Say Yes Portugal
The Girls Trip You’ll Talk About Forever
May 4–11, 2027 | 8 Days, 7 Nights | Lisbon & the Portuguese Coast
Portugal in May is warm, golden, and blooming. The summer crowds haven’t arrived yet, the ocean glows at sunset every night, and for one week, it’s ours.
We’ll spend three nights in Lisbon, wandering tiled streets with a warm custard tart in hand, then head to the coast for four nights in a little white-and-blue surf town where nobody wears heels, and the sun sets over the Atlantic outside your window.
We’ll bake Portugal’s famous custard tarts with a chef and eat them warm from the oven, sail past Lisbon’s rooftops at golden hour, ride quad bikes along coastal ridges, take a surf lesson and laugh harder than we have in years, and in between, there’s real rest. Slow breakfasts. Free afternoons. A whole day with nothing on the calendar but the beach and wandering.
This is the trip that makes you feel alive again, and this time someone else is handling every detail. No planning the days. No booking the dinners. No managing anyone’s moods. For one week, the only person you have to take care of is you.
All you have to do is say yes.
By booking, you agree to our Trip Terms & PoliciesDates
May 4–11, 2027
Location
Lisbon & Ericeira, Portugal
Group Size
10 travelers + Macey as host & photographer
Investment
$3,850 per person
Why May?
Why Say Yes to
Portugal in May
May is when Portugal is most alive.
The wildflowers are still blooming on the cliffs. The jacaranda trees are starting to turn Lisbon purple. The days are long and warm, the evenings are golden, and the light is the kind photographers dream about.
May is before the summer crowds and summer prices arrive. The cafés have open tables. The viewpoints feel like secrets. The coast still belongs to the locals, and for one week, we get to share it with them.
These dates were planned with intention. Sunshine without the swelter. Beauty without the crowds. A trip to Europe that actually feels relaxing.
Why Women Keep Saying Yes
“You have such a gift for bringing people together. It never feels awkward or cliquey. By the end of the trip, a bunch of strangers feel like old friends. You make everyone feel like they belong. I’d travel with you again in a heartbeat.”
- Andrea
“As women, we shoulder the entire emotional load of vacations, from planning everything to managing everyone’s emotions. To be able to just shut my brain off, get on a plane, and know that I just get to show up and enjoy myself is so exciting.”
- Salena
“I have never traveled before where I get to just be in charge of my own joy. Not having to plan meals and activities is an actual dream.”
- Julie
The Experience
What We'll Experience Together
This trip is built around moments you’ll be retelling at every dinner party for the next decade.
A few highlights you can expect:
Slow mornings with pastries, espresso, and nowhere to rush off to
Sunset sailboat ride as Lisbon turns gold
Hands-on pastel de nata class in a Lisbon kitchen
Tapas crawl that ends in a tiny fado bar where locals sing their hearts out
Day exploring along Portugal’s most dramatic coastline
Beginner surf lesson (dignity optional)
Scenic quad bike ride through pine trails and clifftop viewpoints
Sunset beach picnic
Golden hour photo session so you go home with photos you love
Free time to wander, nap, shop, beach, or do absolutely nothing at all
Accommodations
Where You'll Stay
Two home bases. One repack all week.
In Lisbon, we’ll stay at a charming hotel in the heart of the city, tucked on a quiet square steps from the bookstores, cafés, and tiled streets we’ll be wandering.
On the coast, we’ll settle into a stylish seaside spot a short walk from the old town, with the ocean close enough to hear.
Rooms are shared, two travelers per room, with your own bed. Bring your best friend as your roommate, or come solo and meet her here. Many of our favorite friendships start exactly this way.
