Group Trip: Food-obsessed sailing in Portugal

DATES

August 16-23, 2026 [two spots left!]

August 23-30, 2026 [two spots left!]

there are max 5 travelers on each trip

PRICE 3200 USD per traveler

A 8-day retreat sailing south of Lisbon aboard a 43-foot sailboat. With 3 cabins, a wide open deck for sunbathing, an expert skipper, and a private chef on board.

How to book? Click here to email me at letsgo@monetizabeth.com

The trip starts and ends in Lisbon, a seven-hilled city known for its tascas & tiled buildings. In August, this region is deeply summery: hot, dry days, warm ocean breezes, crowded beach towns, and a rhythm built around late dinners & slow mornings. Each night, we’ll sleep on our moving home: a 43-foot private sailboat.

During the day, we’ll sail between small seaside towns and quiet, secluded bays, hopping off the boat to explore the coastline and visit local fish markets. In the evenings, we’ll linger over fresh seafood, wine, and sunset dinners.

All of this will be accompanied by the knowledge of our guide, Austin, a Portuguese-Canadian scholar with a deep love for the region. Through Austin, we’ll learn about the intertwined history of Portugal’s food, culture, and coastline. An accomplished cook, he’ll also be cheffing up many of our meals on board.

What’s it like to sleep on the boat?

I like to describe our sailing trips as camping-adjacent.

There are three double cabins on board. You can book a room for yourself and a friend, or be paired with another traveler of the same gender.

It’s very similar to sharing a tent. We can sleep head-to-toe, you can have your own blanket, or even a sleeping bag liner if that makes you feel more comfortable.

There are two bathrooms on the boat, both with handheld shower capabilities—the sink faucet is also your shower head! There’s also an outdoor handheld shower available on the back of the boat.

Sailing is one of my favorite ways to experience a place. The boat becomes our floating home, giving us access to secluded bays and beaches that are suddenly just a short swim away.

Arrive in Lisbon, meet the crew, and settle into our floating home. We’ll head into the city for dinner as a group, our first introduction to each other and the slow rhythm of Portuguese evenings.

A relaxed morning sail to Sesimbra with breakfast onboard. In Sesimbra, you can explore with the group or head out on your own: stroll the waterfront, visit the castle, and squeeze in a swim or seafood lunch.

Wake up early to wander Sesimbra’s famous fish market. After breakfast, we’ll sail along the coast to Tróia, known for its miles of pristine golden beaches, crystal-clear waters, and resident dolphins. We’ll spend the afternoon swimming, relaxing onboard, or walking the dunes before dinner together in town.

Today is one of our longer sailing days, giving us time to settle into life at sea. Expect long stretches of coastline, salty air, naps on deck, and the occasional stop for a swim if conditions allow. We’ll arrive in the historic port town of Sines by evening, where whitewashed buildings and quiet streets overlook the Atlantic.

A slower day to enjoy Sines and the surrounding coastline. You can wander the market, relax at the beach, take a swim, or simply enjoy a slow morning with coffee on deck. In the evening, we’ll gather for dinner together.

We’ll sail back north toward Setúbal. Along the way, we may stop in secluded bays for swimming or lunch onboard. Setúbal is known for its fishing culture, lively markets, and excellent seafood, making it the perfect place for a long dinner ashore.

Our final sail takes us back toward Lisbon. We’ll spend the day soaking up the last moments onboard: reading on deck, swimming, sharing meals, and watching the coastline drift by before returning to the city. For our final meal, we’ll experience Lisbon’s fado scene.

After breakfast, we’ll say goodbye and head our separate ways — hopefully saltier and with a few new friends.

This itinerary is subject to change depending on weather conditions.

Not at all. The boat is fully crewed with a professional skipper and host. If you want to learn a little about sailing you’re welcome to, but you can also just sit back, watch the cliffs go by, and enjoy the ride.

No extreme fitness required. You’ll need to be able to get on & off the boat unassisted, and be on your feet for several hours at a time.

We’ll go shopping together to get supplies for the boat, splitting the cost. On past trips this has worked out to under 50 euros per person for the week. Usually, we’ll have breakfast and lunch or dinner on the boat each day. Austin will be our head chef. You can pitch in if you’d like, or just sit back and relax.

It’s a very small group, with a maximum of 5 travelers on each trip.

Click here to email me at letsgo@monetizabeth.com

Hope to see you in Portugal!

Monet