Flea Markets and Fairytales: Portugal with Ashley and Jenasie
Oct 1, 2026 - Oct 8, 2026
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
-
Acta The Avenue Hotel or similar ⭐⭐⭐⭐
🍽️ 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
-
Acta The Avenue Hotel or similar ⭐⭐⭐⭐
🍽️ 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
-
Acta The Avenue Hotel or similar ⭐⭐⭐⭐
🍽️ 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
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/
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