There’s nothing like those trips where the second you step off the plane you’ve lost all sense of time and what day it is, the itinerary is packed, there’s no time to mourn one leg of the trip ending because you’re rolling right into the next one. That’s what this Portugal and Madeira honeymoon trip was. Read this for a 9 day travel guide to maximizing your time in these two countries.

Quick Itinerary:

Day 1 – Fly to Lisbon: afternoon 4 hr walking tour of Lisbon + Fado dinner
Day 2 – Lisbon to Madeira: afternoon walk and gondola round Funchal + check into hotel
Day 3 – Madeira: hike and west side of island sight see drive + poncha stop
Day 4 – Madeira: PR1 hike + top floor dinner at Savoy Palace
Day 5 – Madeira –> Lisbon: morning relax at hotel + fight to Lisbon
Day 6 – Lisbon: 8 hr tour Sintra x Casicas
Day 7 – Drive Lisbon –> Lagos: Cliffs + beaches
Day 8 – Lagos: cliffs and Alvor beaches
Day 9 – Lagos: return home –> Lisbon – Home

Where we stayed:

Lisbon: Hotel Britania
Madeira: Savoy Palace
Lagos: Cascade Wellness

Things we’d do differently:

Choose a different hotel in Lagos. Cascade Wellness was gorgeous and is worth staying at for proximity to having the costal cliffs right outside your door. We did go just before peak season when things were extremely quiet and for what we were looking for it was just a bit too quiet at Cascade for our taste.
Consider a more sexy Lisbon hotel or not going back to Britania for the sake of seeing somewhere new in the city. Britania staff and service was incredible, but it was a bit tucked in the streets and felt congested at times.
Plan a rental car from Lisbon to Lagos. We originally thought we wouldn’t rent a car for that leg of the trip and it would have been impossible not to despite there being affordable transportation options.

Things we are glad we did:

Savoy Palace was absolutely wonderful on Madeira island, would stay again perfect for a honeymoon.
Cancelled our Algarve caves boat day. We were toured out at that point of the trip. If you opt out of some of the walking/city tours earlier in this itinerary then I would suggest including an Algarve boat day.
Rented a car to algarve we wouldn’t have discovered Alvor otherwise. In general having a car was a life saver and allowed us to see as much as possible.
Wind down from the week south at the beaches. Ending in the southern part of the country was the right decision.
Learned to NOT accept the conversion rate in processing credit card transactions and which ATMs were recommended (look for MB logo for ATMS that don’t have as high of a conversion rate)

Detailed Itinerary:

Day 1 – Fly to Lisbon:

What you do: Afternoon 4 hr walking tour of Lisbon + Fado dinner

If you are coming from the USA you’ll likely catch an overnight flight to Lisbon. This is the perfect decision because you will land mid-morning/early afternoon.

Upon arrival you will check into Hotel Britania and head out on a 4 hour walking tour of the city. We found having this experience booked and ready upon our arrival made sure we fought jet-lag and got to maximize our half day in the city.

We vet and book most of our tours through Viator and have yet to be dissapointed. Our tour guide Daniel was incredible.

On the 4 hour tour you get to hit high points of the city and surrounding areas like:

Barrio Alto
Miradouro Sao Pedro de Alcantara
Rua da Bica
Igreja de Sao Roque
LX Factory
Alfama
Se de Lisboa
Museu do Fado
Castelo de São Jorge

While we were on the tour we let our guide Daniel know we’d love his suggestions for a dinner spot. We learned most of the better spots require reservations and since it was nearly high season most were booked. Daniel was kind enough to call in a favor and get us a table at Trovas Antigas.

This wound up being such a unique experience with multiple acts of Fado dinner performances from highly talented artists in the intimate dinner setting.

Day 2 – Lisbon to Madeira:

What you do: afternoon walk and gondola round Funchal + check into hotel

We flew TAP Air from Lisbon to Madeira and it wound up being an excellent and reliable choice. Sometimes smaller domestic or lesser known airlines can be a gamble but we were pleasantly surprised by TAP Air.

Tip: Upgrading to TAP premium seats gets you fast track and lounge access. When we were heading back to Lisbon, fast track access saved us from potentially missing our flight due to unexpected delay in returning the rental car.

We picked up the rental car at Madeira airport. Recommend booking your rental car in advance. We booked ours somewhat late and the ones at the airport weren’t available. We wound up renting our car through Drive on Holiday which turned out to be easy enough. Keep track of the return address, once you are on the ground there are a few companies with similar names, and it was very easy to mix up where exactly you needed to drop off the car.

After dropping our bags at our hotel Savoy Palace, we walked and explored the city of Funchal. We recommend grabbing lunch at any of the local cafes which all serve easy and affordable snack options and then heading to the town gondola for an aerial view of the city.

Day 3 – Madeira:

What you do: hike and explore the west side of the island capping the day off with some poncha

We started the day hiking levada nova which turned out to be an excellent choice. This hike can get crowded so start early. Hiking counter clockwise made sure we were able to see the highest most scenic views on the last half of the hike however there are no bad vies the entire way. Hiking along the levada will leave you with some exposure so wear good shoes and tighten down the backpack.

