10 Best Mediterranean Multiday Tours in May 2027

Accommodations

BudgetSimple stays with essential amenities. Typically guesthouses, hostels or hotels rated below 3 stars — clean, no-frills, and great for value-conscious travelers.
Mid-rangeComfortable and reliable 3-star stays. Expect private rooms, en-suite bathrooms, and solid amenities — a great balance between comfort and cost.
PremiumUpscale 4-5 star hotels and lodges. Enjoy high-end service, refined comfort, and premium locations — ideal for travelers seeking extra indulgence.

Amazing Spain - May 2027

Trip customizable

Best price guaranteed

Experience the essence of Spain on this immersive tour, from the vibrant capital of Madrid to the cultural treasures of Andalusia. Begin in Madrid with a guided city tour and tapas dinner before traveling south to explore Mérida’s ancient Roman ruins and Cordoba’s iconic Mosque. Discover Seville’s captivating history and indulge in Andalusian cuisine, then journey through scenic villages to Jerez for an experience of wine and equestrian art. Delight in Ronda’s charm and savor organic olive oil, followed by a historical exploration of Málaga. In Granada, marvel at the majestic Alhambra and learn flamenco before a farewell dinner back in Madrid. This journey weaves together Spain’s history, culture, and cuisine, offering unforgettable memories at every stop.

Cultural, religious and historic sites

Tour Type

Group Tour

Accommodation

Hotel, Villa

Age Range

8-99 yrs

Operated in

english

Destinations

Seville, Madrid, Granada, Cordob

Seville, Madrid, Granada, Cordoba, Costa del Sol

Duration9 days

From

USD 2,939

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Premium Split to Dubrovnik - May 2027

No booking fees

Best price guaranteed

See Croatia’s Dalmatian coast on an eight-day Premium adventure from Split to Dubrovnik. Laze at hidden island beaches and soak in the sunshine, while medieval towns and fishing hamlets make for an incredible backdrops. Get in with the locals on the beautiful island of Korcula, where you’ll be treated to Exclusive Experiences, local tastings, history lessons, panoramic views and loads of free time to soak up the natural beauty at your own pace. Take a sunset cruise off the coast of Dubrovnik, visit Game of Thrones filming locations, take a sustainable Urban Adventure around Split and toast to a trip well-travelled over some local wine. Bursting with culinary delights and cultural wonders – Croatia’s bountiful coast has it all.

Art and architectureChill out

Tour Type

Small Group Tour

Accommodation

Hotel

Age Range

15-99 yrs

Operated in

english

Destinations

Dubrovnik, Split, Lastovo Island

Dubrovnik, Split, Lastovo Island, Korcula Island

Duration8 days

From

USD 3,985

USD 3,865

Saving

USD 120

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Madrid and the enchanting Andalusia - May 2027

Trip customizable

Best price guaranteed

Embark on an enchanting journey through the heart of Spain as you explore the cultural wonders of Madrid, Cordoba, Seville, and Granada. This meticulously crafted itinerary promises a rich tapestry of history, art and architecture, providing you with an immersive experience into the diverse and vibrant heritage of the Iberian Peninsula. Begin your adventure in Madrid, where the energy of a modern metropolis seamlessly intertwines with centuries of regal history. As you venture south to Cordoba, immerse yourself in the city's rich blend of Moorish, Christian, and Jewish influences. Explore the mesmerizing Mezquita-Catedral, a breathtaking mosque-cathedral showcasing the city's complex history. Your journey culminates in Granada, where the crowning jewel is the Alhambra, a palace-fortress that captures the essence of Islamic art in Spain. Then Seville, a city brimming with passion and tradition, awaits with its flamenco rhythms and architectural marvels. This unforgettable journey promises a kaleidoscope of cultural experiences, leaving you with indelible memories of Spain's rich and diverse heritage.

