26 Leisurely Days Exploring Italy

Travel Idea:

26 Leisurely Days Exploring Italy

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Destination for this trip:

Amalfi Coast, Italy; Assisi, Italy; Florence, Italy; Liguria, Italy; Milan, Italy; Piemonte, Italy; Rome, Italy; Tuscany, Italy; Venice, Italy

Length of trip:

26 days

Approximate price of this trip per person:

from $ 4000 to $ 7000

Best travel dates to go:

March, April, May, June, July, August, September, October

Detailed Description of this trip:

On this glorious trip, you will be able to experience all the notable aspects of Italy. From Milan and da Vinci's "Last Supper" to the gorgeous Lakes District and unique Venice, your days will be filled with new sights and sounds to enjoy. Don't forget to visit art and history-drenched Florence within the incomparable Tuscan landscape. Then travel on to ancient Rome, and two breathtaking coastal vistas of Italy--the Cinque Terre and the Amalfi Coast. This trip is truly the complete Italy journey!

Trip Properties:

Trip Itinerary:

  • Day 1 - On the Plane

    depart USA on overnight flight
    overight flight
    Commercial Flight

    Depart the USA on an overnight flight to Milan.

  • Day 2 - Milan

    arrive in Milan, transfer from airport to hotel
    Milan City Tour, Including "Last Supper"
    Group Tour

    Enjoy a guided and personally narrated visit around the highlights of Milan: its fabulous Duoma, La Scala Theater, Sforza Castle, and finish the afternoon with a viewing of da Vinci's infamous "Last Supper" fresco.

  • Days 3-5 - Piemonte

    Lakes Region---train from Milan to Stresa at Lake Maggiore, check into hotel with lake view and enjoy 3 days exploring the Italian Lakes Region
    day at leisure

    Day 3--After your short train trip from Milan to Stresa, enjoy the balance of the day exploring the shores of Lake Maggiore on your own.

    day at leisure

    Day 4--Today you will pick up your rental car to drive to Lake Como where you will spend the day before returning to your hotel in Stresa.

    day at leisure

    Day 5--Use your rental car and visit Lugano, Switzerland today and make any other stops along the way that intrigue you into exploration. Overnight again at Stresa.

  • Days 6-8 - Venice

    Drive from Stresa to Venice, stopping to visit Verona along the way and check into your 4-star hotel near St. Mark's Square.
    Verona self-tour and travel to Venice

    Day 6--After you check out of your Stresa hotel today, use your car to drive to the town of Verona, where Shakespeare's "Romeo and Juliet" takes center stage. Then continue on to Venice where you will drop off your car and enjoy this unique city for 3 nights.

    Venice City Walking Tour
    Group Tour

    Day 7--This morning join a walking tour to explore the highlights of Venice: its Basilica San Marco and Doges' Palace, as well as discover its small canals and meandering "streets." Your afternoon and evening are free to do as you please. How about a stroll and cup of coffee at Piazza San Marco while you listen to the "dueling orchestras?"

    day at leisure

    Day 8--This last day in Venice is yours to do exactly as you please. Will you take a boat trip out to the other lagoon islands of Murano (famous for its ancient glass-blowing techniques), Burano (famous for its hand-made lace), and Torcello (the true origin of Venice)? Will you shop the many glass and Carnevale Mask stores and along the Rialto Bridge? Will you visit any number of other churches and museums? Don't forget to enjoy a ride in a gondola--the main reason everyone comes to Venice!

  • Days 9-11 - Florence

    After traveling by train to Florence, delve into this city rich in history, artistic masterpieces, and Medieval/Renaissance-era ambiance.
    travel from Venice and visits Accademia Gallery

    Day 9--After arrival, use this afternoon to pay a visit to Michelangelo's masterpiece "David." Entrance lines here are always long, but you will be given priority access. Use the balance of the afternoon and evening for exploring this fascinating city on foot.

