Madeira: The Ultimate Portuguese Island Adventure

Funchal is a compact, walkable city with more going on than its size suggests. Its old town, the Zona Velha, is where much of the city’s gay-friendly social life is concentrated: painted doors, candlelit restaurants, and bars with terraces that fill after dark. Art galleries, independent bookshops, and the Mercado dos Lavradores, one of the finest covered markets in Portugal, are all within walking distance of the waterfront.

On your first full day, a private LGBTQ+-friendly walking tour covers the historic centre: the ornate Sé Cathedral, the famous black-and-white mosaic pavements, hilltop neighborhoods with panoramic views across the bay, and the cable car that rises 560 meters from the seafront to the village of Monte in around 15 minutes.

In Monte, the Tropical Garden offers one of the most serene hours available anywhere on the island, and the legendary wicker toboggan ride back down through the narrow streets has delighted visitors since 1850.

Your second day in Funchal moves at whatever pace you choose.

The Zona Velha is the natural place to spend a morning: Rua de Santa Maria’s famous hand-painted doors, the covered market with its stalls of tropical fruit and fresh Atlantic fish, and the kind of independent cafés that make you reassess your relationship with coffee.

Later, a private guided Madeira wine tasting arranged by our team gives the afternoon shape and purpose: the island’s remarkable fortified wine, produced using a centuries-old aging process unique to Madeira, is explored in depth and without rush.

By the time evening comes, Funchal does the rest; dinner at one of its exceptional restaurants, a drink in the Zona Velha, and a harbor that looks its best after dark.

On day four, a private full-day jeep tour takes you into the island’s volcanic interior: mountain plateaus, dense laurel forest, hidden viewpoints above the clouds, and the extraordinary north coast where cliffs drop hundreds of meters to the sea. Lunch is taken at a traditional local restaurant with views that justify the drive.

The tour moves at your pace and can be shaped around what you want most: the dramatic heights of the Paul da Serra plateau, the thatched houses of Santana, the sugarcane rum distilleries of the north coast, or all three.

Day five is reserved for one of Madeira’s most distinctive experiences: a private levada walk with a specialist guide. The levadas are centuries-old irrigation channels cut into the island’s steep hillsides, and the paths that run alongside them pass through UNESCO-listed Laurisilva forest, one of the last surviving laurel rainforests in the world.

The walk can be chosen to suit your level of confidence and fitness, from gentle valley trails to more dramatic routes at altitude where cloud forest closes in on either side.

Madeira sits in some of the richest cetacean waters in the Atlantic. Pilot whales, bottlenose dolphins, loggerhead turtles, and, in season, sperm whales and blue whales pass through the deep water off the island’s southern coast throughout the year.

On day six, a private luxury catamaran charter takes you out in search of the whales, accompanied by a marine biologist and a small, intimate group, with time to swim in the open Atlantic and a lunch prepared onboard from locally sourced ingredients. Sightings are near-guaranteed; the quality of the day is entirely guaranteed.

Back in Funchal for your final evening, we recommend dinner at Il Gallo d’Oro at The Cliff Bay, a two-Michelin-starred restaurant that has long been considered one of the finest tables in Portugal, with a menu built around the island’s produce and a wine list weighted toward exceptional Madeira.

A private transfer takes you to the airport for your flight home. The week ends here, but Madeira tends to follow people; most visitors start planning a return before the island has even disappeared below the clouds.