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Culture · Lisbon, Portugal

Lisbon & Sintra: 5 Days

A central Chiado hotel, a small-group Sintra day, fado and Belém, with private airport transfers and a food walk as an optional add-on.

  • 5 days / 4 nights
  • Starts at Lisbon (LIS)
  • No car needed
A yellow tram on a sunny cobblestone street in Lisbon

Attractions

What you will see as you travel the route, day by day, and how to make the most of each stop.

6sights on the route
4nights in central Chiado
1small-group Sintra day
1fado show
ChiadoAlfamaSintraBelém
1Day 1

Arrive and settle in

Down to the river

Praça do Comércio

On your own

Why it is worth itLisbon’s grand riverside square, rebuilt after the 1755 earthquake, with its triumphal arch onto Rua Augusta.

Insider tipWalk out to the river steps at the edge of the square at sunset.

2Day 2

The old town, or a food walk

The old town, or a food walk

Alfama viewpoints

On your own

Why it is worth itThe oldest neighborhood in Lisbon, with miradouros such as Santa Luzia and Portas do Sol looking out over the rooftops and the river.

Insider tipThe tram gets crowded at midday; ride it up early or late, and walk back down.

Optional add-on

Lisbon Roots Food and Culture Walk

Taste of Lisboa takes a small group through the old neighborhoods for local tastings and stories, from pasteis de nata to petiscos.

$180 per person

Optional. Not included in the trip price.

3Day 3

Sintra small-group day

Sintra, then fado

Pena Palace and Park

Why it is worth itA brightly painted 19th-century palace on a hilltop above Sintra, part of a UNESCO World Heritage Site.

Insider tipWear comfortable shoes; the park is steep.

Quinta da Regaleira

Why it is worth itAn estate of gardens, grottoes and tunnels, with the Initiation Well, a spiral staircase that winds down into the ground.

Insider tipA phone light helps in the tunnels.

Fado in Chiado

Why it is worth itA 50-minute show of fado, Portugal’s soulful traditional music, listed by UNESCO as Intangible Cultural Heritage.

Insider tipStay quiet during the songs; that is the custom at fado.

4Day 4

Belém

Belém Tower

On your own

Why it is worth itA 16th-century fortified tower on the Tagus river, seen here from the outside.

Insider tipWalk along the river from the monastery to see it.

Optional add-on

Jeronimos Monastery Ticket

Your ticket to the Jeronimos Monastery in Belem and its carved stone cloister, a UNESCO World Heritage site.

$35 per person

Optional. Not included in the trip price.

The order of stops can shift with the weather, and access to some sites can change with the season or local conditions. See Day by day for the full plan.

Why this trip

Portugal ranks #7 on the 2026 Global Peace Index, and Lisbon is one of the easiest European cities to do on your own. You stay in one hotel in Chiado, a central neighborhood where the trams, cafés and viewpoints are a short walk away, and the hotel reception is open 24 hours. A driver meets you at the airport. The days are built around small-group experiences: a Sintra day tour with no more than 8 people and a short fado show, with a food and culture walk as an optional add-on. That means company when you want it and your evenings to yourself. You have one person to message from booking to landing.

  • The old town, or a food walkA slow morning in the old center, or add the Taste of Lisboa "Lisbon Roots" walk (about 3.5 hours, 16 tastings), starting at Largo de São Domingos (optional add-on).
  • Sintra small-group dayA day tour of Sintra with Portuguese For a Day (about 8 hours, max 8 people), meeting at 7:40 AM at Praça da Figueira, about a 10-minute walk from the hotel: Pena Palace and Park, and Quinta da Regaleira.
  • BelémA custard tart at the famous bakery, the riverfront and the Belém Tower from the outside, with a Jerónimos Monastery ticket as an optional add-on.

Trip at a glance

Length
5 days / 4 nights
Starts / ends
Lisbon Airport (LIS)
Getting around
No car needed; private airport transfers booked
Pace
One base, one main plan a day
Best time to go
March to June, and October
Great for
Solo travelers, or two friends sharing
Accommodations
Comfort Plus
Flights
Not included. You book; timing tips in your pre-trip guide

Day by day

Day 1 and day 5 are travel days. The order of the days in between is flexible and can shift with the weather.

