Getting Between Stops
From Lisbon Airport, Sintra is about 30 to 40 minutes by car or taxi. Within Sintra, private cars are not allowed up to Pena Palace and parking in the historic center is limited, so use local buses, tuk-tuks, taxis or the walking trails between sites. Rent a car only for the coastal day, or book a driver.
Lisbon to Ponta Delgada is about a two-hour flight with several departures a day. On São Miguel, rent a car. Roads are good, distances are short and the drive from Ponta Delgada to Furnas takes about an hour.
For the trip home, Azores Airlines flies nonstop from Ponta Delgada to Boston year round, with service to New York JFK as well. United has offered seasonal Newark flights. If you want to fly home from Lisbon instead, you can connect through the capital on the same day.
Where to Stay
In Sintra, the Tivoli Palácio de Seteais sits on the road toward Monserrate, with formal gardens and views across the plains to the sea. Penha Longa Resort, set in a former monastery estate south of the hills, suits couples who want a spa, golf and more modern rooms. Small guesthouses in old townhouses and quintas let you walk to the palaces and to dinner.
On São Miguel, split your nights between two areas. Near Ponta Delgada, White Exclusive Suites & Villas in Lagoa is a minimalist hotel on the shoreline, close to the whale-watching boats and the city's restaurants.
In Furnas, Furnas Boutique Hotel has thermal pools and a spa. On the north coast, Santa Bárbara Eco-Beach Resort sits above a black sand surf beach near Ribeira Grande, with villa-style rooms and a more outdoorsy feel.
When to Go
May to September is the best window for the Azores. Days are longer, the sea is warmer for whale watching and the hydrangeas bloom along the roads from around June to August. Even in summer, plan for changeable weather, because sun, mist and showers can all appear in a single afternoon.
Sintra is at its best in spring and early fall, when the gardens are lush and the crowds are more manageable. The hills catch Atlantic moisture, so mornings can be misty even when Lisbon is sunny.
Winter is quiet, green and cheaper on both stops, but the Azores can be windy and wet, with more flight disruptions between islands. Hot springs are lovely in cool weather, so a shoulder-season trip in May or late September can be a smart compromise between weather and price.
What It Costs
This route offers good value. As an approximate guide, boutique guesthouses in Sintra cost about $150 to $300 a night for two, with the Tivoli Palácio de Seteais higher. On São Miguel, White Exclusive Suites & Villas starts around $300 a night. Most other hotels cost less, though summer prices rise.
The Lisbon to Ponta Delgada flight is usually reasonably priced. Add a rental car on São Miguel and taxis or a driver in Sintra.
Spend on the timed palace entries in Sintra, a whale-watching trip and spa time in Furnas. Meals are inexpensive on both stops, from grilled fish in Azenhas do Mar to volcanic stew in Furnas, which leaves room for a splurge dinner on your last night.
Tips for the Two of You
Pack layers and light rain jackets for both of you, along with shoes that can handle wet trails. Azores weather changes fast, so keep a flexible plan and move hikes to the clearest day. In Sintra, comfortable shoes matter more than anything, since the palaces are spread across steep hills.
Bring dark swimsuits for the thermal pools in Furnas. The iron-rich water can stain light fabrics.
At Ponta da Ferraria and on the north coast beaches, ocean swimming can be rough. Check conditions and swim only where locals do.
The Azores give each of you options. One partner might go canyoning or surfing while the other takes a spa treatment or a slow walk through the botanical gardens in Furnas. Whale-watching boats can be bumpy, so take seasickness tablets if either of you is prone to it.
Make It Shorter or Longer
With a week, spend two nights in Sintra and four on São Miguel, choosing one base near Ponta Delgada or in Furnas.
With two weeks, add a second island. Pico with its vineyards and volcano and Faial with its sailing harbor are a short SATA flight from São Miguel and only a 30-minute ferry apart, which makes them an easy pair. Allow buffer days, since wind and fog sometimes delay inter-island flights.
Couples who want more city time can add two nights in Lisbon between Sintra and the Azores for fado in Alfama and a golden-hour sail on the Tagus. Those who prefer beaches could add three nights on the Algarve before flying to the Azores.