Thanksgiving week is one of the trickiest weeks of the year to run a luxury family trip. Flights are tight, restaurants are at capacity, private chefs are in demand, and every family who lives somewhere cold wants to be somewhere warm. We had the Marx family for eight nights at Raintree, November 20 to 28, 2025. Multi-generational group, two advanced surfers, two beginners, and a finish line on Thanksgiving night. Here is how we built the week.
The villa choice
Raintree was the right call for this group for a few reasons. The main house has five bedrooms and sleeps up to fourteen comfortably, which gave the family room to spread out without bunking the generations together. The kitchen is built for a private chef to actually cook in. The yoga shala over the jungle gave us a place for private morning sessions without anyone leaving the property. And the one-acre estate is gated and quiet, which mattered for the younger kids and for the grandparents who wanted slow mornings.
Raintree was completed in August 2022 by Studio Saxe and is one of the AD-featured properties in our collection. We held the villa with a later checkout on the departure day so the family could ease into the final morning instead of rushing.
Arrival, day one
The family came in on Alaska Airlines from LAX, landing at Liberia (LIR) at 6:20 am on November 21. From Liberia, the move we almost always recommend is the morning flight directly into Nosara, which puts a family at the villa by mid-morning. Our transportation partner met them at the Nosara airstrip and drove them straight to Raintree.
Their private chef had a fresh Costa Rican breakfast waiting: gallo pinto, tropical fruit, and an array of small bites. The two Prado SUVs and the ATVs were delivered straight to the villa by our rental partner, so nobody ran errands after a red eye. By lunch they were at Zest Kitchen inside El Pueblo, easing into the slow rhythm of the town. A Mediterranean tapas-style chef dinner at the villa closed the first day.
Day two, the surf split
Day two is the day a family week stands or falls. Get the first surf lesson right and the rest of the week falls into place. Get it wrong and you lose three days.
Private morning yoga on the villa deck at 9:00 am, a one-hour flow to settle everyone in. Then to Playa Guiones at 11:00 am for a two-hour surf session, split across two ISA-certified instructors. Two advanced surfers worked the outside down the beach, two beginners stayed in the whitewater closer to shore. Nobody waited. Nobody got bored. The group came off the beach hungry, walked to La Ventanita for fresh bowls and sandwiches, and went back to the villa to nap.
Dinner that night was 6:00 pm at Harmony Hotel, in the tropical-garden courtyard. The Harmony kitchen is one of the most consistent spots in town for families, and the 6:00 pm slot works when there are kids in the group who fade by 8.
Day three, the slow day
Every week we plan has a slow day on day three. The travel day and surf day catch up with people, and forcing another structured activity is how families end up tired by Wednesday. We left day three open. Breakfast at Rosi's Soda, the local soda that is the best $8 plate of gallo pinto in Nosara. Pool time at the villa. An easy, laid-back lunch at Howler's, which has, in our opinion, the best tuna carpaccio in town. Dinner at Sendero Kitchen with the crispy rice and tuna pre-ordered. Sendero is one of the bookings we set one to two weeks ahead during high season because the dining room fills nightly.
Day four, the ATV adventure
The ATV waterfall day through the back hills is the activity guests remember most from a Nosara week. We staged it on day four because the group had two travel days, one surf day, and a slow day under their belt, which meant they were rested and ready for four hours of mountains and river crossings.
We started with an early lunch at La Luna at 11:00 am, which sits beachfront on Pelada and runs a watermelon margarita that is locally famous. The ATV team met the group at 1:00 pm at our local ATV partner's shop, ten minutes from the villa. The group got a side-by-side and a six-seater for the riders who wanted two-up, plus individual ATVs for everyone else. Four hours through the back hills, two river crossings, a stop at a waterfall, and a coffee at Beach Blend on the drive home. A quieter technique-driven chef dinner at the villa at 7:00 pm to close the day.
Day five, the catamaran day
Day five was Tuesday, which in Nosara means the Tuesday Organic Market in Guiones is open from 8 am to 3 pm. A few in the group walked over for fresh produce, baked goods, and the local-makers stalls.
The catamaran day was the centerpiece. Down to Garza by 1:45 pm, boarding at 2:00, four hours on the Pacific with snorkeling, dolphin sightings if the day was right, and a piña colada we have, after a lot of testing, decided is the best in Nosara. The group was back at the villa by 6 and headed to Mama Gui for handmade pasta and wood-fired pizza.
Day six, wellness and the sunset table
By day six, the older members of the group had asked for something quieter. We booked a private reformer pilates session for six at Black Cat Studio, a fifty-minute class on top-of-the-line equipment in a small, well-appointed room. Lunch at Sunrise in Pelada after, the smoothies and salads kind of meal that everyone gets behind.
Dinner at Coyol at 5:00 pm is one of the most distinctive sunset tables in Costa Rica. The drive is twenty-five minutes up the hill, the dining room is a wood-fired kitchen with a view that runs from the jungle to the Pacific, and there is a swing at the edge of the property that everybody photographs. We hold these reservations months in advance during high season.
Day seven, the zipline and the Thanksgiving feast
Day seven was Thanksgiving. The morning ran light, breakfast and fresh juices at Go Juice for the kids. At 12:30 pm the group went up the road to the canopy zipline at the Nosara reserve, four hours through a 2,500-acre forest reserve with thirteen cables, the longest stretching 750 meters above the jungle and rivers below. Closed-toed shoes, swimsuits underneath for the waterfall stop, and the family was back at the villa by 5.
The Thanksgiving feast was the anchor of the week. Our private chef for the night specializes in warm, generous, family-style cooking. The menu was a generous homemade feast, family-style dishes built around local produce from the Tuesday market, and a tres leches in place of a pumpkin pie. Long table on the terrace, candles, the family gathered around for the last full night in Nosara.
Day eight, departure
Final breakfast at the villa at 8:00 am, a slow morning, luggage out by 10. Our transportation partner picked the family up directly from Raintree for the drive to Liberia, stopping for one last unhurried Costa Rican lunch on the way. The SUV drop-off and the ATV return were handled in the background so the family did not have to manage logistics on departure day. Alaska Airlines flight 617 left Liberia at 7:10 pm.
What we learned
- The split surf lesson is non-negotiable for mixed-skill groups. Two coaches, two zones of the beach, nobody waiting. The cost is meaningfully higher than a group lesson and worth it every time.
- A slow day on day three saves the rest of the week. We have run this experiment enough times to be sure. The instinct is to pack the schedule. The right move is the opposite.
- Restaurant reservations matter more than people think during high season. Harmony, Sendero, La Luna, Mama Gui, Coyol. All of these were booked one to two weeks ahead. Walking in on a Thanksgiving Tuesday would not have worked.
- Thanksgiving night should be the chef night. We have done it the other way, with the family going to a restaurant for the holiday meal. The villa dinner is warmer, longer, less rushed, and ends with everybody on the terrace instead of in a parking lot.
- Day six is the right slot for wellness. The group has been moving for five days. A pilates session and a sunset dinner pulls everybody back into the slow rhythm before the final day's adventure.
Want a Thanksgiving week like this?
Thanksgiving and Christmas weeks in Nosara fill up early. Villas at the Raintree level book six to nine months out for the holidays, and a private chef for Thanksgiving night needs to be confirmed by late summer. If you are thinking about a family Thanksgiving in Nosara for next year, the conversation starts now.