Pompeii, Naples, and Capri with Toldinstone

Dates

Nov 3–9, 2026

Group Size

12–23 Travelers

Duration

7 days, 6 nights

Activity Level

Exploration

About This Trip

This tour, based in Naples, will explore Pompeii, Herculaneum, and the other Roman cities buried by Vesuvius in 79 AD. We'll also visit the cave of the Sibyl at Cumae, the labyrinth under the Puteoli amphitheater, and the sunken palaces of Baiae. On Capri, we'll see the spectacular villa from which Tiberius ruled the Roman Empire. And in Naples itself - along with the world's best pizza - we'll experience the most impressive collection of Roman art anywhere.
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Meet Your Host

Toldinstone
Toldinstone

I'm Garrett Ryan. I have a PhD in ancient history, and I've written a few books about the Greeks and Romans. I spend most of my time, however, running Toldinstone, a popular YouTube channel about the ancient world. I've been fortunate enough to travel widely. But for me, all roads have always led back to Rome.

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Trip Activities

  • Visit the Underground Naples

  • Guided Naples Walking City Tour

  • Visit the Museo Nazionale Archeologico of Naples

  • Cuma Archaeological Park Tour

  • Baia Archaeological Park

  • Flavian Amphitheater in Pozzuoli

  • Guided Herculaneum Visit

  • Guided Oplontis Visit

  • Guided visit of Pompeii

  • Day trip to Capri

Included in Your Trip

  • Double occupancy in 4-star hotels (single rooms are unavailable on this trip)

  • Local guide throughout trip

  • All city transfers

Not Included

  • International flights

  • Food and alcohol (except as noted)

  • Visas and travel insurance

  • Airport transfers

  • Tips for Guides

What's included by Your Host

Q & A with Toldinstone

Informal Gathering
After we get back from the welcome dinner, I'll try to answer your questions about the Bay of Naples, Vesuvius, and all things ancient Roman.

Hidden traces of Roman Naples

Informal Gathering
A short walk through the historic center of Naples, showcasing some Roman ruins - including the theater where Nero made his debut as a singer - hidden in plain sight.

How the Roman games worked

Informal Gathering
A short talk (and Q & A session) covering the practical side of the Roman games - how exotic animals were sourced, how gladiators were hired, and how the tunnels under Roman amphitheaters made it all possible.

The Villa of the Papyri

Informal Gathering
A discussion about the unique treasures of the Villa of the Papyri, still only partially excavated.

Daily life in a Roman city

Informal Gathering
A brief talk on location in Pompeii, covering various aspects of life in a Roman city - shopping in the markets, eating out at bars, and relaxing in the baths.

Tiberius on Capri

Informal Gathering
Exploring the reign and legacy of this enigmatic emperor, who ruled the Roman world from Capri for a decade.

Itinerary

*All durations are approximate

Day 1

Welcome to Naples!

Welcome! Please be prepared to meet in the lobby at 5:30pm to depart for your welcome dinner. The dinner reservation time will be finalized closer to your trip date. If you plan on arriving today, we recommend flying into Naples-Capodichino International Airport (NAP).

dinner

Tonight you will come together as a group in the lobby of the hotel and walk 10 minutes to your welcome dinner at a local restaurant. Your meal tonight is a set menu that includes an appetizer, main entree and dessert. Alcoholic beverages are not included.

Q & A with Toldinstone

After we get back from the welcome dinner, I'll try to answer your questions about the Bay of Naples, Vesuvius, and all things ancient Roman.

Starhotels Terminus (or similar)

Accommodations may vary based on availability or group size, but no matter what, you can expect the same comfort and quality.

Night 1/6

Overnight in Naples.

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Day 2

Get to Know Naples!

Today offers a deep dive into the rich history of Naples. Begin with a private guided walking tour of Naples including the visit to the renowned Naples Archaeological Museum, home to one of the world’s most impressive collections of Greco-Roman artifacts. Continue with a fascinating tour of Underground Naples, where ancient tunnels and hidden chambers reveal layers of the city’s past. End the day with a leisurely walking tour through the historic center, taking in the vibrant atmosphere, stunning architecture, and local charm that make Naples such a unique and captivating destination.

breakfast

Breakfast is included at the hotel. Your breakfast will be buffet style, and includes both hot foods such as eggs and bacon, as well as a selection of cold cuts, croissants, a selection of pastries. Fruit juices, coffee tea milk with cereal and fruit. Other specific foods can be prepared upon request.

