šŸŒ… The Hawaii of Europe: MADEIRA! šŸŒ¤ļø Private Authentic Thatched Farm Villa, Hiking, Wine Tasting, Beaching and Vibes!!

Hosted by

Jemima

7 Days30 Days!

Extra Cancellation Days
only for the first TripMate

Guided trip
What's special?
special Authentic thatched private farm villa
special Wine tasting
special Rental car for exploring and hiking
Join me exploring this stunning volcanic Portuguese archipelago in the Atlantic - also known as the "Pearl of the Atlantic" and dubbed as 'The Hawaii of Europe'! Nestled into the towering mountains with an eternal spring climate you'll find lush subtropical forests (including UNESCO's Laurissilva), dramatic cliffs, and rich biodiversity. This is the perfect place for anyone looking for stunning landscapes from high peaks to rugged coastlines, alongside a vibrant culture, famous fortified wine, and unique traditions like Poncha. šŸ—ŗ ITINERARY KEY HIGHLIGHTS: 1ļøāƒ£ Pick up and drop off our rental car at the airport 2ļøāƒ£ The "Big Four" Hikes: Each morning is dedicated to one of Madeira’s world class trails - Above the clouds, around Canyons and in the waterfalls! 🄾 3ļøāƒ£ Explore vineyards together! šŸ· 4ļøāƒ£ Mooch around beach towns šŸ›– Community living: We will embrace the true "villa life" by cooking together. We’ll hit the local markets for fresh Atlantic produce and whip up communal breakfasts and dinners in the villa’s kitchen. Lunches will be a mixture of eating in and out based on how we're feeling! šŸ’ø Keeping it fair: To keep things affordable and stress free, we’ll use Splitwise to track all shared costs (groceries, drinks, and fuel). This ensures everyone only pays their fair share of the "kitty." šŸ‘„ OUR GROUP: I am looking for fun TripMates who are laid back in character but ready for an adventure or hike! I hope we end up 4 individuals who enjoy a healthy mix of good conversation in a group but personal time in our own space too. Our group will consist of maximum 4 of us (including myself). Males and females are welcome to apply and there will be individual video calls with each TripMate prior to being accepted to ensure we get a good group who will gel nicely! šŸ“ MEETING POINT: Cristiano Ronaldo International Airport — also known as Madeira Airport, Funchal Airport, and formerly Santa Catarina Airport (confusing right!) šŸ“ VISAS: Please check BEFORE booking that you are eligible for a visa & you have a valid passport – these essentials are down to yourself to check & ensure validity. You will also need to check if Madeira has any alternative entry requirement forms, documents or vaccinations essential to be granted entry to the country for your nationality. Most nationalities can obtain a visa on arrival for Madeira and don't need anything else essential to enter. ā¤ļøā€šŸ©¹ INSURANCE: Travel insurance is included if you are a resident of Germany or Austria. You can view all the inclusions & exclusions of this insurance here: www.joinmytrip.com/en/t/travel-insurance. For any other TripMates, you will need to purchase your own Travel Insurance, which also covers you for Medical expenses should you need it whilst we are away. šŸ“±WHATSAPP GROUP: I will be making a ā€˜Madeira’ specific group WhatsApp before we depart for us to start these conversations where I can answer any questions you may have about the trip.

šŸ‘‹šŸ½ I am 34, British šŸ‡¬šŸ‡§ & have been traveling solo for over 15 years across 80 countries! I used to organise volunteering group trips in International schools before moving into luxury travel for UHNW clients. I co-founded a travel concierge service in Dubai and now I am an independent travel agent organising group trips here alongside vacations for others. I live, sleep, east and breathe travel and I am excited to share my passion with you! You can read more about me & my sustainability focused travels on my profile 🄰

Stay in an authentic Madeiran thatched country house surrounded by 3,000 meters of cultivated land and fruit trees in the charming beach town of Santana. The private house feels like stepping back in time - it’s unique, cosy, and equipped with everything you might need. You will have a private single room and together we will prep meals in the shared kitchen, where we will be passed fresh fruit and veg from the garden from the owner and arrive to local jams & milk in the fridge. This is truly a very special experience! Either relax and connect with nature or use the 513 Mbps fast wifi to work in truly breathtaking scenery. The house even has a washer we can use as part of the amenities!

What's included?
Accommodation
Car rental
Travel insurance (Germans & Austrians)
Experienced & knowledgeable trip leader
Destination specific WhatsApp group
Pre-departure guidance
No booking responsibility
Activities specified in the itinerary
Your Booking includes free protection from Trip cancellations.
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Trip Itinerary
1