Next head out to explore the west side of the island stopping anywhere you please along the way. The following were stops we loved:

Ponta do Sol – excellent post hike breakfast and beach stop
Paul do Mar viewpoint
Miradouro Farol
Miradouro da Boa Morte
Ponta do Tristao
Piscinas Naturais do Porto Moniz
Miradouro da Faja do Barro
Seixal Beach – black sand beach and waterfalls

You can easily drive back through the center of the island vs. going all the way around put us right at sunset and offered some gorgeous mountain views. We will tackle the east side of the island tomorrow.

Finally on this day we recommend you stop for an end of day poncha and some incredible vibes at Taberna Poncha where everyone is celebrating and likely watching the game.

Day 4 – Madeira:

What you do: hike PR1, drive and explore the east side of the island

On this day we woke up before sunrise to hike the iconic PR1 hike which takes you through Pico Areeiro and Pico Ruvio. Watch the weather as this hike while one of the most epic views can easily get socked into the clouds. We planned to leave extra early (4:30am) to get an upper lot parking spot or risk adding an extra mile to the hike at the lower lot. We were glad we did given how hilly and strenuous the hike is. Give yourself about an hour to drive from Funchal to the trailhead parking.

If the weather is variable or cloudy, we recommend not forcing the Pico Ruvio summit. We opted to and wound up not being able to see anything for the last 2 miles. While we got a foggy day for a hike it was still absolutely epic and a bucket list hike for me personally. I hope to go back one day on a clear morning it’s worth it in every way.

Once you’ve completed the hike driving the east side of the island makes for an excellent second half of the way

The best stop to spend time at will be the eastern most point of Ponta de Sao Lucerno. It can get crowded so going early or late afternoon are your better bets to find parking. You pay a small fee (2 euro per person) to hike out to the point for some incredible cliffs and rock formations along the peninsula. While the distance isn’t far, keep in mind there is minimal shade throughout the entire hike so bring sun protection and water.

Day 5 – Madeira to Lisbon:

What you do: morning relax at the hotel and fly to Lisbon

This day is a slight rest day as far as activities are concerned. You will fly back to Lisbon and prepare to head south on day 7 towards the Lagos for the last few days of the trip.

A few callouts:

The breakfast at Savoy Palace is unmatched. Such an incredible luxury feeling, setting and the staff was wonderful
In Lisbon you will pick up a rental car and drive to stay one night in Lisbon. Recommend walking the city shopping the street vendors.
On this night you can choose to stay again at Hotel Britana to keep things simply or pick somewhere new in the city.
Optional: You can head straight from Lisbon to Lagos (3hrs) if you’d like to avoid the stay-over in Lisbon and get an extra night in Lagos, but I have to say after the busy week it was nice to have a simple day with less driving.

Day 6 – Sintra x Cascais:

What you do: Head out for an 8hr private tour of Sintra and Cascais

As mentioned in day 5 you can opt for an extra day at the beaches in the south and skip this last full day in Lisbon. If you like history and the chance to learn of the events and stories that shape the culture of the area this is definitely recommended. I would also recommend the private tour for a few reasons:

Sintra gets extremely crowded, large groups, shoulder to shoulder walking through narrow castle walls
If your guide is anything like ours, Luis, they will make sure you arrive early and get ahead of the crowds.
The chance to see luxe Cascais and check out some of the food and scenery there was an unexpected surprise and felt like a way to truly maximize a jam-packed day.

We almost always book our tours through Viator and this private tour group did an amazing job. Why Viator? The ratings and reviews always seem to be very accurate. Additionally, if you’re like us and don’t love stuffy group tours they offer tons of incredible private activities.

Day 7 – Lagos:

What you do: Drive Lisbon to Lagos to stay at Cascade Wellness in Algarve.

Note: As mentioned above, this is a very quiet family friendly resort. If you are looking for something a bit livelier with a social/party vibe this is likely not your spot. The reason stay here is because it’s right on top of and walkable to some of the most iconic sites on the Algarve a few you will want to hit are:

Ponta da Piedade
Heart rocks
Miradouro do Abismo

Some of the best beached we hit while down in Lagos/Algarve were:

Praia da Marinha
Praia de Odeceixe
Praia Dona Ana
Praia do Camilo

There so TONS more here were some incredible blogs we used to research and find out some of the best beaches int he area:

Day 8 – Lagos x Alvor Beaches:

What you do: Another final beach day to Alvor

One of our favorite beaches in of the entire trip was Prainha. The rock formations were incredible and the size of the area was amazing. The beach bars and restaurants here were exactly what you needed for quick bites throughout the day.

We went into Alvor for dinner at La Fiesta Cantina Mexicana and it was the perfect cap to a beach day with the festive interior and authentic feel. The surrounding streets are very walkable and easy to find any type of dinner you might be looking for in this area.

Day 9 – Drive Lisbon and return home:

What you do: End your incredible trip with the drive Lagos to Lisbon to catch your flight back home wherever that may be.

We hope you enjoyed this itinerary and welcome and comments or notes you might have for us to add to this writeup to strengthen it!

-Riley

Riley Roams

Madeira, Lisbon and Lagos – 9 Day Itinerary