Expatsi Tours: Uruguay
Uruguay Scouting Trip Itinerary
Whether you’re seeking a cosmopolitan lifestyle or laid-back beach living, this 6-night scouting trip through Uruguay blends city sophistication with coastal charm. You’ll explore Montevideo’s vibrant neighborhoods and culture, travel the scenic coastline to glamorous Punta del Este and artistic La Barra, and tour real estate, markets, and local hubs that define life here. With expert seminars, hands-on guidance, and connections to expats already thriving in Uruguay, you’ll return home inspired and equipped to plan your next chapter abroad. The best part is, you don’t even have to leave if you don’t want to — we’ll be ready to handle your paperwork on the spot.
Day 1 – Montevideo (Pocitos & Punta Carretas)
Arrive in Montevideo and settle into the Pocitos neighborhood, then enjoy an orientation seminar with wine and local cuisine in Punta Carretas, two of the city’s most popular coastal districts.
Day 2 – Coastal Drive to Punta del Este
Travel from Montevideo along the coast, passing through friendly towns like Atlántida, Piriápolis, and Punta Ballena, before arriving in glamorous Punta del Este.
Day 3 – Punta del Este
Discover Punta del Este with real estate visits, coworking hubs, and local schools, with opportunities to connect with expats who call this chic resort city home.
Day 4 – La Barra
Continue exploring the Punta area before transferring to La Barra, a lively beach town known for its surf, art galleries, and vibrant social scene.
Day 5 – Expat Barbecue
Enjoy a special event for fellow expats in Uruguay plus experts in immigration, taxes, concierge services, and more.
Day 6 – Montevideo
Enjoy a last day in Montevideo to explore its neighborhoods, cultural attractions, and real estate options, with optional evening entertainment such as a tango dinner show.
Day 7 – Departure
Transfer to Montevideo’s airport, or extend your stay with optional tours to Colonia del Sacramento, vineyards, or rural estancias.
What to Expect
Community: Meet other people who want to move abroad and enjoy exploring and getting to know each other. There will also be opportunities to meet locals and other expats.
A learning experience: Stay in neighborhoods and live as locals to get a feel for how you might like living in each of our destinations. Meet local experts like realtors, immigration attorneys, and financial planners who know the ins and outs of moving to the local country. Get used to the currency, customs, and transportation.
Life as a local, not a tourist: We’ll bypass the touristy parts of town and experiences like visiting museums and landmarks. Instead, we’ll see livable neighborhoods, markets, and where the locals hang out. It’s easy to enjoy the monuments on your own: just add on a day or two at the beginning or end of your journey, bypass an excursion, or visit them in the evening.
Fun!: We’re all moving abroad for a better life, so we’ll work on giving you a taste of what that means to you.
Meet the Experts
Karen A Higgs, author of the best selling Guru’Guay guidebooks to Uruguay and website, moved there 25 years ago, and relocation experts Sierra Atlantica are trusted friends who’ve helped thousands of people move to Uruguay. They’ll share advice and can get you moved as soon as you’re ready.
Claire, a New Zealander living in Uruguay for 17 years, and her husband Gabriel are co-owners of Tekoa Viajes, your Uruguayan transfer and tour experts.
You’ll be in good hands in Uruguay!
What’s Included
- Seven nights of lodging in Montevideo and Punta del Este, choice of single or double occupancy, breakfast included.
- Tickets to expat barbecue with food and drink.
- Seminar to meet experts in immigration, taxes, and healthcare with food and drink.
- Orientation session before the trip to meet other guests and ask questions.
- Whats App group and Trip Plans app to ask questions, get to know your fellow guests, and follow the itinerary.
- Access to travel agent for booking flights.
- Contact info for experts to schedule appointments to get started on your move abroad.
- Guided tours of popular towns and neighborhoods with a focus on lifestyle.
- Real estate tours of typical homes for sale or rent in each area.
- Private ground transportation for tours and transportation between cities.
- Information on immigration and taxes.
What’s Not Included
- Airfare & airport transfers
- Food or drink not mentioned
As Featured in:
Testimonials
Thank you Jen and Brett for putting this all together. You guys did a great job and we appreciate all of your time and effort to create this experience for us to have. I will never forget it and especially not the connections I made on this journey.
This is such an amazing idea and I’m excited to see how it and we evolve. I look forward to reunions and celebrations as each of us find our new homes.
You realize you’re stuck with us forever, right?
You guys did the damn thing! Group dynamics are tricky but you two showed leadership in both tactical and energetic ways. You exemplified that the path will appear when you take the first step ?
Jen and Brett, with all of the expat resources you and your team provided, a few of us may already be moved by the time we reunite ?
I am full of gratitude for the time I spend with each of you. To Jen and Brett for the drive, vision, tenacity and care to make your dreams and ours, a reality.
Jen and Brett, what you all organized was hard. And all of us stretched. When you do hard things together and succeed, the results are amazing. I feel like we’ve made potential lifelong friends.
Feeling the love over here ? y’all have been amazing and I hope there’s a way to keep in contact as people make moves on their plans. It would definitely help keep me motivated and I believe I can do it!
I feel more like my old self than I have in years. Thank you for taking on the straggler and helping with the healing.
Jen and Brett – thank you so much for following your inspiration and creating Expatsi. You’ve created something very special and it’s been an honor to be a part of it. I sincerely appreciate the feeling of connection, authenticity, and like mindedness we got to share on this trip.
Next Steps
- Attend a Q&A session if you have questions
- Make sure your passport is valid for six months after the trip ends
- FYI, ETIAS may go into effect in 2026 (EU only)
- Book your trip with us
- Complete required forms from us
- Attend trip chats and use Whats App to ask questions and meet fellow travelers
- Schedule your flight, and book your rooms
- Get excited!
Got Questions?
Join virtual Q&A sessions to meet others considering the trip and ask us questions about the cost, itinerary, and more. You can also join our Facebook Group to meet people who’ve gone on past trips or people considering an upcoming excursion.