Santana

Day 1-2
DAY 1: After meeting at the airport, our journey begins when we leave the Funchal region of Madeira in our rental car (Renault Clio or similar) to wind up in the lush, emerald hills of North-East Madeira! We'll also stop for groceries en route to our accommodations for our welcome feast tonight. šŸ›–šŸ Our authentically thatched Madeiran private villa is located on a working farm with fruits, veggies and roaming goats and chickens. We'll be surrounded by 3,000 meters of cultivated land in the charming beach town of Santana. There are 360 panoramic views of the mountains towering into the valley - it’s the ultimate "home base"! You’ll drop your bags, settle into your room and immediately feel the pace of life slow down. The private house feels like stepping back in time - it’s unique, cosy, and equipped with everything you might need. You will have a private single room and together we will prep meals in the shared kitchen, we'll grab the produce from the local markets and supermarkets. Although we will receive seasonal fresh fruit and veggies from the garden courtesy of the owner. I've heard it's common to arrive to local jams & milk in the fridge from them too! As I am sure you've already worked out.. this is truly a very special experience! 🌊 We'll head into Santana beach town to take a look around, Santana is Madeira’s iconic cultural beach town, famous for its triangular, straw-roofed cottages that look like something out of a fairytale. Nestled in a UNESCO Biosphere Reserve, it’s a town where tradition meets dramatic nature, offering a peaceful glimpse into the island’s rural soul. We'll be taking a ride on the Rocha do Navio cable car and visiting the 'hidden waterfall' of Santana. šŸ½ļø The welcome feast: To kick things off, when we get back to the villa we'll cook a delicious welcome feast together and spend the evening playing games, enjoying a tipple and settling into our new environment before hitting the hay!
2

Pico do Arieiro

Day 2-3
DAY 2: Above the clouds & into the surf! 🄾 We'll have a quick breakfast before heading early for the "King of Hikes" - Pico do Arieiro to Pico Ruivo! This isn't just a walk; it’s a journey across the spine of the island. You’ll start at Pico do Arieiro (1818m) as the sun begins to burn through the morning mist. The trail, known as the PR1, is a masterpiece of stonework carved directly into volcanic ridges. The Highlights: You’ll traverse narrow ledges with 1,000 meter drops on either side (all safely railed!), pass through dark tunnels cut into the mountain, and climb the famous "Stairway to Heaven" - a steep set of steps that feels like it’s leading straight into the blue. At the top, we'll have reached Pico Ruivo (1862m), the highest point in Madeira! From here, you can see both the north and south coasts simultaneously, a sea of white clouds usually swirling at your feet. It's raw, rugged, and completely unforgettable. After descending from the peaks, we'll find somewhere local to devour some Mediterranean food before trading the thin mountain air for the salt spray of the North Coast. The north is Madeira’s "wild side," characterized by lush emerald cliffs that drop vertically into the Atlantic. šŸ„ā€ā™€ļøšŸŒŠšŸ˜Ž Surfing at Porto da Cruz: If you’re still craving adventure, we'll head to the nearby village of Porto da Cruz for the afternoon. Unlike the dangerous reef breaks elsewhere, the beaches here (Alagoa and Maiata) have soft volcanic sand bottoms, making them the safest and most iconic spots on the island to learn to surf. Chill out in the sun tanning or reading, book a surf lesson, mooch around the town - the afternoon is yours!
3

Levada do Caldeirão Verde

Day 3-4
DAY 3: Enchanted Forests & High-Altitude Vines 🄾 Today's hike is Levada do CaldeirĆ£o Verde - The Fairytale Walk! Step into a world that looks like a scene from Jurassic Park. This trail follows a levada (an ancient stone irrigation channel) deep into the heart of the UNESCO-protected Laurissilva forest. You’ll wind through emerald-green canyons where water drips from the mossy walls and sunlight filters through giant ferns. You’ll navigate four hand-carved tunnels (don't forget your flashlight!) that feel like portals to a hidden world. The trail culminates at the CaldeirĆ£o Verde (Green Cauldron). Here, a massive, thin ribbon of water plunges 100 meters down a circular rock wall into a crystal-clear, ice-cold lagoon. It is one of the most serene and photographed spots on the island. The vibe is just pure, untouched nature with the sound of the waterfall echoing. šŸ‡šŸ· After the forest trek, we emerge from the green canopy and head to visit Quinta do Barbusano - a vineyard with a jawbreaking backdrop perched on a steep slope overlooking the SĆ£o Vicente valley. The vines are framed by dramatic mountain peaks and the Atlantic Ocean, making it arguably the most scenic winery on the island. This isn’t just a tasting; it’s an education in volcanic wine. You’ll tour the terraces to see how the grapes survive the salty Atlantic winds and then head to the stone cellar or the sun-drenched patio whilst sampling 4 wines each with a small palate cleanser snack board.
4

Ponta de São Lourenço

Day 4-5
🄾This morning set off on the Ponta de SĆ£o LourenƧo route (Madeira’s wild "Dragon’s Tail") - a dramatic volcanic peninsula that looks like Mars meeting the Atlantic. Unlike the rest of the green island, this is a raw landscape of fiery orange cliffs, jagged rock formations, and crashing turquoise waves. It’s a sun-drenched trek where you can stand on narrow ridges and see both the north and south coasts of the island at once. šŸ“ā˜€ļøšŸ™ļøā›°ļø Take a free afternoon to enjoy the island you feel best. Take a bus to Funchal for the afternoon if you're not visiting before or after the trip or perhaps you could book an activity such as horseback riding?
5

