away the days.
Finish your holiday in the beating heart of Hawaii: Hilo, a diverse, colourful, and lush destination that’s less touristy but decidedly worth your time. For a conveniently placed and budget-friendly stay, hit up Arnott’s Lodge & Hiking Adventures. From there, trek around the Hawaii Volcanoes National Park, Mauna Kea volcano, the free-spirited town of Puna, and the idyllic Hamakua Coast.
5. Philippines: Iloilo > Cebu City > Bacolod
Island-hopping in the Philippines takes some serious preparation. There are 2,000 inhabited islets in the country’s archipelago and its turquoise-surf beaches are the stuff of dreams. Begin on rustic Panay Island, whose largest city Iloilo boasts both the urban comforts and the airport needed to kick things off – you won’t go far wrong staying at the comfortable Grand Dame Hotel.
When you’re all set to explore, take the hour’s flight to Cebu. Cebu City is the second largest city in the Philippines and the jumping-off point for 167 small islands that make up the Cebu province. Take your time pottering between them by boat, swimming and snorkelling at every opportunity. For a central city base, Cebu Parklane International Hotel is our pick and has an amazing pool.
It costs next to nothing to fly from there to Bacolod, which, although highly urbanised, also makes a handy base for visiting Mt Kanlaon Natural Park. Here you’ll find some 24,000 hectares of cool, dense forest, home to both an enormous active volcano and diverse wildlife. Spot deer, leopards, hawk eagles, and wild boar on a day-long, challenging trek. Then retire to the smart and comfortable beachside lodging, Palmas Del Mar Conference Resort Hotel.