    Morning Florence City Walking Tour
    Group Tour

    Day 10--This morning join a walking tour of Florence as your guide offers you insights into Florence's glorious (and tumultuous) history, esteemed citizens in the political, scientific, and artistic world, and famous landmarks. Use the afternoon to pay visits on your own to the Medici Chapels, perhaps the Pitti Palace and Boboli Gardens. See if you can resist buying something sparkly as your cross the Ponte Vecchio lined with goldsmiths and jewelers!

    Uffizi Gallery and day at leisure

    Day 11--Today enjoy a visit to Florence's other illustrious museum--the Uffizi Gallery. Your visit will be unguided, but you will be given priority entrance, thus avoiding the massive lines of tourists waiting for admission outside. The rest of the day is yours to enjoy Florence; enjoy its street markets, performances, and innumerable other famous churches and sights.

  • Days 12-14 - Liguria

    Cinque Terre---Leave Florence on your way to the Cinque Terre coastline, with a quick stop in Pisa as you go. Enjoy a seaview room in the larger of the towns, Monterosso al Mare.
    Pisa and Cinque Terre

    Day 12--After you check out of your Florence hotel, board a train to Pisa where you will view the infamous Leaning Tower before you continue on to the Cinque Terre coastal villages.

    Cinque Terre exploration

    Day 13--There are 5 coastal villages here, each with its own distinct personality. You can hike, train, or boat between all 5 of them at your leisure over the next 2 days. Enjoy sweet local wine, fresh pesto, and seafood caught only that morning as you use this time to simply relax in the middle of your vacation.

    Cinque Terre exploration

    Day 14--Same as day 13. Treat this remote and laid-back destination as a vacation from your vacation and rejuvenate yourself.

  • Days 15-17 - Tuscany

    Travel inland again to enjoy the history and green vistas of Tuscany, with Siena as your base and a rental car to aid your independent explorations.
    travel to Siena

    Day 15--As you leave the Cinque Terre and pick up a rental car, take your time and visit one or two Tuscan villages on your way to finding your home base in Siena. The many-towered town of San Gimignano is little-changed from medieval times, as if it was frozen in history. Once in Siena, enjoy a stroll along its streets until you reach il Campo, the "town square" and location of Siena's Palio horse race.

    driving day at leisure through Tuscany

    Day 16--Use your car today to simply drive. Tuscan towns are too many to mention, but you might try to visit anything with "chianti" in its name, Pienza, Montalcino (famous for its Brunello red wine and plenty of free tastings), Montepulciano, and more. Are you also a WWII buff? Did you know there is an American Cemetery just outside of Florence (less than an hour away)? Sticking with more Italian pursuits, find the bucolic and ruined Abbey at San Galgano and view a true "sword in the stone." Return to your Siena hotel.

    driving day at leisure through Tuscany

    Day 17--Yesterday you barely scratched the surface of the many places and towns that are a worthwhile stop throughout Tuscany. Since most places are within 30-90 minutes of your base in Siena, see what else you can discover! Frances Mayes' book "Under the Tuscan Sun" (only vaguely resembling the movie of the same name) was set in the town of Cortona; you can definitely see why she fell in love with this region. Overnight in Siena.

  • Day 18 - Assisi

    Enjoy a night in the city that was home to the revered St. Francis

    As you leave Tuscany today and drive east toward Umbria (the "Green heart of Italy"), enjoy the beautiful scenery. Assisi has been a pilgrimage site for hundreds of years and is full of both pilgrims and tourists by day. But by night, the town is quiet and seems to be completely yours. Visit the Basilica of St. Francis and explore its medieval streets.

  • Day 19-21 - Rome

    Enjoy the most famous of Italy's cities--Rome. Home of the ancient Caesars and seat of the Holy Roman Catholic Church.
    Car Rental

    Day 19--As you drive from Assisi to Rome, you will again pass though any number of smaller Italian towns. Deruta is known for centuries for its hand-thrown and hand-painted ceramics. Eventually you will have to drop off your car and check into your Rome hotel.

