Two parts. The front end is shared (Sicily → Rome). After Fat Freddy's in Rome you pick one back end: Route A London only or Route B Madeira only (the island hike) — not both. Both are costed below. All prices are for 2 people in USD, rough ranges to refine once you lock route + flight class.
Hardened from live fare + market research — every line's source & confidence is in §07. Toggle lodging style (Airbnb vs hotel); lodging & food scale with nights. Includes UK ETA, intra-Europe bag fees, CFAR insurance & an 8% buffer.
Live-pulled from Booking.com (your exact dates, 2 adults, USD) — these bands now feed the calculator. Each city has a pre-filtered search plus real verified picks. Liverpool match-night already shows 72% sold out — book it first.
Airbnb · Ortigia · Booking · Ortigia
Live value: Life Hotels Residence ($91/nt), Casa Calles ($95), CASADELMAR ($118). Boutique: Algilà Ortigia.
Airbnb · Trastevere · Booking · Rome center
Live value: Villa Riari Garden ($145/nt), Sonnino Suite ($209), Trastevere Colors ($220). Boutique: Elizabeth Unique.
Airbnb · Shoreditch · Booking · Soho
Live value: citizenM ($197/nt), Peloton apt ($194). Boutique: Boundary ($317), The Hoxton, Batty Langley's.
Airbnb · Funchal · Booking · Madeira
Live value: Social Lodge ($77/nt), São Pedro Boutique ($110), Studios Funchal ($124). Eco/glamping: Canto das Fontes.
★ Our pick: Hope Street Hotel — 4★ boutique, Georgian Quarter, 8.9 score / 9.5 location. Live Oct 10, 2 adults (Booking): Deluxe Twin £359 (~$456) · Studio £363 · Studio Suite £387 · Lounge Suite £443 · Corner Suite £481 — non-refundable; ~$24 more for free-cancel. +£19.50 pp breakfast, +£2.40/nt city tax. 0.7 mi to centre, ~2 mi taxi to Anfield. Match-night surge — book first.
Cheaper fallbacks if it sells out: Liverpool Inn (~$149/nt), Duke St Boutique (~$175), 62 Castle St (~$246).
For 17+ nights, Airbnb weekly/monthly discounts (often 10–25%) can beat the nightly rate — the modeled numbers don't assume them, so real cost may land lower. Filter for "Entire place," superhost, and free cancellation where you can.
| Date | What | Detail |
|---|---|---|
| Sep 22–24 | HBMA Revenue Cycle Conf. | The M Resort, Las Vegas. Board meeting = Day 1 (Sep 22, must-attend). Fly out Sep 23–25 from LAS or home via SBP. |
| Thu Oct 1, 9pm | Fat Freddy's Drop | Atlantico, Rome — you hold tickets. |
| Sat Oct 10 | Liverpool v Man City | Anfield. PL resumes from the intl break with this fixture. Provisional 3pm KO — will likely move to a TV slot (12:30 / 17:30 GMT); confirmed ~6 wks out. |
| Oct 11–13 | Home to SLO | Fly Manchester Oct 11; flexible to Oct 13. Hard deadline: in SLO by the 13th. |
| Oct 14 → 15–18 | SLO → Houston, ASPS | PSTM 2026, George R. Brown CC. |
You're flexible on the exits: leave Sep 23, 24, or 25, from Vegas (LAS) or home via SLO (SBP), and return Oct 11–13. Earlier out = more Sicily — the Rome anchor (Oct 1, depart Oct 2) and the Oct 10 match are fixed, so the front end flexes. Board-meeting Day 1 (Sep 22) is the only HBMA must-attend.
| Depart | From | Arrive Sicily | Sicily nights | Read |
|---|---|---|---|---|
| Sep 23 · daytime | Vegas (LAS) | Sep 24 | ~6 | Most Europe time; leave after Day 1. |
| Sep 23 · end of day | Home via SLO | Sep 24/25 | ~5–6 | Go home first, repack out of conference mode; SLO adds a connection. |
| Sep 24 | Vegas or SLO | Sep 25 | ~5 | After ~full conference. |
| Sep 25 | Vegas or SLO | Sep 26 | ~4 | Latest start — compresses Sicily. |
Fly home from Manchester Oct 11 (lands same day) — or spend the Oct 11–13 slack on a post-match night in Manchester/London, then home. Must be in SLO by Oct 13 for the Oct 14 Houston flight; that slack is your delay insurance.
From Vegas: LAS → Catania (CTA) 1-stop via Frankfurt/Zurich — Lufthansa · SWISS. From SLO: SBP has no international service — fly home LAS→SBP after the conference, then SBP→LAX/SFO→Europe→CTA (2 stops). Either origin also includes the SLO→LAS hop to reach HBMA (~$150–320 pp). Open-jaw the whole trip either way: home out of Manchester — don't pay to backtrack. Live fares (Google Flights, your dates): LAS→Catania ~$415–525 pp economy (Lufthansa/SWISS/Iberia, "$112 below usual"); premium economy ~$950–1,450 pp. Ex-SLO adds the SBP→LAX hop.
Sicily gets room to breathe — east-coast base, the volcano, baroque old towns, a beach/boat day, and a slow start to beat jet lag.
