Getting Between Stops
The only transfer is a short flight. Lisbon to Madeira takes under two hours, with several departures a day. Porto also has flights to the island if you prefer to start in the north.
In Lisbon, walk and use cheap ride-hail cars on the hills. Do not rent a car there. The trains to Sintra and Cascais take about 40 minutes and are easier than driving.
On Madeira, rent a car to see the island properly. Modern tunnels and expressways connect most areas, but local roads are steep and narrow, with tight hairpins. An automatic is worth the extra cost. If neither of you wants to drive, book a private driver for the sunrise and levada days and use taxis in Funchal. Ask your hotel about parking and the steepness of the access road before you book.
Where to Stay
In Lisbon, choose your neighborhood first. Alfama has staircases and fado. Chiado and Príncipe Real have the most restaurants. The Bairro Alto Hotel sits on Chiado's edge with a rooftop terrace. Memmo Alfama has a small pool terrace looking over the rooftops to the river.
On Madeira, most couples stay in or near Funchal, the most convenient base for restaurants and day trips. Belmond Reid's Palace is the grand choice, famous for its gardens and afternoon tea. Quinta da Casa Branca is a calmer contemporary hotel in the gardens of an old family estate. Les Suites at The Cliff Bay offers all-suite rooms with ocean views.
For more seclusion, look at small rural hotels and quintas in Calheta or Ponta do Sol on the sunny southwest coast.
When to Go
This is one of the few European honeymoons that works in any month. Madeira's coast stays mild all year, so winter weddings can still have sunshine, flowers and outdoor dinners. Lisbon is cooler and wetter from November to March but rarely cold by US standards.
April to October is the best window overall. Lisbon is at its most pleasant in late spring and early fall. Madeira's mountain trails are more reliably clear. Late April and May bring Madeira's flower season, when Funchal fills with blooms.
Peak summer is busy in Lisbon and warm in the city, while Madeira stays comfortable. Mountain weather on the island changes fast in any season. Keep the sunrise and levada days flexible, since the high peaks can sit inside cloud while the coast is sunny.
What It Costs
Portugal is good value for Western Europe. As an approximate guide, good boutique hotels in Lisbon cost about $250 to $450 a night for two, with the Bairro Alto Hotel starting in the $400s. On Madeira, Belmond Reid's Palace starts around $500 a night, while quintas and rural hotels cost far less.
The Lisbon to Madeira flight is usually inexpensive when booked early. Add a rental car for five days, fuel and parking.
The experiences worth paying for are the Tagus sunset sail, a fado dinner, a guide or driver for the levada day and a Madeira wine tasting that compares dry Sercial with sweet Malmsey. Afternoon tea on the Reid's Palace terrace is a smaller splurge that gives you the famous setting without the room rate.
Tips for the Two of You
Madeira is an active island, so pack proper walking shoes with grip, a rain layer and a warm top for each of you. Pico do Arieiro at sunrise can be near freezing even when Funchal is warm. Levada paths often run beside steep drops, so stick to well-known routes, start early and check conditions before you go.
At the Porto Moniz pools, swim only inside the protected areas and stay away from the outer walls when waves are big.
Both of you will find your own highlights. One partner might add a longer hike or a canyoning trip while the other spends a morning at the Funchal markets or a spa, then meet for lunch by the sea. In Lisbon, watch for pickpockets on the crowded trams and keep phones zipped away. Late taxis and ride-hail cars are easy and inexpensive.
Make It Shorter or Longer
With a week, spend two nights in Lisbon and four on Madeira. Keep at least one flexible day on the island for weather.
With 12 days, add the Azores for three or four nights, either flying from Madeira or connecting through Lisbon, for crater lakes and hot springs. The Azores also have nonstops to Boston, which can make the trip home simpler. Another option is two nights in Sintra before Lisbon, sleeping among the palaces to see them before the crowds arrive.
If beaches matter, Porto Santo, Madeira's sister island, has a long stretch of golden sand. It is about 2.5 hours by ferry or a short flight, so two nights there make a calm beach finish before you fly home.
