These are tips from Kelly’s luxury 8 night trip to Rome and Positano.  You’ll get tips on great restaurants, hotels and tours.

Where do you live when you’re not traveling?   Boston, MA.

Who went on the trip?  Couple in their 30s.

What was the Trip?    2 nights in Rome, 4 nights in Positano and 2 more nights in Rome. In mid-October 2016.

What were your interests/goals on the trip?
We had a wedding in Positano and wanted to make it into a week-long trip. We combined Positano with Rome, because although I had studied abroad in Rome, my wife had never been. We wanted to check out the must sees in Rome. But we have a toddler, so we mostly wanted to relax didn’t want to be rushing places. Because we both work a lot, we also wanted to splurge on a hotel and restaurants.

Anything especially awesome?


Portrait Roma  With only 14 rooms, so it was some of the best service we’ve ever experienced. The deluxe studio was bright, roomy and stylish. It also has a spectacular roof deck where you can take your breakfast. The location was perfect, right off of Via del Corso, the famous high end shopping street. Andrea’s only complaint was that it didn’t have a restaurant in the hotel.

JK Place  We were split on whether we liked JK Place or Portrait Roma Better. My wife likes having a restaurant in the hotel, so she liked JK Place better. But I preferred Portrait Roma. JK Place was bigger than Portrait Roma, so the service was excellent but it felt less personal. The rooms were also decorated in a darker style, so everything just seemed dim. There also wasn’t really a view at JK Place. The prices are similar, so if a hotel in the restaurant doesn’t matter to you, stick with Portrait Roma!

Dilla  An awesome restaurant in Portrait Roma. We still talk about the Tiramisu.

Tour under St. Peter’s Basilica  This tour is amazing and you can only book it through Vatican City. It’s one of the hardest tours to get, you have to book it months ahead of time. Don’t book the tour on your first day as you’ll likely be tired from all the travel.

Walks of Italy Tour (Crypts & Catacombs: Underground Tour of Rome)  A great tour, would definitely use the company again. Probably only 8-10 people on the tour.


Le Sirenuse  The best hotel we’ve ever stayed at. It’s super luxurious and the staff is very attentive, but it’s also unique because it’s an old mansion that’s been turned into a hotel. The views are beyond spectacular. Supposedly Mark Zuckerberg and Tom Brady stay there.

La Rada  The most amazing view ever. The food was decent, but we ate mass produced meals for a wedding.

La Sponda  A Michelin star restaurant with excellent food, which we thought was better than La Pergola. We did the tasting menu.

Any tips that might be helpful to future travelers?

  • If you’re going on a weekend or in the summer, you should make reservations at any restaurants you really want to eat at (or ask your hotel to).
  • Book the Scavi Tour of St. Peters as soon as you know your dates as those tours book up very quickly!
  • If you taking the train to Positano, book your train ticket ahead of time
  • Arrange for the car transfer from the airport, and we find that it’s easier to book your car transfers ahead of time instead of trying to arrange for them on the trip.

Anything you disliked or things you would have done differently?

La Pergola  A 3-star Michelin restaurant. The food was good, but only a couple of the 12 courses were spectacular. We’d never been a 3 starred restaurant, so the experience was really cool and the service was phenomenal. Go if you want to be treated like royalty, but you can find better, less costly, food.

What would you do if you had one more day? If you had one less day?

We would have rearranged the itinerary to give us one more day in Positano.  If you want to hit all the big sites in Rome, then give yourself enough days to not feel rushed.

Average cost per night of one hotel room and cost of an average entree:
$1150/night per room (you could spend half that in Rome if you’re not staying at the nicest room) and about $50 per entree.