Where are you flying from? Have you been to Europe before (and had that long of drive after arrival)? I would look at flights into Pisa or Florence. If you fly into Pisa, you could catch the train to CT, spend a few days, pick up a car in La Spezia and go to Santa Margherita (keep car) a few days and then drive south to Tuscany. Return your car at the Pisa airport.

You need to define "spend for good places". does that mean 300 euros a night? 400? And what are you looking for? An agriturismo that does all meal? Or a small luxury inn?

I would not change rooms--you can easily get to CT and back in a day.
Just curious--have you checked flights into Genoa so you don't have to drive from Milan? I know it's only a couple hours, but I found some affordable flights to GEN last year. Also, perhaps you can fly open jaw so you don't have to back track. Pisa can be a good bet for flights.
Don't overlook the fabulous hiking you will have at your doorstep in SML. I stayed on the other side of Portofino National Park in San Rocco (above Camogli), mere steps from the park, and the hiking was wonderful. We'd cross the park every day to SML, but I only was there long enough for gelato, to catch the bus or ferry, etc.
If you are not set on SML, allow me to plug where I stayed, and which I absolutely adored:
http://www.larosabiancadiportofino.com/
It has a million dollar view, but if you were looking for something more luxe, I eyed this place:
http://www.villarosmarino.com
Buona fortuna!

Fast responses! Thank you everyone. To answer some of the questions-
I have been to Europe before and both myself and my fiance fly very frequently so don't generally mind a drive after a flight. The reason I picked Milan was because we will be using miles (from all that flying) and that was a route listed for the airline. I would definitely be up for looking at alternate routes if it made more travel sense.

As far as spending, I apologize, that was vague. I would say we would top out at around 300 euros. What we'd like (and I'm not sure if I can have it all, but...) would be somewhere smaller with nice, clean rooms, great views, great food. We would like to have some excursions during the day to vineyards and surrounding small to

I have been to CT but my fiance has not and I wanted to share it with him but I also don't want to go out of our way just to stop there, as I know there are so many other gems on the riviera. At this point I'm still very open to suggestions for an itinerary (which is why I'm posting here).

Hope this clarifies things and thanks again for all the help!

Ashley,

I have a slightly different take on the transpotation piece. Since you fly into Milan, why not takt the train to Liguria. The transfer from Milano to Milano Centrale is quite easy.2 years ago my wife and I got a direct train (no changes in Genoa) to Rapallo. We rented an appartment in Rapallo so I cannot comment on hotels in the area. SML is a very short bus ride from Rapallo and the bus station is right across the street from the train station. A couple of days in SML with easy train access to CT could work. Again train to La Spezia for your rental car.

Happy planning and congratulations on your getting married

Rolo

If you haven't booked your flight yet, I would see if you can get a flight into Milan and out of Rome. Rome's airport would be easier to reach after Tuscany.

We stayed in the Metropole in SML last year and enjoyed it very much. It's placed at one end of the village on the way into SML from Rappallo.

http://www.metropole.it/en?id=

Usually I would suggest staying in one of the Cinque Terre towns (I prefer Monterosso because there are more restaurants there), but it is close enough to Santa Margherita Ligure to just visit as a day trip; that will cut down on your need to move from hotel to hotel.

Or, if you're comfortable with driving and the pricing of cars vs. trains works out, you could rent a car from Milan, and keep it for the entire trip. It seems like most people take a train to the Cinque Terre, but we've always driven, because we visit that area in the middle of other driving destinations. For example, one time we started our vacation in rural Tuscany (San Gimignano), drove all over, then drove to the Cinque Terre, then drove on up the coast into France. Some hotels (Hotel Villa Steno) have (limited) parking; there's also a public lot in Monterosso.

Depending on how many days you plan to spend in rural Tuscany, you might want to stay in two places, one a little more in the northern part of Tuscany (San Gimignano and thereabouts), and one further south (Pienza / Montalcino / Montepulciano).

For Tuscany, we were there in October and stayed at Frances Lodge in the countryside outside of Siena. It was beautiful and centrally located. We took day trips to MONTERRIGIONI, COLLE DI VAL D’ELSA, VOLTERRA, SAN GIMIGNANO one day, ABAZZIAS OLIVETO MAGGIORE & SANT ANTIMO, MONTALCINO, PIENZA another day, Siena itself one day, and CASTELLO DI BROLIO, RADDA, CASTELLINA IN CHIANTI the final day. You can check my trip report for details. We loved Frances Lodge and I think it would be luxe enough for a honeymoon...! Congrats.

I am very interested in the responses, as we are planning a similar trip also in September for 2 couples celebrating our 50th birthdays (or 2nd honeymoons), we also were thinking of hiring a car, but maybe the train idea would work better. Is there a favourite spot to stay in the Siena area.

gawlergirl (and ashleylanderson)

If you decide you want to take a car from Milan, it is better to stay in Lerici than drive to Santa Margeheria Ligure. It is an easier drive, plus easier parking when you get there, and you are close to le Cinque Terre. If it rains and you have a car in Lerici, you can visit nearby interesting towns in Tuscany. If it rains and you have a car in Santa Margherita Ligure, the most interesting nearby spots (Genova, Nervi or Chiavari are best reached by train, not car).

There is no place in the Siena are that makes it possible to visit the Mediterranean coast easily, especially not the Riviera. And while it is possible to go to Siena by train from Milan, once you are in Siena, if you want to tour the area, it is difficult to do without a car.