Visit the Underground Naples

1 Hour 15 Mins

A visit to Napoli Sotterranea reveals a hidden world beneath the city, with ancient Greek-Roman tunnels, aqueducts, and wartime shelters. Walking through narrow passageways and underground chambers offers a unique perspective on Naples’ history, blending archaeology, mystery, and centuries-old legends in a captivating and atmospheric experience.

Guided Naples Walking City Tour

2 Hours

Get ready to explore the city center with your local guide. From your hotel you will discover the narrow alleys of Naples city center and the elegant shopping streets. The exact starting point will be determined based on the confirmed hotel. Some of the highlights of this tour include Duomo of Naples, Decumano Maggiore, San Lorenzo Church and San Gregorio Alley with handcrafted nativities. Amaze yourself in the tiny streets of the old town, and the elegant shopping streets such as Via Toledo, Galleria Umberto, and Piazza del Plebiscito. You will be walking along a city route for 2 hours, and a total distance of about 2 miles so please remember to wear comfortable shoes.

Visit the Museo Nazionale Archeologico of Naples

2 Hours

The Archaeological Museum of Naples offers a fascinating journey through ancient history, showcasing remarkable Greek and Roman artifacts, including mosaics, sculptures, and relics from Pompeii and Herculaneum, all housed in an elegant historic building.

Hidden traces of Roman Naples

A short walk through the historic center of Naples, showcasing some Roman ruins - including the theater where Nero made his debut as a singer - hidden in plain sight.

Starhotels Terminus (or similar)

Accommodations may vary based on availability or group size, but no matter what, you can expect the same comfort and quality.

Night 2/6

Overnight in Naples.

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Day 3

Day Trip to Capri

A day trip in the Phlegraean Fields explores volcanic landscapes, ancient ruins, and seaside charm. Visit Cuma to see the legendary Sibyl’s Cave and archaeological remains, then continue Baia Archeological Park, and finally to Pozzuoli to admire the Roman amphitheater and the fascinating Solfatara crater. History, nature, and mythology blend in this unique experience near Naples.

breakfast

Breakfast is included at the hotel. Your breakfast will be buffet style, and includes both hot foods such as eggs and bacon, as well as a selection of cold cuts, croissants, a selection of pastries. Fruit juices, coffee tea milk with cereal and fruit. Other specific foods can be prepared upon request.

Cuma Archaeological Park Tour

2 Hours

Take a private tour through the evocative ruins of Cuma Archaeological Park, the oldest Greek settlement on mainland Italy. Explore ancient temples and shadowed passageways where myth and history intertwine — from the fabled Cave of the Sibyl to the enduring traces of Hellenic civilization.

Baia Archaeological Park

2 Hours

Continue to Baia Archaeological Park, once an opulent Roman seaside retreat for emperors and elites. Though partially claimed by the sea, its hauntingly beautiful ruins still whisper of ancient indulgence, political intrigue, and thermal pleasures, offering a rare glimpse into the lavish world of imperial leisure.

Flavian Amphitheater in Pozzuoli

1 Hour

Conclude the day at the awe-inspiring Flavian Amphitheater in Pozzuoli, one of Italy’s largest and best-preserved arenas. Step beneath its towering arches and into the subterranean chambers where gladiators once prepared for battle, and feel the enduring pulse of Roman spectacle and architectural brilliance.

How the Roman games worked

A short talk (and Q & A session) covering the practical side of the Roman games - how exotic animals were sourced, how gladiators were hired, and how the tunnels under Roman amphitheaters made it all possible.

Starhotels Terminus (or similar)

Accommodations may vary based on availability or group size, but no matter what, you can expect the same comfort and quality.

Night 3/6

Overnight in Naples.

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Day 4

Discover Pompeii

In the morning take an excursion to the remarkably well-preserved ruins of Herculaneum, a Roman town buried by the eruption of Mount Vesuvius in 79 AD which you will visit with a private guide. Unlike Pompeii, Herculaneum reveals vivid details of daily life through its intact buildings, mosaics, and wooden structures. The tour continues with a private guided tour of the nearby Villa of Poppaea at Oplontis, a lavish Roman residence believed to have belonged to Emperor Nero’s wife. Richly decorated with frescoes and surrounded by gardens, the villa offers a striking example of Roman luxury and architecture. This day provides a unique and immersive glimpse into ancient life along the Bay of Naples.

breakfast

Breakfast is included at the hotel. Your breakfast will be buffet style, and includes both hot foods such as eggs and bacon, as well as a selection of cold cuts, croissants, a selection of pastries. Fruit juices, coffee tea milk with cereal and fruit. Other specific foods can be prepared upon request.