7 nights in well-loved, walkable hotels
Daily breakfast, plus hosted food experiences
Private airport transfers in Lisbon on arrival and departure days
All group transportation, including our private van and driver for the coastal day
Sunset sailboat ride on the Tagus
Hands-on pastel de nata cooking class
Tapas crawl and fado night
Wine tasting experience
Beginner surf lesson
Scenic guided quad bike tour
Sunset beach picnic
All entry fees for group activities
Professional photography throughout the trip
A thoughtfully planned week so all you have to do is show up and enjoy
What's Included
International flights to and from Lisbon (LIS)
Travel insurance (strongly recommended)
Meals not listed as included, roughly five lunches and three dinners (see Meals below)
Alcohol
Personal shopping and souvenirs
What’s Not Included
Meals
About Meals on This Trip
Most meals are taken care of. The rest are yours to discover.
That balance is intentional.
Every breakfast is included, slow and unhurried. So are a handful of hosted food moments I didn’t want you to miss: a welcome toast, dinner after our sunset sail, a tapas crawl through Lisbon’s best little counters, a picnic on the beach, and a farewell dinner with our toes in the sand.
The rest of your lunches and dinners are open for discovery. Portugal is full of tiny family-run spots, and half the joy is wandering into one and feeling like you found it. You won’t be guessing, though. You’ll have my personal shortlist of the places worth your appetite.
20 Years of Professional Experience
You'll Be in the Photos
I’m Macey, a professional photographer with 20 years of experience, and I’m on every single trip.
One of the things women tell me most often is this: “I realized I’m never actually in the photos.” That changes here.
You can put your phone in your pocket and stay completely present. No stopping to document moments you should be living. No asking strangers to take photos that never turn out right. I’ll be there the whole time, capturing the tiled streets, the sail at golden hour, the laughter, and the look on your face when the sun drops into the Atlantic and you realize this is your real life right now.
You’ll leave with a full gallery that captures how this trip felt, not just what it looked like.
Fit Check
Is This Trip For You?
This trip was made for you if:
Europe has been on your list for years, and somehow you’ve still not booked it
You’re always the one who plans the trip, books the dinners, and manages everyone’s moods, and you are ready to hand that job to someone else
You want the trip where you try new things: surfing, quad bikes, singing along in a fado bar
You also want the trip where you rest: slow mornings, beach afternoons, no alarm clocks
You want photos of yourself living your actual life, not just photos of scenery
A heads up: Lisbon is a city of hills and cobblestones, and we explore on foot. Nothing extreme, but comfortable sneakers are a must. If you can walk a few easy miles with café stops built in, you’ll be great.
The Details
Trip Details
Location: Lisbon & Ericeira, Portugal
Dates: May 4–11, 2027 (8 days, 7 nights)
Accommodations: Walkable, well-loved hotels. Two travelers per room, your own bed.
Group Size: Up to 10 travelers + Macey as host and photographer
Investment: $3,850 per person with just a $550 deposit to reserve your spot.
Flights: Fly in and out of Lisbon (LIS). On arrival day, aim to land by early afternoon, before 2:00 pm ideally, so you have time to settle in and join our welcome toast. On departure day, we drive back to Lisbon from the coast together, so book your flight home for 11:30 am or later. That keeps your last morning relaxed instead of rushed. Want a slower goodbye? You can add a night in Lisbon on your own, and we'll drop you in the city instead of at the airport.
A note for the moms: You may notice this trip takes place over Mother's Day in the US. If you're a mom, consider this your permission slip to spend the day however you like. The best Mother's Day gift is the one where nobody needs anything from you.
Due to the nature of small group travel, refunds are not available. You may transfer or sell your spot to another traveler. Say Yes will share your available spot with our community and waitlist to help you connect with someone.
Investment
Ready to say yes to Portugal?
There are only 10 spots available.
Every detail is handled; all you have to do is get to Lisbon.
There are two ways to book.
Either way, your spot is yours the moment you reserve it.
$3,850
Pay in Full
$550
Reserve with Deposit
With three equal payments of $1,100, invoiced 12/5/26, 1/4/27, and 2/3/27By booking, you agree to our Trip Terms & Policies