John & Ruth Reay — First-Class Greece & Italy
First-Class Private Journey

John & Ruth's
Greece & Italy

14 days of private cooking, five-star suites, bespoke shopping, and dinners lit by 400 candles.

14Days
4Private Classes
5Luxury Hotels
$30KAll-In

The First-Class Route

Business class into Athens. A 17th-century Venetian mansion in Chania. Private cooking over wood fire. The Ferragamo family's art collection in Florence. Dinner under 400 candles at Le Sirenuse. Custom linen tailored same-day in Positano. A private boat around Capri. Home through Naples, never backtracking.

The Route

SRQ/RSW → Athens (1 night) → Chania, Crete (4 nights, Casa Delfino Penthouse) → Naxos (2 nights) → Athens → Bologna (2 nights, Grand Hotel Majestic) → Florence (3 nights, Hotel Lungarno) → Positano (2 nights, Le Sirenuse) → Naples → Home

What Makes This First-Class

Every cooking class is private — just you two with the chef. Every hotel is the best in its city. A private boat replaces the ferry at Balos and Capri. Shopping means same-day tailoring delivered to your suite. The Italian food tour is a private van with your own guide.

Ruth's Wardrobe Stops

Florence: Boutique Nadine (ask for Irene), AquaFlor (bespoke perfume with Sileno), Angela Caputi (handmade jewelry). Positano: Casa Mastro (ask for Ivan or Esther — same-day tailoring to Le Sirenuse), Antonio Viva (bespoke sandals in 15 min), La Bottega di Brunella. Capri: La Parisienne (Jackie Kennedy's tailor).

John's Highlights

Parmigiano factory at dawn, private guide. 25-year balsamic in a family attic. Wood-fire Cretan lamb (Meat Wagon technique theft). Whole fish grilled Greek-style. Bistecca alla Fiorentina 3 inches thick. Italian linen shirts from Casa Mastro. Borgo San Jacopo Michelin dinner with 900 wines.

Greece — Days 1 through 8

Crete's Venetian old town, a private farmhouse cooking class, mountain villages, and the Cycladic island Greeks keep for themselves.

Day 1Travel

Sarasota to Athens — Business Class

Morning
Depart SRQ/RSW business class. Delta One via ATL → ATH nonstop (lie-flat, lounge access). Open-jaw: fly INTO Athens, OUT OF Naples Day 14. ~$4,500-6,500/pp
Late PM
Arrive Athens. Private transfer to Hotel Grande Bretagne. Rooftop wine overlooking the Acropolis lit at night. Bed.
★Night 1: Hotel Grande Bretagne, Athens — rooftop Acropolis view. ~$400-600/night.
Day 2Crete

Athens to Chania — Into the Venetian Quarter

8:30 AM
Flight Athens → Chania (Aegean Airlines, 55 min). Private transfer to hotel.
10:30 AM
Check into Casa Delfino Hotel & Spa. 17th-century Venetian mansion, six generations same family. Penthouse Suite — private rooftop terrace, panoramic harbor and lighthouse views. Owner Margarita is on-site daily. Concierge team Chrissy and Eleni arrange everything. ~$350-500/night
12:00 PM
Private food walk through Chania's Agora market. Graviera cheese aged in caves, mountain herbs, thyme honey from the beekeeper. Walk the Venetian harbor. Lunch at a hidden taverna — dakos, grilled octopus, copper-pitcher wine.
4:00 PM
Splantzia quarter. The neighborhood nobody visits. Find a kafeneio — Greek coffee and raki. Sit for an hour.
8:30 PM
Dinner at Glossitses. Modern Cretan tasting menu with wine pairing. ~$200-280/couple
★Nights 2-5: Casa Delfino Penthouse, Chania — 4 nights. Harbor views, marble hammam, concierge-arranged privates.
Day 3Crete

