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Old Jul 21st, 2023, 01:28 PM
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Need help filling a gap in itinerary

My husband and I are planning a trip this September/October. We are both novice trip planners.

We're currently set to visit Italy and Santorini, Greece. What should we do from September 27-October 3? I'm open to anything a vacation has to offer, so I would love to hear your personal recommendations!

(I'd also love to hear the why behind your recommendations!)

Our current itinerary:

September 21: Fly out

September 22 @ 9:35 a.m.: Land in Venice

September 22-24: Venice

September 24: travel to Florence

September 24-27: Florence (with a day trip to the Tuscan countryside)

September 27: travel to next destination

September 27-October 3: Undecided itinerary

October 3: travel to Santorini

October 3-7: Santorini

October 7: fly home

We have places already booked in Venice, Florence, and Santorini. Originally, we were going to do the Amalfi Coast September 27-30 and Naxos September 30-October 3. But I'm doubting if that's the best decision and want to hear from experienced travelers. We're still learning!
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Old Jul 21st, 2023, 03:10 PM
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For first-time visits, I would want more time in Venice and Florence and more than a single day trip from Florence. Sept. 22nd won't be a terribly useful day, so you'd only have one uninterrupted day in Venice. Sept. 24th will equate to about a half day in Florence, and then you'd have only one uninterrupted day in Florence and one day out of the city. I would distribute some (if not all) of your additional days to both Venice and Florence. Beyond that, I'd go to Rome or back to Venice for a direct flight to Santorini.
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Old Jul 21st, 2023, 05:27 PM
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Welcome to Fodors. I agree with Jean -- too little time in too many places.

You have less time in places than you may be thinking - there is no accounting for travel time, and are counting the same days in two different locations. Not counting 9-22 and 10-7 (arrival and departure days) you have 14 days free to see/do things (though It is usually best to think in terms of nights rather than days).

What you actually have is:

Arrive in Venice September 22 - likely jet lagged and not able to access your hotel room until mid to late afternoon.
Nights of September 22-23: Venice = 1 full day in Venice
Nights of September 24-26: Florence = 2.5 days for Florence and a full day trip to the countryside
Nights of September 27-October 2 = 5.5 days Undecided location(s)
Nights of October 3-6: Santorini = 3 full days on Santorini
October 7: fly home
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Old Jul 21st, 2023, 06:04 PM
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Part of your consideration of what to do with Oct. 3rd (and the night of Oct. 2nd) is figuring out/deciding how you're going to get to Santorini.

Also, do you need to get to Athens to fly home? If so, how early is the departure? Do you need to spend the previous night in Athens?
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Old Jul 21st, 2023, 06:38 PM
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Oh -- yes -- I missed that. Assuming you are flying home from ATH you probably need to be in Athens the evening of the 6th, meaning you'll have about 2.5 days on the island. (It is best to be in the departure city the night before flying)
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Old Jul 21st, 2023, 06:39 PM
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Do you have flights booked? I assume you will travel by train from Venice to Florence? It’s more convenient than flying in this case. How do you intend to get to Santorini from Florence? Do you need to consider a night in Rome or Milan, or will you fly to Athens from Florence with a stop over?
Also, If your Santorini flight home requires you to catch another flight in Athens, plan on spending the night in Athens the night before so that you won’t miss your flight home. There is always a chance of delays or canceled flights.
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Old Jul 21st, 2023, 07:44 PM
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Jean and Janisj are giving good advice and laying out out much time you actually have.
General rule of thumb. Never count the same day twice or don’t count any travel days as days in a place. It makes it seem as if you have longer than you do and is not clear cut.
Example: you are returning home on October 7. It is purely a travel day, no time anywhere. Don’t count or put it with Santorini. Travel from Venice to Florence will eat up at least 1/2 day. You have to check out of hotel and travel to train station in Venice, train time, then travel and check into hotel in Florence. same with other places. It adds up.
A fast pace is fine for a week or so, but a longer trip needs a more relaxing pace, plus there are amazing places near your major stops. Keep your trip to four bases, with less time spent traveling, more time sightseeing.

List travel days separately, or list by nights in a place, knowing it takes 2 nights to give you 1 full day, 3 nights to give you 2 days, etc.

9/21, depart home
9/22, 23, 24, Venice, 3 nts. 2&1/2 days. Considering possible jet lag the first day and how much there is do in and around Venice, I would definitely add this one day and spend at least part of one day on the lagoon, visiting Burano and other islands. If you find when you are there, that Venice just is not for you, you can day trip to Padua, Vicenza or even Verona.
9/25, 26, 27, 28, Travel to Florence, at least 1/2 day of travel, 4 nts. 3 &1/2 days. (I would add this day here, especially if you want a day trip to the countryside, because I would definitely do a day trip to Siena.)
9/29, Travel to? It is almost a full day of travel from Florence to the AC, 1/2 day to Rome or any place else
9/30, & 10/1, 2, Next Place.
Realistically, if you have added days to Venice and Florence, you have left a maximum of 4 nts, 3 days.
10/3, Travel to Santorini

Questions that make a difference: Are any flights to Santorini booked?
Is the flight home from Santorini booked from Santorini or through Athens?

