Winter 2026 – 2027 · Confirmed Itinerary

Four Spanish home bases, then a week in Morocco.

Barcelona, Madrid, Sevilla, and Granada, each held for one to four-plus weeks, with day trips and satellite stays woven in between. Closes with 2 nights in Tangier and 3 in Chefchaouen before flying home to Chicago from Casablanca.

Window
Jan 4 – Mar 16 2027
Total length
70+ nights
Relocations
5 + flight home
Route
BCN→MAD→SVQ→GRX→Morocco
The Shape of the Trip

4 home bases + satellite trips, then Morocco.

The logic: minimize full relocations — packing, re-settling, losing a transition day — by keeping an apartment as "home" while taking shorter trips out of it. A satellite trip is a stay away with the home-base apartment still held, not a relocation. The Morocco close is different: a real, final relocation, not a satellite, since there's no Spanish apartment to return to afterward. Placeholder start is Monday, Jan 4, 2027 — shift every date once real dates are set.

🏠

Home Base

An apartment held for the full stay — settle in, cook, find a café. Day trips and satellite stays happen out of it without ever checking out.

🚶

Day Trip

Out and back the same day, home-base apartment untouched. Girona from Barcelona, Toledo from Madrid, Córdoba from Sevilla — no packing required.

🎒

Satellite Trip

A few nights away with the home-base apartment still held — Valencia from Madrid, Cádiz and Ronda from Sevilla, the Alpujarras from Granada.

Getting Between Bases

Rail through Spain, then the ferry and Al Boraq into Morocco.

Every Spanish base-to-base leg runs on the AVE high-speed network. The Morocco leg switches to ferry, road, and Morocco's own high-speed train — then a direct flight home from Casablanca, so there's no backtracking into Spain at the end.

Barcelona
Jan 4–14
🚄
AVE ~2h25–2h45
Direct to Madrid Atocha
Madrid
Jan 14–25
🚄
AVE ~2h33–2h51
Direct to Sevilla Santa Justa
Sevilla
Jan 25–Feb 19
🚄
AVE ~2h31 fastest
Direct, via Antequera line
Granada
Feb 19–Mar 10
🚌⛴️
Bus ~3h + ferry ~53min
Via Tarifa
Tangier
2 nights
🚌
Bus/taxi ~2–2.5h
CTM bus or grand taxi
Chefchaouen
3 nights
🚄✈️
Al Boraq ~2h10 + flight
Via Casablanca (CMN)
Chicago
Home
The flight home: fly out of Casablanca (CMN), not Tangier. Royal Air Maroc runs a direct CMN → Chicago O'Hare (ORD) route — the only realistic one-stop-free option back to Chicago from Morocco. From Chefchaouen, backtrack to Tangier (~2–2.5h by bus or grand taxi), then take the Al Boraq high-speed train Tangier → Casablanca (~2h10, departures roughly hourly 6am–9pm) to connect to the flight. Budget a full travel day for the Chefchaouen → Tangier → Casablanca → airport chain — don't schedule the flight same-evening as leaving Chefchaouen. Fares and schedules should be rechecked closer to the date; Royal Air Maroc's US network has shifted before.

Within Sevilla's satellites: Sevilla ⇄ Cádiz is regional AVE-class ~1h20; Sevilla ⇄ Ronda has no direct fast train (via Antequera with a transfer, or drive) — see Practical Intel below.

At-A-Glance

Five stops, one thread.

Each Spanish base's night count already includes its satellite trips. Morocco is listed separately since it's a real relocation, not a satellite of anything.

