Skip to main content
New Pending Creator

Flea Markets and Fairytales: Portugal with Ashley and Jenasie

Oct 1, 2026 - Oct 8, 2026

Cultural Cultural

$3,799 USD

BOOK WITH $750 DEPOSIT

Flea Markets and Fairytales: Portugal with Ashley and Jenasie

Oct 1, 2026 - Oct 8, 2026

$3,799  USD

BOOK WITH $750 DEPOSIT

From the cobbled laneways of Porto to the sunlit plazas of Lisbon, this journey through Portugal is a celebration of color, culture, and timeless charm. With its azulejo-tiled facades, bright yellow trams, and ocean-blue horizons, Portugal dazzles the senses at every turn – a place where vivid hues and soulful energy bring centuries of history to life.

Hosted by Ashley Wilson together with co-host Jenasie Earl, this handcrafted itinerary reveals the heart of the country through its artistry, creativity, and warmth. You’ll wander through colorful neighborhoods, meet local makers, explore lively markets, and uncover the architectural masterpieces that define Portugal’s rich identity. From painting your own tiles to tasting traditional dishes, this trip invites you to experience the country’s vibrant palette – one that’s as expressive as its people.

Along the way, enjoy welcoming 4-star stays, warm hospitality, and meaningful cultural encounters that capture the essence of authentic Portugal. Whether you’re sipping coffee by the Douro River or wandering through Lisbon’s creative corners, this journey invites you to slow down, savor, and truly connect – with the colors, the culture, and the spirit of Portugal.

Trip Start: Porto, Portugal - Tuesday October 1st, 2026

Trip Finish: Lisbon, Portugal - Tuesday October 8th, 2026

Trip Duration: 8 Days / 7 Nights

Accommodation: 7 Nights Hand-picked ⭐⭐⭐⭐ Hotels (Shared & Private Available)

Included Meals: Breakfast Daily, Lunch x 2, Dinner x 2

Group Size:

Inclusions

7 Nights in⭐⭐⭐⭐ Hotels in Porto and Lisbon

Included Meals: Breakfast Daily, Lunch x 2, Dinner x 2

Trip Hosted by Ashley Wilson with Co-host Jenasie Earl

English-Speaking Local Guides Throughout

All Ground Transport as Detailed in Itinerary

All Entrance Fees for Listed Attractions

Welcome Dinner with Host Ashley

Guided Walking Tour of Porto’s Historic Center

Visit to Livraria Lello Bookstore

Tile Painting Workshop with Local Artisan

Entry and Guided Tour of Palácio da Bolsa

Visit to Feira da Vandoma Flea Market

Junk Journaling Night with Ashley & Jenasie

Lisbon City Walking Tour and Traditional Tram Ride

Full-Day Excursion to Sintra Including Quinta da Regaleira and Palácio de Monserrate

Included Lunch in Sintra

Private Coach Transfer from Porto to Lisbon

Visit to Feira da Ladra Flea Market in Lisbon

Visit to Ler Devagar Bookstore

Visit to Palácio Nacional de Queluz

Visit to National Tile Museum (Museu Nacional do Azulejo)

Included Farewell Dinner in Lisbon

Exclusions

Arrival/Departure Flights

Airport Transfers

Visa/Entry Requirements

Meals Not Mentioned in Inclusions

Personal Expenses incl Tips

Travel Insurance (Required)

Hotel City Taxes

Your Host

Ashley Wilson

I’m Ashley – decorator, DIYer, and travel lover behind At Home with Ashley! When I’m not transforming my home in Logan, Utah, I’m exploring beautiful places around the world. My happy places? Flea markets, charming bookshops, and colorful interiors that tell a story. I’ve hosted group trips to Paris, Florence, Morocco, and Charleston, and nothing makes me happier than connecting with creative, like-minded travelers along the way. I love seeing the world together – laughing, shopping, and soaking up all the inspiration each destination has to offer.

Itinerary

Day 1 Arrival in Porto & Welcome Dinner

Welcome to Porto – a city of color, charm, and creative spirit. Upon arrival, make your way to the joining hotel for check-in and some time to relax. With its hillside neighborhoods, blue-and-white tiled churches, and the shimmering Douro River below, Porto is the perfect place to begin your journey through Portugal’s artistic soul.

In the evening, gather with Ashley and your fellow travelers for a special welcome dinner at a traditional Portuguese restaurant. Enjoy your first taste of local cuisine, share stories, and toast to the week of discovery ahead.

🏨 Accommodation

🍽️ Included Meals

  • Dinner

✅ Activities

  • Welcome Dinner at a Traditional Restaurant

Day 2 Porto Essentials & Tile Workshop

After breakfast, set out on a guided walking tour with your experienced and knowledgeable local guide to explore Porto’s historic heart – a patchwork of colors, textures, and stories. Wander through the cobbled lanes of the Ribeira district, where pastel buildings rise above the riverfront and laundry flutters from iron balconies. Visit the majestic São Bento Station to admire its stunning azulejo murals, depicting Portugal’s history in brilliant blue and white tiles. Cross the iconic Dom Luís I Bridge for panoramic views of the city’s terracotta rooftops and the sparkling Douro below.

