And not necessarily in that order.
When we started planning a 2-week trip to Italy almost a year ago, we had big ambitions. Lots of different destinations. We would have 2 full weeks to fill with wine, food, adventure, and friends.
Then there were the details. How many different regions could we hit while also experiencing each place to the fullest? Where were the best places to stay on a realistic budget? How would we even get from point A to point B to point C?
By the time the trip came around in May, we had a solid itinerary, thanks to regularly scheduled brainstorming and planning sessions where we researched activities in each destination while sampling Italian red wines (a form of training, if you will). And in the end, the trip exceeded all expectations.
Having gone through planning such a complicated endeavor, here’s my advice.
Mix It Up
Plan for different types of experiences. Our friends enjoy "the good life" so to speak, so we knew going into it that we wanted to mix activities like hiking and exploring with lots of food, wine, and relaxing in each locale to take in the views and the culture. We wanted to spend minimal time indoors and maximum time outdoors taking in views of the countryside and the coast. So we paced ourselves to keep things balanced: we started the trip with more time being active and finished with more beach and boat time.
Of course, we always found time along the way when we encountered wine bars, or enotecas. You always stop for a glass of wine. No need to mix that up.
Don't Move Too Fast
Don't stay less than 3 days and 3 nights in any spot. That said, you will have some distance to cover in between destinations, so figure out how to minimize hassle and time spent in transit. We purchased train tickets and booked private drivers in advance to make sure we could get from point A to point B, including wine tours and dinner reservations.
Plan, But Don't Overplan
It's important to leave down time to explore or act on recommendations received from locals, hotel staff, or even other travelers. In each spot, we left open mornings, afternoons, and/or evenings to fill in additional activities or to simply relax.
Prepare For The Elements
Two notes here: 1) Bring Claritin if you have allergies, particularly for Tuscany, and 2) Bring dramamine. This will be important for any driving pretty much everywhere, as the roads are very, very curvy.
At Meals, Order Lots of Things And Share
Because when the food is that good, you should try as many different things as you can.
Come Up With A Color Scheme
My family makes fun of me for this, but I think it’s good to have everyone pack clothes within a tighter color palette for vacations where a lot of group photos are happening. It gives the entire series of vacation photos more of a connective thread.
It’s also fun to build anticipation for a trip by pinning inspiration photos from your destination that you want to snap once you’re there.
Looking for some more specific suggestions by location? Scroll for my Italy vacation gallery along with recommendations by location.
It’s a hop, a skip, and a jump to get there, but it’s worth it.
The headline activity in Cinque Terre is hiking the 5 towns. The hikes are not super difficult, but the views are super incredible. On our first day, we hiked from Monterosso al Mare to Vernazza and Corniglia.
We planned to do the other towns on the following day, but mudslides had closed the trails and there was a train strike at the same time. So, we swung at the curveball and caught a boat to Portovenere, a town further down the coast from Cinque Terre, for the day instead.
Portovenere was beautiful in its own right, but the real bonus was that the boat ride gave us views from the water of Cinque Terre during our journey, which proved to be one of the best ways to see the coast.
Our headlining dinner in Cinque Terre was at L'Ancora Della Tortuga, a restaurant in Monterosso carved into the cliffs in a former WW2 bunker. So cool.
Throughout all the towns, we stopped for lemon granitas (with limoncello and vodka, obviously) and gelato. When in Italy!
We found and stayed at the most charming and picturesque villa in Monticchiello, a small town in between Montepulciano and Siena in the Val D’Orcia region of Tuscany. The villa was one of the reasons Tuscany was probably our favorite leg of the trip.
The one thing that was missing was a pizza float in the pool. Luckily, we came prepared.
If you happen to be able to make it to Monticchiello, I'd recommend lunch at La Guardiola for amazingly fresh farm-to-table food, including burrata, tomatoes, and wild boar.
For dinner, Osteria La Porta was so great that we dined there two nights in a row.
The wine was honestly great everywhere, and most of the wineries are able to ship back to the States. These were the ones we went to (and would recommend):
Castello di Ama (Chianti) - This is a winery that also has 11 modern art installations (they commission artists to come to their site and design based on how the grounds inspire them).
Barone Ricasoli & Castello di Brolio (Chianti) - The oldest winery in Italy, and they are affiliated with a nearby castle that is beautiful for walking around. They actually set up a picnic lunch for us on the vineyard grounds complete with wine and local foods, then drove us up to the castle for a tour.
Avignonesi (Cortona) - Biodynamic with lots of inventive techniques for grape growing and wine production (the tour kept us very intrigued to hear about the entire process). We actually reserved a spot for their Wine Lover’s Lunch, which was a 3 course meal with unlimited wine pairings. Food, wine, and view were incredible. Cortona is where "Under the Tuscan Sun" was filmed.
We stayed in Praiano, which is a few tiny towns south of Positano. We liked it because it felt a little more off the beaten path, was a lot less crowded, and was a lot less expensive.
Be prepared to WALK. It was like 400 steps down to the water from us (there was a beach club called One Fire Beach Club with fun orange umbrellas) and along the way there are cute little alleys and steps and the occasional place to grab a drink.
We rented a private boat to Capri for the day through La Sibilla. The boat ride felt both adventurous and relaxing against a backdrop blue sea and steep cliffs, and Capri lived up to expectations.
Once we arrived on the island, we took a chairlift up to the peak for some spectacular panoramic views. I was scared to death given the height, but the scenery was so to-die-for that it was well worth it.
Even more chic than the boat ride was lunch at La Fontelina, a beach club and restaurant only accessible by boat. Frequented by celebs and bloggers, you know, people like Gwyneth Paltrow and Gray Malin. Advice when dining on the water on the Amalfi Coast: When in doubt, order as much seafood pasta as you can. We didn't have a dish we didn't like.
There are several beach clubs on the Amalfi Coast between Positano and Praiano, but I’m partial to Da Adolfo. You have to make a reservation ahead of time, and they run a free shuttle boat from Positano pier (or you can take a water taxi, as we did directly from Praiano). They serve lunch, which was one of the best we had, and then you can lie on the beach or climb on rocks.
Hiking the Path of the Gods is a must. But don’t let the locals fool you; parts of this trail are actually quite difficult, particularly the ascent from Praiano.
Lastly, no trip to the Amalfi Coast is complete without spending a little time in Positano. We mostly dined, grabbed drinks, and wandered the streets to shop. If you are into it, there are a few places to get shoes or sandals made where they make them while you wait.
Or make a beeline for Le Sirenuse, one of the most photographed hotels on Pinterest. If you can afford it, stay there; if you’re like us, you might just want to dine and drink at one or all of their restaurants and bars.
You know what?
I think it might be time to start planning a trip back.
Photos courtesy of Jonathan Steinitz, Marc Humphrey, Joshua Secrest, Morgan Naseef, Allison Shivers, John Pfabe, waiters, boat drivers, and other tourists.