Stop Dates Nights Satellite Trips Day Trips
Barcelona
Base 1 · Catalonia
Jan 4 – Jan 14
10
None — day trips only
5 (Girona, Besalú, Montserrat, Sitges, Cadaqués/Figueres)
Madrid
Base 2 · Castile
Jan 14 – Jan 25
11 (8 + 3)
Valencia — 3 nights
5 (Toledo, Segovia, Aranjuez, Chinchón, Alcalá de Henares)
Sevilla
Base 3 · Andalusia
Jan 25 – Feb 19
25 (17 + 8)
Cádiz/Carnaval — 4 nights · Ronda + white villages — 4 nights
2 (Córdoba, Carmona)
Granada
Base 4 · Andalusia
Feb 19 – Mar 10
19+ (15 + 4)
Alpujarras — 4 nights
5 (Priego de Córdoba, Guadix, Baeza + Úbeda, Santa Fe, Montefrío)
Morocco
Closing leg · Tangier + Chefchaouen
Mar 10 – Mar 15
5 (2 + 3)
Not applicable — sequential, not nested
Optional: Tétouan or Asilah en route
Worth noting: Granada's 19 nights are a firm minimum with room to extend "if it's going well." Extending Granada pushes the Morocco dates back by the same amount — Morocco isn't losing its own 5 nights, the whole back half of the trip just shifts later.
The Stops

What each leg actually covers.

Day trips (no overnight, apartment untouched) and satellite trips (a few nights away, apartment still held) for each Spanish base, plus the Morocco close.

Home Base 1 · 10 nights

Barcelona

Jan 4 – Jan 14 · day trips only, no satellites

The opener — no relocation logic to lean on yet, just a hub for a cluster of easy day trips into Catalonia's medieval towns, a mountain monastery, and Dalí's Costa Brava.

🌤️ Weather: Mild Mediterranean winter — highs ~55–57°F (13–14°C), lows ~41–45°F (5–7°C). Some rain days, otherwise walkable and mild; a warm coat covers it.

Nights
10
Day trips
5
Satellites
0

Day Trips

  • Girona — Jewish quarter, cathedral, far fewer crowds than Barcelona itself
  • Besalú — near-perfectly preserved medieval town, fortified bridge
  • Montserrat — mountain monastery, reached via the slow, scenic FGC rail line
  • Sitges — coastal town, real local life outside peak weekends
  • Cadaqués / Figueres — Dalí country; Cadaqués keeps a fishing-village feel most of the year
10 nights Day trips only FGC to Montserrat
Home Base 2 · 11 nights

Madrid

Jan 14 – Jan 25 · Madrid ~8 nights + Valencia satellite 3 nights

Central Spain's culture-and-day-trip hub — three cultures layered into Toledo, a Roman aqueduct still standing in Segovia's town center, and a quieter royal-garden alternative in Aranjuez. A 3-night satellite pulls out to Valencia by AVE without giving up the Madrid apartment.

🌤️ Weather: Colder, continental — highs ~48–50°F (9–10°C), lows near freezing 32–36°F (0–2°C). Clear skies common but chilly mornings; pack a proper coat, not just a jacket.

Nights
11
Day trips
5
Satellites
1

Day Trips

  • Toledo — "city of three cultures," dense Christian/Jewish/Islamic layering; best early or overnight to beat day-trip crowds
  • Segovia — Roman aqueduct still standing in the town center
  • Aranjuez — royal gardens/palace, quieter than Toledo or Segovia
  • Chinchón — small town built around a circular plaza once used as a bullring; mostly a locals' day out
  • Alcalá de Henares — Cervantes' birthplace, easy half-day

Satellite: Valencia — 3 nights (Jan 22–25)

City of Arts and Sciences, Albufera, Manises (ceramics town, 700-year pottery tradition). AVE train, ~1h55 each way from Madrid.

AVE hub Valencia satellite 3 cultures — Toledo
Home Base 3 · 25 nights incl. satellites

Sevilla

Jan 25 – Feb 19 · Sevilla proper 17 nights + Cádiz 4 + Ronda 4

The longest stop and the anchor of the whole trip — seventeen nights in Sevilla itself, split around two satellite trips: Carnaval in Cádiz (fixed to the real Feb 5–9 dates), then the white villages around Ronda to close out the base. The Cádiz satellite was shortened from an earlier draft specifically to free up more time in Sevilla proper.