Veerna's Kitchen — Private Cooking Class

10:30 AM
Private cooking class at Veerna's Kitchen. Universally rated #1 experience in western Crete. Veerna and brother Kostas welcome you into their family property. Private session — just you and Ruth. Cook "The Thieves' Dinner": boureki, slow-roasted herb lamb, dakos, kaltsounia. Recipes from their grandmother. Raki flows. Eat everything under the trees. ~$250-350 private
3:30 PM
Nea Chora Beach. The local beach. Swim. Nap.
5:30 PM
Couples spa at Casa Delfino. Marble hammam + massage.
8:30 PM
Light meze dinner on the rooftop. After cooking all day, keep it simple.
Book now: chaniacookingclass.com — request private session. Tell them you're at Casa Delfino; they coordinate transfer.
Day 4Crete

Private Driver — Mountains, Olive Oil & Wine

9:00 AM
Private car + driver for the day. Via Casa Delfino concierge. ~$350-400
9:45 AM
Private olive oil estate. Family press, single-varietal Koroneiki tastings. Buy tins.
11:30 AM
Theriso village. Population ~50, one taverna, grandmother cooks wood-fire lamb. John: study the technique — herbs in joints, slow over wood, no sauce.
2:30 PM
Botanical Park & Gardens of Crete. 20-hectare garden, on-site restaurant using only estate ingredients.
5:00 PM
Manousakis Winery. Private tasting. Rhone varietals in Cretan volcanic soil. Nostos Syrah on the terrace.
Day 5Crete

Balos Lagoon, Beach & Cretan Shopping

7:00 AM
Private boat to Balos Lagoon. Skip tourist ferry. Captain drops you before crowds. Turquoise shallow water, pink sand, wild goats. ~$400-600
12:30 PM
Falassarna Beach. Wide, uncrowded. Beachside taverna lunch.
3:30 PM
Ruth's Cretan shopping. Stivanadika street — custom leather sandals (~$40-80). Halidon street — hand-embroidered linen. Ask Casa Delfino concierge which specific cobbler they recommend this season.
8:30 PM
Farewell Crete: Palazzo al Mare. Terrace table, tasting menu, wines from producers you actually visited. ~$220-300/couple
Day 6Naxos

The Island Greeks Keep for Themselves

Morning
Fly or ferry to Naxos via Athens. High-speed ferry is the more memorable option (~4 hrs, Cycladic views).
PM
Arrive Naxos Chora. Boutique suite in the Kastro (Venetian castle quarter). Private terrace, Aegean views.
7:00 PM
Sunset at the Portara. Temple of Apollo marble gate, peninsula causeway. Free and unforgettable.
★Nights 6-7: Naxian Collection or 18 Grapes — boutique luxury. 2 nights. ~$300-450/night.
Day 7Naxos

Private Naxian Cooking & Mountain Villages

9:00 AM
Private cooking with a Naxian family. Harvest herbs, cook gemista, cheese pies, slow-cooked lamb. Eat under the grape arbor. ~$200-300 private
2:30 PM
Interior Naxos. Tragaea valley, Byzantine churches, marble quarries. Halki village — Vallindras Distillery kitron tasting.
4:30 PM
Apiranthos village. Marble-paved, zero tourism, old men playing tavli. Buy wild honey.
Meat Wagon Intel: Study the Greek charcoal fish technique — olive oil, lemon, oregano, nothing else. Transfers directly to your setup.
Day 8Crossing

Greece to Italy

Morning
Naxos → Athens → Bologna (Aegean direct, ~2.5 hrs). Or fly to Rome, Frecciarossa Executive to Bologna (2 hrs, leather seats, complimentary drinks).
Evening
Grand Hotel Majestic già Baglioni. Only 5-star in Bologna. 16th-century palazzo, Carracci frescoes, Michelin restaurant. Walk the porticoes. First real tortellini in brodo. ~$400-550/night
★Nights 8-9: Grand Hotel Majestic, Bologna — 2 nights.

Italy — Days 9 through 14

Bologna's artisan food factories. The Ferragamo family's Florence. Positano's Le Sirenuse. Every detail elevated.