After laying it out with days and nights, seeing precisely how much time you have, my suggestion is to spend those 4 nts, 3 plus days in one place.
Options:
1. Amalfi Coast, because it is breathtakingly beautiful, you seem to favor coastal places and islands, there is so much to do like Pompeii, it will be cooler for walking, and you can likely get a flight from Naples to Santorini (but have to check this) on 10/3.
2. Rome, because it is one of Europe’s great cities, it is a shorter trip from Florence, the weather will be nice for walking, great day trips to places like Orvieto, etc. probably direct flights.

Just noticed more good concerns from others about travel and flights.

Last edited by Sassafrass; Jul 21st, 2023 at 07:46 PM.
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Old Jul 22nd, 2023, 12:00 AM
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Absolutely you want to use the train for travel city to city centres. Be aware of ZTL if you decide to hire a car for the Tuscany bit around Florence

For me the obvious is to split the time between Venice and Florence. Around each city are many many ancient city wonders, all reachable by train or, in Venice's case, ferry.

The list should include at least Siena, Lucca, Pisa for Florence
and Padova/Padua for Venice plus the likes of Murano etc

You don't need to move any more (way to much moving on this trip as it is) what you need to do is holiday in the environment you have chosen.

If it helps, it looks like you decided to spend 2 days in Boston, 2 days in New York and now were wondering about spending an extra 4 days in Florida or San Francisco in between. Enjoy Northern Italy all of which is fascinating.

You are also missing out on encountering Italians, who are generally, pretty nice people. If you just stay in hotels you will meet the desk clerk..... if you stay in a B&B or an agriturismo.it you will at least get a little feeling of the society that makes this glorious place work. Sometimes holidays can be about looking at the view and sometimes you benefit from meet-the-folks and you don't want that to be just retaurant hustlers and clerks, get to meet a father and mother running their own business who want to help you enjoy your holiday

trains, read seat61.com
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Old Jul 22nd, 2023, 04:51 AM
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If this were my trip, I would drop Santorini (assuming your accommodations are refundable) because it’s a lot of travel and money for a view when Italy has so much to offer. Florence would make a great base. It’s so much more enriching to stay in one area and absorb the culture, the language, the food as well as all the impressive sights you will miss if you leave. Florence is one of the most beautiful towns in the world with so many art museums and beautiful walks to occupy several weeks. My favorite area to stay is south of Ponte Vecchio (covered bridge) because it’s more charming and yet still close walking distance to the sights and train station. I like to run in the mountains in this area to see the gorgeous villas and vineyards. I also buy a pass to the Boboli Gardens and run there in the mornings. Florence makes a terrific base for day trips to Venice and Rome and Tuscany and villages like Lucca, all reachable by train. It’s always nice to come back to a VRBO at the end of the day because you don’t have to travel with luggage, pack and unpack or wait for check in time. It’s also cheaper if you don’t want to eat out every meal.

From Florence it’s two and a half hours by car to Cinque Terre. I believe the train is very efficient but I don’t know how to do that. This could be your gorgeous coastal area. Like Santorini it can get crowded, but in Cinque Terre the crowds are day trippers. In Santorini you can’t get a break from the crowds. It’s horrendous.

If your goal is to see as many sights in one trip as possible, I would wait until 2024 and book a cruise. There are several that include Italy and Greece. The benefit of a cruise is that you sleep during the travel part and you don’t have to deal with train delays, flights, luggage, hotels. Mediterranean cruises are port intensive, so less time is spent on the ship, so don’t worry about being bored. A cruise is also good for a novice traveler who is uncomfortable with the logistics of international travel.

Anyway, your trip will be fantastic whatever you do. I hope you have a great time.
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Old Jul 22nd, 2023, 07:44 AM
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Welcome, baker2er! Imho, you could add 2 days each to Venice and Florence, and spend a night in Athens at the end for airport ease.. Make Amalfi your next trip...you will return to Bella Italia.
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Old Jul 22nd, 2023, 11:25 AM
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I think as others do that some of the recommendations would depend on how you are getting to Santorini and how you are getting homeDo not think you have enough time for Venice and would add at least a night there and probably most of your remaking nights for Florence and Tuscany. There is a lot to see in Tuscany with a car.
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Old Jul 22nd, 2023, 01:08 PM
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You could easily also go to Milan and reserve in advance to see The Last Supper. I agree with the above posters. Adding on Santorini to a trip to Venice/Florence makes no sense to me.
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Old Aug 28th, 2023, 10:06 AM
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Just traveled to Santorini in May. That could be another trip give the time involved in traveled. Missed our flight due to tardiness on flight prior to that, arrive in Santorini at 1 AM while others couldn’t get out at all. They missed an entire day and we missed a 1/2 day.
So please don’t depend on perfect travel with airlines.
You could stay in Italy, expand to Verona, Lake Garda, etc.
When I use Booking.com So easy to change arrangements.
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Old Aug 28th, 2023, 02:11 PM
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There is no hole in your schedule. Just spread the unscheduled days to the places that really need more time. Please also give us the details for your transfer from Florence to Santorini and your transfer from Santorini to home. Those two transfers may use up a day each, not including the flight home. Also, considering the fires in Greece, Santorini may not be a good idea.
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