Getting there: Catania → Rome direct flight (CTA→FCO, ~1h10, ITA/Ryanair/Vueling, ~$50–120 pp) on Sep 30. Depart Rome Oct 2 for the back end.
Relaxed, simplest logistics. ~8 nights London — the big food + shopping + sights run.
All-in on the island traverse — ~7 nights to hike across Madeira, then fly straight to the match. No London. (Ends up cheaper than A.)
My read: your "hike across the island / glamping" wording leans Route B (Madeira). Pick A if a London food-and-shopping week wins instead — it's one or the other now.
Route A: London Euston → Liverpool Lime St on Avanti (~2h15, ~£35–90 pp). Route B: you land at Manchester and hop ~45 min to Liverpool. Either way — stay over, fly home from Manchester next day.
Liverpool v Man City is the season's hottest fixture — non-member general sale is near-impossible, so this is hospitality (or vetted resale).
Manchester → LAX direct on Virgin Atlantic (seasonal, runs through Oct; ~$580–1,200 pp econ), then LAX → SBP regional hop (~$150–250 pp). Depart Oct 11 → land Oct 11, leaving Oct 12–13 as buffer before the Oct 14 Houston flight. That buffer is deliberate — it absorbs any delay so ASPS isn't at risk.
The ★ calculator up top is authoritative; this is where every number comes from. HARD = current published/market data · MED = benchmarked estimate · SOFT = heuristic. At ~3 months out, fares are loaded and prices are firming — book soon, they climb from here. Scope: Europe only — no HBMA/Vegas or ASPS/Houston costs except the departing flight.
| Line | Figure (2 ppl) | Hardness | Basis / source |
|---|---|---|---|
| Flights · economy | per-leg, see calc | LIVE | Live Google Flights/Kayak, your dates: LAS→Catania $415–525 (cheapest $377), MAN→LAX $389–553, CTA→Rome $30–95, Rome→London $53–160, Rome→Madeira $251–417, Madeira→Manchester $170–303. Google flags both transatlantic legs "below usual." |
| Flights · premium econ | +~$3–4k | SOFT | interpolated ~2.5–3× economy — verify at booking |
| Flights · date deltas | ±$200–600 | SOFT | day-of-week heuristic (Wed/Tue cheap, Fri/Sun premium) |
| Lodging · Airbnb/night | Sicily $120–210 · Rome $140–230 · London $180–300 · Madeira $110–190 · L'pool $200–400 | MED-HARD | 2026 market medians (AirROI): Rome $167, Sicily $147, London $175–230, Funchal $151; L'pool = match-night surge |
| Lodging · boutique hotel | ~1.6–1.8× Airbnb | HARD | named hotels in §02/§04 (Algilà, Casa Angelina, eco-lodges) |
| Food | $180–280/day | MED | ~$90–140 pp/day incl. several standout dinners — your dial |
| Ground | $900–1,600 | MED | rental car(s), Avanti L'pool train £35–90, transfers, transit |
| Liverpool | $1,600–2,500 (your cap) | HARD | hospitality from ~$1,063/pp (Hospitality Centre); your budget = std/resale tier |
| Activities | $300–850 | HARD | Etna cable car €30 self / €78 guided summit; PR1 permit €10.50 pp (SIMplifica); levadas free; Colosseum €18, Vatican €20 |
| Shopping | $2,000 (set) | YOURS | sneaker / streetwear earmark |
| Insurance · CFAR | $700–1,400 | MED | base 4–10% of trip + CFAR ~3%/+40% (Squaremouth) — coverage explained below |
| Entry, bags & data | $300–700 | HARD | UK ETA £20/$26 pp (req. since Feb 2026); intra-EU checked bags £45–85 ea; T-Mobile data ~$0 (below) |
| Buffer | 8% of subtotal | — | FX, tips, surprises |
T-Mobile Magenta / Go5G includes 5GB high-speed in Italy, UK & Portugal plus unlimited slower data & texting in 215+ countries — all three of your countries covered. Add an International Pass (~$5/day or $50 / 30-day 15GB) only if you want more high-speed. Budget $0–70.
UK ETA: required for US citizens since Feb 2026 — £20/$26 pp, 2-yr validity, apply online (minutes). EU ETIAS: not required for this trip — launches Q4 2026, not mandatory until ~Apr 2027. Italy + Portugal = just your passport.
Four things, in order of why they matter here: (1) Medical evacuation — an air-ambulance off Sicily or Madeira can run $50k–250k; this is the real reason to carry it. (2) Emergency medical abroad — your US plan / Medicare generally won't cover you overseas. (3) Trip cancellation / interruption — reimburses prepaid, non-refundable spend (flights, Airbnbs, and the non-refundable Liverpool tickets) if you can't go or must cut it short. (4) CFAR recovers 50–75% even for reasons standard policies exclude. Given non-refundable match tickets + the tight Houston turnaround, I'd carry comprehensive + CFAR — and buy within ~14–21 days of your first deposit to qualify.
Give me those five and I'll lock an hour-by-hour version with named hotels, sample flight itineraries + live fares, every reservation link, and a single fixed total.