Day 9Bologna

Private DOP Food Tour — Parmigiano, Balsamic & Prosciutto

7:00 AM
Private food tour — just you two, driver, guide. Emilia Delizia or Bologna Gourmet (guide: Ilaria). ~$500-700 private
7:45 AM
Parmigiano Reggiano factory. 80-lb wheels pulled from copper vats at dawn. Aging warehouse worth millions. Taste 15-month vs 25-month. "Breakfast of Champions": mortadella, salami, pastries, real Lambrusco, espresso.
11:00 AM
Family acetaia — Traditional Balsamic Vinegar of Modena. One of 310 authorized families. Attic aging, 5-7 barrels of different wood. Taste 6, 12, and 25-year. The 25-year on vanilla gelato is transcendent.
1:00 PM
Prosciutto factory. Two ingredients: pig + salt. Fresh hand-cut slices with Lambrusco Grasparossa.
2:30 PM
Private 8-course lunch at a countryside agriturismo. Homemade pasta, local wine. You will not need dinner.
Day 10Bologna → Florence

Private Pasta Class & Oltrarno Shopping

8:30 AM
Private pasta with a Bolognese sfoglina. Roll sfoglia by hand with a 3-foot pin. Fill tortellini. Make tagliatelle + ragu. ~$200-300 private
12:30 PM
Frecciarossa Executive, Bologna → Florence. 37 minutes. Espresso, prosecco, countryside views.
1:30 PM
Check into Hotel Lungarno. Ferragamo-owned, on the Arno, 100m from Ponte Vecchio. 450+ artworks including Picasso and Cocteau. Premium River View room. Ferragamo bath products. Borgo San Jacopo Michelin restaurant + 900 wines. ~$550-750/night
3:00 PM
Ruth's Oltrarno shopping. See Ruth's Style Guide tab for full details — who to ask for by name, what to say, and pre-arrival contact info for Boutique Nadine (Irene), AquaFlor (Sileno), and Angela Caputi.
8:30 PM
Dinner at Borgo San Jacopo. Michelin star, window table over the Arno and Ponte Vecchio at night. Tasting menu. ~$400-550/couple
★Nights 10-12: Hotel Lungarno, Florence — 3 nights.
Day 11Tuscany

Private Tuscan Villa Cooking & Chianti

9:00 AM
Private car to Chianti farmhouse. Market, then cook: pappardelle, ribollita, bistecca, cantucci. ~$400-600 private
1:30 PM
Feast on the terrace overlooking vineyards. Estate Chianti Classico.
3:30 PM
Private wine tasting at a small Chianti estate. Riserva, Super Tuscans, vin santo.
6:30 PM
Aperitivo at Piazzale Michelangelo. 360-degree Florence view at golden hour.
8:30 PM
Trattoria Sostanza. Cash only, communal tables, best butter chicken in Italy. The deliberate contrast.
Day 12Florence → Positano

South to Le Sirenuse

11:30 AM
Frecciarossa Executive to Naples (2h45). Private Mercedes transfer Naples → Positano (~75 min). ~$200-250
4:00 PM
Check into Le Sirenuse. The Sersale family since 1951. Junior Suite Sea View — private balcony, entire bay of Positano, double whirlpool with ocean view. Michelin La Sponda. Champagne & Oyster Bar. ~$1,000-1,400/night
5:00 PM
Ruth's Positano shopping. See Ruth's Style Guide tab — full details on Casa Mastro (ask for Ivan or Esther), Antonio Viva, Maria Lampo, La Bottega di Brunella. Same-day tailoring delivered to Le Sirenuse.
8:30 PM
Dinner at La Sponda. 400 candles lit every evening. Guitar and mandolin. Terrace overlooking Positano's lights. Ruth in her new dress, candlelight, the bay below. The dinner she talks about for 10 years. ~$450-650/couple
★Nights 12-13: Le Sirenuse, Positano — Junior Suite Sea View. 2 nights.
Le Sirenuse perk: Book a Suite for 2+ nights June-Sept and they include a 2-hour sail on their Riva Aquarama Special — classic Italian wooden speedboat. Don't skip it.
Day 13Capri

