Female Only Small Group Trip to Portugal 2025: Lisbon, Obidos, Cascais & Sintra

Portugal

September 28th to October 6th 2025

8 Nights / 9 Days

The image shows a woman standing in a city street, wearing a light lace cardigan over a red dress. She is holding a beige tote bag that reads "A Solo Woman Traveling" with the tagline "Group Trips & Travel Guides" and a website link. The backdrop features a vibrant red building with white-framed windows, and the street has some parked cars, giving the setting a casual, urban vibe, likely in a European city. The woman looks thoughtful as she gazes into the distance.

Let’s Travel Solo Together!

Spend 9 unforgettable days in Portugal connecting with fellow solo female travelers from around the world.

We’ll begin our journey in the exciting capital city of Lisbon, where we’ll explore historic neighborhoods, enjoy incredible cuisine, and take in sweeping views from the city’s iconic miradouros. Then it’s off to the chic coastal town of Cascais for some seaside relaxation, followed by day trips to the fairytale palaces of Sintra and the medieval charm of Óbidos.

This tour is designed for women who love:

Food – Enjoy guided food tours and meals at some of Portugal’s best restaurants, handpicked to give you a true taste of the region.
Wine – Visit local vineyards and indulge in tastings that highlight Portugal’s rich winemaking traditions.
History and Castles – Step into Portugal’s past with guided tours of castles, palaces, and UNESCO-listed sites.
Scenic Cruising – Take in the beauty of Lisbon and the coast with a relaxing boat cruise along the Tagus River.
Free Time – While each day includes a thoughtfully planned group activity, we’ve also built in free time so you can unwind, explore, or simply soak in the moment.:

How it works

Reserve

A non-refundable deposit of 20% is required at the time of booking.

Pay

Set up your payment installements or pay in full. Trip must be paid in full 45 days prior to departure.

Bon voyage!

Prepare for your trip! We will send you travel details and add you to our group chat and private group webpage.

Hotels

Where We Are Staying

We’re kicking off our Portugal adventure with 4 nights in Lisbon, staying at the beautiful Pestana Palace Lisboa, a historic hotel with all the charm and elegance you’d expect in the capital.

After exploring the city’s vibrant neighborhoods, tiled streets, and amazing food scene, we’ll head to the coast for 4 nights at the Hilton Legacy in Cascais—a relaxing seaside town known for its beaches, fresh seafood, and laid-back vibe.

A modern hotel room with a neatly made king-sized bed, two bedside tables with lamps, and a softly lit, textured wall panel behind the headboard.

A cozy lounge area with two red-patterned armchairs, a round beige table, and a decorative wall shelf displaying books, vases, and statues, all set against a floral-patterned backdrop with accent lighting.

An outdoor pool area with white lounge chairs and umbrellas, surrounded by manicured hedges and trees, with construction cranes visible in the background under a clear sky.

A stylish hotel bar with a hanging glass rack, bottles of liquor, and plush armchairs, with natural light coming through large windows and a wine display on the back wall.

A vibrant hotel restaurant with colorful upholstered chairs, neatly set tables with glassware and napkins, and decorative shelving with vases and plants separating dining spaces.

A sailboat with a tall mast glides under a large red suspension bridge at sunset. The water ripples gently, and the sky transitions from blue to a soft orange glow, casting reflections on the water. The bridge’s structure looms above, framing the serene scene.

A historic stone tower, known as the Belém Tower, stands majestically on the waterfront under a bright blue sky with wispy clouds. The water below is gently rippling, reflecting the sunlight. The tower’s detailed architecture is illuminated by the afternoon light, and lush green trees can be seen in the background, along with parts of the Lisbon shoreline.

A steep, cobblestone street in Lisbon, lined with beautifully tiled buildings and balconies, with tram tracks running down the center. The street curves gently toward the horizon, where the bright blue sky and the Tagus River can be seen in the distance. Overhead, a network of tram cables crisscrosses against a backdrop of clouds.

This image captures a stunning view of Lisbon with its iconic red rooftops, the Tagus River in the distance, and the prominent dome of the National Pantheon. The scene is framed by lush greenery under a bright blue sky.

Urban park with a large palm tree and a pond, with ducks swimming.

Cheese display at a deli counter with various types of cheeses and breads.

Tall, pointed white church under a clear blue sky.

A quaint cobblestone street in Óbidos, lined with small traditional houses, one of which has a rustic red facade with a decorative gable. Souvenir shops add color and vibrancy to this medieval town.

