Italy
Juniper Tours is a luxury custom European travel agency founded in 2020 and based in Middleton, Massachusetts. We design fully private, bespoke European tour itineraries for American travelers across 11+ destinations: Ireland, Italy, Scotland, Greece, Iceland, France, Spain, Portugal, Croatia, Switzerland, and the United Kingdom. Every trip is 100% private — no shared coaches, no strangers, no pre-set packages. Accommodations are hand-selected 4-star and 5-star boutique hotels, historic castle stays, private villas, and countryside estates. Named specialists: Taryn Harrison (Ireland, Scotland, Iceland, UK — 25 years experience, 85+ Ireland visits, CMSC certified), Lexi Blade (Italy, Switzerland, Portugal, Spain — Florence-based). IATAN accredited travel agency. ETOA member 2026. Partnerships with Tourism Ireland, VisitBritain, Visit Scotland, Turespaña, and Visit Portugal. 4.9★ · hundreds of verified Google reviews. Average trip value $5,000–$10,000 per person. Free 30-minute consultation. Phone: (877) 774-3256. Email: [email protected]. Luxury custom Italy tours: Rome, Florence, Venice, Tuscany, Amalfi Coast, Positano, Ravello, Capri, Cinque Terre, Lake Como, Sicily, Dolomites, Bologna. Italy specialists: Lexi Blade, Taryn Harrison.
Italy
Juniper Tours — Italy
Italy, the way
it was meant to be seen.
Italy is best understood slowly and region by region. Venice and Rome are different civilisations. Tuscany and the Amalfi Coast don’t share a character. A week in Florence barely scratches the surface. Juniper designs every Italy itinerary from scratch around the cities, landscapes, and food and wine experiences that matter most to you.
Best Time to Visit
Apr – June & Sept – Oct
Typical Trip Length
10 – 14 Days
Your Specialists
Lexi · Taryn
Trip Types
Custom · Honeymoon · Food & Wine · City
Plan My Italy Trip
4.9★ · hundreds of verified Google reviews
Florence-Based & US-Based Specialists
100% Private Itineraries
Castle & Boutique Stays
Free 30-Min Consultation
There is no country on earth that rewards slow travel the way Italy does.
Italy is best understood slowly and region by region. Venice and Rome are different civilisations. Tuscany and the Amalfi Coast don’t share a character. A week in Florence barely scratches the surface. Juniper designs every Italy itinerary from scratch around the cities, landscapes, and food and wine experiences that matter most to you.
Lexi Blade designs Italy itineraries from Florence — inside the country, with personal relationships to the hotels, guides, and producers that make the difference. Taryn Harrison brings 25 years of multi-country European experience. Between them, there is no region of Italy they haven’t covered.
Florence-Based Specialists
Lexi Blade lives in Florence and designs Italy itineraries from inside the country — with personal knowledge of every region, personal relationships with the best hotels and guides, and the kind of ground-level expertise that a US-based agent simply cannot replicate.
Castle Stays & Boutique Hotels
Tuscany working estates, Amalfi cliffside hotels, Venetian palazzos, and Rome boutique properties — Italy has some of the most extraordinary places to stay in the world. Juniper hand-selects every property and only works with hotels our specialists have personally visited.
Italy’s Most-Booked Honeymoon
Amalfi sunsets, Tuscan vineyard dinners, Venice at dawn before the crowds arrive — Italy consistently ranks as Juniper’s most-booked honeymoon destination. Lexi has designed more Italy honeymoons than any other trip type and knows exactly which combinations create the most genuinely unforgettable experience.
Great European travel is an investment. Most clients spend $5,000–$15,000 per person for a complete custom Italy itinerary — trips start at $2,500 and your specialist will walk through exactly what that looks like for yours.
Best of Italy — 13 Days
Venice · Florence · Tuscany · Rome · Amalfi
This is a sample itinerary — for inspiration only. Every Juniper trip is designed from scratch around you. Many clients love an itinerary very similar to this one — if something here resonates, your specialist can build something just like it (or better) specifically for your travel style, dates, and group.