Private Boat to Capri

9:00 AM
Private boat charter. Captain picks you up from Positano marina. Hidden coves, swim stops, Faraglioni rocks. ~$1,000-1,800
11:00 AM
Capri. Ruth: La Parisienne (Jackie Kennedy's tailor — bespoke Capri pants). John: artisanal limoncello tastings. Carthusia perfume. Gardens of Augustus.
1:00 PM
Lunch: Il Riccio (Michelin star beach club) or Da Paolino (lemon-tree canopy).
5:30 PM
Le Sirenuse spa. Couples massage. Then Franco's Bar terrace at sunset.
8:30 PM
Farewell dinner: Aldo's Champagne Bar at Le Sirenuse. Oysters, seafood, champagne. End with limoncello.
Day 14Home

Positano → Naples → Home

9:00 AM
Final breakfast at Le Sirenuse. Bay terrace. Take your time.
11:00 AM
Private transfer to Naples Airport. 90 min coast road.
2:00 PM
Business class: Naples → hub → SRQ/RSW. Open-jaw, no backtracking. Lie-flat home.

Ruth's Personal Style Guide

Who to ask for by name at every boutique, size conversion, style preferences, and pre-arrival email templates so they're pulling pieces before Ruth walks in the door.

Fill In Once, Use EverywhereMeasurements

Ruth's Sizes & Preferences

US Dress Size
Italian Size (US + 6)
Height
Bust (in)
Waist (in)
Hips (in)
US Shoe Size
EU Shoe Size (US + ~31)
Foot Width
Style — What Ruth gravitates toward
Colors She Loves
Colors to Avoid
Fit Notes

Quick Size Conversion

USITUKBustWaistHips
238632-33"24-25"34-35"
440834-35"26-27"36-37"
6421035-36"27-28"38-39"
8441237-38"29-30"39-40"
10461439-40"31-32"41-42"
12481640-42"33-34"43-44"
14501842-44"35-37"45-46"
Italian sizing runs small and narrow. When in doubt, size UP. Every boutique below does on-site tailoring — better to start larger and take in. Show staff your measurements; they handle the rest.
Florence — Day 10Boutique

Boutique Nadine — Curated Fashion & Vintage

IZ
Irene Zarrilli — Owner & Founder
Founded 2006 at age 22. Personally sources every piece across Italy/Europe. Also designs her own line Odette — romantic dresses with feminine silhouettes, fabrics from small Florentine textile houses. Her partner Matteo co-runs the shop. Ask for either by name.

What they carry: Emerging Italian designers (clothes made in Florence — rare today), vintage Pucci/Chanel/Dior/YSL, Irene's Odette line. Silk, cashmere, floral motifs, wrap dresses, handmade jewelry. Staff puts pieces in the dressing room and styles without being pushy.

Address: Lungarno Acciaiuoli 22r, Florence
Hours: Mon-Sat 10-8, Sun 12-7:30
WhatsApp: +39 320 690 6660
IG: @boutiquenadine
Pre-arrival: WhatsApp Irene 1 week ahead. "We're at Hotel Lungarno [dates]. My wife loves [style]. Italian size [X]. Could you set aside pieces?" She will.
Florence — Day 10Perfumery

AquaFlor — Bespoke Perfume

SC
Sileno Cheloni — Master Perfumer & Owner
Works from a 15th-century palazzo with 1,000+ raw materials. His team interviews Ruth about memories, moods, what she wants to feel — then blends a fragrance unique to her. 45-minute consultation. ~$150-300 for bespoke.
Address: Borgo Santa Croce 6, Florence
Book: Through Hotel Lungarno concierge (direct relationship)
Florence — Day 10Jewelry

