Luxury 5-Day Sicily Road Trip from Taormina traveling south to Syracuse

Your luxury holiday in Sicily begins as soon as you reach the city of Taormina. There, you’ll pick up the luxury rental vehicle of your choice and hit the roads!

The first destination of your luxury vacation in Sicily is Taormina - a city with many fantastic attractions to explore. Catch an early flight to enjoy as much time as possible discovering Taormina.

Tonight you will be treated to a stay at one of best luxury hotels in Taormina. We have picked out three of the most exclusive luxury lodging and hotel options for you to choose from.

Exploring new places can make you hungry. When you’re ready for dinner, we recommend trying one of the finest restaurants in Taormina.

For a culinary experience you will remember, have a look at the menu at Mezzaparola Cocktail Art Bar. With an average rating of 4.6 out of 5 stars by 855 customers, it’s truly one of the best restaurants in the whole of Taormina.

If you feel like having something slightly different, check out Lettera 82 Risto Pub. This is one of the most recommended restaurants in the city. Considering its average rating of 4.3 out of 5 stars by 631 customers, it’s one that most guests enjoy.

As your day in Taormina is coming to an end retreat to a bar where you can celebrate the start of your exciting luxury holiday in Sicily.

Make your way to Caffè Europa. This bar promises a great atmosphere for your celebrations and has an average rating of 4.3 out of 5 stars by 4,459 customers.

Or, why not continue your evening at First Lounge Bar, rated an average of 4.5 out of 5 stars among 1,328 guests.

Another bar where you can have a great time tonight is DOC - DUOMO OF CATANIA. This bar has an average rating of 4.4 out of 5 stars by 946 customers.

Raise a toast to the start of your 5-day luxury vacation in Sicily and look forward to more fantastic days to come!

On day 2 of your luxury road trip holiday in Sicily you will have the opportunity to experience two destinations in one day, the city of Taormina and the city of Syracuse. You’ll stay in Syracuse for 2 nights.

Your day starts in Taormina. Give yourself time to see some of the city’s very best attractions before it's time to hit the road.

Make the amazing Elephant Fountain your first stop of the day. The average rating of 4.6 out of 5 stars by 7,587 visitors gives you an idea of what to expect from this fountain and attraction before you head there.

Next up, make a stop at the incredible Catania Cathedral. With an average rating of 4.7 out of 5 stars by 6,668 visitors, it's easy to understand why so many people visit this cathedral and attraction.

Another unforgettable travel destination you can visit on this day of your luxury holiday is the outstanding Giardino Bellini. This urban park has an average rating of 4.4 out of 5 stars by 16,413 visitors.

When you’re finished at the must-see tourist destination, the perfect next stop is the popular Piazza Università. This spectacular must-see tourist destination and attraction is rated an average of 4.6 out of 5 stars in 7,354 reviews.

If you’re keen to explore even more, then consider a visit to the fantastic Castello Ursino. This hohenstaufen castle in southern italy is a remarkable attraction with an average rating of 4.3 out of 5 stars from 10,039 visitors.

Make the most of your day in Taormina by joining exclusive tours and activities that take your luxury holiday in Sicily to the next level. This is only one of many experiences you can include in your luxury travel package in Sicily. So make sure to check out the other options too, to find the best way to spend your time in Taormina today.

By the end of the day, you will drive to the city of Syracuse, where you will choose among some of the best luxury hotels.

After a long day of driving and exploring, we recommend you try A Putia, one of the best restaurants in Syracuse. This restaurant has an average rating of 4.6 out of 5 stars by 2,277 customers.

If you feel like having something else, locals also recommend Ristorante Sicilia in Tavola as one of their top choices in the city. Ristorante Sicilia in Tavola is rated an average of 4.4 out of 5 stars by 861 customers.

Another restaurant you could try in Syracuse is Trattoria del Buongustaio. This lovely restaurant has a fantastic menu and has been rated an average of 4.3 out of 5 stars by 928 customers.

If you’re not yet ready to head back to your hotel, we recommend you check out the nightlife of the city.

Fratelli Burgio is one of the best bars you can visit in Syracuse tonight. This bar is rated an average of 4.7 out of 5 stars by 537 customers.

You can also enjoy a glass or two at a popular place like Bar Pasticceria Midolo. This bar has an average rating of 4.4 out of 5 stars from 1,581 customers.

Alternatively, try Koala Pub. Koala Pub is the perfect place to get to know some locals in the city. This top-recommended bar is rated an average of 4.4 out of 5 stars by 1,089 customers.

Raise a glass in celebration of your fantastic luxury holiday in Sicily! Head back to your hotel for some much-needed rest in preparation for tomorrow’s adventures.

On day 3 of your luxury holiday, you’ll get the opportunity to experience the spectacular city of Syracuse. You’ll stay in Syracuse for 1 night, which gives you enough time to discover some of the most amazing things to see and do in the city. Start your morning with a hearty breakfast and get ready for an entire day of enjoying Syracuse to the fullest.

Today you will have the opportunity to visit multiple popular travel destinations in Syracuse. Begin your sightseeing with a visit to the outstanding Ear of Dionysius. This attraction has an average rating of 4.5 out of 5 stars by 8,144 visitors.

When you’re finished at Ear of Dionysius, make a stop at the wonderful Neapolis Archaeological Park. This incredible attraction is a park, rated an average of 4.3 out of 5 stars by 18,306 visitors.