You’ll also step into the magical Livraria Lello, one of the world’s most beautiful bookstores, where stained glass, carved wood, and a sweeping red staircase have inspired artists and writers for over a century. In the afternoon, channel your own creativity during a tile painting workshop led by a local artisan. You’ll paint two traditional azulejos, which will be fired overnight and ready for collection the next day – a perfect keepsake from Portugal’s artistic heart.

🏨 Accommodation

🍽️ Included Meals

  • Breakfast

✅ Activities

  • Porto Walking Tour
  • Visit to Livraria Lello
  • Tile Painting Workshop

Day 3 Local Treasures & Cultural Heritage

This morning, immerse yourself in Porto’s local life with a visit to Feira da Vandoma – the city’s oldest and most colorful flea market. Stroll among the bustling stalls filled with antique books, retro posters, ceramics, and vintage treasures. It’s a photographer’s paradise and a cultural time capsule that captures the city’s creative and quirky spirit. After exploring and picking up a few unique finds, return to the hotel to drop off your discoveries.

In the afternoon, continue your journey through Porto’s cultural heritage with a guided visit to the Palácio da Bolsa, a 19th-century architectural masterpiece once used by merchants and dignitaries. Its Arab Room, inspired by Moorish design, shimmers with gold leaf and intricate detail. Later, collect your beautifully glazed tiles from the workshop – a lasting reminder of your creative connection to the city.

After a day of treasure-hunting at the flea market, unwind with an evening of creativity and connection. Gather with Ashley and Jenasie for a relaxed junk journaling session – the perfect way to capture the beauty and inspiration of your travels. We’ll start with a little “show and tell” to share favorite finds from the market, then get crafty assembling our own Portugal-inspired travel journals with kits provided by your hosts. This cozy creative night is all about slowing down, laughing together, and turning your travel memories into art.

🏨 Accommodation

🍽️ Included Meals

  • Breakfast

✅ Activities

  • Visit Feira da Vandoma Flea Market
  • Guided Tour of Palácio da Bolsa
  • Collection of Finished Tiles
  • Junk Journaling Night with Ashley & Jenasie

Day 4 Porto to Lisbon

After breakfast, board your private coach for the scenic journey south to Lisbon, passing rolling vineyards, sun-drenched hills, and picturesque coastal landscapes. Along the way, you’ll see how Portugal’s beauty extends far beyond its cities – a tapestry of rural charm and coastal elegance.

Upon arrival, set out on a guided walking tour of Lisbon’s historic center. Explore the elegant boulevards of Baixa, the boutique-lined lanes of Chiado, and the maze-like alleys of Alfama – where brightly painted houses and street art blend into a kaleidoscope of color. End the day with a ride on Lisbon’s iconic yellow tram, an enduring symbol of the city’s old-world charm and everyday creativity.

🏨 Accommodation

🍽️ Included Meals

  • Breakfast

✅ Activities

  • Private Coach Transfer to Lisbon
  • Lisbon Walking Tour
  • Traditional Tram Ride

Day 5 Day Trip to Sintra

Today’s adventure takes you to Sintra – a dreamlike town tucked among misty forests and fairytale palaces. Begin at the mystical Quinta da Regaleira, where winding tunnels, hidden towers, and lush gardens tell stories of myth and symbolism. Then visit Palácio de Monserrate, a masterpiece of romantic architecture blending Moorish, Gothic, and Indian influences in soft pinks and ivory whites.

Surrounded by tropical gardens bursting with color, Monserrate feels like a painter’s dream. Enjoy an included lunch at a local restaurant, soaking up the charm of this UNESCO World Heritage town before returning to Lisbon in the late afternoon.

🏨 Accommodation

🍽️ Included Meals

  • Breakfast

  • Lunch

✅ Activities

  • Visit to Quinta da Regaleira
  • Visit to Palácio de Monserrate
  • Included Lunch in Sintra

Day 6 Lisbon’s Creative Corners

Discover Lisbon’s artistic and bohemian heart, starting at Feira da Ladra – the city’s famous open-air flea market where locals sell everything from antique tiles and vintage vinyl to handmade crafts. It’s a kaleidoscope of colors and creativity, nestled in Alfama’s historic streets.

Later, visit Ler Devagar, one of Europe’s most beautiful bookshops, housed in a former printing factory. Its soaring ceilings, floating bicycle sculpture, and shelves of art and literature create an atmosphere that celebrates imagination and culture. The rest of the day is free to explore Lisbon’s galleries, boutiques, or colorful street murals that reflect the city’s creative pulse.