Angela Caputi — Handmade Statement Jewelry

AC
Angela Caputi — Designer & Owner (in-shop daily)
Hand-making bold Italian resin jewelry since the 1970s. Shock of white hair, assembles every piece herself. Chunky, colorful statement necklaces and earrings. Happy to chat. Just walk in.
Address: Borgo Santi Apostoli 44-46/r, Florence
Positano — Day 12Atelier

Casa Mastro — Handmade Linen, Same-Day Tailoring

IM
Ivan Mastro — Co-Owner & Front of House
Third-generation Positano tailor. Father Raffaele was a founding Moda Positano tailor for 30+ years. Ivan runs the floor, styles customers, coordinates same-day tailoring. The person most reviewers rave about.
CM
Cristiana Mastro — Co-Owner & Head Tailor
Ivan's sister, the production genius. She cuts, sews, and does same-day alterations in the back atelier. Hem, taper, adjust — delivered to Le Sirenuse by evening.
E
Esther — Senior Stylist
Named in more Google reviews than any other staff member. "A joy," "not pushy," "made my shopping experience special." If Ivan is busy, ask for Esther — she'll style Ruth head to toe and show multiple ways to wear each piece.

What they make: 100% linen, designed and handmade in Positano by the Mastro family. Dresses, wide-leg pants, tunics, blouses. Fabrics are layered and dimensional. Custom embroidery and lace. John: Beautiful men's linen shirts here too — ask Ivan.

The superpower: They measure, pin, tailor, and deliver to Le Sirenuse same day. Ruth picks pieces in the morning, they're tailored by afternoon, delivered by evening.

Address: Via dei Mulini, Positano
IG: @casamastro_positano
Phone: +39 368 946 191
Web: casamastropositano.com
Pre-arrival DM (1 week before): IG or phone. "My wife and I are at Le Sirenuse [dates]. She's US size [X] / Italian [Y], loves [style] in [colors]. Can you pull pieces? We need same-day tailoring with delivery to Le Sirenuse." They will say yes.
Positano — Day 12Sandals

Antonio Viva — Bespoke Leather Sandals Since 1958

AV
Antonio Viva — Master Sandal-Maker
Hand-assembles bespoke sandals from morning to night. Choose style, strap width, color, heel, embellishments. He measures Ruth's feet, builds them on the spot — done in 15 minutes. 100% Italian leather, non-slip rubber sole. ~$80-150/pair. Go before 2pm when it's less crowded.
Address: Via Pasitea, Positano
No appointment needed — walk in
Positano — Day 12Boutique

Maria Lampo — The Original Positano Boutique

ML
The Lampo Family — 3rd Generation
Maria and husband Alfonso opened one of the first shops post-WWII when Positano was a fishing village. Sign read "Made-to-Measure Trousers — ready after an afternoon at the beach." Maria was so fast she earned the name "Lampo" — Italian for lightning. Three generations later, family still runs it.

Style: Bold patterns, vivid Mediterranean colors, flowing skirts, Positano peasant blouses. More bohemian and color-forward than Casa Mastro — good complement.

Address: Via Pasitea 12-16, Positano
Capri — Day 13Bespoke

La Parisienne — Where Jackie Kennedy Got Her Capri Pants

LP
La Parisienne Team
This is where Jackie Kennedy had the famous Capri pants made — giving the world the term "Capri pants." Still producing bespoke pieces. Walk in, get measured, choose fabric. Just say "I'd like something made" — they know the drill.
Address: Piazza Umberto I (the main piazzetta), Capri
No booking needed — walk in
Crete — Day 5Artisan

Stivanadika Street — Custom Leather & Linen

S
The Cobbler Families of Stivanadika
Historic leather-workers' street in Chania Old Town. Multiple family workshops making custom sandals, bags, belts for generations. Walk the street, sit with whoever's work catches your eye. Custom sandals while you wait (~$40-80). Ask Casa Delfino concierge (Chrissy or Eleni) which cobbler they recommend this season.

