Expatsi Tours: Costa Rica
Costa Rica Scouting Trip Itinerary
Whether you’re picturing a peaceful retirement by the beach or a flexible lifestyle as a digital nomad, this 6-day scouting trip through Costa Rica offers the perfect mix of discovery, clarity, and inspiration. From the cultural heart of San José to the sun-soaked Pacific coast of Tamarindo, you’ll experience daily life as a local—touring diverse neighborhoods, visiting real estate options, exploring markets and healthcare, and connecting with professionals who can guide you through the legal and financial steps to make your move with confidence.
Day 1 – San José Seminar
Arrive in San José and be welcomed by your local guide, then join an information seminar in Escazú on how to move to Costa Rica before gathering with your group for a welcome dinner of traditional cuisine.
Day 2 – Pretty Suburbs
Explore the vibrant neighborhoods of Escazú, Santa Ana, and Heredia with real estate tours, then enjoy a relaxed evening with free time for dinner on your own.
Day 3 – Country Life
Visit the charming mountain towns of Atenas, Grecia, and San Ramón to get a feel for daily life and housing options before returning to San José for a restful evening.
Day 4 – Make Way to the Coast
Depart San José and travel toward the coast, stopping for lunch and exploration in Nosara before arriving in Tamarindo and settling into your new hotel.
Day 5 – Coastal Havens
Spend the day exploring Costa Rica’s stunning Pacific coastline with tours in Tamarindo, Conchal, Flamingo, and Potrero, then unwind in the evening or sample the local nightlife.
Day 6 – Q&A Then Home (Or Not!)
Enjoy your final breakfast in Tamarindo and an informal Q&A with Zach from Start Abroad before transferring to Liberia International Airport for your flight home, or stay in Costa Rica and apply for residency.
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 Your Guides
Zach and Anna from StartAbroad and Pablo from International Relocation Partners are trusted friends who’ve helped hundreds of people move to Costa Rica. They’ll share advice and can get you moved as soon as you’re ready.
What’s Included
- Five nights of lodging in San José and Tamarindo, choice of single or double occupancy, breakfast included.
- 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.
- Airport transfer to San José at specified time, airport transfer to Liberia airport.
- Information on immigration and taxes.
What’s Not Included
- Airfare
- Food or drink, aside from what’s served at the seminar and daily breakfast
As Featured in:
Testimonials
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!
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.
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.
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.
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.
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 ?
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.
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 ?
You realize you’re stuck with us forever, right?
I feel more like my old self than I have in years. Thank you for taking on the straggler and helping with the healing.
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.