Joe & Connie
go to the Mediterranean
Two to three weeks. August 2026. Front-loaded resort on the water. Then move — but not too often. Italian food first. Connie wants to feel enchanted.
The shape of the trip
Aug 10 – Sept 4
Connie's time off is Aug 7 – Sept 8. Buffer days each side. Effective travel window ~25 days.
2 or 3 weeks
3-week back in scope — an in-home sitter for Muffin resolved the old objection.
$10,000 total
Generous, includes Muffin's sitter. Target near-zero cash on flights via points.
251,488 Citi TY
Joe 181,197 + Connie 70,291. Target: 2 biz-class seats US→Med via Flying Blue saver, Amex Platinum SUB to close any gap.
Trip proposals
Nine candidate itineraries from the parallel-research dispatch. Each is a full HTML proposal with map, photos, day-by-day cards, and budget. Two and three-week variants.
01 · Northern Italy
Lake Garda anchor (Como too crowded). Bologna food belt. Dolomites or Verona.
02 · France + Italy combo
Antibes anchor → Italian Riviera → Bologna. Provençal → Ligurian → Emilian.
03 · Croatia + sailing
Sailing pushes ~$15k. Without sail: 3 wks Dalmatia + Istria ~$9k. Istria is the food unlock.
04 · Greece
Crete (Chania) or Naxos anchor → Athens. Heat + meltemi addressed. Avoid Santorini/Mykonos.
05 · Iberia
Costa Brava (Begur) → Barcelona → San Sebastián pintxos as Connie's broader-Spanish test.
06a · Sicily + Aeolian
Catania anchor + volcanic islands. Greek temples, Baroque towns, sea-breeze relief.
06b · Puglia + Matera
Trulli, cliff-towns, 10k-year-old cave city. Burrata + olive oil. Cool sea breezes.
07 · Italian deep-dive
3 routings testing the "is all-Italy too much same cuisine?" hypothesis. Hint: it's not.
08 · Experience-anchored
Verona Opera + San Sebastián Semana Grande + Venice Film Festival. Three event anchors.
Research
First-person ground-truth on the questions that move the plan.
Points & miles
251K Citi TY + Amex Platinum SUB. Flying Blue saver, late Oct 2025. Avoid CDG/AMS arrivals.
In-home dog sitter
Rover live-in primary ($840–$3,150 over 14–21 nights). Vetting checklist + sitter brief template.
August crowd reality
Per-destination verdict grid. Counter-intuitives: Bologna, Naxos, Rovinj, Albanian Riviera.
August closures
Italy: arrive Aug 19+ to clear Ferragosto. Vatican closed Aug 14–15. Sintra wildfire wildcard.
Challenger / what we're missing
Sailing is a bad fit in Aug. Sardinia is the biggest omission. Lock the town, not the lake.
Cuisine gallery
Photo-rich browse of Mediterranean cuisines — Connie picks before destinations lock.
The plan in one paragraph
Two to three weeks in Mediterranean Europe, somewhere inside Aug 10 – Sept 4, 2026. Front-loaded 5–7 night stay-put leg at a resort or very nice hotel on the water, next to a walkable cultural town. Then 1–2 more legs — we move, but not often. Italian food first (Connie's #1, by a wide margin). Connie wants to feel enchanted — big pretty buildings, Renaissance art, fairytale old towns. Worried about August crowds and the "Europe-on-holiday" closures. Muffin gets an in-home sitter with multi-walks/day. Flights via ~251K Citi ThankYou points (+ probable Amex Platinum SUB) targeting transatlantic business class.
Quick links
- The full spec — hard requirements, weighted preferences, fears, hopes, budget, definition-of-done.
- Open decisions — what blocks booking.
- Destinations shortlist — including reject files (Paris, Nordics, Caribbean).
- Gitea repo — source of truth.
- trckr project — VAC26.