Also nearby (Halidon Street): Hand-embroidered linen dresses, woven textiles, silver jewelry. Casual beach cover-ups and unique Cretan pieces.

Pre-TripAction Item

Copy-Paste Pre-Arrival Message

Send to Casa Mastro (IG DM or phone) and Boutique Nadine (WhatsApp) 1-2 weeks before arrival:

Casa Mastro: IG DM @casamastro_positano or phone +39 368 946 191. Boutique Nadine: WhatsApp +39 320 690 6660. AquaFlor: Book private consultation through Hotel Lungarno concierge. La Parisienne & Antonio Viva: Walk in, no pre-booking needed.

Budget & Booking Plan

The full financial picture and exactly what to book this week.

First-Class Budget — Two People, All-In

CategoryEstimate
Business class flights — open-jaw SRQ→ATH / NAP→SRQ (2 pax)$9,000 – $13,000
Internal flights, ferries, exec trains$600 – $900
Hotels — 13 nights (Grande Bretagne 1, Casa Delfino 4, Naxos 2, Majestic 2, Lungarno 3, Le Sirenuse 2)$7,500 – $9,500
Private cooking classes — 4 sessions$1,100 – $1,600
Private DOP food tour, Bologna$500 – $700
Private boats — Balos + Capri charter$1,400 – $2,400
Private drivers & luxury transfers$1,000 – $1,500
Dining — splurge + everyday$3,500 – $5,000
Shopping — Ruth's wardrobe + John's leather/linen$2,500 – $5,000
Spa, wine, olive oil, gifts, tips, misc$1,100 – $2,000
Total (2 people)$28,000 – $41,000
Sweet spot: $30,000-$32,000. Every experience on the itinerary, no compromises. Ruth wakes up in Le Sirenuse, dines under 400 candles in a dress tailored that afternoon, and comes home with a perfume that exists nowhere else in the world.

Booking Sequence

This Week
1. Business class open-jaw flights (Google Flights alerts)
2. Le Sirenuse Jr Suite Sea View — sirenuse.it
3. Veerna's Kitchen private — chaniacookingclass.com
4. Private Bologna food tour — emiliadelizia.com
Week 2
5. Casa Delfino Penthouse — casadelfino.com
6. Hotel Lungarno Premium River View — lungarnocollection.com
7. Grand Hotel Majestic, Bologna
8. Internal flights (Aegean Airlines)
9. Naxos hotel + Tuscan cooking class
Week 3-4
10. Frecciarossa trains — trenitalia.com
11. Private boat charters (via hotel concierges)
12. Restaurant reservations: La Sponda, Borgo San Jacopo, Glossitses, Il Riccio
13. Pre-arrival messages to Casa Mastro + Boutique Nadine
14. AquaFlor consultation via Lungarno concierge

When to Go

Best
Late May – mid June or September – mid October. Warm enough to swim (75-85°F), everything open, 40-60% lighter crowds, 20-35% cheaper flights/hotels. The light is golden. This is when seasoned travelers go.
Avoid
Mid-July to August. Intense heat, peak pricing, Le Sirenuse books 6+ months ahead, Amalfi road is a traffic nightmare. You'd pay $35-45K for a worse experience.

Packing

Ruth
Pack light — you're buying in Italy. One dinner dress for early nights, walking shoes, elegant sandals, swimwear, cashmere wrap. Leave half the suitcase empty. Buy a leather bag in Florence to carry everything home.
John
Linen pants (2), polos, one collared shirt for Michelin nights, leather shoes, swim trunks, light jacket. You'll grab linen shirts at Casa Mastro. Bring a soft cooler for transporting olive oil and balsamic home.
Essentials
EU adapter (Type C/F). Airalo eSIM (~$15, Greece + Italy). Polarized sunglasses. Reef-safe sunscreen. Crossbody day bag. Passport (6+ mo validity). Travel insurance with Cancel For Any Reason.