Day 1Arrive and settle in
Your Welcome Pickups driver meets you in arrivals and takes you to Lisboa Pessoa Hotel in Chiado. Check-in is from 3 PM; reception will store your bags if you arrive early. Take an easy afternoon walk down to Praça do Comércio and the river, and have an early dinner nearby.
Day 2The old town, or a food walk
A slow morning in the old center, or add the Taste of Lisboa "Lisbon Roots" walk (about 3.5 hours, 16 tastings), starting at Largo de São Domingos (optional add-on). Free afternoon: ride the tram up to the Alfama viewpoints, or rest.
Day 3Sintra small-group day
A day tour of Sintra with Portuguese For a Day (about 8 hours, max 8 people), meeting at 7:40 AM at Praça da Figueira, about a 10-minute walk from the hotel: Pena Palace and Park, and Quinta da Regaleira. Back in time for a 50-minute fado show at Fado in Chiado in the evening.
Day 4Belém
A custard tart at the famous bakery, the riverfront and the Belém Tower from the outside, with a Jerónimos Monastery ticket as an optional add-on. Tram 15E or a short taxi from Chiado (paid locally). Evening free; the hotel's rooftop restaurant has views over the city.
Day 5Home
Check out by noon (or earlier for your flight). Your driver takes you to LIS.

What’s included

Included

  • 4 nights in your own room at Lisboa Pessoa Hotel, Chiado, with the Lisbon tourist tax
  • Private airport transfers both ways (Welcome Pickups)
  • Portuguese For a Day Sintra small-group tour (Pena Palace and Park, Quinta da Regaleira)
  • Fado in Chiado show ticket
  • A day-by-day plan, a one-page solo safety sheet, and one point of contact from booking to landing

Not included

  • International flights
  • Rental car (not needed)
  • Meals; hotel breakfast is extra (about €15)
  • Local trams, metro and taxis
  • Travel insurance
  • Tips and personal spending

Optional add-ons: Lisbon Roots Food and Culture Walk ($180 per person), Jeronimos Monastery Ticket ($35 per person). Add them in the booking box or in Attractions.

Your hotels, experiences, transfers and guides are booked for you. Flights are up to you, and your pre-trip guide includes timing tips.

Questions

What if I need to cancel?
Plans change. If you need to cancel, you'll receive trip credit toward another itsTripEasy trip: within 24 hours of payment, 100% trip credit, so you can swap to a different destination; 90 or more days before your trip start date, 100% trip credit; less than 90 days before, no trip credit, unless you added Flexible Cancellation: with it, you get 100% trip credit if you cancel at least 10 days before your trip start date, for a trip you take within 12 months. Other trip credits never expire. To cancel or change your dates, use the cancellation request form. For a date change, choose the reason "I'd like to change my dates".
Do I need a car?
No. Car-free. A private driver meets you at arrivals and takes you back on the last day. Everything else is walkable or a short tram, metro or taxi ride. The Sintra tour picks up in central Lisbon.
Are flights included?
Flights are up to you, and your pre-trip guide includes timing tips so your arrival and departure fit the plan.
Can the trip be customized?
Yes, right in the booking box: add up to 3 extra nights at the start or end of your trip and choose how many travelers share each room.

Good to know

  • Weather and nature. Weather, road and natural conditions are outside anyone’s control and can change quickly. They may change the plan, close roads, or delay, shorten or cancel tours and activities, and the order of days may shift.
  • Your choices. You are responsible for your own decisions, safety and choices while traveling, including which activities you take part in, and following local guidance, posted warnings and your guides’ instructions.
  • Photos. Photos on this page are for inspiration. They may not show the exact location, hotel, season or conditions of your trip.
  • Not included. Flights aren’t included; you book those yourself.
$4,358
2 travelers · 5 days / 4 nights
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