Solo vacation after 50: How to plan the trip of your life with confidence.

Every woman’s reason for taking a solo vacation is different.

Maybe you want a break from routines, or maybe you’re ready for something new and just need a little push.

Whatever your reason, a solo vacation after 50, can open doors you didn’t even know were there.

Since my first solo trip, I’ve met so many women who tell me they dream of traveling alone but never quite get around to it. I always say the same thing: Don’t wait. you don’t need a perfect plan, you just need to start. 

A travel guide for your solo vacation

This guide will help you see all the places you want without feeling rushed or overwhelmed by mixing travel, discovery, and simple pleasures.

Start with a wish list

Before any logistics, begin with your wish list. Write down what you dream of in a vacation, then use it as a compass for planning.

It’s never final, and it changes many times even in the middle of your trip. 

Are you traveling to Lisbon in the winter?

Are you coming in June?

Your wishlist for a solo vacation may include:

• Slow travel
• Good restaurants
• Comfortable hotels that don’t break the budget
• Walking, swimming, and easy hikes
• Photography and painting time
• A workshop or class
• Opportunities to meet people, balanced with solo time group tours for specific days
• Public transport and car rental options

What is Slow Travel?

• Slow travel is about connecting to the places you visit.  
• It’s about the depth instead of speed. 
• Visit fewer places and stay longer.

Sample 14-Day Portugal Itinerary (keep it flexible!)

Day 1 Arrival in Lisbon

• Morning: Arrive, get settled.
• Lunch: Mezze at the Arroios Market (Middle Eastern food in a lively local market).
• Late afternoon:  Walk along the Tejo River near Cais do Sodré.
• Evening: Light dinner near your hotel, rest.

Day 2  Lisbon Group Tour

• Morning: Take a walking or city highlights tour. Read: One day in Lisbon.
• Evening: Rooftop drink at Independente in Príncipe Real.
• Dinner: Tapisco Restaurant (tapas and petiscos). Alternative: Book a dinner with Fado music.

Day 3 – Toino Abel Atelier

Pick up a rental car.

• Drive to the atelier near Óbidos to learn to weave and make your own straw bag at Toino Abel. (Book in advance.) You will be learning about one of the oldest craft traditions in Portugal.
• Overnight at the atelier’s cottage or nearby.

Day 4 – Óbidos and Nazaré

• Morning: Explore medieval  Óbidos.
• Lunch in town.
• Late Afternoon: Drive to Nazaré.
• Dinner in Nazaré.

Day 5 – Nazaré Slow Day

• Morning: Walk  coastal paths, sketch and photograph.
• Lunch: Fresh seafood in Nazaré.
• Afternoon: Walk up the hill to see upper Nazaré (Sitio or Sitio de Nazaré) and photograph the church and the gorgeous views. 
• Evening: Dinner in Nazaré

Day 6 Road trip

• Morning: Day trip to Alcobaça, visit the monastery solo or join a tour.
• Lunch: in Alcobaça
• Afternoon: Explore the city. Eat the typical pastries from this area.
• Dinner in Nazaré.

Day 7 – Aveiro

• Morning: Drive north to Aveiro. Walk around the city, check out the famous canals, eat their pastries and walk on the boardwalk near the beaches.
• Dinner in Aveiro.

Day 8 – Porto Slow Day

• Morning: Drive to Porto.
• Join a foodie walk for a fun way to explore Porto.
• Afternoon: Visit bookstores, coffee shops, sketch, or just wander.
• Evening: Dinner at one of Porto’s many small restaurants.

Day 9 – Douro Valley

• Tour Full-day guided tour with wine tastings and a boat ride (seasonal).
• Dinner: On the road or Porto

Day 10 – Braga

• Explore Braga. 
• Dinner: Porto

Day 11 – Tomar and Almourol

• Spend the night in Tomar
• Visit the Convent of Christ, once a Templar stronghold. Walk around the city.
• Drive to Almourol.
• Dinner in Tomar.

Day 12 – Return to Lisbon

• Slow day in Lisbon. Optional tours or rest. Option: Hire a private guide.
• Dinner in Lisbon.

Day 13 – Sintra or Nature Walk

Option 1: Hire a hiking guide to go to the Sintra hills.

Option 2: Drive to Quinta do Pisão near Cascais for a gentle walk.

Evening dinner in Cascais or back in Lisbon.

Day 14 – Last Day in Lisbon

Revisit favorite spots, and check out my favourite hidden gems in Lisbon. 

Evening: Rooftop drinks and dinner

For women over 50, travel is about freedom and choosing how you want to spend your days.

This schedule will help you organize your solo vacation to Portugal, and best of all, it’s flexible.

Personalize your trip: You can stay longer in one place, skip another, or add something new.

Tips for a confident, fantastic solo vacation

Here are a few ideas I keep in mind during every solo trip:

• Stay safe, stay alert, share your itinerary with family or friends, trust your gut.
• You are safer among people, do not go hiking in nature alone, keep your documents and credit cards safe and hidden! Be attentive in crowded areas and public transport.
• Mix solo days and social days, balance is key.
• Give yourself creative time to sketch, photograph, journal, or your favorite hobby.
• Flexible planning! Skip or linger whenever you feel like it.
• Lean into the local rhythm and try local markets, cafes and walking tours.

Return home renewed

Travel changes you. On a solo vacation after 50, you’ll come home with:

• A deeper sense of self.
• Stories you can’t wait to tell.
• A fresh lens on your everyday.
• Renewed energy and curiosity.

You don’t have to plan an epic trip right away. Even one solo weekend away can shift your perspective.

If you are planning your first solo trip to Lisbon

Check out my guides on packing for Lisbon in the fall, summer and Day trips from Lisbon.

And if you enjoy stories and tips like this, subscribe to The 50 and Rising Edit on Substack for weekly inspiration on travel, creativity and living deliciously after 50.

I’m Marguerite Beaty, artist, photographer, and founder of 50 and Rising.

I write for women over 50 who are curious about travel, creativity and who want to live deliciously!.

Updated October 2025

New itinerary, travel ideas, and more down time on this update!

FAQ solo vacation