A wooden wall display in Óbidos, adorned with medieval-style goblets, figurines of knights, and shields bearing the red cross of the Knights Templar. This display gives a glimpse into the medieval culture of the town.

The cobblestone path leading to the castle walls of Óbidos, Portugal. A small archway and banner can be seen on the ancient stone walls, reflecting the town’s medieval charm.

A charming cobblestone street lined with whitewashed houses with colorful accents. Vibrant red flowers cascade down from vines along the walls, adding a burst of color to the peaceful and quiet village scene.

A rustic stone house with a cobblestone courtyard in a small village. The walls of the house are made of weathered stone, and various pots with plants decorate the outdoor area, giving the scene a cozy, historical feel.

A group of people holding pastel de nata, Portugal’s famous custard tarts, wrapped in napkins. The freshly baked tarts are shared among friends, with the golden tops of the pastries showing off their delicious, slightly caramelized appearance.

A small Jack Russell Terrier stands confidently on top of a stone wall, overlooking a vast, rural landscape. The view includes rolling hills with scattered greenery and trees under a cloudy sky.

A vibrant view of the National Palace of Sintra, framed by lush gardens with blooming pink flowers and greenery. The palace's iconic twin chimneys rise in the background, with colorful houses dotting the hillside.

A beautiful scene in Cascais, Portugal, featuring a cove with clear green waters, rocky outcrops, and people relaxing by the sea. A striped lighthouse stands in the background, framed by palm trees and a historic building, all set under a clear blue sky.

A sandy beach in Cascais, Portugal, with calm blue-green waters gently touching the shoreline. In the background, picturesque seaside buildings and a few visitors enjoying the beach under a bright blue sky.

A serene view of the waterfront in Cascais, Portugal. Small boats are floating peacefully in the calm harbor, with the town's buildings visible in the background, under a pastel sky as the evening sets in.

Tour Itinerary (What We’re Doing!)

Below is an example of our tour itinerary. Most days we have free time as well as an organized activity.

Day 1: Antique car tour of Lisbon, welcome drink and tapas
Day 2: Walking food tour in local neighborhood, sunset boat cruise with snack & wine.
Day 3: Tuk-tuk tour of Belém & Fado show + dinner
Day 4: Day trip to Obidos for castle tour
Day 5: Private transfer to Cascais, coastal tour & wine tasting
Day 6: Free day to explore Cascais, go to the beach or casino
Day 7: Private transfer to Sintra, visit 2 famous Sintra monuments
Day 8: Free time in the morning followed by hidden villages of Sintra tour with wine and tapas
Day 9: Departure day

What’s Included

Pricing

Inclusions

Arrival & Departure Day Airport Transfers
9 Nights Accommodation
1 Dinner
10 Breakfasts
Local Guides
Ferries & Ground Transportation
Entry Fees & Tickets

Exclusions

International Airfare
Travel & Medical Insurance (Required)
Tips for Guides
Alcohol
Meals Unless Mentioned
Gifts

Pricing

€4499 for Single Occupancy
€3899 for Double Occupancy
Includes 20% Non-Refundable Fee
Payment Plans Available

ITINERARY DISCLOSURE

THE PUBLISHED ITINERARY FOR THE GREEK ISLANDS TRIP IS A SAMPLE ITINERARY. ACCOMMODATION, ACTIVITIES, AND EXPERIENCES MAY BE MODIFIED BASED ON WEATHER, AVAILABILITY, OR OTHER UNFORESEEN CIRCUMSTANCES.

TRAVEL INSURANCE DISCLOSURE

A TRAVEL INSURANCE POLICY THAT COVERS MEDICAL EXPENSES, TRIP CANCELLATION, AND OTHER TRAVEL-RELATED ISSUES IS REQUIRED FOR ALL TOURS. POLICIES OFFERED BY TRAVEL CREDIT CARDS DO NOT MEET THIS REQUIREMENT FOR COVERAGE.

Travel medical insurance is mandatory for all participants. To join us, your insurance policy must include at least $100,000 USD coverage for medical emergency evacuation and repatriation.

Credit Card insurance will not be accepted as valid travel insurance for our tours. Therefore, we strongly advise securing a travel insurance policy BEFORE you make any payments towards the trip.

While many of our guests prefer Faye, it’s important to find a policy that aligns with your specific needs. Other reputable providers include Allianz Travel Insurance, Nationwide Travel Insurance, and John Hancock Travel, among others.

