7 days in sorrento

Pompeii is one of the #1 day trips from Sorrento: 30 minutes by local train (Circumvesuviana).

You could also go into Naples for a day (about an hour via the same train), visit Herculaneum along the way, and see the excellent archeological museum in the city where many treasures from both excavations are displayed.

Good thing about having a big group is that no one will mess with you on the Circumvesuviana...

Just kidding, it's fine. Just ride it during the day, with your group, and you'll love all the great scenery, weird people, and how inexpensive it is.

For a walking trip, I'd take the SITA bus from Sorrento station over to Positano (45 min) and just walk around, maybe even get off a little early--as we inadvertently did--and walk the cliff road downhill for awhile. That's something to remember!

There's a restaurant just outside the Sorrento station called Il Leone Rosso with really solid food and it's big. In March I saw a couple big parties (15+) seated there. BTW, I was there for my 60th as well!

And...I don't know if you can book it for that many people because it's small, but TavernAllegra is a trip-and-a-half, in the Old Town not far from Piazza Tasso. The owner, in his seventies, likes to sing Frank Sinatra songs to the crowd. And so does the chef...and the waitress sings along, to a strumming guitarist. It's like a floor show. I would say it's kinda touristy and cheesy--which it is--but the food is absolutely fabulous, so it's really a lot of fun.

There's a restaurant just outside the Sorrento station called Il Leone
Rosso with really solid food and it's big.

Good suggestion from Jay: we had a really good meal there as well. But with a big group, you're going to want to make reservations at any restaurant well in advance: you don't want to just try and land into them without prior notice as they'd be unlikely to accommodate you. Exactly how big is your group?

Sorrento is IDEAL for daytrips like Pompeii, Herculaneum, Capri, and Naples. If everyone in the group has good knees, an nice local outing is to take the bus to the top of the hill, Sant' Agata (stops opposite the Cirvumvesuviana station in Sorrento) and walk two hours down back to Sorrento, 99% paved and with streetlights and some steps, but somewhat steep. Don't wear sandals because of the grade. The beginning of the walk is hard to find, but you can't get lost on the way down.

Thanks everyone for great suggestions. My group started with my family of 6 extending to friends traveling in Europe at that times Will make up to 20 We will do our own thing a bit and having a lunch day already booked for everyone. Should be fun Great suggestions and will look into those walks and restaurants.