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Swanson Family Trip 2026

Italy Travel Itinerary

Rome · Florence · Taormina · August 22–31, 2026

10 daysAugust 22–31
3 basesRome, Florence, Taormina
26 stopsTaormina places + reservations

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Tripsy MCP connected 15 activities 4 stays 10 Italy moves + 1 other
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Base city

Before departure

Trip starts Aug 22 0%
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Route

Rome, Florence, Taormina, Rome

Aug 22-24 Rome Arrival, Colosseum, Vatican
Aug 24-26 Florence Duomo, pizza class, Strozzi Airbnb
Aug 26-30 Taormina Castelmola, Etna, boat day, beach club
Aug 30-31 Rome Final hotel night and return flights

Departure Day — August 22, 2026

Saturday · Embark on your Italian journey

Prepare for an exciting adventure ahead!

Arrival in Rome & Ancient Wonders — August 23

Sunday · Welcome to Rome

  • 10:50 AM
  • Transfer
    Get Airport Taxi to Rome Marriott Grand Hotel Flora.
  • 4:00–7:00 PM
    The Best of Colosseum & Ancient Rome with Exclusive Arena Access with LivTours.
    Order number: LVO-662359 · Booking number: LVB-667009.
    Meet in Largo Gaetana Agnesi, underneath the red Metro “M” sign outside the upper-floor entrance of Colosseum Metro Station, Line B. The station has upper and lower entrances; use the upper-level entrance.
    Bring photo ID to guarantee entry.
  • Evening
    Settle in and enjoy a relaxing stroll.
  • Dinner ideas
    Reddit + local tourism shortlist: Trastevere for the liveliest dinner-and-bars night; Monti if you want to stay near the Colosseum for wine bars and trattorias; or Testaccio for classic Roman food and a more local nightlife feel.

Vatican City & Journey to Florence — August 24

Monday · Spiritual and scenic transitions

  • 8:30–11:45 AM
    Vatican Highlights, Sistine Chapel & St. Peter's Basilica | Semi-Private Tour with LivTours.
    Order number: LVO-648781 · Booking number: LVB-653085.
    Meet at Viale Vaticano 100, in front of Cafè Vaticano, right across the street from the Vatican Museums entrance.
    Bring photo ID to guarantee entry.
  • Lunch ideas
    Easy after Vatican: Borgo Pio for characteristic streets near St. Peter's, or Prati / Via Cola di Rienzo for restaurants, wine bars, and shopping before hotel checkout.
  • 1:30 PM
    Check out from the hotel.
  • 3:30–6:42 PM
    Travel to Florence by train. Booking platform: Trainline.
  • 7:15 PM
  • 8:00 PM
    Dinner reservation at Osteria Santo Spirito. Reservation #943.

Florence’s Artistic Heart — August 25

Tuesday · Renaissance discoveries

  • 12:00 PM
    Florence Duomo Tour: Dome & Terraces or First Entry Dome Climb via Viator.
    Meeting point: Via dei Lamberti, 1, 50123 Firenze FI.
    Travelers: 4 adults · Language: English guide · Duration: 2 to 4 hours.
    Experience: Duomo, terraces, and dome climb at 12:00. Ticket ready; show ticket on arrival.
    Booking ID: 1404362763.
  • 6:00 PM
    Pizza-making excursion with Viator.
  • Evening ideas
    Keep it simple after the pizza class: Santo Spirito / San Frediano for the strongest Reddit consensus on lively local food, bars, and aperitivo; or Mercato Centrale / San Lorenzo for casual food-hall options if the group wants easy choices.
Enjoy the vibrant atmosphere of Florence!

Arrive in Taormina — August 26

Wednesday · Ciao Sicilia

  • 6:30 AM
    Check out from the Florence Airbnb.
  • 7:00 AM
    Taxi to Florence Airport — to be scheduled.
  • 1:50 PM
    Brady and Elise arrive in Sicily, take a taxi to the Taormina Airbnb, and check in.
  • Afternoon
    Swansons land shortly after and meet at the Airbnb.
  • Airbnb
  • 6:30 PM
    Leave the house and walk to dinner.
  • 7:00 PM
    Dinner reservation at Ristorante Da Giovanni, Via Nazionale, 117, 98039 Taormina ME.
  • 10:00 PM
    Reservation at Morgana club, Scesa Morgana, 4, 98039 Taormina ME.

Castelmola & Sunset Wine Tour — August 27

Thursday · Explore Taormina and Etna

Savor the unique flavors of Sicily!

Boat Day & Al Saraceno — August 28

Friday · Coast, dinner, and views

  • 8:30 AM
    Taxi pickup for boat day.
  • Boat day
    Isola Bella boat tour; taxi drops everyone back at the house afterward.
  • 6:45 PM
    Taxi pickup for dinner.
  • 7:00 PM
    Dinner reservation at Al Saraceno, Via Madonna della Rocca, 16/18, 98039 Taormina ME.
  • After dinner
    Walk home.