Cultural, religious and historic sites

Tour Type

Private Tour

Accommodation

Hotel

Age Range

1-79 yrs

Operated in

english

Destinations

Madrid, Andalucia, Cordoba, Gran

Madrid, Andalucia, Cordoba, Granada, Seville

Duration10 days

From

USD 2,263

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Morocco Activity & Wellness Tour - May 2027

Trip customizable

Best price guaranteed

It is not just the history and culture of Morocco that intrigues travelers. The country is also endowed with natural beauty and an amazing variety of terrain, which add to its appeal. Book this seven-day, private tour and explore the rich cultural and natural diversity that Morocco has to offer. Your journey starts on arrival in Casablanca from where we will drive you to Rabat. Continue to Meknes, Volubilis, Fez and Chefcouaen followed by the Atlas Mountains. As part of this trip, you will also get the chance to learn more about the culture and lifestyle of Berber highlanders, enjoy a cooking class with an excellent Moroccan chef and relax in a hammam. Similarly, all your meals will be prepared with organic and natural produces. We understand that there is more to wellness than meets the eye. Therefore, we have designed this itinerary with as much attention to spiritual enrichment as physical. Delve into sufism during a hiking trip in Mount Zerhoune and meet the musicians of Joujouka, known for their sufi trance performances Since we want this trip to be ecologically friendly and sustainable in nature, we will prioritize reducing, reusing and recycling as much as possible. You will spend most of the nights in guesthouses and get plenty of opportunities to mingle with locals. For more details, please scroll down.

City sightseeing

Tour Type

Private Tour

Accommodation

Hotel, Guest House

Age Range

18-79 yrs

Operated in

english, french, german, spanish

Destinations

Casablanca, Fez, Rabat, Chefchao

Casablanca, Fez, Rabat, Chefchaouen, Moulay Idriss Zerhoun

Duration7 days

From

USD 1,665

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Unesco Puglia & Matera wonder holiday package - May 2027

Trip customizable

Best price guaranteed

In 6 amazing days, visit the 3 most beautiful UNESCO sites in southern Italy! Explore Matera, Alberobello and Castel del Monte in addition to the cities of Bari, Ostuni, and Lecce, all in a single organized tour that includes tour guides, hotels, and transfers. Learn more about the culture, history, and region, and recharge your batteries in the open air, while hunting for authentic wonders. This tour is perfect for couples, solo travelers, and for those who prefer a great quality, comprehensive, organized trip. If you would like an unforgettable holiday but without the worry of doing all the organizing, or if you simply don’t want the stress of driving, this holiday is for you! Make it easy on yourself and worry-free. This tour departs from Bari every Saturday and finishes in Lecce.

City sightseeing

Tour Type

Private Tour

Accommodation

Hotel

Age Range

18-79 yrs

Operated in

english, italian

Destinations

Matera, Puglia, Bari, Trani, Alb

Matera, Puglia, Bari, Trani, Alberobello, Ostuni, Lecce

Duration6 days

From

USD 2,494

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Premium Morocco Highlights with Essaouira - May 2027

No booking fees

Best price guaranteed

Take in the rich history and diverse culture of Morocco on a 12-day journey through this North African gem. Marvel at the Mosque of Hassan II in French-infused Casablanca, discover the charming streets of the Medina in magical Meknes, uncover ancient history at the Roman ruins of Volubilis, wander through the labyrinth of twisting alleyways in Fes el Bali, relax in the lakeside settlement of Bine el Ouidane and as the sun goes down, watch Djemaa el-Fna come to life with markets and magicians in Marrakech. End your adventure by relaxing in the coastal, European-inspired Essaouira where you can kick back, feast on fresh seafood and take it all in.

Cultural, religious and historic sites

Tour Type

Small Group Tour

Accommodation

Hotel, Villa, Resort, Guest House, Tent

Age Range

15-99 yrs

Operated in

english

Destinations

Marrakech, Casablanca, Meknes, F

Marrakech, Casablanca, Meknes, Fes, Bine El Ouidane, Essaouira

Duration12 days

From

USD 3,940

USD 3,822

Saving

USD 118

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27% OFF TODAY

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Exploring the Amalfi Coast - May 2027

(8 reviews )

No booking fees

Best price guaranteed

All in all this was a great week for us. We liked the itinerary and especially the fact it was two nights at each place. We did struggle with some of the other people in our group, but not so much that it impacted too much on our holiday. We just found them very loud and quite self centred which can be difficult in a group environment. We simply spent more time alone when we could. We would have liked some more detailed information about what to do in our free time as most of the group wanted to go shopping but that’s not our thing.

