Five for Fifty · Trip one
Tamarindo
Itinerary
November 9 – 15, 2026
El Chante · Playa Tamarindo, Costa Rica
Don't forget your passport.
The house
El Chante
A Balinese-style hilltop villa of eight detached bungalows around an open-air living room and infinity pool, about 300 meters above the north end of Tamarindo beach. Give this address block to your driver, your family, and anyone who asks.
Address
Villa El ChanteGated hillside community, across from Pangas Beach ClubPlaya Tamarindo, Santa CruzGuanacaste 50309, Costa RicaGPS 10.304726, -85.835216Open in Google MapsCosta Rica doesn't use street numbers; the GPS pin and “across from Pangas” is how locals and drivers find it. Pangas Beach Club is also our nearest beach access.
- Check-in
- Wed Nov 11 · 3:00 PM
- Guests arriving before Wednesday stay in town until check-in
- Check-out
- Sun Nov 15 · 10:00 AM
- Airport
- Liberia (LIR)
- About 1 hr 15 min by road
- Sleeps
- 16 – 19
- 8 bedrooms · 8.5 baths
- Included
- Breakfast & housekeeping
- Mon – Sat, with a concierge
- Getting around
- Golf carts
- Rented for the group; the hill is steep, so don't plan on walking it
Day by day
The plan
Headcounts show the group present for each activity or meal; overnight totals count only house guests. Matt and Rachel join Wednesday activities and dinner, stay elsewhere, and leave Thursday. Times in Costa Rica (Central Standard, no daylight saving; one hour ahead of Denver this week).
- 4:10 PM2landing
Katie & Dex arrive at LIR
- 10:00 AM Denver → 4:10 PM LIR · United UA 1917 — Katie Lake, Dex Sexton
- After landing
Katie picks up her rental car
Own transport for Katie & Dex; stay in town until Wednesday check-in
- 4–7 PM3landing
Early arrivals
- 4:10 PM · United UA 1917 — Sam Reed, Kaylie Reed
- 6:35 PM · Alaska AS 616 — Ro the Pro
- Evening
TBD
House check-in is Wednesday; early arrivals stay in town
- Midday12landing
Who's coming in
- 11:54 AM · United UA 1876 — Michael Downes
- 12:45 PM · Delta DL 1898 — Anna Hudson, Jason Chaifetz, John McGraw
- 1:10 PM · United UA 1512 — Kevin Taggart
- 1:50 PM · Southwest — Jill O'Keefe, Ryan O'Keefe
- 4:10 PM · United UA 1917 — James Smith, Julie Smith, Julie Echter, Brandon, Darren Lake
- Before 3
TBD for early arrivals
Lunch in town while the house gets ready
- 3:00 PM
Check-in at El Chante
- 5:00 PM16here
Sunset drinks & snacks at the house
- 7:30 PM19RSVP
Dinner at Tabu Tamarindo
- Late19here
Explore the nightlife
- Morning17here
Breakfast at the house
- TBD
Matt & Rachel leave
Own transport; not staying at the house
- 1–3 PM9surfing
Surf lessons
One hour
- 3:00 PM17here
Late lunch on the beach
- Afternoon17here
Leisure time
- 5:00 PM17here
Sunset drinks at the house
- 6:00 PM17RSVP
Private chef dinner at the house
A Taste of Costa Rica
- Late
Post-dinner TBD
See how we're all feeling
- Morning17here
Breakfast at the house
- 10:00 AM
Katie & Darren leave for LIR
Rental car · 1:00 PM United UA 1918
- 1–3 PM9surfing
Surf lessons
One hour
- 3:00 PM14here
Late lunch on the beach
- Afternoon14here
Leisure time
- 5:00 PM
Sunset drinks before dinner
- 8:00 PM14RSVP
Dinner in town at Chiquitas
- Late14here
Discoteca
- Morning14here
Breakfast at the house
- 10:00 AM
James & Julie Smith leave for LIR
Jason follows at 12:25
- Afternoon11here
Beach time
- 4:00 PM11here
Beach bar pub crawl
- 5:00 PM
Sunset drinks before dinner
- 7:30 PM11RSVP
Dinner at Pangas Beach Club
- Late
TBD
- 6:40 AM
Ro leaves for LIR
- Morning10here
Breakfast at the house
Last one; checkout is 10 AM
- 10:00 AM
Main group leaves for LIR; house checkout
Six in the later van; Jill & Ryan use own transport, Dex's onward plans to confirm
Airport shuttles
Arrivals & departures
All flights are into and out of Liberia (LIR). Monday's two arrivals need no van: Katie takes the rental car and Dex makes his own way. Tuesday's vans go to the first-night lodging in town; everything from Wednesday on goes to El Chante. Vans are grouped by who lands or leaves close together. Arrival pickups allow about 45 minutes after the last flight in the group for immigration and bags; departure vans leave the house three hours before the first flight in the group.