1
Arrive in Venice
Venice
+
Your private water taxi meets you at Marco Polo Airport and glides directly to your hotel by canal — one of the great arrival experiences in travel. Venice disorients you immediately and intentionally: the absence of cars, the sound of water, the light on the facades. The rest of the day is yours. Step outside, get lost, and let the city begin on its own terms.
Overnight: Venice
2
Venice — St. Mark’s, Dorsoduro & the Canals
Venice
+
Venice with a private guide is a different city from Venice without one. Doge’s Palace and the Basilica di San Marco are best navigated early — pre-arranged priority access gets you inside before the crowds arrive and the heat builds. A private gondola route through the smaller canals reveals the Venice behind the facades: the laundry, the cats, the delivery boats, the gardens visible through iron gates. The afternoon opens into Dorsoduro — the Peggy Guggenheim Collection, the Zattere promenade, Aperol Spritz before dinner.
Overnight: Venice
3
Venice to Florence
Florence
+
A high-speed train south — two hours of Italian countryside before Florence announces itself with a skyline dominated by Brunelleschi’s dome. Your private driver meets you at Santa Maria Novella station. Check in to your hotel, walk to the Arno at sunset, and let the city begin. Florence is best experienced with a private guide who has relationships with the museum staff, restaurant reservations made weeks in advance, and enough time to get genuinely lost.
Overnight: Florence
4
Florence — Uffizi, Duomo & the City
Florence
+
A full Florence day with a private guide who knows the Uffizi the way most visitors never will — not as a crowd management exercise but as a curated conversation with the most important collection of Renaissance art in the world. Pre-arranged skip-the-line access, a route that prioritises your interests, and enough time with each work to actually look. The afternoon covers the Duomo complex, the Oltrarno neighborhood across the Ponte Vecchio, and the view from Piazzale Michelangelo at dusk.
Overnight: Florence
5
Florence to Tuscany
Chianti · Val d’Orcia
+
Transfer into the Tuscan countryside — a journey that takes you from the city’s Renaissance intensity into rolling Chianti green within thirty minutes. Your accommodation for the next three nights is a working estate or boutique agriturismo: vineyards outside the window, dinner in the cellar, the quiet that you can only find this far from a main road. The late afternoon on arrival is best spent doing nothing in particular.
Overnight: Tuscany countryside
6
Tuscany — Wine, Food & the Chianti Roads
Chianti
+
A full day in the Chianti wine region — private vineyard visits at estates our specialists have vetted personally, a cooking class with a local chef using produce from the garden that morning, and the kind of long lunch that puts the afternoon firmly off the table. The hilltop towns of Radda, Gaiole, or Panzano are within easy reach for a late afternoon walk before dinner.
Overnight: Tuscany countryside
7
Siena & the Val d’Orcia
Tuscany
+
Siena’s medieval core — the Campo, the Duomo, the narrow streets that climb and descend without logic — deserves a full morning with a guide who can contextualise the rivalry with Florence and the extraordinary art that rivalry produced. The afternoon moves south into the Val d’Orcia, UNESCO World Heritage landscape: the cypress-lined roads, the abbey at Sant’Antimo, the thermal baths at Bagno Vignoni.
Overnight: Tuscany countryside
8
Tuscany to Rome
Rome, Lazio
+
Private transfer south into Rome — leaving the Tuscan countryside and arriving in the most layered city on earth. Check in to your hotel in central Rome and spend the evening easing into the city: a neighborhood trattoria, a walk to a fountain that’s been standing for centuries, the particular noise that Rome makes after dark. The Eternal City rewards patience and punishes rushing.