Transfer to Herculaneum

45 Mins

A 45 minutes transfer will bring you from your accommodation in Naples to Herculaneum

Guided Herculaneum Visit

2 Hours

A two-hour guided tour of Herculaneum offers an immersive journey into one of the best-preserved ancient Roman cities. Walking through the archaeological site, you will explore remarkably intact houses, frescoes, mosaics, and public buildings, all buried by the eruption of Mount Vesuvius in 79 AD. The guide will bring the past to life, explaining daily life, social customs, and architectural details of this once-thriving town. You will see the ancient baths, shops, and the impressive Villa of the Papyri, providing a vivid picture of Roman civilization. The visit is both educational and fascinating, offering a deeper understanding of history and archaeology.

Guided Oplontis Visit

1 Hour 30 Mins

After some time at leisure for lunch embark on a guided tour of Oplontis. The tour offers a fascinating glimpse into the luxurious lifestyle of ancient Rome. The visit focuses on the impressive Villa Poppaea, believed to have belonged to Emperor Nero’s wife, beautifully preserved under volcanic ash from the eruption of Mount Vesuvius. As you walk through spacious rooms, elegant frescoes, and tranquil gardens, the guide explains the villa’s history, art, and architecture, bringing to life the opulence of Roman aristocracy. The tour also highlights daily life, leisure, and the significance of this magnificent residence within the Roman world. Return to Naples after the visit (transfer approx 45 minutes)

The Villa of the Papyri

A discussion about the unique treasures of the Villa of the Papyri, still only partially excavated.

Starhotels Terminus (or similar)

Accommodations may vary based on availability or group size, but no matter what, you can expect the same comfort and quality.

Night 4/6

Overnight in Naples.

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Day 5

Head to the Amalfi Coast

After breakfast transfer to Pompeii, where you will explore one of the world's most significant archaeological sites. Explore the archaeological site of Pompeii with the guidance of a private and knowledgeable guide.

breakfast

Breakfast is included at the hotel. Your breakfast will be buffet style, and includes both hot foods such as eggs and bacon, as well as a selection of cold cuts, croissants, a selection of pastries. Fruit juices, coffee tea milk with cereal and fruit. Other specific foods can be prepared upon request.

Transfer to Pompeii

40 Mins

Transfer from your accommodation in Naples to Pompeii

Guided visit of Pompeii

3 Hours

Explore the archaeological site of Pompeii with the guidance of a private and knowledgeable english speaking guide. Before the devastating eruption of Mount Vesuvius in 79 A.D., Pompeii was a thriving commercial hub. The eruption buried the city under layers of ash, preserving it for nearly 2,000 years and offering an extraordinary glimpse into ancient life. Your tour will begin at Piazza del Foro, once the vibrant center of Pompeii, and take you through the city’s temples, thermal baths, bustling marketplace, and grand theatre. You will step inside the opulent homes of Roman aristocrats like the House of the Faun or the house of Vettii, to marvel at some of the most exquisite frescoes and mosaics of the Roman era. Return to Naples after the visit of Pompeii for an afternoon at your leisure.

Daily life in a Roman city

A brief talk on location in Pompeii, covering various aspects of life in a Roman city - shopping in the markets, eating out at bars, and relaxing in the baths.

Starhotels Terminus (or similar)

Accommodations may vary based on availability or group size, but no matter what, you can expect the same comfort and quality.

Night 5/6

Overnight in Naples.

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Day 6

Free Time in Sorrento

Get ready for an adventure to Capri, the shining gem of the Bay of Naples! With its breathtaking natural beauty and a vibrant atmosphere filled with bars, cafes, and restaurants, Capri is one of the most sought-after destinations in Italy. After exploring this dazzling island, head back to Naples and get ready to indulge in some delicious Neapolitan cuisine.

breakfast

Breakfast is included at the hotel. Your breakfast will be buffet style, and includes both hot foods such as eggs and bacon, as well as a selection of cold cuts, croissants, a selection of pastries. Fruit juices, coffee tea milk with cereal and fruit. Other specific foods can be prepared upon request.

Day trip to Capri

8 Hours

After breakfast a short transfer will take you to the port of Naples, where you will board on a public boat to Capri for a full-day excursion to this enchanting island, known for its stunning cliffs, crystal-clear waters, and timeless beauty. Board on the funicolar linking the port of the island with the iconic village of Capri and explore the island’s charming streets and natural wonders before heading to Villa Jovis (approx 45 minutes walk one way from Capri – no transportation possible), the imperial residence of Emperor Tiberius. Perched dramatically on a cliff, the villa offers both archaeological significance and breathtaking views over the sea. Return to Capri and time at leisure before boarding on the public boat to Naples

dinner

Time to say goodbye and with a last toast all together share stories from the memorable week during your farewell dinner at a local restaurant. Your meal tonight is a set menu that includes an appetizer, main entree and dessert. Alcoholic beverages are not included.

