This trip blends dreamy coastlines, laid-back beach time, delicious cuisine, and rich cultural discovery. 

Expect sunny days, picture-perfect towns like Positano and Matera, and plenty of time to unwind over spritzes, seafood pasta, and gelato with new friends.

It’s a well-balanced itinerary with a mix of activity and leisure. 

You’ll explore ancient cities like Matera, stroll seaside promenades, take a private boat to Capri, and enjoy group dinners in postcard-worthy settings. 

Free time is built in, so you’ll have space to relax or venture out on your own.

You'll stay in hand-picked hotels that reflect the charm of each destination. Rooms may be smaller than U.S. standards, but they’re clean, well-located, and full of character. 

• In Lecce and Sorrento, enjoy centrally located hotels near the action. 

• In Matera, expect a more atmospheric stay — with some rooms built into the historic stone landscape.

• The final night in Rome offers a comfortable base for your departure.

Yes! Italy is generally accommodating of dietary restrictions, with plenty of fresh produce, pasta varieties, and vegetarian-friendly and gluten-free options. In coastal areas, seafood is common, and some local specialties may include cheese or cured meats — but there are usually workarounds.

If you have strict dietary needs, we always recommend bringing a few snacks just in case and letting us know in advance so we can help you navigate meals along the way.

Southern Italy boasts over 300 days of sunshine a year. Expect hot, dry summers with temps ranging from the high 70s to low 90s °F (25–34°C). Bring plenty of sun protection, and plan for cooler evenings in hill towns like Matera.

Pack light, breathable clothing for sunny Mediterranean days, plus a few dressier options for dinners and evenings out. Comfortable walking shoes are a must for exploring hilly towns like Matera and cobblestone streets in Lecce and Sorrento. Don’t forget a swimsuit, sunscreen, sunglasses, a sunhat, and insect repellent just in case.

Italy’s food scene is both delicious and diverse — from rustic, budget-friendly trattorias to upscale seafood restaurants along the coast, offering meals that can range from €10–15 for a simple pasta dish to €50 or more for a gourmet dining experience.

We typically recommend that you budget around $200 USD for meals not included in the itinerary, depending on your personal consumption and spending habits.

Our trip kicks off in Lecce where the closest airport is Brindisi Airport (BDS). A convenient direct bus connects Brindisi Airport to Lecce in about 45 minutes for approximately €10. If you're flying into Brindisi, please ensure you arrive at BDS by 2:45 PM to allow enough time to get settled in before the festivities begin.

If you find more affordable round-trip flights through Rome Fiumicino Airport (FCO), you also have the option to book a domestic flight or train to Lecce ahead of the trip.

Our trip ends in Rome and you are free to depart at anytime on Day 8 - or hop on over to another nearby FTLO trip.

We highly recommend packing light, as you'll be responsible for carrying your own luggage throughout the trip. While a standard European carry-on and one checked bag are generally acceptable, keep in mind that you'll be moving between cities via private & public transport and navigating narrow streets, cobblestones, and hotel stairs. For ease and comfort, rolling suitcases or travel backpacks are ideal.

If you’ve got a few days to keep traveling, you can head north to Tuscany & Rome, catch a local flight to Sardinia, take a train west toward Barcelona & the South of France, or stay in the Mediterranean and join our Greek Islands trip.