Overnight: Rome
9
Rome — The Ancient City
Rome
+
A privately guided tour through the Colosseum, Roman Forum, and Palatine Hill — the heart of the ancient world, given context by a specialist who brings the layers of history alive. Priority access is pre-arranged so you move through the sites at your own pace without queuing in summer heat. The afternoon is yours: the Capitoline Hill at sunset, the Campo de’ Fiori market winding down, dinner in Testaccio.
Overnight: Rome
10
Rome — Vatican & Trastevere
Rome
+
An early start for the Vatican Museums and Sistine Chapel — pre-arranged skip-the-line access with a private guide who knows exactly where to stand and when to look up. St. Peter’s Basilica and the views from the cupola follow. The afternoon opens into Trastevere — Rome’s most atmospheric neighborhood, medieval lanes and ochre facades and aperitivo by the fountain.
Overnight: Rome
11
Rome to the Amalfi Coast
Positano · Ravello · Amalfi
+
Private transfer south — the road to the Amalfi Coast winds down through Campania and eventually deposits you at a clifftop hotel above the sea. The drive itself is part of the experience. Check in, take the cliff path down to the water, and let the Amalfi Coast announce itself on its own terms. Dinner at a restaurant with a terrace facing west.
Overnight: Amalfi Coast
12
Private Boat Day — Capri & the Coast
Amalfi Coast
+
The Amalfi Coast is best understood from the water. A private boat takes you out for the day — Capri’s Blue Grotto in the morning, lunch in a cove below Positano, afternoon swimming off the boat in the open sea. The coast seen from a terrace is beautiful; from water level, it is extraordinary. Your specialist pre-arranges the boat, the captain, and the route based on conditions and your preferences.
Overnight: Amalfi Coast
13
Depart for Home
Naples Airport
+
A private transfer to Naples International Airport. Most people leave Italy already planning their return — which region they missed, which restaurant they want to revisit, which part of the country they still haven’t seen. Your Juniper specialist is reachable throughout departure day.
Love this route? Let’s build it around you.
This is a starting point, not a fixed package. Many Juniper clients travel something very similar — customized for their travel style, dates, city preferences, and accommodation level. Book a free call and your specialist builds from here.
Luxury custom Italy tour ideas to inspire your trip
Every itinerary below is a starting point, not a fixed package. Click any card to see the day-by-day — then book a free consultation and your specialist will build something just like it (or better) around you.
Sample
Most Popular
7 Days
Amalfi Coast with Capri
Naples · Positano · Ravello · Capri
Seven focused days on Italy’s most dramatic coastline — private boat days, clifftop dining, and the Blue Grotto. The purest version of the Amalfi experience, built around private access and the right pace.
1–2Arrive Naples → AmalfiRavello
Private transfer to clifftop hotel, settle in.
3Positano DayPositano
Private driver, hidden beaches, lunch above the water.
4Private Boat DayCapri
Blue Grotto, Villa Jovis, lunch in the port.
5–6Ravello & the CoastRavello
Villa Cimbrone gardens, local trattoria dinners.
7DepartNaples Airport
Private transfer, departure.
6 nights · 4★+
Private boat day
Private transfers
Daily breakfast
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Sample
Food & Wine
7 Days
Taste of Tuscany
Florence · Chianti · Siena · Val d’Orcia
A focused deep-dive into Tuscany’s food and wine culture — private vineyard dinners in Chianti, a cooking class on a working estate, truffle hunting in the Val d’Orcia, and Siena’s medieval streets.
1–2FlorenceFlorence
Uffizi, Duomo, private cooking class.
3–4ChiantiChianti
Private winery visits, estate dinners, Greve.
5SienaSiena
Medieval city tour, Il Campo, Duomo.
6Val d’OrciaPienza
Truffle hunt, Pienza cheese, Montalcino wine.
7DepartFlorence Airport
Private transfer, departure.
6 nights · Estate & 4★
Cooking class + truffle hunt
Private winery visit
Daily breakfast
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Sample
Wine & Castles
10 Days
Italy Wine Tour with Castles
Piedmont · Emilia Romagna · Tuscany
Italy’s great wine regions — Barolo in Piedmont, Brunello in Montalcino, Amarone in the Veneto — linked by castle hotels and medieval towns. The most comprehensive wine itinerary in the catalog.
