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We’ve created the ULTIMATE 1-week itinerary for adventurous travelers that want to get off the beaten path and have unforgettable experiences in Madeira, Portugal.
This done-for-you itinerary is everything you need!
I'm ready to plan my trip!
26
pages
7
fully-planned days
1
exciting location
Completely DONE-FOR-YOU Itinerary!
CONFESSION:
I have major trip FOMO.
I hate coming home from a trip only to realize I missed an epic hike or a hidden restaurant I was just around the corner from.
Can you relate?
If so, you are in the right place because we have literally spent hundreds of hours creating this itinerary (no exaggeration) so that you don’t have to worry about missing out.
This is packed with advice (from actual on-the-ground experience) as well as hidden gems most travelers miss.
Here’s a sneak peak at what’s included!
- bucket list hikes with views around every corner
- some of the most magical sunset views we’ve ever seen
- where the find the most delicious local foods
- dining with views from all over the island
- iconic lookouts and viewpoints with suggestions to beat the crowds
- swimming in stunning natural pools filled by the sea
- a thrilling ride in a traditional wicker toboggan
- accommodation recommendations that will have you pinching yourself (they’re that good)
- fully interchangeable days so you can be entirely flexible and adjust this itinerary to fit the weather you experience on your trip!
Our itinerary style…
Explore the island in your rental car to get off-the-beaten path.
Visit a mix of iconic sights and hidden gems that see far fewer tourists.
Hike some of the most stunning trails with epic views around the island.
Immerse yourself in authentic Madeiran culture—from local foods to friendly small towns.
A mix of splurge-worthy experiences and free activities that immerse you in nature.
Super unique accommodation recommendations you can choose from.
Are you in?!
If you’re ready to embark on the Madeira trip of your dreams, grab your itinerary now & you’ll soon be on your way.
Cheers to the trip of a lifetime!
This is a brand new itinerary and doesn’t have reviews (yet!).
Here a few testimonials from our other itineraries.
It was such a vital part of our planning!
“After researching several travel blogs for [an itinerary], I purchased the TWS itinerary and use it as a guide to help [with planning]. It was such a vital part of our planning and was such an amazing thorough packet of not only recommended places but packing list, campervan rentals, food recs and so much great info and had everything we needed to plan our trip.“
Well worth the money!
“I was hesitant to pay for an itinerary however I’ve found that [TWS itineraries are] well worth the $! It’s FAR more detailed that anything I could find free & has shaped the backbone of our trip. Thanks for all the info!”
It’s an inspiration and such a help!
“I wanted to say thank you for your amazing [itinerary] guide! Me my husband and our 9 month old son just came back one week ago and we had the most amazing time! And as the first bigger trip with a baby it was such a help to have that guide and didn’t need to do my own research! Thank you for everything you guys do! It’s an inspiration and such a help!”
Interactive Google Map
Be sure to grab the interactive map with all places pinned for easy access!
Getting Around
We’ve provided driving directions, distance and timing for your road trip around the country
Restaurant recommendations
You’ll love our restaurant recommendations throughout the itinerary as we’ve done plenty of on the ground “research” to find the best spots.
Where to stay
We’ve carefully chosen unique and special accommodation options in the most central parts of the island for your trip.
A 1-week custom itinerary based on all of our research and experience in Madeira would cost upwards of $750.
We know that is not feasible for everyone, so we decided to take our experience and turn it into a totally affordable and downloadable PDF guide!
Let us help save you SO MUCH TIME.
Madeira Itinerary
Overview
This itinerary includes detailed plans for each of these places and activities (+ a whole lot more!) and is customizable based on your interests & travel style.
Funchal
Madeira’s lively capital, known for its charming old town, oceanfront promenade, and sweeping hillside views.
Madalena do Mar
A seaside village surrounded by dramatic cliffs and lush banana plantations you can walk through.
Fanal Forest
Visit the magical, mist-covered laurel forest where ancient trees twist into otherworldly shapes.
Seixal
Walk the famous black sand beach and swim in natural pools in this picturesque coastal town.
Porto Moniz
Swim in Madeira’s iconic natural pools, perfect for a refreshing dip with ocean views.
São Vicente
A charming northern village known for its volcanic caves, lush scenery, and serene riverside setting.
Levada hikes
Uniquely Madeiran, we’ve included a few of these scenic walking trails that follow ancient irrigation channels.
Santana Old House
A colorful traditional thatched house offering a glimpse into Madeira’s rural past.
Ponta de São Lourenço
A stunning coastal trail across Madeira’s eastern peninsula, showcasing rugged cliffs and endless ocean views.
