Madeira, Portugal 2026

Frequently Asked Questions

Why are you doing this?

In short, I love travel, planning travel, sharing travel, and I understand that some people find travel planning challenging and/or want to travel with others. And, of course, it’s Madeira! Our past trips were absolutely incredible and an amazing experience for each traveler, and I am super excited to share one of my favorite places on the planet with others.

Is this trip for me?

Planning: I’ve planned everything for you! All you have to do is show up and trust that you will have an amazing adventure waiting for you. If you love going on adventures but don’t enjoy planning all the details, this trip is perfect for you.

Fitness Level: The hiking trails on Madeira range from “easy” to “hard”. Because of the unique way we will be visiting the island, all hiking will be optional. While there are no extremely technical climbs, hiking requires a reasonable level of fitness and we may be doing 1-2 hikes per day of varying lengths and difficulty. If you're comfortable with regular walks or hikes, you should be able to manage the trails with proper preparation.

Hiking Experience: While prior hiking experience is not essential, some familiarity with walking on uneven terrain and carrying a daypack is beneficial. If you're a novice hiker, consider training beforehand to build endurance and get accustomed to hiking gear.

Enjoyment of the Outdoors: Madeira offers a rich immersion in nature, with diverse landscapes ranging from serene seaside locations to rugged mountains. If you appreciate spending time outdoors, relish fresh air, and find beauty in natural surroundings, this trip will likely resonate with you.

Sense of Adventure: The Madeira trip is an adventure that calls for a spirit of exploration and a willingness to embrace the challenges of a multiple day hikes. If you're eager to step out of your comfort zone, discover new places, and challenge yourself physically, this trip could be an enriching experience. There are also other unique opportunities like cultural activities and boat excursions.

Appreciation for Portuguese Culture: This trip provides a glimpse into a unique part of Portuguese culture, with charming villages, historic sites, and opportunities to interact with locals.

Desire for Camaraderie: A group trip offers a unique opportunity to bond with fellow travelers, share experiences, and create lasting memories. If you enjoy socializing and connecting with others, this trip could provide a fulfilling group dynamic.

If you find yourself nodding along to these factors, then the Madeira group trip could be an excellent fit for you. It's a chance to immerse yourself in the beauty of the island, challenge your physical limits, and forge new connections with like-minded adventurers. Embrace the spirit of exploration and embark on a journey that will leave a lasting impression.

Why should I travel with this group?

Forget impersonal, organized group travel. This is a unique, small-group, personalized travel experience. Travel with a diverse but similarly-minded group of people together on this once-in-a-lifetime journey!

How much will it cost?

Total cost for all 15 days is $1890 USD (see below for what is included/excluded). I am doing everything I can to maximize the experience while keeping costs as low as possible. Trip prices may increase for late bookings if space is still available.

What’s included?

7-night’s stay in a beautiful Airbnb with stunning coastal views and a pool

All dinners with an option to choose a starter, a main, a drink, and dessert (additional items will be at your own expense)

Preplanned group activies (see final itinerary). There may be additional activities available at own expense

Transportation, driver, and fuel while on the island during the inclusive dates of the trip

Fully guided trip by an experienced hiker and guide

What’s not included?

Airfare to and from Madeira at the start and end of trip

Meals, food, and drinks unless otherwise indicated as included

Travel Insurance. More details below

Personal hiking equipment /gear

Optional activities not included

How large will the group be?

In order to maximize the experience, I have limited the maximum group size to 8 people (including myself).

Do I need to be in good shape? How difficult is the walking/hiking?

You should be in reasonably good shape prior to starting this trip. During the experience and on hiking days, we will be hiking on average 2-6 hours a day over varied terrain. The island has easy to more difficult level trails and should be suitable for most hikers with a reasonable level of fitness. While some trails may be well-maintained and easy to follow, there may be others that will be more challenging with some rock scrambles and muddy sections. As each hike will be optional, we will discuss in detail before starting each day so that you can make an informed decision about the hikes planned for that day.

Jogging, biking, swimming, yoga, or whatever your favorite exercises are great to keep up (or start) well before the trip (at least 3-6 weeks prior). If you have any concerns related to your health and ability to complete this experience, please consult your physician.

What kind of pace will we hike?

We’ll tailor the pace each day based on everyone’s abilities, how much hiking we want to accomplish, start time, weather conditions, and breaks. Please don’t be afraid to speak up if you think we need to slow down or take a break. We’ll do our best to accommodate everyone and ensure the pace we walk is enjoyable.