Arrivals
LIR → El Chante
Mon Nov 92 arriving · no van needed
Own transport · no van
4:10 PM after the 4:10 PM landing
- Katie LakeRental car · no shuttle4:10 PM · United UA 1917
- Dex SextonOwn transport · no shuttle4:10 PM · United UA 1917
2 landing · rental car for Katie; Dex makes his own way
Tue Nov 103 arriving · to town, not the house
Van 1 · Pickup
4:55 PM after the 4:10 PM landing
- Sam Reed4:10 PM · United UA 1917
- Kaylie Reed4:10 PM · United UA 1917
2 passengers · in Tamarindo around 6:10 PM
Van 2 · Pickup
7:20 PM after the 6:35 PM landing
- Ro the Pro6:35 PM · Alaska AS 616
1 passenger · in Tamarindo around 8:35 PM
Wed Nov 1112 arriving
Van 1 · Pickup
1:30 PM after the 12:45 PM landing
- Michael Downes11:54 AM · United UA 1876
- Anna Hudson12:45 PM · Delta DL 1898
- Jason Chaifetz12:45 PM · Delta DL 1898
- John McGraw12:45 PM · Delta DL 1898
4 passengers · at the house around 2:45 PM
Van 2 · Pickup
2:35 PM after the 1:50 PM landing
- Kevin Taggart1:10 PM · United UA 1512
- Jill O'Keefe1:50 PM · Southwest
- Ryan O'Keefe1 board bag · 2 boards1:50 PM · Southwest
3 passengers · at the house around 3:50 PM
Van 3 · Pickup
4:55 PM after the 4:10 PM landing
- James Smith4:10 PM · United UA 1917
- Julie Smith4:10 PM · United UA 1917
- Julie Echter4:10 PM · United UA 1917
- Brandon4:10 PM · United UA 1917
- Darren Lake4:10 PM · United UA 1917
5 passengers · at the house around 6:10 PM
Departures
El Chante → LIR
Sat Nov 143 leaving
Van 1 · Leave house
10:00 AM for the 1:00 PM flight
- James Smith1:00 PM · United UA 1918
- Julie Smith1:00 PM · United UA 1918
2 passengers
Van 2 · Leave house
12:25 PM for the 3:25 PM flight
- Jason Chaifetz3:25 PM · Delta DL 1784
1 passenger
Sun Nov 157 leaving
Van 1 · Leave house
6:40 AM for the 9:40 AM flight
- Ro the Pro9:40 AM · Alaska AS 617
1 passenger
Van 2 · Leave house
10:00 AM for the 1:00 PM flight
- Sam Reed1:00 PM · United UA 1918
- Kaylie Reed1:00 PM · United UA 1918
- Julie Echter1:00 PM · United UA 1918
- Anna Hudson2:00 PM · Delta DL 1820
- John McGraw2:00 PM · Delta DL 1820
- Kevin Taggart2:20 PM · United UA 1516
6 passengers
Own transport
- Jill and Ryan O'Keefe · Fly home Tue Nov 17 at 2:45 PM (Southwest), after the house checks out. Ryan has 1 board bag with 2 boards. Own transport.
- Dex Sexton · Departs Denver Mon Nov 9 at 10:00 AM on United UA 1917, landing at LIR at 4:10 PM with Katie. Onward travel after Sunday checkout to confirm. Own transport.
- Matt Stewart and Rachel Lamanna · In Costa Rica from Nov 7. Join Wednesday Nov 11 dinner and all other Wednesday activities; stay elsewhere and leave Thursday Nov 12. Own transport.
- Darren Lake · Lands Wed Nov 11 at 4:10 PM on United UA 1917 and rides Wednesday's Van 3 to the house. Leaves Fri Nov 13 with Katie in her rental car for the 1:00 PM United UA 1918; no departure van. Own transport.
- Katie Lake · Departs Denver Mon Nov 9 at 10:00 AM on United UA 1917 and lands at LIR at 4:10 PM. Rental car; no shuttles needed either way. Flies home Fri Nov 13 at 1:00 PM (United UA 1918). Own transport.
The weather
What to expect in mid-November
The tail end of green season. Expect highs around 88–90°F, nights in the mid-70s, humid, with most rain arriving as a late-afternoon or overnight shower rather than all-day wash-outs. The sun sets around 5:30 PM and it's fully dark by 6. The ocean is bath-warm and the swell is friendly for lessons. Pack light and quick-dry, bring reef-safe sunscreen and bug spray, and one outfit for dinner.
Reservations
Headcounts for the restaurants
Wednesday, Nov 11 · 7:30 PM
Tabu Tamarindo
19confirmed guests
Thursday, Nov 12 · 6:00 PM
Private chef · El Chante
17confirmed guests
Friday, Nov 13 · 8:00 PM
Chiquitas
14confirmed guests
Saturday, Nov 14 · 7:30 PM
Pangas Beach Club
11confirmed guests