Monte
Visit the lush palace gardens and do the iconic traditional wooden toboggan ride through the streets of this hilltop village.
Valley of Nuns
Have lunch in a dramatic mountain valley once hidden from pirates, now a peaceful village surrounded by towering peaks.
Câmara de Lobos
A vibrant fishing town beloved by Winston Churchill, with colorful boats and waterfront restaurants.
Ponta do Sol
Known as the “sunniest place on the island” with pastel buildings, sea views, and a laid-back local vibe.
Pico do Arieiro
Madeira’s third-highest peak, offering breathtaking sunrise views and access to the island’s most spectacular hikes.
“We’ve packed this with insider tips that’ll make the difference between a great trip & the most unforgettable trip of your life!”
– Katie & Ben Zweber
Why trust our Madeira advice?
Before our Madeira adventure, we spent months researching the island—scouting hikes, viewpoints, villages, and figuring out how to get around those winding mountain roads.
We spent a week exploring Madeira—hiking levadas, soaking in volcanic pools, chasing waterfalls, and tasting all the local treats. And thanks to our team member Amanda, who visited just before us, we had insider tips that made our trip even smoother.
Between the three of us, we experienced the island in different ways, which helped us create what we think is the ultimate Madeira itinerary: a perfect balance of adventure, relaxation, and can’t-miss highlights, thoughtfully paced for an unforgettable trip.
-Katie & Ben Zweber
Your dream trip awaits…
Let’s turn your dream Madeira trip into reality!
We’ve done all the hard work for you. This itinerary will truly save you SO MUCH time and headache. All you’ve got to do is pack your bags and you’ll be off on the trip of a lifetime!
Grab your itinerary!
IF THIS YOUR VIBE, THIS ITINERARY IS FOR YOU…
Charming local villages & iconic cities + epic hikes + local eats + off-the-beaten-path adventures + once-in-a-lifetime experiences
Get ready to make core memories!
FAQs
Who is this itinerary for?
This is a perfect route for anyone who has roughly 1 week to spend in Madeira and wants to see the top sights as well as some little-known gems. This would make an amazing honeymoon or special trip.
This itinerary is for you if you:
- want a mix of bucket list spots and off-the-beaten-path gems
- enjoy hiking, outdoor adventures, and jaw-dropping landscapes
- prefer traveling independently (not on a tour)
- like having flexibility, but also appreciate a well-thought-out plan
- are comfortable driving a rental car
- want to make the most of your time in Madeira without the pressure of planning
What is the budget?
The accommodation, experiences, and activities recommended are for those with a mid-range budget.
Portugal is pretty affordable, and we’ve done our best to keep costs reasonable.
We’ve included a handful of (optional) worthy splurges, but have mostly stuck with mid-range prices.
What type of accommodation is recommended?
We’ve included a mix of Airbnbs and hotels in our accommodation recommendations (including the exact Airbnb we stayed at).
Do I need a car to follow this itinerary?
This itinerary was created as a road trip, and therefore you will need your own vehicle.
You DO NOT need a 4×4 for this itinerary, but we do suggest getting an automatic car (even if you know how to drive manual—Madeira has lots of steep roads and intersections on hills).
How much physical activity does this itinerary require?
This itinerary is pretty hiking-forward, but we’ve done our best to spread out the hikes so you’re not hitting the trails every single day.
That being said, we think anyone with a moderate level of fitness should be able to enjoy this itinerary, and you can always swap out of a hike for another less strenuous activity if you’re not feeling up for it.
What time of year can I follow this itinerary?
Madeira is a year-round destination so in theory you could do this itinerary for any time of year.
In the winter months (November – March), you’ll have a higher chance of rain, but you’ll also be able to see the winter blooms. Conversely, the summer months (June – August) are the hottest months of the year, and also the busiest season.
We’d suggest following this Madeira itinerary during the spring or fall months (April/May or September/October). We went in the first week of June and had pretty ideal weather for our trip!
What if I have less time?
Each of the planned days in our Madeira itinerary is standalone, so you can mix them up or skip one if you like.
What is your return policy?
Since this is a digital download and we cannot revoke access to it, we have a no refund policy.
For this reason, we have made it incredibly affordable.
We stand by this product 100% and have put countless hours into putting it together for you. We are confident that this will be extremely helpful in planning your trip.
The itinerary includes various easy to moderate level hikes, but nothing too demanding or requiring extra gear.
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Still have questions?
If you still have questions, feel free to reach out and ask away!
Get in touch!