Porto to Lisbon | Our 2027 Hosted Trip

I once planned an AmaWaterways river cruise through France for an amazing group of women. I worked on every detail for months. Then I got to go.

Seeing it all come together in person was the best part. I knew right away I wanted to do it again, this time with Randy along.

So here we go. Portugal, fall 2027.

Jess Peterman with a group of women travelers outside a chateau in France
Our group in France – the trip that started all of this

Portugal in Full Color at a glance

Dates
September 26 to October 7, 2027 (12 days, 11 nights)
Route
Porto, the Douro Valley, Óbidos and Lisbon
Group size
12 travelers maximum
Hosts
Jess and Randy Peterman, with the group the whole trip
Fly in / out
Into Porto (OPO), home from Lisbon (LIS)
Full details
jesspeterman.com/portugal2027

What is Portugal in Full Color?

Portugal in Full Color is a 12-day hosted small group trip to Portugal from September 26 to October 7, 2027. It is planned and hosted by luxury travel advisor Jess Peterman of Jess Peterman Travel and her husband, Randy Peterman, who travel with the group for the entire trip. The route includes five nights in Porto, a full day in the Douro Valley, a stop in the medieval village of Óbidos and six nights in Lisbon, with a maximum of 12 travelers.

Travel is better with people who love it as much as you do

You know that feeling when you meet someone who loves travel as much as you do? You start swapping stories and suddenly an hour has gone by.

That’s what I want for this trip. A small group of people who get excited about the same things. Who want to stop and look at the tiles. Who order the regional dish without being talked into it. Who are still sending each other photos months after we’re home.

Randy will have the whole table laughing. I’ll make sure the details are handled. You get to enjoy Portugal with people who are on the same page.

Why Portugal?

Randy and I have wanted to go to Portugal for a long time. Here’s what sold me while I was researching:

  • The tiles. They’re on train stations, churches and the outside of buildings. I already know I’m going to stop every five minutes to look.
  • The history. Castles, monasteries and a red and yellow palace on a hilltop in Sintra.
  • The food. Fresh seafood, the original pastéis de nata in Belém and port in the city it’s named after.
  • The coffee. Portugal takes its cafés seriously and you know I’ll find the good ones.

It’s also really doable. The drives are short, one train ride gets us into the Douro and you only change hotels once.

Colorful buildings along the river in Porto's old city Yellow vintage tram on a street in Lisbon

Why late September in Portugal?

We picked these dates on purpose. Summer in Portugal is hot and packed. By late September it cools off, the crowds thin out and the locals have their cities back.

It’s also harvest season in the Douro Valley. The grape harvest, called the vindima, runs through September into early October, so the vineyards are busy and we get to see it happening.

Pro tip: Sintra is one of the busiest day trips in Portugal. Going after the summer rush makes a big difference at Pena Palace

Terraced vineyards along the Douro River seen from a train window
The Douro Valley by train

Why two home bases?

I’m not a fan of packing up every other morning and I’m guessing you aren’t either. So we stay put in two places and make one move south.

Porto: 5 nights

The Bolhão Market, port blending, a tuk tuk tour and a full day in the Douro Valley by train and riverboat. There’s also an open day to sleep in and have that second coffee.

Óbidos on the way south

A walled medieval village with flowers over the doorways. It turns a travel day into a highlight.

Lisbon: 6 nights

Sintra, tile painting, a cooking class, Belém and a farewell dinner with live fado, plus open time to wander Alfama and Chiado.

Flowers over a doorway on a stone street in Óbidos, Portugal Front stairs of the colorful Pena Palace in Sintra, Portugal

What’s the difference between a hosted trip and a group tour?

This is the question I get the most, so here’s the short version.

Large group tourDIY tripPortugal in Full Color
Group sizeOften 30 to 50 peopleJust you12 travelers maximum
Who plans itA tour companyYou, with a lot of open tabsJess, with vetted local partners
Who’s with youA tour director you just metNo one if something goes wrongJess and Randy, all 12 days
PaceFixed schedule, lots of bus timeWhatever you can figure outGuided days plus two open days
HotelsOften outside the centerYour best guess from reviewsChosen for location and character

On a big tour, you’re following a flag. On your own, you’re the one up at 6am figuring out the train schedule. On this trip, I’ve got the details, local guides have the stories and Randy’s got the jokes.

What I’m most excited about

  • Blending our own port. We each make a bottle and label it ourselves. A nonalcoholic option is available.
  • The Douro Valley. A scenic train, a riverboat, a winery and a long lunch with no reason to rush.
  • Painting tiles. After a week of staring at them everywhere, we finally get to make one.
  • The cooking class. We shop the market, then we cook. Not a demo.
  • Fado on our last night. Live music, a small restaurant and all of us together one more time.
Hand-painted blue azulejo tiles in progress at a workshop in Lisbon

Is this trip for you?

My first question for anyone interested is, “What are you most excited to do in Portugal?”

If you said Sintra, the Douro Valley or the food, you’re going to love this trip. It’s a great fit if you:

  • Love history and culture and always try the regional dish
  • Want the research done right without doing it yourself
  • Like the idea of a small group that turns into friends
  • Are comfortable walking on cobblestones, hills and stairs

If you’re more of a shopping-and-pool traveler, that’s totally okay. I’d love to help you plan a trip that fits you better.

A travel group sharing a long outdoor meal under trees

Frequently asked questions

When is the Portugal in Full Color trip?

Portugal in Full Color runs September 26 to October 7, 2027. It is 12 days and 11 nights, starting in Porto and ending in Lisbon.

How many people are on the trip?

The group is capped at 12 travelers. Hosts Jess and Randy Peterman travel with the group for all 12 days.

Where do travelers fly in and out?

Travelers fly into Porto (OPO) and home from Lisbon (LIS). International airfare is not included. Jess provides flight guidance before booking.

Do I need to drink wine to enjoy this trip?

No. Wine and port are part of a few experiences. A nonalcoholic option is available for the port blending workshop.

Can solo travelers join?

Yes. Solo rooms are limited, so solo travelers should contact Jess before reserving.

How active is the trip?

The trip includes walking tours on cobblestones, hills and stairs, plus full sightseeing days. It is best for travelers who walk comfortably on uneven ground.

What’s included in the trip?

Hotels, private airport transfers, guided touring, the listed meals and tastings, gratuities for included guides and drivers plus Jess and Randy hosting the full trip. The complete list is on the trip page.

How do I reserve a spot?

Reservations are made through the Portugal in Full Color trip page. Travelers who want to talk it through first can schedule a trip fit call with Jess.

Come to Portugal with us

Next fall, we could be sitting on a rooftop in Lisbon together.

Everything you need to know is on the trip page: the full itinerary, the hotels and how to reserve. Not sure if it’s for you? Let’s chat and I’ll tell you if it’s a good fit.

See the Trip Details Book a Trip Fit Call

Want more trip ideas and planning tips? Come join my Facebook group.

Warmly, Jess

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