🏨 Accommodation

🍽️ Included Meals

  • Breakfast

✅ Activities

  • Visit Feira da Ladra Flea Market
  • Visit Ler Devagar Bookstore

Day 7 The Versailles of Lisbon

Begin your final full day with a private transfer to the stunning Palácio Nacional de Queluz, often called the “Portuguese Versailles.” Stroll through its pastel-pink halls and formal gardens adorned with fountains, statues, and gilded detail – a glorious reflection of Portugal’s royal artistry.

In the afternoon, visit the National Tile Museum (Museu Nacional do Azulejo), where centuries of color and craftsmanship come to life through intricate tilework. You’ll see everything from 16th-century religious panels to bold contemporary designs that prove Portugal’s creative spirit is as vibrant as ever. Tonight, gather with your group for a farewell dinner – a final toast to art, friendship, and the colors of Portugal.

🏨 Accommodation

🍽️ Included Meals

  • Breakfast
  • Lunch
  • Farewell Dinner

✅ Activities

  • Visit to Palácio Nacional de Queluz
  • Visit to National Tile Museum
  • Farewell Dinner

Day 8 Fond Farewell

Enjoy a leisurely breakfast before saying goodbye to Lisbon’s light and color. Take one last stroll through its elegant boulevards or relax at a café as you reflect on a week filled with creativity, culture, and connection.

As you depart, carry home not just your painted tiles and photos – but the spirit of Portugal’s artistry, warmth, and joy.

🍽️ Included Meals

  • Breakfast

✅ Activities

  • Departure Day

Trip Photos

Important Notes

ARRIVAL:
You will need to make sure your travel plans allow you to arrive at the meeting point by the scheduled guest meeting time. More information on this will be provided once the trip is confirmed. Your arrival airport is Francisco Sá Carneiro Porto Airport (OPO/LPPR).

DEPARTURE:
On the final day, you are free to depart at any time. Your departure airport is Humberto Delgado Lisbon Airport (LIS).

AIRPORT TRANSFERS:
Airport transfers are not included as part of this trip, so you will need to make your own arrangements. More specific information on transport options for your arrival and departure airports will be available on the airport websites.

Pre-booked airport transfers are available for most airports via Expedia – please select “Cars” and then “Airport Transportation”: https://bit.ly/expedia-best-in-travel-vip

ADDITIONAL NIGHTS ACCOMMODATION:
We are unable to organise additional nights accommodation on your behalf. Our exact hotels will be finalised and advised roughly 2-3 months prior to the trip starting. We will advise guests once that happens, and we then recommend booking accommodation via our affiliate link at https://bit.ly/booking-com-best-in-travel

ENTRY REQUIREMENTS:
Be sure to check entry requirements based on the passport that you will be travelling with. It is your responsibility to ensure that your passport meets minimum requirements, and that you have arranged any required visas before arrival. Visa information is available in the destination guide linked below.

DESTINATION GUIDE:
For a detailed destination guide for this trip’s location, head to https://bestintravelgroup.com/portugal-destination-guide/

TRIP CONFIRMATION:
A trip is listed as PENDING until the minimum guest numbers are reached, at which point the trip becomes CONFIRMED. Guests will be notified when a trip becomes CONFIRMED.

BOOKING FLIGHTS:
We do not recommend booking flights until your trip is CONFIRMED.

BOOKING T&Cs:
We recommend you familiarise yourself with our Booking Terms & Conditions for more information about our booking, deposit and cancellation policies.

TRAVEL INSURANCE:
Travel insurance is required, and this will need to organised independently. There are a number of travel insurance comparison websites available. We do not recommend organising this until your trip is CONFIRMED.

For more information on travel insurance head to https://bestintravelgroup.com/protect-your-adventure-best-in-travels-guide-to-travel-insurance/

ISSUES & CONTACTS DURING THE TRIP:
If you experience any issues that you need resolved during this trip, please chat to your host or your local driver/guide. Emergency contact details for your local trip operator will be provided prior to the trip starting.

For more information on the correct process for handling issues during a trip, including emergency situations, please read the following guide: https://bestintravelgroup.com/managing-emergencies-other-issues-on-your-best-in-travel-adventure/

INCLUSIVITY:
For information on how Best In Travel creates a welcoming space for all travellers, please head to: https://bestintravelgroup.com/everyones-welcome-inclusivity-on-best-in-travel-group-trips/

Recent Reviews

Click the button below and be the first to review this.

Taken this trip before?

Click the button below and be the first to review this.

Leave a review

Leave a review by completing the form below

Rating:
Got questions?

Register your interest for

Flea Markets and Fairytales: Portugal with Ashley and Jenasie



    Contact us

    Please fill in this form and we’ll be in touch soon.



      INSTAGRAM

      @bestintravel