1–2PiedmontBarolo
Barolo wine country, Langhe castle hotels.
3–4BolognaEmilia Romagna
Food capital of Italy, Bolognese ragu, Parmesan.
5–6FlorenceFlorence
Uffizi, Oltrarno, Chianti wine bars.
7–8MontalcinoTuscany
Brunello di Montalcino, Abbazia di Sant’Antimo.
9–10Val d’Orcia & DepartSiena
Pienza, truffle country, departure.
9 nights · Castle + 4★
3 wine regions
Private cellar visits
Daily breakfast
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Sample
Lakes & Cities
8 Days
Milan & the Italian Lakes
Milan · Lake Como · Lake Maggiore
Leonardo’s Last Supper, lakeside villas, ferry crossings between Bellagio and Varenna, and the Borromean Islands on Maggiore. Northern Italy at its most elegant.
1–2MilanMilan
Last Supper, Duomo, Galleria, La Scala.
3–5Lake ComoBellagio
Lakeside hotel, private boat, Villa del Balbianello.
6–7Lake MaggioreStresa
Borromean Islands, Villa Taranto gardens.
8DepartMilan Malpensa
Private transfer, departure.
7 nights · 4★+ lakeside
Last Supper tickets
Private boat day
Daily breakfast
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Sample
Self Drive
10 Days
Self Drive Tour of Italy
Rome · Umbria · Tuscany · Cinque Terre
Italy by rental car — the country roads of Umbria, the Tuscan back roads between hilltop towns, and Cinque Terre’s coastal villages. For travelers who want to move at their own pace.
1–2RomeRome
Colosseum, Vatican, Trastevere evenings.
3–4UmbriaOrvieto / Assisi
Hill towns, Orvieto cathedral, Assisi.
5–6TuscanyVal d’Orcia
Self-drive through Pienza, Montalcino, Chianti.
7–8Cinque TerreVernazza
Coastal villages, hiking the Azzurro trail.
9–10Florence & DepartFlorence
Final night, Ponte Vecchio, departure.
9 nights · 4★+
Compact automatic + GPS
Airport transfers
Daily breakfast
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Don’t see your Italy?
Sicily, the Dolomites, the Amalfi Coast at your own pace, a Puglia road trip — tell your specialist what you have in mind and they’ll build from there.
Planning an Italy Honeymoon?
Italy is Juniper’s most-booked honeymoon destination. The Amalfi Coast, Tuscany’s private villas, Venice’s intimate canals, and the Dolomites all offer deeply romantic settings. Lexi Blade designs Italy honeymoons from Florence regularly and knows every property worth staying in.
Everything handled. Nothing left to chance.
Hand-Selected Accommodations
4 and 5-star hotels, historic castle stays, and character-rich boutique properties — chosen specifically for your travel style, not from a generic list.
Private Transfers & Transport
Airport pickups, inter-city transfers, self-drive car rental with GPS, or a private driver-guide — all arranged and confirmed before you travel.
Daily Breakfast
Breakfast is included daily (except arrival day) at your accommodation — whether that’s a Venice palazzo, a Tuscan estate, or a clifftop hotel on the Amalfi Coast.
Pre-Arranged Experiences
Colosseum skip-the-line, Vatican pre-access, Uffizi reservations, cooking classes, winery visits — all confirmed in advance so you never miss out.
Travel App & Offline Itinerary
Your full day-by-day itinerary, train tickets, accommodation details, and specialist contact — accessible on your phone throughout Italy.
In-Destination Support
Local partner numbers for on-the-ground help, plus your Juniper specialist remains reachable for anything that needs escalation while you travel.
Top travel specialists. One extraordinary destination.