Speaking of start times, when will start each day?

Again, we’ll consider a variety of factors each day, such as weather, driving distances, activities, etc.

Is this a luxury tour?

This is not a luxury tour, at least in the traditional sense. The luxuries will come in the form of the very unique experiences we’ll have on this journey.

What are sleeping accommodations like?

We will be staying in a beautiful Airbnb on the island with a pool. All rooms have two single beds. You will also have the opportunity to purchase any food and beverage items you would like to have on hand.

What do I need to bring?

I’ll provide a more detailed list later, but here are some items you will likely need to bring (keep in mind that the weather may vary wildly from warm sunny periods to cold and rain):

Hiking shorts, trekking pants, lightweight underwear, t-shirts (ideally quick drying), light waterproof jacket, fleece jacket or pullover, gloves, hat, daypack, electricity adapters (EU), e-book reader, glasses and sunglasses, medications for the whole trip, toiletries, quick-drying towel, soap, sanitizer, refillable water bottles and/or bladders, hat, sunscreen, lip balm, trekking poles (optional depending on preference), portable device charger/battery, good hiking boots or shoes, lighter shoes/sandals to wear post hike on trek, sweatpants/joggers, tennis/walking shoes, an eye mask (if sensitive to light), swimwear and water shoes

Do I need trekking poles?

Again, the choice is really up to you. I personally have mixed feelings about them. People who carry two and walk with them on regular/flat terrain tend to walk more slowly than those without. However, there are times on steep or unstable terrain that they can be helpful. My personal preference is to (sometimes) carry one and only use it when necessary.

What’s the weather going to be like?

In May, Madeira's weather is generally very pleasant and marks a transition into the warm summer months. It's often considered one of the best times to visit, as the weather is consistently warm but not yet hot, and the island is in full bloom. The average high temperature is around 21-22°C (70-72°F), while the average low is around 15°C (59°F). The days are comfortably warm, and the evenings are mild. You can expect plenty of sunshine, with an average of 7 to 8 hours of sunshine per day. The days are long, and it's a great time for outdoor activities. May is a relatively dry month, especially compared to the winter season. The average rainfall is low, with only a few days of light rain expected throughout the month. The ocean temperature is still on the cooler side, around 19°C (66°F). While it may be a bit chilly for some, it's still suitable for swimming.

If it’s raining, will we still hike?

Most likely yes. There is a chance we will have some rain at some point during our hikes. Waterproof gear is helpful. If the weather is very bad or dangerous during a hike, we will try to find shelter and wait for it to clear. Also, we may delay or omit certain hikes in the event of inclement weather. Rainy days/periods could be a good opportunity to take an easier hike, check out a museum or cafe, or simply relax in a cozy spot with a good book and a hot tea.

How much do I need to put as a deposit to hold my space? When is the balance due?

I kindly ask that you pay a $300 deposit as soon as possible to secure your space on the trip. Your space on the trip is not guaranteed until you pay the deposit, but it is fully refundable up to 10 Dec 2025. The balance is due 1 Feb 2026 and is non-refundable. Trip insurance can help cover any unforeseen obstacles to travel. If you have a unique situation and need some flexibility with this, please contact me directly. Thank you for understanding!

Do I need insurance?

Although not mandatory, it is HIGHLY recommended in the event you need to cancel or alter your travel plans. It is also helpful in the extremely unlikely event you need medical care or evacuation while you are traveling. There are many options available out there. I recommend World Nomads; however feel free to chose whomever you like.

What time should I arrive into Madeira on the first day?

The choice is yours; however please keep in mind that we will have a welcome dinner for the group that first night. You are welcome to arrive as early as you like. I can help you make hotel arrangements if arriving before the start of the group trip. Please do let me know once you make your arrival and departure arrangements or if you have any questions during the process.

I have dietary restrictions, can you accommodate them?

We will do our best to accommodate, but please communicate any restrictions or concerns prior to booking.

How do I reserve a spot???

Just let me know! Once you share all of your pertinent details and pay the $300 (refundable up to 10 Dec), you’re in!!

Anything else I should know?

Here are some additional pointers to make sure you get the most of this experience:

Expect the unexpected. Although this trip is fairly structured, this is adventure travel

As mentioned above, try to be more of a traveler and less of a tourist

Always seek the beauty and fun of an experience and people. There’s charm everywhere

Try everything you can (be openminded) and be open to pushing your boundaries

Breathe deeply and fully

Pack some patience and a lot of kindness