City sightseeing

Tour Type

Small Group Tour

Accommodation

Hotel

Age Range

12-100 yrs

Operated in

english

Destinations

Naples, Sorrento, Amalfi

27% OFF TODAY

Duration7 days

From

USD 1,849

USD 1,344

Saving

USD 505

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Cycling the Mediterranean Coast in Spain - May 2027

(2 reviews )

No booking fees

Best price guaranteed

Such an amazing trip with an excellent guide!

Bicycle tours

Tour Type

Small Group Tour

Accommodation

Hotel

Age Range

16-99 yrs

Operated in

english

Destinations

Barcelona, Valencia, L'ampolla

Barcelona, Valencia, L'ampolla, Sant Carles De La Rapita, Alcossebre

Duration8 days

From

USD 3,600

USD 3,492

Saving

USD 108

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12% OFF TODAY

Rome and Tuscan Highlights - May 2027

4.7

(51 reviews )

No booking fees

Best price guaranteed

I chose this trip because of the 6 nights in Tuscany - Montecatini Terme. Cinque Terre, Lucca, Siena and San Gimignano were highlights of this tour. The food for the special dinners was amazing. Rosella and Massimo kept things on track. Organizing and coordinating tickets, transportation (2 ferries, train and bus) and firsthand knowledge of the areas visited was well exhibited by Rosella. The specialty tour guides were knowledgeable and added extra flair to the excursions. Enjoyed the trip immensely.

City sightseeing

Tour Type

Group Tour

Accommodation

Hotel

Age Range

5-99 yrs

Operated in

english

Destinations

Rome, Montecatini, Florence, Vin

Rome, Montecatini, Florence, Vinci, San Gimignano

12% OFF TODAY

Duration9 days

From

USD 2,750

USD 2,430

Saving

USD 320

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Italy Coast to Coast by E-bike: Puglia to Amalfi Coast - May 2027

(4 reviews )

No booking fees

Best price guaranteed

This was the first time that this trip had been run using E-bikes, so everyone was keen to see how the trip would unfold. We were introduced to our bikes on the first evening, and because of a change of hotel we had the opportunity to cycle into Monopoli, and return in the dark after an amazing first meal. When I checked the itinerary I could see that the first two rides were going to be the most challenging in terms of ascent and distance, but I quickly realised that E-bikes are a great leveller. There are four levels of assistance, with turbo being the most powerful. The motor rewards effort, the faster you peddle, the more assistance it gives you, up to its maximum speed - these bikes are not chipped like the delivery cycles that whizz around around our streets bringing takeaways to the masses. Each person in the group decided how much effort to put in, getting up the many hills, but hats off to the one person in the group who rode the whole way on an ordinary bike . . . . and he was not at the back. Respect!! With uphills come downhills, and there were plenty of those. Long sweeping downhills that went on and on. Great fun. We were well fed and watered on this trip, both at lunchtime and in the evenings, and for the most part the weather behaved itself.

Bicycle tours

Tour Type

Small Group Tour

Accommodation

Hotel, Hut, Resort, Villa

Age Range

16-99 yrs

Operated in

english

Destinations

Sorrento, Monopoli, Matera, Cast

Sorrento, Monopoli, Matera, Castelmezzano, Monte Sant'Angelo, Paestum, Salerno

Duration8 days

From

USD 5,850

USD 5,675

Saving

USD 176

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Greece Island Hopper featuring Athens, Mykonos and Santorini - May 2027

No booking fees

Best price guaranteed

In Greece, discover a place where age-old legends and monuments intertwine with warm sunshine and island-style living. Tour Athens with a local guide. Explore the Acropolis, home to the famous Parthenon and the city’s best lookout. Enjoy three days at leisure on the island of Mykonos, an Aegean paradise of sandy beaches and bustling energy. Uncover the past at the excavation site of Akrotiri. Make the most of a free day on the picture-perfect island of Santorini. From to the ruins of Athens to the bright rooftops of Mykonos and Santorini – embrace the country at its best.