Lexi Blade designs Italy itineraries from Florence — inside the country, with personal relationships to the hotels, guides, and producers that make the difference. Taryn Harrison brings 25 years of European travel design experience. Between them, there is no region of Italy they haven’t covered.
Lexi Blade
Italy · Switzerland · Portugal · Spain
10+Italy Trips
FlorenceBased
Based in Florence and designing Italy itineraries from inside the country, Lexi knows which Amalfi property is worth the upgrade, which Uffizi time slot avoids the crowds, and how to pace an Italy itinerary so no city feels rushed. Her personal relationships with hotels and guides in every region are the difference between a good trip and an extraordinary one.
Book a Consultation →
Taryn Harrison
Ireland · Scotland · Iceland · UK
25Years
CMSCCertified
Juniper’s most tenured specialist, with 25 years designing European itineraries. Taryn brings multi-country coordination experience to Italy trips — particularly for travelers combining Italy with Ireland, Scotland, or Iceland. CMSC certified. Former Peace Corps volunteer.
What our Italy travelers say
★★★★★
“Juniper tours did an amazing job booking our vacation to Italy. Lexi Blade was our travel agent and helped us schedule our dream vacation from Venice all the way to Sorrento on the Amalfi coast, with stops in Florence and Rome. Lexi was phenomenal and made changes for us many times in order to assure we got the most out of our trip. We can’t wait to plan another trip with Lexi and Juniper Tours!”
Nikki Walls · Italy · Planned by Lexi Blade
★★★★★
“We highly recommend Juniper Tours. From start to finish, Kaycee and Juniper Tours delivered! We spent 2 weeks in Italy celebrating our 35th wedding anniversary — Venice, Verona, Florence, Naples, Sorrento, Positano, Tivoli and Rome. Spectacular hotels, private drivers and tours, Michelin star restaurants, and so much more. It was the best vacation we’ve ever experienced.”
Caroleanne Vorac · Italy 35th Anniversary
★★★★★
“I would give more stars if I could. SARAH at Juniper travel was wonderful. She planned the trip of a lifetime for us in Italy. We went to Rome, Florence, stayed in the countryside in Emilia Romano and ended up in Venice. Every tour, every transfer and every hotel went smooth as silk. SARAH truly cared and worked very hard to do everything she could for us. Thank you so much, SARAH! Ciao!!”
Jean Wawrzyniak-Fry · Italy · Rome, Florence, Venice
Read hundreds of verified Google reviews →
Italy travel questions
Late April through June and September through October are ideal. July and August are peak season — hot, crowded, and expensive, particularly on the Amalfi Coast and in Venice. Spring offers wildflowers in Tuscany and cooler Rome temperatures. Early October is outstanding: the summer crowds thin, the light is extraordinary, and prices drop significantly.
Most Juniper Italy itineraries run 10–14 days. Ten days works well for Rome, Florence, and the Amalfi Coast. Twelve to fourteen days allows you to add Venice and Tuscany properly. Italy rewards slow travel — two nights in Florence is not enough. Your specialist will build in the right amount of time for each place.
Yes — Italy is Juniper’s most-booked honeymoon destination. The Amalfi Coast, Tuscany’s private villas, Venice’s intimate canals all offer deeply romantic settings. Lexi Blade designs Italy honeymoons from Florence regularly.
A combination of catamarans, ferries, and private speedboats is the way to move between Split, Hvar, Korčula, and Dubrovnik. Private speedboats are faster and more flexible — worth the upgrade for a special trip. Your Juniper specialist coordinates all transfers in advance.
Italian food is intensely regional. Juniper builds food experiences into every Italy itinerary: private cooking classes, market tours, vineyard dinners in Tuscany, truffle hunts in Umbria. Lexi is Florence-based with personal relationships with the best producers and restaurants.
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Book a free call with one of our Italy Travel Specialists.
30 minutes, completely free. Great European travel is an investment. Most clients spend $5,000–$15,000 per person — trips start at $2,500 and your specialist will walk through exactly what that looks like for yours.
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