🌤️ Weather: Mild Andalusian winter — highs ~59–61°F (15–16°C), lows ~41–43°F (5–6°C). The sunniest of the mainland bases, with some rain likely in late Jan/early Feb.

Nights
25
Day trips
2
Satellites
2

Day Trips (from Sevilla)

  • Córdoba — Mezquita, the Judería; best late afternoon, after Sevilla day-trippers clear out
  • Carmona — 15 min by train, Roman necropolis, almost no tourists

Satellite: Cádiz · Carnaval — 4 nights (Feb 5–9)

Targets the Gran Cabalgata main parade — first Sunday of Carnaval, Feb 7, 2027 — with a day either side. Gets the full-street atmosphere and at least one chirigota competition night without the full 10-day arc. Cádiz's official 2027 Carnaval window runs Feb 4–14, though the day-by-day event program hasn't been published yet — re-verify closer to the date.

Day trips from Cádiz: Jerez de la Frontera (sherry bodegas, Royal Andalusian School of Equestrian Art), Arcos de la Frontera (clifftop white hill town, far less visited than Ronda).

Satellite: Ronda + White Villages — 4 nights (Feb 15–19)

Zahara de la Sierra, Grazalema, Setenil de las Bodegas (houses built into an overhanging rock face).

Getting around: rent a car for just this 4-night stretch — the villages sit 20–45 min apart with thin rail service, and returning to the same city avoids one-way fees. Train only really works for Sevilla↔Ronda (more transfers now, often via Antequera); bus is a workable backup between the larger towns but doesn't reach the villages well.

Longest base Carnaval Feb 7 Rental car for white villages
Home Base 4 · 19+ nights, flexible

Granada

Feb 19 – Mar 10 · Granada proper ~15 nights + Alpujarras 4 · 19 nights firm minimum

Closing Spanish base, with the same flex logic as the Japan decision: 19 nights firm, then extend a week at a time if it's going well rather than pre-committing now — which pushes the Morocco dates back correspondingly. The plan favors multiple unhurried Alhambra visits over one marathon day, plus an under-visited cluster of olive-country towns.

🌤️ Weather: Cooler, elevation-driven — highs ~57–59°F (14–15°C) by March, lows can dip near freezing overnight. Snow often visible on the Sierra Nevada; layers recommended.

Nights
19+
Day trips
5
Satellites
1

Day Trips

  • Priego de Córdoba — Baroque architecture, olive-oil country, essentially undiscovered by foreign tourists
  • Guadix — cave-house neighborhood carved into the hillside, still inhabited
  • Baeza + Úbeda (paired) — Renaissance towns in olive country
  • Santa Fe — 15 min out, where Columbus's capitulations were signed
  • Montefrío — ~45 min, white town built into a rock outcrop, church perched on top

Satellite: Alpujarras — 4 nights (Feb 27–Mar 3)

Trevélez, Capileira, Bubión — mountain villages on the Alhambra's southern flank.

In Granada Itself

  • Alhambra + Nasrid Palaces — multiple visits, not one marathon day
  • Albaicín — wander unscheduled
  • Sierra Nevada — only if skiing interests
Flexible Alhambra × multiple visits Olive-country day trips
Closing Leg · 5 nights

Tangier + Chefchaouen

Mar 10 – Mar 15 · Tangier 2 nights, then Chefchaouen 3 nights

The one genuine relocation-with-no-return on the trip — after Granada, cross via Tarifa instead of heading back toward a Spanish base. Two days in the port city, then three in the Blue City up in the Rif Mountains, before backtracking to Tangier and on to Casablanca for the flight home.

🌤️ Weather: Mild spring-like — Tangier highs ~63–64°F (17–18°C) tempered by Atlantic breeze; Chefchaouen slightly cooler in the mountains, ~59°F (15°C) days, ~46–50°F (8–10°C) nights. Generally sunny by mid-March.