Tao Beach Club & Velvet Rooftop — August 29

Saturday · Beach beds and sunset drinks

  • 10:45 AM
    Taxi pickup for Tao Beach Club.
  • 11:00 AM
    Day-bed reservations confirmed at Tao Beach Club, Via Nazionale, 175, 98039 Taormina ME. Order #30362.
  • 3:00 PM
    Taxi pickup from beach club back to the house.
  • 6:00 PM
    Leave the house and walk to drinks.
  • 6:30 PM
    Reservation for drinks at Velvet Rooftop Cocktail Bar, Via Nazionale, 147, 98039 Mazzarò.

Return to Rome — August 30

Sunday · Early flight and farewell dinner

Enjoy your final evening in Rome, with time for souvenirs or a leisurely walk.

Departure Day — August 31

Monday · Arrivederci, Italia

Buon viaggio!

Taormina Places & Reservations

Places from the shared Google Maps list plus reservations from the Taormina itinerary: open full list.

Loading Taormina map... The place cards below still open directly in Google Maps.
Residence San Giorgio
Via Mario e Nicola Garipoli, 4, Taormina
Stay
Ristorante Da Giovanni
Via Nazionale, 117, Taormina
Reservation
Morgana Taormina
Scesa Morgana, 4, Taormina
Nightlife
Villa Comunale
Taormina public gardens
Landmark
Piazza IX Aprile
Corso Umberto, Taormina
Landmark
Velvet Rooftop Cocktail Bar
Via Nazionale, 147, Mazzarò
Drinks
Ristorante Da Fabiana
Via Michelangelo Garufi, Letojanni
Restaurant
Lido Tao Beach Club
Via Nazionale, 175, Taormina
Beach
LAMURI cocktails & food
Lungomare IV Novembre, 69, Giardini-Naxos
Drinks
Osteria Pizzeria Le Tre Vie
Via Crocefisso, 4, Taormina
Restaurant
Mamma Mia
Via Bagnoli Croci, 52, Taormina
Restaurant
La Romana
Via Cappuccini, 1, Taormina
Cafe
Bam Bar
Via di Giovanni, 45, Taormina
Cafe
Time Out Pub
Viale S. Pancrazio, 21, Taormina
Drinks
Incanto
Via Leonardo Da Vinci, 60, Taormina
Restaurant
PierdeCat Sicilian Bistro di Saglimbene Piero
Via Sottotenente Leto, 12, Castelmola
Restaurant
Pizzeria Nina
Via Tutti I Santi, Castelmola
Pizza
Malvasia
Viale Apollo Arcageta, 8, Taormina
Restaurant
Ristorante Pizzeria Porta Messina
Largo Giove Serapide, 4, Taormina
Pizza
Ristorante Pirandello 2.0
Via Luigi Pirandello, 20, Taormina
Restaurant
Al Saraceno
Via Madonna della Rocca, 16/18, Taormina
Restaurant
TreQuarti Taormina Antipasteria Siciliana
Salita Guglielmo Melivia, 7, Taormina
Restaurant
Taverna Don Nino
Via Bagnoli Croci, 19, Taormina
Restaurant
Liola Osteria and Bar
Viale S. Pancrazio, 10, Taormina
Restaurant
Nui Restaurant
Via Nazionale, 161, Taormina
Restaurant
Ristorante Le Grand Bleu
Via Nazionale, 105, Taormina
Restaurant

Important To-Do List

Taormina confirmations from attached itinerary

Reddit-Tested Italian Phrases

The practical words travelers kept recommending: polite greetings, ordering, transit, payment, and quick help.

BuongiornoGood morning / good day; polite for shops and restaurants
BuonaseraGood evening; use later in the day
ArrivederciGoodbye; polite when leaving
Buona giornataHave a good day
CiaoHi / bye; more casual
Per favorePlease
Grazie / grazie milleThank you / thank you very much
PregoYou are welcome / go ahead / after you
No, grazieNo, thank you
Mi scusiExcuse me; polite way to get attention
PermessoExcuse me; let me pass
Mi dispiaceI am sorry
Sì / NoYes / no
Non parlo italianoI do not speak Italian
Non capiscoI do not understand
Lei parla inglese?Do you speak English? Polite form
Può parlare più lentamente?Can you speak more slowly?
Questo, per favoreThis, please
Vorrei questo, per favoreI would like this, please
Quanto costa?How much does it cost?
Sto solo guardando, grazieI am just looking, thanks
Un cappuccino, per favoreA cappuccino, please
Un cornetto, per favoreA croissant, please
Siamo in quattroThere are four of us
Ho una prenotazioneI have a reservation
Il conto, per favoreThe check, please
Ci può portare il conto?Could you bring the check?
Posso pagare con carta?Can I pay by card?
Tenga il restoKeep the change
Acqua naturale / frizzanteStill / sparkling water
Senza glutineGluten-free
Senza lattosioLactose-free
Sono vegetariano/aI am vegetarian
Dov'è il bagno?Where is the bathroom?
Dov'è la stazione?Where is the station?
Come arrivo a...?How do I get to...?
A che ora parte il treno?What time does the train leave?
BinarioTrain platform
UscitaExit
EntrataEntrance
Vorrei un taxiI would like a taxi
Mi consiglia un posto qui vicino?Can you recommend a nearby place?
CopertoCover charge; common on restaurant bills
ScontrinoReceipt
BancomatATM / debit card
AiutoHelp
EmergenzaEmergency