Tiberius on Capri

Exploring the reign and legacy of this enigmatic emperor, who ruled the Roman world from Capri for a decade.

Starhotels Terminus (or similar)

Accommodations may vary based on availability or group size, but no matter what, you can expect the same comfort and quality.

Night 6/6

Overnight in Naples.

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Day 7

Wave Goodbye to Your Newfound Friends!

All good things must come to an end, but only until your next adventure! Enjoy a final breakfast and then make your own way onward. If departing directly from the hotel, we recommend flying out of Naples-Capodichino International Airport (NAP).

breakfast

Breakfast is included at the hotel. Your breakfast will be buffet style, and includes both hot foods such as eggs and bacon, as well as a selection of cold cuts, croissants, a selection of pastries. Fruit juices, coffee tea milk with cereal and fruit. Other specific foods can be prepared upon request.

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Physical Activity Level:Exploration

These trips require some movement, but slow and steady is the name of the game. Maybe a mid-length walking tour or at-your-pace sightseeing. No rush.

Cancellation Policy

We get it—life happens. Here's how cancellations work depending on where you're at in the process:

Spot Pending

100% refundable
Not confirmed yet? No worries. You can cancel at any time for a full refund.

Spot Confirmed With 91 or More Days Before Your Trip

Partially refundable + credit towards a future trip
You'll receive a future trip credit for the amount of your down payment (minus a $100 cancellation fee per Traveler). This trip credit is valid for one year from the date it is issued. Additionally, any payments made beyond the original 25% down payment will be refunded to your original form of payment.

Spot Confirmed With 90 or Fewer Days Before Your Trip

Non-refundable
At this point, all payments are non-refundable because your experience is already in motion behind the scenes. By this time, our operating partners will be working with local businesses to secure your accommodations and finalize your activities.

HIGHLY RECOMMENDED: Protect Your Adventure-Invest in Peace of Mind

We strongly encourage purchasing travel insurance with trip cancellation coverage to safeguard your investment. With travel insurance, you're covered in case of unexpected events—from illness to emergencies—that could affect your plans. Life is unpredictable, but your dream trip doesn't have to be.

After booking, you'll receive a personalized recommendation for coverage tailored to your trip. For full details on our cancellation policy, please refer to our Terms & Conditions.

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FAQ

Traveling with TrovaTrip

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Trova Trips are curated group travel experiences designed to help you see the world, meet new people, and connect over shared interests. Each trip is hosted by a community leader you know and trust, and run by professional local Operators who handle the logistics. Expect meaningful experiences, authentic activities, and a like-minded group to share it all with.

What's the difference between the Host, the Operator, and Trova?

Great question! Each plays a key role in bringing your experience to life:

  • The Host is your community leader who brings the group together, fosters connection, and perhaps leads a workshop or two. They're there to bring the vibes, not the logistics. That's the Tour Operator's job.
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In short: The Host brings the vibe, the Operator runs the trip, and we make it all happen. Read more about who does what here.

I'm nervous to book. How can I feel more confident?

First, let us say—it's totally understandable, and you're not alone! Travel can feel intimidating, but we built Trova to take the guesswork out of group travel and earn your trust every step of the way:

    • Every trip is run by licensed Tour Operators with vetted local Guides.
    • Hosts are there to foster connection, meaning you'll arrive solo but never feel alone.
    • Itineraries are clearly outlined so you know what to expect, including activity level, example accommodations, and what's included.
    • Our team is available to support you pre-departure, and Operators—plus your local Guide—are on the ground to assist during the trip. And rest assured, all our Operating partners are trained in crisis management.
    • We always recommend travel insurance for extra peace of mind, whether you're traveling with Trova or solo. It can cover medical issues, lost luggage, or even cancellations.

We know it takes trust to book a trip with new people, and we're here to make sure you feel ready, supported, and excited!”

Can I book solo?

Absolutely! As of 2025, almost 84% of TrovaTrip Travelers go solo. (And yes, we may be a little biased, but we think group travel is one of the best ways to meet new people!) You'll have your own bed and the option to book a private room on most trips. Plus you'll be traveling with others who are just as excited to explore and connect.

What if I need to cancel?