Nights
5
Tangier
2
Chefchaouen
3

Tangier (2 nights)

  • Kasbah and the old medina, Grand Socco and Petit Socco markets
  • Cape Spartel and the Hercules Caves — about an hour out
  • Arrival via ferry from Tarifa, ~53 min crossing

Chefchaouen (3 nights)

  • The Blue City — every wall, doorway, and staircase washed in cobalt blue, in the Rif Mountains
  • ~2–2.5h from Tangier by CTM bus or grand taxi
  • One of the most photogenic towns in Morocco — worth the extra day over a rushed day-trip version

Getting home: Casablanca, not Tangier

Backtrack Chefchaouen → Tangier (~2–2.5h), then take the Al Boraq high-speed train to Casablanca (~2h10, roughly hourly). Royal Air Maroc flies direct Casablanca (CMN) → Chicago O'Hare (ORD) — budget a full travel day for the chain rather than same-day connections.

Blue City Ferry from Tarifa Fly home via Casablanca
Jan–Mar 2027 Festival Calendar

What's actually happening while you're there.

Trimmed to what intersects the actual route — no Tenerife, no Fallas this time, since neither city is on the itinerary this trip.

Pin these dates to your itinerary

Jan 5 eve
Cabalgata de los Reyes Magos
Barcelona — while you're there
Three Kings parade with elaborate floats and candy thrown to children, right in the middle of your Barcelona stay.
Jan 6
Día de los Reyes Magos (bank holiday)
Nationwide — Barcelona
Families exchange gifts, eat Roscón de Reyes. Many businesses closed. The end of Spain's long Christmas season.
Feb 2
La Candelaria (Candlemas)
Sevilla and many towns — early in your Sevilla stay
Processions, pageantry, and in some pueblos mock bullfights. Minor event but atmospheric if you're there.
Feb 4–14
Carnaval de Cádiz
Cádiz — your satellite trip is timed for this
Spain's most famous and satirical Carnaval — chirigota chorus groups at the Gran Teatro Falla, costumed street revelry, plaza parties. Official 2027 window confirmed as Feb 4–14; the Gran Cabalgata (main parade) falls on the first Sunday, Feb 7, 2027, which your Feb 5–9 Cádiz stay is built around. Full daily program still pending official release — re-verify before locking travel dates.
Feb 28
Día de Andalucía
Regional holiday — Granada, during your Alpujarras satellite trip
Official Andalusian regional holiday. Some businesses and services may close or run reduced hours — worth checking if it affects the mountain villages while you're out there.
The Confirmed Route

Five stops, no wasted relocations.

How the pieces connect — order, length, and what's nested inside each stop. See the Gantt-chart schedule for a visual timeline.

Base 1 · Jan 4 – Jan 14

Barcelona

Length
10 nights
Day trips only — Girona, Besalú, Montserrat, Sitges, Cadaqués/Figueres.
While there
Reyes Magos, Jan 5–6
Falls right in the middle of this stay.
Next: Madrid by AVE (~2h25–2h45), same day Barcelona wraps up — no gap between bases.
Base 2 · Jan 14 – Jan 25

Madrid

Length
11 nights (8 + 3)
Toledo, Segovia, Aranjuez, Chinchón, Alcalá de Henares.
Satellite
Valencia — 3 nights
AVE ~1h55 each way. City of Arts and Sciences, Albufera, Manises.
Next: Sevilla by AVE (~2h33–2h51).
Base 3 · Jan 25 – Feb 19

Sevilla

Length
25 nights (17 + 4 + 4)
Sevilla proper, plus Córdoba and Carmona day trips.
Satellites
Cádiz (Carnaval) + Ronda
Cádiz Feb 5–9 brackets Gran Cabalgata (Feb 7); Ronda Feb 15–19 wants a rental car.
Next: Granada by AVE (~2h31 fastest, via Antequera).
Base 4 · Feb 19 – Mar 10