Keep in mind, all payments made towards the tour are non-refundable. Travel insurance typically covers cancellations only for covered reasons, which may include unexpected illness (yours or a family member’s), severe weather conditions, or job loss.

For those interested in “cancel for any reason” coverage—which is pricier but can reimburse you for 50-75% of the trip’s total cost—consider options like John Hancock’s “Gold” Travel Insurance or Nationwide’s “Prime” Travel Insurance. Note that these policies often need to be purchased within 14 days following your initial trip deposit.

IMPORTANT: When arranging your travel insurance, please account for any extra days you might be traveling outside our official tour dates, such as arriving a day early or staying an additional night at our suggestion. For instance, if you plan to fly out on October 2nd to ensure your timely arrival for the tour’s start, make sure your insurance coverage begins from October 2nd.

NON-REFUNDABLE PAYMENT DISCLOSURE

ALL PAYMENTS MADE TOWARD THE GREEK ISLANDS TRIP ARE NON-REFUNDABLE AND NON-TRANSFERABLE. WE STRONGLY RECOMMEND PURCHASING COMPREHENSIVE TRAVEL INSURANCE TO PROTECT YOUR INVESTMENT AGAINST ANY UNEXPECTED EVENTS OR CIRCUMSTANCES.

COVID-19 VACCINATION DISCLOSURE

FOR OUR 2025 GREEK ISLANDS TOURS, PARTICIPANTS WILL NOT BE REQUIRED TO BE FULLY VACCINATED AGAINST COVID-19. OUR PRIMARY GOAL IS TO SAFEGUARD THE HEALTH AND WELL-BEING OF OUR TOUR PARTICIPANTS WHILE ALSO PROTECTING THE COMMUNITIES WE VISIT. ALTHOUGH MANY DESTINATIONS HAVE RELAXED THEIR VACCINATION REQUIREMENTS, WE ADVISE ALL TRAVELERS TO STAY INFORMED OF AND COMPLY WITH LOCAL HEALTH GUIDELINES AND REQUIREMENTS. PARTICIPANTS MUST UNDERSTAND AND AGREE TO FOLLOW ANY DESTINATION-SPECIFIC COVID-19 REQUIREMENTS, WHICH MAY VARY FROM OUR GENERAL POLICY.

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Sit back & relax, you’re in good hands

I had the pleasure of being on Melissa’s Portugal trip September 2024. It was OUTSTANDING. The value for the money beyond exceeded my expectations. First of all, Melissa takes all the stress, planning, booking and things you don’t think of out of your mind. Second, everything she selected and booked was beyond perfect. There is an excellent balance of tours and free time. The tours Melissa hand picks are not mainstream and “touristy”, they are a blend of seeing all the right things and the hidden treasures. She is so well connected and focused in on creating a community with the local people that she has developed a unique, boutique style of travel. I can’t say enough about my experience. I wish I could give more than five stars. The amount of work that she puts in and takes away from you is mind blowing. WELL, WELL worth the money. I can’t wait for my next tour!!!!

Tania R.

Portugal Trip 2024

I would give this trip ten stars if I could. Everything was so well organized. It was the perfect balance of planned activities and free time. We stayed at boutique hotels that had personality. We dined at a number of great restaurants. We were spoiled with boat trips, wine tastings and jeep tours. I can’t say enough wonderful things about how Melissa conducted this trip. It was the vacation of my dreams.

Lisa B.

Greece 2025

I had a wonderful time. Melissa was the epitome of a fantastic guide, great organiser and happy travelling companion. Everything ran so smoothly, the accommodation was lovely and the organised activities and free time were perfectly balanced. Melissa could not have been more accommodating, she is very knowledgeable about the areas we travelled to. I can one hundred percent recommend a trip with Melissa and look forward to travelling with her in the future.

Trudy Z.

Portugal 2025

I had the pleasure of traveling to Greece with Melissa and eleven other amazing women during the first week of October, and I can’t say enough good things about the experience. Every day felt like the best day ever, but my absolute favorite was the day Melissa rented a private, ten-hour boat trip for island hopping. Everything was perfect, from the stunning scenery to the seamless organization. Melissa’s attention to detail and dedication to ensuring everyone had a fantastic time was evident throughout the trip. Anytime someone had an issue or needed assistance, Melissa was right there to help. Her enthusiasm and passion for creating memorable experiences made this trip truly unforgettable. I highly recommend Melissa for anyone looking to have an incredible travel experience. She goes above and beyond to make sure everything runs smoothly and that everyone has the time of their lives. Thank you, Melissa, for an extraordinary adventure in Greece!!

