How To Plan An Epic Trip To Lisbon

How To Plan An Epic Trip To Lisbon

Lisbon is one of the most popular budget destinations in Europe. Is a trip to Lisbon on your bucket list? If not, consider adding it. Because the city wraps grit and beauty comfortably like a warm blanket. You’ll see and feel it the moment you arrive.

Lisbon also brazenly embraces its’ adventurous roots. Museums and statues salute a glorified history of pursued opportunity and conquest. Strolling along the cobbled streets feels as though you’re walking back through history.

Read on as I provide the travel resources I’m using. See how my process works for the trips I take.

Ready to start planning? Let’s get you motivated to plan an epic trip to Lisbon.

Get Flights

I have a 5-guy travel crew and we’ve talked about taking a trip to Lisbon for years. Finally, this is the year we’re making a 5-day trip happen.

Flights are the very first item to check off. Everything else falls into place from there.

Franc Tip: Once you start telling friends about your great trip to Lisbon, some may want to join. As awesome as it sounds, know it’s all talk until they book their flights. Once they commit and buy tickets, then get excited.

Chicago’s O’Hare Airport has non-stop destinations all over the world. Luckily for us, the Portuguese airline TAP airlines fly direct to Lisbon.

Budgeting is a key component. After a few group texts back and forth, everyone was comfortable spending $600 round-trip.

We were about a month before our desired departure date. Less than 6 weeks before a trip can be problematic in getting cheap flights to Europe. Since February is not high season, I anticipated demand would be lower. And it was.

A quick Google flights check showed TAP was the cheapest and fastest to Lisbon. Not a surprise to those us spending countless hours following airfare trends. The basic economy flight was a shade under $600. Perfect!

Informed the group via text. The flight confirmations rolled in.

Franc Explanation: Basic economy is the lowest fare airlines publicly offer. Usually, you can’t pick your seats. Only get a carry-on. And, you get next to nothing mileage-wise towards free flights.

Find A Place To Snooze

Where you rest your head can make or break a trip. Are you a soft sleeper? Make sure you have a quiet space. Know what you need to be comfortable with. You’re on vacation. Get good snooze-time!

Once again budgeting is key. You have to know what you want and how it fits the budget.

We anticipate some late nights. Since we’re 5 dudes, a quiet, romantic bed and breakfast won’t work.

A 24-hour hotel is a solid option.

I did check Airbnb. Pricing was similar to many hotels. However, limited access to the hosts and early quiet times wasn’t the best for us either.

One of our crew has access to employee rates at certain hotels. Where we were able to secure a $30/night per person rate at the Holiday Inn Express – Saldanha. It’s hard to beat that deal.

However, I did check Booking and Trivago to compare. We saved about 10% with the employee rate. Even without the employee rate, Lisbon during the off-season is very reasonable.

Franc Tip: If your plans are not flexible, opt for the non-refundable hotel rates. You can save 10% or more.

The Fun Stuff

With flights and hotel checked off, I could concentrate on the revelry. This being my 2nd time to Lisbon, I know the typical touristy spots. But, I want the crew to have a local experience.

In our chats, the crew wanted one planned group activity. A food and wine tour. I decided to find a local guide to show us around the first night. To get us comfortable in Lisbon.

Mass tours following umbrellas or flags around tourist areas are not what I had in mind. I wanted a local to give us insider tips. A more personal experience. To enjoy Lisbon more like a local.

While researching the best tours on Tripadvisor, I discovered WithLocals. It appears to be a new-ish company operating in the last few years. The concept of connecting locals with tourists in the right way was appealing.


They must have a decent amount of funding to back their company. They have mobile app versions for both Android and Apple. The app is very intuitive and easy to use. It has a texting/conversation feature which makes it convenient to arrange tour requests with local guides. I took the plunge and joined.

I connected with a local named Ana via the app. After a few texts, we agreed on a 3-hour tour of her favorite foodie spots with drinks included. She’ll be fun, enthusiastic and fantastic based on her reviews. We’ll maintain flexibility for the following days based on Ana’s expertise on what else to do. Perhaps we’ll do a winery tour as well.

Franc Tip: In Lisbon, there are free, get to know Lisbon tours. You pay the guide a tip afterward. It could be a good option if you have low expectations for a free service.

Post Trip Update: Ana certainly took a local restaurant on the northeast corner of Rossio Plaza. We sat outside which was enjoyable. We had a typical chicken dish along with other meats and octopus. We sampled the Ginjinha (Portuguese berry liqueur). Ate the famous Bifana sandwich at O Trevo. And, ended the tour eating the delectable custard tart (Pasteis de Nata). The tour was enjoyable and Ana was nice. I’m unsure we would use WithLocals again.

Planning Continues

Lisbon has a few “must-see” touristy sites and activities. I’ll plan to take the crew on the famous Tram 28. Visit the Sao Jorge Castle. And, see the Jeronimos Monastery.

The town of Torres Vedras is around 40 minutes from Lisbon by car. It also hosts their version of Carnival. Based on Youtube videos, it looks fun and the party rolls on to the early morning.

We may also take a day trip to Cascais and Sintra.

4 nights isn’t a lot of time. We need to balance maximizing time and relaxing.

Post Trip Update: Carnival was a stop to remember. Definitely find a store close by the grounds and buy some costumes. Immerse yourself in the revelry. Beer, shots and sandwiches can be bought in kiosks lining the streets. Amazingly cheap as all are priced around 2 Euros.

Planning what to do depends entirely on interests. Know you can’t see everything. Pick your top must-see items. Take your time to enjoy it.

If you’re looking for help planning a trip to Lisbon, contact Franc.

Read. Plan. Travel. Repeat!


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