Granada

Length
19+ nights (15 + 4)
Firm minimum, extend week by week if it's going well.
Satellite
Alpujarras — 4 nights
Trevélez, Capileira, Bubión.
Next: Tangier via bus to Tarifa (~3h) + ferry (~53min). Extending Granada pushes this back.
Closing Leg · Mar 10 – Mar 15

Morocco

Tangier
2 nights
Kasbah, medina, Cape Spartel.
Chefchaouen
3 nights
The Blue City, ~2–2.5h from Tangier.
Trip closes here — fly Casablanca (CMN) → Chicago O'Hare (ORD) direct on Royal Air Maroc, via Al Boraq train from Tangier (~2h10).
Practical Intel

Logistics worth sorting now.

Booking timing

  • Cádiz Carnaval accommodation — book 4–6 months ahead. Prices 2–3× normal, and the daily event program isn't published yet.
  • Rental car for Ronda + white villages — book the 4-night stretch well ahead; small-town supply is limited during peak season.
  • Alhambra tickets — book online as soon as dates are firm.
  • Royal Air Maroc CMN → ORD — book well ahead; it's the linchpin of the whole Morocco close, and fares/schedule details should be reconfirmed closer to the date.
  • Long-stay apartments — Spotahome and Flatio price at genuine monthly/lease rates (Nestpick is just a Spotahome-inclusive meta-search, not separate inventory), but both are built around a 30-day minimum stay. None of the four bases hit that on their own — even Sevilla's 25 nights falls just short — so check each listing's actual minimum rather than assuming it applies; for anything under 30 nights, licensed Airbnb/Booking apartments (VFT/HUT verified, monthly-discount toggle if offered) are the more realistic route.

Getting around: Ronda & the white villages

  • Rental car — best option. Villages sit 20–45 min apart, rail service is thin, and returning the car to the same city avoids one-way fees.
  • Train — works for Sevilla↔Ronda only, with more transfers now, often via Antequera.
  • Bus — a workable backup between the larger towns, but doesn't reach the villages well.
  • Bottom line — rent a car for just this 4-night stretch; train or bus covers the Sevilla–Ronda legs on either end.

Transport spine (Spain, high-speed rail)

  • Barcelona ⇄ Madrid — AVE, ~2h25–2h45, direct
  • Madrid ⇄ Sevilla — AVE, ~2h33–2h51, direct
  • Sevilla ⇄ Granada — AVE, ~2h31 fastest, direct via the Antequera line
  • Madrid ⇄ Valencia — AVE, ~1h55, direct
  • Sevilla ⇄ Cádiz — regional AVE-class, ~1h20
  • Sevilla ⇄ Ronda — no direct fast train; via Antequera with a transfer, or drive

Getting into and out of Morocco

  • Granada ⇄ Tarifa — bus, ~3h (ALSA)
  • Tarifa ⇄ Tangier — ferry, ~53 min, frequent daily sailings
  • Tangier ⇄ Chefchaouen — CTM bus or grand taxi, ~2–2.5h
  • Tangier ⇄ Casablanca — Al Boraq high-speed train, ~2h10, roughly hourly 6am–9pm
  • Casablanca ⇄ Chicago — Royal Air Maroc, direct
  • Check passport validity (6-month rule is common for Morocco entry) and any visa requirements well before booking.
Beyond the Itinerary

Meeting other English-speaking travelers.

Four home bases of a week-plus each is enough time to actually build a small social rhythm in each city, not just pass through.

Platforms & groups

  • InterNations — expat platform, active in Barcelona/Madrid/Sevilla, skews long-term.
  • Meetup.com — hiking, photography walks, book clubs; strong in Barcelona/Madrid, thinner in Sevilla/Granada.
  • Facebook expat groups — "Expats in Barcelona," "Sevilla Expats," first to post pop-up events.
  • Expat-run coworking spaces — recurring social events, active in Sevilla and Granada.