Liz. S

Greece Trip 2024

I had a better time than I could ever imagine! It was a wonderful experience. All of the women in our group were so fun and inspiring. I can’t wait to travel on another solo woman trip . Melissa thought of everything and made everyone feel special!

Cassie H.

Greece Trip 2024

This trip was fantastic. Melissa did a wonderful job planning such that I just had to show up! I would not have been able to organize this kind of a trip by myself and been able to experience all that we did, yet the pace was relaxed. The chosen accommodations were excellent, the small group of ladies were a pleasure to travel with and I just loved Portugal! So many great memories and friendships made. Thanks A Solo Woman Traveling!

Cindy O.

Portugal Trip 2024

I recently went on a tour of Portugal (Lisbon, Cascais and Sintra) with Melissa that she organized and it was amazing!!! The communication leading up to the trip and during was clear and concise. My time was being pulled in various directions before the trip and never once did I have to worry about a thing. During the trip the tours, restaurants, activities and recommendations were thoroughly thought out with care and thought about each of us on the tour. I will be looking forward to new trips and will join again in a heartbeat.

Katherine S.

Portugal Trip 2024

The trip was amazing and for a first timer doing a group trip I could not have expected that I would have enjoyed it as much as I did.

Melissa organized this to perfection, from the arrival pick up at the airport to the last day. The hotels were perfect and the locations of each suited all of our needs and easy access to the ferries, boat rides and central to where we needed to go.

The organization of all the tours, trips and the extra special ones like the sunset cruise and taking photos of the most amazing sunsets! A day on the Aegean Sea with a private boat that included a few stops to swim in the Sea, a cave experience, traditional Greek lunch and even some dancing. The most beautiful sunsets on the boats that one could ask for! read more

Ana Marie P.

Greece Trip 2024

This experience exceeded all my expectations. To meet some of the most amazing woman and to experience this journey together was life changing. From authentic Greek cuisine to historical sites to sunset sails and some of the most beautiful accommodations. Melissa(A solo woman traveling) our host beautifully crafted the perfect itinerary combining leisure time with historical site seeing and fun activities. Her seamless planning and attention to details showed in every way possible. Melissa provided us with experiences beyond my expectations and I cannot thank her enough. I would highly recommend A Solo Woman Traveling to anyone wanting a fun, relaxing and educational journey with great company.

Lauren P.

Greece 2024

I joined the trip to Athens, Naxos, Paros and Mykonos. I was an amazing trip and experience. Melissa is the most patient person and best travel guide I could ever imagine. She had everything planned out for transportation, lodging, activities and places to go for meals. This was my first trip out of the country and Melissa made me so comfortable knowing that she had thoroughly planned and researched everything down to all the smallest details. She left us with free time but also planned activities that made me feel like I got to experience a lot of what Greece has to offer. I would love to join another trip lead by Melissa. I appreciate her so much and think she is great at what she does.

Lauren T.

Greece 2024

We had an amazing, seamless trip. Everything was more than we ever expected. All the tours, hotels, and restaurants were top notch. Will definitely book another trip with Melissa in the future.

Ashley B.

Greece 2024

The trip was perfect. All the excursions were well planned and appealed to all the different individuals in our group. Our travel guide, Melissa, even added a personal touch by planning the naming ceremony/activity. The day on a private boat was magical. I never imagined myself swimming in caves and exploring quaint seaside villages. The trip exceeded my expectations.

Pat K.

Greece 2024

A Transformative Journey Through Greece: Embracing New Experiences and Lifelong Friendships Travel has always been a pathway to self-discovery and personal growth, and my recent adventure to Greece exemplified this truth. On October 1, 2024, I embarked on a journey that would take me deeper into both the waters of the Adriatic Sea and the rich cultural tapestry of Greece. This trip, inspired by following the blog of A Solo Woman Traveling – Melissa Leigh, was not only a tribute to my late husband, who passed away unexpectedly at the age of 63, but also a leap towards reclaiming my independence and zest for life. read more

Coco M.