    Colosseum and Palatine Hill Tour
    Group Tour

    Day 20--Join a pre-reserved guided visit inside the Colosseum and avoid the terrible lines of tourists (waiting in the heat) who didn't know better. Learn how the gladiators fought, how the crowds reacted, and why this was all so entertaining for ancient Roman citizens. Be amazed at its thoughtful construction and you'll see why we still build stadiums in this fashion today! Your visit will also include a tour of Palatine hill palaces and the adjacent Roman Forum, the seat of Roman government and commerce. The balance of your day is at leisure to explore the Pantheon and other classical Roman sights.

    Vatican City Tour
    Group Tour

    Day 21--While technically its own independent principality, Vatican City is by and large considered part of Rome for our touristic purposes. With a trained guide, skip the lines that stretch for blocks waiting for entrance to the Vatican Museums. Enjoy commentary from a well-informed and professional guide as you wind your way through the Vatican's Raphael Rooms, Map Rooms, Tapestry rooms, and more, with your visit culminating in Michelangelo's ultimate masterpiece, the Sistine Chapel. You will also be enthralled by a visit inside St. Peter's Basilica and learn details of Bernini's creation, St. Peter's Square outside the basilica. The rest of your day is yours to enjoy, and don't forget a nighttime visit to the Trevi Fountain and Spanish Steps to enjoy the romantic side of Rome.

  • Day 22-25 - Amalfi Coast

    No words can accurately describe the beauty of Amalfi Coast. Enjoy 4 nights (1 night Capri, 3 nights Sorrento in a seaview room) here and you might just refuse to return home!
    Capri, Italy

    Day 22--Travel today by train, private driver, and ferry from ancient Rome to splendid Capri--where Rome's emperors and wealthy built their vacation villas. Ferry through the Bay of Naples, viewing Mt. Vesuvius in the distance, to a world of stunning beauty on the Isle of Capri, where you will stay for one night. Your mid-afternoon arrival will allow you plenty of time to explore this tiny island.

    Blue Grotto and Sorrento, Italy

    Day 23--Get up early to experience a thrilling boat ride and visit inside the legendary Blue Grotto. Your boat "driver" will shoot your tiny dinghy through the 3 foot opening at precisely the right moment so you aren't drenched with waves. Once inside, you might be serenaded while sunlight through the cave opening bounces off the limestone floor of the pitch-black cave and reflects back as the most magnificent shade of turquoise blue you have ever seen. Later, check out of your hotel and ferry the short distance over to Sorrento to relax and enjoy the view you will have of the Bay of Naples, Mt. Vesuvius, and passing boats.

    Pompeii Visit
    Group Tour

    Day 24--Today you will join a guided excursion to the ruins at Pompeii, all but obliterated by the 89A.D. eruption of nearby Mt. Vesuvius. Return to Sorrento in the afternoon and spend the rest of the day at leisure and exploring. Sorrento itself is famous for hand-crafted linens, ceramics, inlaid wood furniture, and limoncello (a wonderful lemon liqueur, best served chilled).

    Amalfi Coast Drive
    Group Tour

    Day 25--Today will be devoted to a scenic drive along the breathtaking Amalfi Coast. You will have stops in Amalfi Town, Ravello, and Positano, with the opportunity of exploring these small towns and their highlights.

  • Day 26 - Rome

    Return to Rome and prepare for departure.
    Rome, Italy

    Day 26--Today you will train from Sorrento back to Rome and on to your hotel (city or airport location is up to you). You can enjoy one last afternoon in this ancient city, or simply retire to a hotel near the airport and rearrange your luggage in preparation for your homebound flight tomorrow. Arrivaderci, Italia!

  • Day 27 - On the Plane

    Depart Rome for the USA.
    Rome to USA
    Commercial Flight

    After your hotel-airport transfer, you will be on you way back to the USA.

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