Lower-key options

  • Small-group walking tours — cluster English speakers, no ongoing commitment.
  • Long-stay/aparthotel rentals — some have shared courtyards or terraces; worth asking the host.
  • English-language church congregations — e.g. the American Church in Madrid.
  • Photography/craft-specific meetups — likely a better fit given your interests than general mixers.
Rough Cost Estimate

What this might run, roughly.

Sizing math, not quotes. All figures in USD, for 2 travelers sharing accommodations. Lodging is a shared cost — one apartment or room, not doubled — while transportation (train tickets, ferry, flights) doubles since each traveler needs their own seat; the Ronda rental car stays flat since it's shared. The $225/night rate ($4,500 per 20 days) applies only to the four Spanish home bases themselves — long-stay apartment logic, Spotahome/Flatio-style monthly discounts. Satellite trips, Morocco, transportation, food, and entertainment run on different pricing logic, so they're estimated separately below.

Main home bases — 50 nights @ ~$225/night

  • Barcelona — 10 nights → $2,250
  • Madrid (proper) — 8 nights → $1,800
  • Sevilla (proper) — 17 nights → $3,825
  • Granada (proper, firm min.) — 15 nights → $3,375
  • Subtotal — $11,250

Satellite trips + Morocco — 20 nights, short-stay rates

  • Valencia — 3 nights @ ~$180 → $540
  • Cádiz (Carnaval surge) — 4 nights @ ~$300 → $1,200
  • Ronda — 4 nights @ ~$170 → $680
  • Alpujarras — 4 nights @ ~$140 → $560
  • Tangier — 2 nights @ ~$110 → $220
  • Chefchaouen — 3 nights @ ~$90 → $270
  • Subtotal — $3,470

Transportation — 2 travelers, trains, ferry, rental car, flights

  • Barcelona → Madrid, AVE (×2) — ~$140
  • Madrid → Sevilla, AVE (×2) — ~$140
  • Sevilla → Granada, AVE (×2) — ~$100
  • Madrid ⇄ Valencia round trip (×2) — ~$140
  • Sevilla ⇄ Cádiz round trip (×2) — ~$60
  • Rental car, Ronda (4 days, shared) — ~$200
  • Granada → Tarifa, bus (×2) — ~$70
  • Tarifa → Tangier, ferry (×2) — ~$90
  • Tangier ⇄ Chefchaouen round trip (×2) — ~$40
  • Tangier → Casablanca, Al Boraq (×2) — ~$60
  • Casablanca → Chicago, Royal Air Maroc (×2) — ~$2,000
  • Chicago → Barcelona, opening flight (×2) — ~$1,100
  • Subtotal — $4,140

Rough total & daily average — both travelers

  • Lodging (shared — main bases + satellites/Morocco) — $14,720
  • Transportation (2 travelers) — $4,140
  • Food & dining (2 travelers; ~2 home-cooked dinners/week at the 4 main bases, eating out everywhere else) — $4,200
  • Entertainment ($300/week for 2, × 10 weeks) — $3,000
  • Trip total, both travelers — ~$26,060
  • Per traveler (of the total above) — ~$13,030
  • Blended daily average (70 confirmed nights, both travelers) — ~$372/day (~$186/day each)
Not included: travel insurance, visas, shopping/souvenirs, and any extension of Granada past its 19-night firm minimum. Attraction tickets and nightlife are meant to be absorbed by the $300/week entertainment line, though a big-ticket week (guided tours, splurge dinners) could push it higher.
How rough is rough: only the $225/night main-base rate came from you — everything else (satellite/Morocco nightly rates, every transport fare, the food/dining split, the entertainment budget, and the assumption that lodging is shared while transport doubles for 2 people) is a ballpark estimate for sizing purposes, not a researched quote. Real AVE/ferry/flight prices and grocery/restaurant costs vary a lot — recheck closer to booking.