Escorted Tour to Rome, Positano, Capri, Florence, Siena & More
Explore our extensive galleries featuring stunning photos from an actual honeymoon tour to Rome, Tuscany, Positano & Capri and a Spring tour to Rome, Tuscany, the Amalfi Coast & Venice. The galleries will open in new tabs while you read here.
These trips are the perfect choice for a honeymoon or a first trip to Italy. They commence and conclude in Rome, utilizing bullet trains for quick transitions between regions, and feature a diverse array of touring options centered around art, gastronomy, wine, history, and of course, shopping!
“You may have the universe if I may have Italy.”
Giuseppe Verdi, Composer
Day 1 – Arrival at FCO & Orientation Walk
Your flight is expected to arrive in the morning (Rome time). One of our trusted drivers will greet you at the exit gate and transport you to your hotel in the heart of downtown.
Once you’ve checked in and had a chance to freshen up, we will meet for a 90-minute orientation walk near your hotel, offering you suggestions for shopping and dining, as well as information on how certain things operate in Italy.
Day 2 – Highlights of Rome
The following day will focus on Rome’s iconic highlights, including the Trevi Fountain (recently restored and breathtaking), the Pantheon, Piazza Navona, the Campidoglio, the Roman Forum, and the Colosseum.
In the morning, we will leverage a car to navigate distances that would be challenging to walk. Expect plenty of photo opportunities along the ancient Roman walls, the enchanting orange garden of Aventine Hill, its secret keyhole, and stunning views from Piazza del Popolo and Janiculum Hill.
Of course, we’ll pause for a leisurely lunch at a charming trattoria! 😉
Day 3 – Ostia Antica & the Borghese Gallery
We’ll take a commuter train to Ostia Antica, the ancient port city of Rome, which is reminiscent of Pompeii—but arguably even better preserved. You will be amazed by its theater, baths, synagogue (the oldest in Europe), apartment complexes, restaurants, and shops.
Enjoy a seafood lunch in the shade of a nearby Renaissance castle before heading back to Rome.
In the afternoon, we will visit our favorite gallery: the Borghese Gallery. We often refer to it as “All killer, no filler.” Though small, this is the queen of private art collections and is absolutely spectacular. The villa is set within a vast park, providing an ideal setting for a cocktail and a stroll to end the day.
Day 4 – Vatican Museums, Sistine Chapel & St. Peter’s Basilica
This day is fully dedicated to Vatican City, the heart of the Roman Catholic Church. A guide will meet you with your VIP passes for a two-hour tour highlighting the museums, featuring Michelangelo’s stunning frescoes in the Sistine Chapel.
After your visit to the chapel, you will explore St. Peter’s Basilica, the largest church in the world, renowned for its artistic and architectural treasures.
Optional: If you contact us at least four months in advance, we may be able to arrange a visit to the Vatican “scavi” (excavations)—what was once an outdoor pagan cemetery is now a site beneath the basilica, accessible with prior permission and a guided tour.
“All potential clients are welcomed to reach out by phone or e-mail for any specific inquiries. Thank you for arranging a wonderful family vacation for us. We have come to think of you as part of our family. Best of luck with your endeavors, and we hope to see you again soon. With warm regards; Howard & Sue Cowan.”
Day 5 – Rome to Positano (or Capri)
We will travel by high-speed train from Rome to Naples (50 minutes). From there, our driver will take us to our hotel in Positano (or to the hydrofoil to Capri), where we will base ourselves for the next few days.
An orientation walk and dinner will follow.
Day 6 – Boat Ride, Swimming & Amalfi
After breakfast at the hotel, our captain will meet us at the dock for a fun private boat excursion along the coast.
Marvel at the beautiful views from the water, and enjoy some time swimming in the stunning blue Mediterranean waters.
We will make a stop at Amalfi, a charming town that once was one of the four Italian maritime republics. The tour will highlight its main attractions, culminating in a visit to the Church of Sant’Andrea and its cloisters.
Lunch will be enjoyed in a quaint trattoria, accessible only by boat.
Day 7 – Capri & Anacapri
We will take a high-speed hydrofoil to Capri (30 minutes). First, we will explore the quieter, more authentic side of the island, where you’ll have the chance to shop, get custom jeweled sandals made, and take a lift up to Monte Solaro—offering breathtaking views across the Mediterranean.
We’ll then return to the heart of Capri for lunch at a hidden trattoria known only to locals.
Following lunch, a walking tour will take you through Capri’s highlights: the piazzetta, San Giacomo, the Gardens of Augustus, Via Krupp, and a walk out to the iconic Faraglioni—three towering rock formations that are symbols of Capri.
We will return to Positano by hydrofoil in the late afternoon.
Day 8 – Leisure Day
Enjoy a relaxed day for shopping, reading, writing postcards, hiking in the hills above Positano, or participating in a cooking class.