Chill outBeach Holidays

Tour Type

Group Tour

Accommodation

Hotel, Resort

Age Range

1-99 yrs

Operated in

english

Destinations

Athens, Mykonos, Santorini

Duration11 days

From

USD 3,599

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15% OFF TODAY

Northern Italy Including Cinque Terre - May 2027

4.5

(98 reviews )

No booking fees

Best price guaranteed

Very enjoyable, with a variety of interesting locations.

City sightseeing

Tour Type

Group Tour

Accommodation

Hotel, Villa

Age Range

5-99 yrs

Operated in

english

Destinations

Milan, Baveno, Italian Riviera

Milan, Baveno, Italian Riviera, Cinque Terre, Lake Maggiore

15% OFF TODAY

Duration8 days

From

USD 2,395

USD 2,037

Saving

USD 358

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13% OFF TODAY

Best of Italy and Sicily - May 2027

4.7

(55 reviews )

No booking fees

Best price guaranteed

The Hotel were ok but did not cater to the tourist. The rooms did not have the use of the fans and found the air stagnant. A little air moving would helped. The Hotel in Sicily in Jiardini Naxos, Caeser palace, found the hotel desk determinitly unhelpful.

City sightseeing

Tour Type

Group Tour

Accommodation

Hotel, Resort

Age Range

5-99 yrs

Operated in

english

Destinations

Rome, Venice, Palermo, Assisi, L

Rome, Venice, Palermo, Assisi, La Spezia, Florence, Monreale, Agrigento, Taormina, Sorrento, Capri, Vatican City

13% OFF TODAY

Duration15 days

From

USD 5,225

USD 4,559

Saving

USD 667

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Super Sales

Highlights of Crete - May 2027

No booking fees

Best price guaranteed

The island of Crete has so much history and natural wonder to offer, and in seven days on its shores, you’ll see what’s known as Europe’s oldest city, taste some of the region’s best food and wine, and discover some of the world’s most beautiful beaches. Visit the Knossos archaeological site and unwind in the secluded seaside village of Sougia. Join a boat trip with a local family through the region’s islands, sip wine in the vibrant port city of Chania and indulge in local dishes like fresh seafood or bougatsa (warm flaky pastry with creamy semolina custard or cheese).

Beach

Tour Type

Small Group Tour

Accommodation

Guest House, Hotel

Age Range

15-99 yrs

Operated in

english

Destinations

Chania, Heraklion, Knossos, Sougia

Duration7 days

From

USD 1,740

USD 1,688

Saving

USD 52

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All Mediterranean Tours in May 2027

Page 39 of 1,029 Trips in Mediterranean during May 2027 with 10,141 Reviews

Amazing Spain - May 2027

Premium Split to Dubrovnik - May 2027

Madrid and the enchanting Andalusia - May 2027

Morocco Activity & Wellness Tour - May 2027

Unesco Puglia & Matera wonder holiday package - May 2027

Premium Morocco Highlights with Essaouira - May 2027

Exploring the Amalfi Coast - May 2027

Cycling the Mediterranean Coast in Spain - May 2027

Rome and Tuscan Highlights - May 2027

Italy Coast to Coast by E-bike: Puglia to Amalfi Coast - May 2027

Greece Island Hopper featuring Athens, Mykonos and Santorini - May 2027

Northern Italy Including Cinque Terre - May 2027

Best of Italy and Sicily - May 2027

Page 39 of 1,029 Trips in Mediterranean during May 2027 with 10,141 Reviews

Highlights of Crete - May 2027

Europe

Asia

South America

Africa

North America

Oceania

Polar

Food, wine, events and nightlife

Adventure and sport

Wildlife, landscapes and nature

Boat tours, water sports and marine wildlife

Sightseeing, attractions, culture and history

Air tours, road trips and transfers

Beach, romance, getaways and relaxation

Special interests and hobbies

All Mediterranean Tours in May 2027

Page 39 of 1,029 Trips in Mediterranean during May 2027 with 10,141 Reviews

Page 39 of 1,029 Trips in Mediterranean during May 2027 with 10,141 Reviews