Greece 2024

I stumbled upon Melissa’s blog in early 2024, then joined her FB page and saw she had a female group trip to Greece in October 2024. I had no expectations, other than just wanting to explore a new country that I had not been to before without having to plan the trip myself. Been there, done that and takes a lot of time to do if you’re not familiar with the area/country. So I loved the idea that it was all planned out and all I had to do was book my flight and pack my bags! The trip was beyond anything I could have imaged. From the excursions, tours, dinners, etc., I could not have asked for a better trip. Some of the things that drew me in to her trip was that you had group and alone time to explore, stayed at boutique hotels and a variety of different tours/excursions. I loved the trip so much, that I am going on my second trip through A Solo Woman Traveling to France in August 2025!

Kristina A.

Greece 2024

Traveling with Melissa Byron of A Solo Woman Traveling was an absolute dream. From the moment the tour began, every detail was taken care of with care and precision. The only decision I had to make was what to order from the menu—everything else was flawlessly handled. What made this women-only tour truly unforgettable: • Stress-free logistics: Accommodations, local transportation, daily schedules—completely taken care of. I never had to think about what was next or how we’d get there. • Incredible excursions: Each day brought a new adventure—jeep tours through stunning landscapes, breezy boat rides along the coast, tastings at local wineries, and guided walks through remarkable historical sites. Every experience felt curated just for us. • Beautifully chosen accommodations: Every hotel and guesthouse felt like a hidden gem—comfortable, charming, and perfectly located. • Supportive group atmosphere: There’s something special about traveling with a group of women. The camaraderie, laughter, and shared curiosity made it even more meaningful. • Impeccable planning: Every element felt intentional and seamless. I was able to be fully present, knowing everything was in good hands. I can’t recommend Melissa enough. If you’re looking for a worry-free, inspiring, and joy-filled way to explore the world—this is it. I’m already looking forward to my next trip!

Cindy C.

Greece 2025

I had the pleasure of joining the Portugal tour in May, and it was truly an unforgettable experience! Melissa has a real gift for curating unique, meaningful travel moments that go beyond the typical tourist path. Every detail felt intentional and special. I’m already looking forward to the next one!

Ana M.

Portugal 2025

This was my second trip with Melissa, and once again, she exceeded all expectations. Every detail—from the beautiful accommodations to the amazing food and curated experiences—was perfectly planned and effortlessly executed. When unexpected weather rolled in, Melissa quickly adjusted our itinerary without missing a beat. What could’ve been a washout turned into one of the most memorable days of the trip, thanks to her flexibility and thoughtful planning. Her restaurant recommendations were fantastic, and her deep knowledge of the islands added so much richness to the experience. There’s a reason I keep coming back—Melissa makes travel easy, enjoyable, and truly unforgettable. This won’t be my last trip with her!

Katherine S.

Greece 2025

This was a fabulous trip. Melissa was a great host and planned the best itinerary. I think I saw the high points and intend to return.

Sara P.

Portugal 2025

Got Questions?

While the tour isn’t considered adventurous, our destinations do have their fair share of hills and inclines. I do my best to arrange transportation that minimizes stairs.

The hotel in Cascais does have a pool.

Our tour begins in the at 4pm on the first day, so it be nice to arrive one day prior to the start of the trip. I can help you coordinate accommodations.

In Portugal, the cost of food varies depending on the type of dining experience you choose. For a casual meal at an inexpensive restaurant, you can expect to pay around €8 to €15 per person. If you opt for a mid-range restaurant, a three-course meal might cost between €20 and €40 per person. Fast food and street food are generally cheaper, costing about €5 to €10.

Breakfast is included each day of the tour except the start day. Additional meals are included, which are specified on the itinerary above.

While many travelers can enter on a tourist visa with no extra steps it is important to confirm on the government website.

Meet Your Host!

I’m Melissa

Your go-to girl for all things travel

I’ve traveled to over 40 countries solo! And I’m passionate about helping you explore the world.

My favorite part about traveling is trying the local cusine, taking photographs and making new friends!

I’m a big believer that anyone can achieve their goals if they are willing to work at it!.

Melissa, the founder of A Solo Woman Traveling

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Ready to begin your voyage?

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Five women posing on large rocks surrounded by lush greenery, with a colorful castle visible in the distance atop a hill under a clear blue sky.

Portugal 2024

Highlight Reel

Take a journey through our 2024 adventures in Portugal! From stunning landscapes to unforgettable experiences, this highlight reel on Instagram brings it all to life.

>> Watch now and get inspired to join our next trip!

Female Only Small Group Trip to Portugal 2025: Lisbon, Obidos, Cascais & Sintra

Portugal

Let’s Travel Solo Together!