Fanal Forest

Day 5-6
🄾Fanal Forest - The hike through Fanal Forest is widely considered the most atmospheric experience on the island. It is part of the ancient Laurissilva forest, a UNESCO World Heritage site that dates back millions of years, offering a landscape that feels completely detached from the modern world. Fanal Forest is famous for its "mystical" quality, primarily due to the thick fog that frequently rolls over the plateau, swallowing the 500-year-old Til trees. These ancient trees have grown into expressive, twisted shapes, creating a natural gallery of silhouettes that change as you walk through the mist. It is often described by visitors as eerie, silent, and fairytale-like; it is one of the few places where hikers actually hope for "bad" weather, as the heavy fog is what creates the iconic, ghostly atmosphere. šŸŒ‹Volcanic Pools: Enjoy a relaxing afternoon in Porto Moniz, swimming in natural infinity pools carved out of the coastline by ancient lava flows.
6

Funchal

Day 6
DAY 6: We'll be packing up and leaving our little slice of Hawaii! Funchal is the vibrant capital of Madeira, Portugal - a sun drenched island that feels worlds away from the rest of Europe. While Funchal isn't part of our itinerary, it is the perfect "add-on" if you're looking to balance rural adventure with some Atlantic island charm to finish off your trip! Here is how you can spend a day or more in this glorious city if you only have one day: āž”ļø Morning: Head to the "Forgotten" fort and gardens. Skip the main Monte cable car and head to the Fortress of SĆ£o Tiago. This bright yellow sea-fort in the Old Town is often overlooked. After exploring the ramparts, walk up to the Jardim OrquĆ­dea (Orchid Garden). Unlike the massive Botanical Garden, this is a more intimate, "hidden" botanical gem that feels like a private jungle in the middle of the city. āž”ļø Lunch: The saltwater secret head to Doca do Cavacas. It’s a small set of natural volcanic pools linked to the sea. There is a tiny restaurant perched right above the water where you can eat fresh limpets (Lapas) with garlic butter while the Atlantic spray literally hits the windows. It’s a favorite for locals who want to stay away from the harbor crowds. āž”ļø Afternoon: Wine and workshop Instead of just a tasting, visit Blandy’s Wine Lodge for their "Behind the Scenes" cooperage tour. Rather than just drinking, you’ll see the master coopers repairing the massive ancient barrels. It’s a gritty, fascinating look at the craftsmanship that keeps the wine industry alive. āž”ļø Afterward, head to the ArmazĆ©m do Mercado. This is a repurposed warehouse that now houses modern art galleries, local designer shops, and a hidden courtyard cafe. It’s the best place to find a souvenir that isn't a fridge magnet. āž”ļø Early Evening: The highest toast for your final sunset, skip the seaside bars and head to the rooftop at the Vine hotel. It’s one of the chicest spots in the city with 360-degree views of the Funchal lights turning on against the mountain backdrop. Order a "Madeira Mojito" and watch the city transform. If you have longer, then check out the below top experiences: ā–¶ļø The Monte toboggan: Take a cable car up to the Monte district for breathtaking views, then ride back down the steep streets in a traditional wicker basket sledge pushed by "Carreiros" in straw hats. ā–¶ļø Mercado dos Lavradores: A sensory explosion of color. This Art Deco market is where you’ll find exotic fruits (like the "pineapple-banana"), fresh-caught scabbard fish, and local flower sellers in traditional dress. ā–¶ļø Old Town (Zona Velha): Wander through the "Painted Doors Project," where local artists have turned the neighborhood's doors into permanent murals. ā–¶ļø Blandy’s wine lodge: šŸ· This is the beating heart of Madeira wine history. Located in a 200-year-old former monastery, it has been run by the same family for seven generations. You can walk through aging rooms filled with massive wooden vats where the wine is matured using the traditional "Canteiro" method (using natural heat from the sun). Ask for a tasting in the Vintage Room, where you can see rare bottles dating back to the 19th century. The smell of aged wood and sweet wine in the cellar is unforgettable. ā–¶ļø Barreirinha bar cafĆ©: tucked away at the edge of the Old Town, this is where the locals hang out. It’s a cliffside bar overlooking a swimming complex. It’s the best place in the city to grab a Poncha (the local rum and honey drink) and watch the sunset away from the main tourist crowds. ā–¶ļø Quinta das Cruzes viewpoint: most tourists head to the Pico dos Barcelos, but for a "secret" view, head to the gardens of the Quinta das Cruzes museum. It offers a beautiful, intimate perspective over the red-tiled roofs of the city and the harbor. ā–¶ļø Design centre 'Nini Andrade Silva': Located at the end of the harbor pier inside an old fort, this spot is part gallery, part restaurant. Even if you don't eat there, head to the rooftop bar for a unique view of the Funchal skyline from the water looking back at the land.
Trip Summary
Accommodation
Other
6 days trip
Santana, Pico do Arieiro & 4 more
Transportation
Car
What's excluded?
Flights
Souvenirs
Petrol
Food, Drinks & Snacks
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