Next up, make your way to one of the best places to see according to travelers in Syracuse, the extraordinary Diana fountain. This fountain is rated an average of 4.6 out of 5 stars by 5,848 visitors.

As the day moves along, another attraction you will probably want to visit is the incredible Ortygia. Up to 5,807 visitors have rated this island an average of 4.8 out of 5 stars.

If you’re up for one last attraction today, check out the popular Cathedral of Syracuse.

Tonight you will stay at one of the best luxury hotels in Syracuse. We have selected the perfect options for you to have the loveliest experience in Syracuse.

Treat yourself to an overnight stay at the wonderful Grande Albergo Alfeo, a highly recommended 4-star hotel in the city. This hotel has an average rating of 4 out of 5 stars by 1,329 guests and guarantees you a pleasant break from your self-drive luxury vacation.

Another excellent luxury accommodation alternative in Syracuse is the fantastic Grand Hotel Villa Politi. This 4-star hotel is the ultimate place to lay back and treat yourself to some well-deserved downtime after a busy day exploring. Grand Hotel Villa Politi is rated an average of 4.2 out of 5 stars by 1,037 guests.

Alternatively, check in at the outstanding Grand Hotel Ortigia. This 5-star hotel is warmly recommended by previous guest and has an average rating of 4.2 out of 5 stars from 906 reviews to prove it. Get cozy and rest before it’s yet again time to hit the roads.

Our flexible booking system will automatically provide you with the best luxury hotel alternatives if these are not available.

After a long day of exploring, it’s time for indulging in some food. Make a reservation at one of the best restaurants in Syracuse.

We recommend you eat at a restaurant that locals enjoy, like the fantastic La Lisca Cucina e Bottega. This excellent restaurant has an average rating of 4.6 out of 5 stars by 679 customers.

Alternatively, check out the menu at Trattoria o' Scinà. Considered one of the best restaurants in Syracuse, it has an average rating of 4.3 out of 5 stars by 444 customers.

If you’re curious about more of the best restaurants in Syracuse, Civico Maltato is one to check out. Civico Maltato is rated an average of 4.6 out of 5 stars by 325 customers.

As the day is coming to an end, retreat to your hotel for some rest, or head out to a bar to celebrate your time in Syracuse.

Many locals go to Bar Tunisi to have a good time. This bar is rated an average of 4.5 out of 5 stars by 903 customers.

If you feel like going somewhere else, another popular option in the city is Verga Courtyard - Cafeteria. This bar has an average rating of 4.6 out of 5 stars by 566 customers.

EVOÈ is another great option in Syracuse. This bar is rated an average of 4.9 out of 5 stars by 404 customers.

Enjoy an amazing evening in Syracuse, and get ready for more fantastic days to come of your luxury vacation in Sicily!

On day 4 of your luxury holiday in Sicily, wonderful attractions await. Today you have the opportunity to discover two places in one day, the city of Syracuse and Sicily. You’ll stay in Taormina for 1 night.

Begin your adventures of the day with a visit to the outstanding Temple of Apollo. This attraction is an ancient greek temple and has an average rating of 4.4 out of 5 stars by 16,056 visitors.

Joining a top-rated tour in Syracuse is another excellent way to spend your luxury holiday in Sicily. The best tours in this destination will take you on a discovery of some of Sicily’s most well-known attractions and best-kept secrets.

Make your way to the incredible Temple of Apollo in Sicily for some sightseeing. This popular attraction is an ancient greek temple and has been rated an average of 4.4 out of 5 stars by 16,056 visitors.

Another unforgettable travel destination you’ll want to pay a visit in Sicily is the outstanding Riserva Naturale Cavagrande del Cassibile. Rated 4.6 out of 5 stars by 6,913 visitors, this remarkable park and attraction definitely deserves a spot on travelers' bucket lists in Sicily.

We also recommend a visit to the popular Nature reserve of Vendicari. This attraction, a stunning regional nature reserve, has been rated an average of 4.6 out of 5 stars by 11,686 travelers.

If you’re keen to explore even more, then consider a visit to the fantastic Giardino Ibleo. With an average rating of 4.5 out of 5 stars from 8,600 travelers, this is a highly recommended stop on your luxury road trip through Sicily.

For the night, you’ll have the choice of the best luxury hotels and places to stay in the city of Taormina.

After dinner, you can enjoy some downtime at your hotel or head out to a bar for a couple of drinks.

If you’re not yet ready to call it a day, pop into the top-rated Bohéme Mixology Bar. This bar is considered one of the best in Taormina and is rated an average of 4.6 out of 5 stars by 634 customers.

You can also enjoy drinks at a popular bar like Collage Boutique Bar. This bar has an average rating of 4.7 out of 5 stars by 455 customers.

Alternatively, go to Mezzaparola Cocktail Art Bar. This is one of the most frequently recommended bars by locals in Taormina and is rated an average of 4.6 out of 5 stars in 855 reviews.

Go over your photos from the day, raise a toast, and rest your tired legs. A new adventurous day of your luxury road trip in Sicily awaits!

Today is the last day of your 5-day luxury holiday in Sicily and it’s soon time to start your journey home. This is your chance to get one last glimpse of Taormina before saying goodbye.

Catch a later flight to enjoy some extra time for exploring. If you have a late departure, we recommend doing some last-minute shopping or sightseeing.

Don’t end your vacation hungry.

You will then say farewell to Taormina and begin your journey home. We wish you safe travels and a warm welcome home, with unforgettable memories and incredible photos from your luxury holiday in Sicily in your luggage!