Bespoke
Portugal Islands Bespoke
Discover Portugal’s islands of adventure and charm
Country
Portugal
Accommodation Options
Boutique hotels & rural estates
Things to See & Do
Hiking, whale watching, biking, sailing, gastronomy & wine tastings
Best Time To Go
April – June, September – October
Carbon Neutral Trip
Leave the mainland behind and discover a world where volcanic peaks meet lush forests, and ocean breezes carry the scent of wildflowers and salt. In the Azores and Madeira, nature takes center stage. Hike the crater rims of ancient calderas, taste wines grown in volcanic soil or sail between islands. This island playground invites you to slow down and tune into the rhythm of the waves, the rustle of the forest and your own sense of wonder.
Be immersed in the natural beauty of the islands, where volcanic landscapes, waterfalls, crater lakes and botanical gardens create the perfect backdrop for active exploration.
Dive into the unique heritage of each island, from sipping Azorean tea and Madeira’s fortified wines to walking the levadas. Tradition here comes with a distinctly local flavour.
From boutique stays to exclusive experiences, we unlock the raw beauty of the islands—for those who crave adventure, without compromising on luxury.
Experience Designer
Trip Inspiration
Snapshot of a Day
Begin your morning on São Miguel with an early hike around the crater lakes of Sete Cidades, ending in a scenic picnic with views to remember.
Trip Inspiration
Hike the Volcanic Trails of the Azores
The Azores are a hiker’s paradise, with trails that wind through volcanic landscapes, lush cloud forests, coastal cliffs and ancient calderas. Each island offers a different kind of adventure—whether it’s São Miguel’s crater lakes, Pico’s towering volcanic cone or Faial’s fields of lava and ash. Evenings are for soaking in thermal springs, savouring island cuisine and perhaps sipping a glass of local Verdelho.
Recommended Duration: 7-11 days
Best Time To Go: May – mid-June, September – October
Things to See and Do: Whale watching, hiking, kayaking and traditional culinary experiences.
Don't Miss Out On: A dip in the Furnas hot springs, surrounded by lush greenery.
Snapshot of a Day
Paddle together in a crater lake, then watch your kids help prepare a traditional "cozido" cooked underground by geothermal steam.
Trip Inspiration
A Family Adventure in the Azores
The Azores are made for families with an adventurous spirit. From paddling serene crater lakes to spotting whales just offshore, each day invites wonder. Lava tubes, dolphin encounters and lush forests offer endless opportunities to explore, while parents will appreciate the warm hospitality and rich island flavours. Kids will remember the colour of the water, the smell of eucalyptus and the thrill of whale watching in the open sea.
Recommended Duration: 7-10 days
Best Time To Go: May – July, September – October
Things to See and Do: Whale and dolphin watching, biking, swimming and lava cave visits.
Don't Miss Out On: Swimming in natural hot springs at Caldeira Velha.
Snapshot of a Day
Walk along narrow stone channels that trace ancient water routes through the heart of Madeira’s cloud forests, ending with fresh grilled espada and a poncha in a coastal village.
Trip Inspiration
The Levadas & Lush Trails of Madeira
Madeira’s levada paths weave through cliffs, waterfalls and deep green valleys, creating an incredible network of hikes. The island’s subtropical charm and mountain culture come together in a landscape where every turn reveals a new vista. Botanical gardens, cable cars and oceanfront picnics complete this journey of constant wonder.
Recommended Duration: 6-9 days
Best Time To Go: March – June, September – October
Things to See and Do: Levada hikes, sailing, wine tasting, botanic gardens and canyoning.
Don't Miss Out On: Private tasting of Madeira wines in a 17th-century estate.
Featured stays
Sensi Azores Nature & Spa
Location: Sao Miguel Island, Portugal
White Exclusive Suites & Villas
Location: Sao Miguel Island, Portugal
Santa Barbara Eco-Beach Resort
Location: Sao Miguel Island, Portugal
Azores Wine Company Lodging
Location: Pico Island, Portugal
Reid’s Palace
Location: Funchal, Portugal
Process
Step 1
Let's connect
Have a trip in mind or just starting to dream? Share your travel preferences with us and we will reach out to kick off the planning.
Step 2
Detailed Brief
We'll set up a conversation to get to know you and your group. From there, you'll receive a journey proposal—destinations, activities and accommodation options shaped around what matters most to you. An initial Trip Development Fee is collected before moving to the next stage.
Step 3
Tailored Itinerary and Confirmation
Your Experience Designer will share a detailed trip plan, then work closely with you to refine it until every detail is right. When you're ready, a per-person deposit confirms your trip, with full payment due 95 days* before departure.
Step 4
Support, Start to Finish
Before you leave, you'll receive a full breakdown of your journey. On the road, you'll have dedicated support throughout. When you return, the same Traveller Experience team will be ready to hear how it went—and to start thinking about what comes next.
* Final payment terms may vary based on destination and type of trip.
Good to know
Accommodation
Azores offers simpler accommodations, including charming boutique hotels. B&R has access to the best in the region, where luxury presents itself in the form of local charm, comfort and great service.
Inter-Island Travel
Flights between islands are best booked in advance and may require flexible scheduling.
Food
While vegan dining options are available, they can be limited—especially outside urban areas. If vegan meals are essential during your trip, please let your Experience Designer know.
Weather
Weather on the islands can be unpredictable, so we recommend dressing in layers to stay comfortable.
Why choose a Bespoke trip?
An Effortless Journey
Our expert Experience Designers are perfectionists, using first-hand knowledge of routes, restaurants and hotels to create an unforgettable experience. This means you’re in the best hands to plan your dream trip.
Lifelong Memories
Our Bespoke trips are often described as lifechanging. When every detail and magical moment is planned just for you and your group – you'll get exactly what you’re after, and more. The perfect addition to the memory book.
Years of Local Friendships
We’ve been at this since 1966, and our Experience Designers have been planting seeds and building friendships around the world since day one. The loyalty we share with our connections is invaluable and is what allows us to give access exclusive to B&R.
Creativity and Spontaneity
From our office to our guides on the road, every person who touches your trip pours their passion and creativity into it. When you travel Bespoke, you’ll work closely with passionate planners to create the perfect fit for you and your travelling companions.
Discover further
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Portugal | Best Time To Go : April – June, September – October
Contact an Expert
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