We understand that life happens. Our cancellation policy is designed to provide flexibility while balancing the logistics of group travel:

  • Spot pending100% refundable. Not confirmed yet? No worries. You can cancel at any time for a full refund.
  • Spot confirmed with 91 or more days before your tripPartially refundable + credit towards a future trip. You'll receive a future trip credit for the amount of your down payment (minus a $100 cancellation fee per Traveler). This trip credit is valid for one year from the date it is issued. Additionally, any payments made beyond the original 25% down payment will be refunded to your original form of payment. 
  • Spot confirmed with 90 days or fewer before your tripNon-refundable. At this point, all payments are non-refundable because your experience is already in motion behind the scenes. By this time, our operating partners will be working with local businesses to secure your accommodations and finalize your activities.

HIGHLY RECOMMENDED: Protect Your Adventure–Invest in Peace of Mind
We strongly encourage purchasing travel insurance with trip cancellation coverage to safeguard your investment. With travel insurance, you're covered in case of unexpected events–from illness to emergencies–that could affect your plans. Life is unpredictable, but your dream trip doesn't have to be.

After booking, you'll receive a personalized recommendation for coverage tailored to your trip. For full details on our cancellation policy, please refer to our Terms & Conditions.

What's included in the trip cost?

Most trips include accommodations, daily activities, ground transportation, some meals, and a dedicated local Guide. Because Travelers are coming from all around the world, flights to and from your destination are not included. Each trip page breaks it all down for you.

Will I have free time?

Yes! While we pack in incredible experiences, most itineraries include built-in free time so you can relax, wander, or check out personal must-sees.

What do the activity levels mean?

Every trip has a physical Activity Level from 1 to 5 so you can find the right fit for your travel style:

  • Level 1 – Relax + Unwind: Minimal movement (spa days, beach lounging, local markets)
  • Level 2 – Low-Key Movement: Light, easy-paced activity (snorkeling, boat tours, gentle hikes)
  • Level 3 – Moderate Activity: Ready to move (multi-day hikes, skiing, camping)
  • Level 4 – Get Your Heart Rate Up: More intense movement (long hikes, biking, active days)
  • Level 5 – Extreme Adventure: High-adrenaline travel (challenging hikes, dives, technical climbs – experience may be required)

You'll find the Activity Level clearly listed on each trip page, and a more in-depth explanation of each level here.

Who can I contact with more questions?

Our support team is here to help! Visit trovatrip.com/company/contact-us to reach out. You can expect to hear back within 2 business days, but probably sooner—our Trova elves are pretty speedy!

Accommodations

What does "or similar" mean next to the accommodations?

When we say “or similar,” it means the hotel listed is an example of what you can expect—not always the exact spot you'll be staying. Sometimes Operators adjust accommodations due to seasonal availability or group size. But rest assured: the quality and comfort will match what's shown.

Why would the accommodations change from time of booking?

Flexibility allows Operators to choose the best-fit accommodations closer to your trip—based on availability, logistics, and what works best for the group (like the number of Travelers and room configurations). This ensures a smooth experience without sacrificing comfort or quality.

Finalized hotel info is typically shared about 30 days before departure in your Traveler Portal, along with your final itinerary.

Trip Operations & Compliance

Who actually runs my trip, and how does Trova keep things safe?

Your trip is operated by licensed, certified Tour Operators who manage all trip logistics and safety—from accommodations and local Guides and day-to-day logistics. All trips comply with local legal and regulatory standards. We vet each Operating partner carefully so you can travel with confidence.

Who do I talk to if I have questions about safety or compliance?

If you have any questions about safety protocols or trip compliance, reach out to us at safety@trovatrip.com. We're here to help.

General Travel Questions

Do I need any documentation to travel?

It depends on where you're headed. Though it is not a universal requirement, many countries require that your passport be valid for at least six months beyond your arrival date. This ensures Travelers have sufficient time to return home even if their visas are extended or if unexpected circumstances arise. 

Some destinations may also require a visa. Check our visa page to consult your country's travel resources.

Do I need any vaccines?

It's always best to check with your healthcare provider or a travel doctor before your trip. You can also visit the CDC website (or your local government's travel health resource) for destination-specific vaccine guidance. Health and safety first!

Are flights included in the trip cost?

Because our Hosts and Travelers are coming from all around the world, flights to and from your destination are not included. Some trips include internal flights (like a short domestic hop), and those details will always be listed on the trip page if applicable.

Can you accommodate my dietary needs?

We’ll do our very best! Our Operators aim to accommodate dietary restrictions, though availability varies by destination. For example, some places offer plenty of vegan and vegetarian choices, while others might be quite limited. The earlier you let us know—through your trip form or by contacting our support team—the better we can prepare. Once you arrive, be sure to remind your local Guide about any allergies or restrictions so they can help you enjoy your meals safely and comfortably.