20 days in Greece, Spain & Lisbon Itinerary
Created using Klarna Trips Europe tour planner
Start: Chicago, United States
Fly
1
Lisbon, Portugal
— 3 nights
Fly
2
Madrid, Spain
— 3 nights
Fly
3
Athens, Greece
— 2 nights
Fly
4
Fira, Greece
— 3 nights
Ferry
5
Naxos Town, Greece
— 4 nights
Fly
6
Barcelona, Spain
— 3 nights
Fly
End: Chicago, United States
Sun, Jun 11 - Fri, Jun 30
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Lisbon, Portugal — 3 nights

City of Seven Hills
Built on seven hills, Lisbon has experienced a renaissance in recent years, making it the cultural star of Portugal.Museum-lovers will appreciate National Coach Museum and Museu Colecao Berardo. Mosteiro dos Jeronimos and Castelo de S. Jorge will appeal to history buffs. Change things up with these side-trips from Lisbon: Quinta da Regaleira (in Sintra) and Praia de Carcavelos (in Carcavelos). There's still lots to do: take a stroll through Chiado, explore the world behind art at Museu Nacional do Azulejo, take an in-depth tour of Carmo Archaeological Museum, and make a trip to Belém Tower.
For more things to do, other places to visit, reviews, and tourist information, read Lisbon online trip builder.
Chicago, USA to Lisbon is an approximately 12.5-hour flight. The time zone changes from Central Standard Time to Western European Standard Time, which is usually a 6 hour difference. In June, daily temperatures in Lisbon can reach 81°F, while at night they dip to 60°F. Wrap up your sightseeing on the 15th (Thu) early enough to fly to Madrid.
Side Trips
Find places to stay Jun 12 — 15:
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Madrid, Spain — 3 nights

Cultural Capital of Spain
Madrid is known for its cultural and artistic heritage, lively nightlife, and a dynamic culinary scene.Prado National Museum and Royal Palace of Madrid are good opportunities to explore the local culture. Deepen your sense of the past at sights like Plaza de Toros de Las Ventas and Catedral de Sta Maria la Real de la Almudena. Next up on the itinerary: indulge your senses at some of the top wineries in the area, explore the world behind art at National Archaeological Museum of Spain, wander the streets of La Latina, and don't miss a visit to Paseo del Prado.
To see reviews, traveler tips, and other tourist information, go to the Madrid driving holiday planner.
Traveling by flight from Lisbon to Madrid takes 4.5 hours. Alternatively, you can drive; or take a bus. The time zone changes from Western European Standard Time to Central European Standard Time, which is usually a 1 hour difference. When traveling from Lisbon in June, plan for a bit warmer days in Madrid, with highs around 87°F, while nights are about the same with lows around 61°F. Wrap up your sightseeing on the 18th (Sun) early enough to fly to Athens.
Find places to stay Jun 15 — 18:
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Athens, Greece — 2 nights

The Birthplace of Democracy
One of the world's most ancient cities, Athens remains Europe's undisputed historical and cultural capital.Kick off your visit on the 19th (Mon): wander the streets of Anafiotika, delve into the distant past at Erechtheion, then contemplate the long history of Acropolis of Athens, and finally delve into the distant past at Temple of Hephaestus.
To find where to stay, reviews, and more tourist information, read Athens trip builder site.
Traveling by flight from Madrid to Athens takes 7 hours. Alternatively, you can drive; or do a combination of train and bus. Due to the time zone difference, you'll lose 1 hour traveling from Madrid to Athens. Traveling from Madrid in June, plan for somewhat warmer nights in Athens, with lows around 70°F. Finish your sightseeing early on the 20th (Tue) so you can fly to Fira.
Find places to stay Jun 18 — 20:
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Fira, Greece — 3 nights

Fira, the busy capital of Santorini, sits on the very edge of a volcanic caldera.Wine Museum Koutsogiannopoulos and Cultural Village are good opportunities to explore the local culture. Get some historical perspective at Castelli of Pyrgos and Ekklisia Panagia Platsani. The adventure continues: do a tasting at Venetsanos Winery, admire the masterpieces at MATI Art Gallery, steep yourself in history at The Castle of St Nicholas, and relax and rejuvenate at some of the best spas.
Start your trip to Fira by creating a personalized itinerary on Klarna Trips.
You can fly from Athens to Fira in 2.5 hours. Other options are to do a combination of taxi and ferry; or ride a ferry. Expect a daytime high around 82°F in June, and nighttime lows around 70°F. Finish your sightseeing early on the 23rd (Fri) so you can ride a ferry to Naxos Town.
Side Trips
Find places to stay Jun 20 — 23:
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Naxos Town, Greece — 4 nights

Naxos Town tops the itinerary of most visitors exploring the Aegean islands, drawing their attention with taverns, shops, beaches, and ancient ruins.Popular historic sites such as The Temple of Apollo – Portara and Old Town are in your itinerary. Fish & Olive and Panagia Drossiani Church are good opportunities to explore the local culture. Change things up with these side-trips from Naxos Town: Kastraki Beach (in Kastraki) and Temple of Demeter (in Sangri). There's still lots to do: kick back and relax at Finikas Beach, admire the landmark architecture of Church of Agios Georgios Diasoritis, stroll through Maragas Beach, and examine the collection at Theatrical Museum Iakovos Kampanellis.
For ratings, more things to do, traveler tips, and more tourist information, you can read our Naxos Town trip planner.
Traveling by ferry from Fira to Naxos Town takes 2.5 hours. Alternatively, you can fly. In June, daily temperatures in Naxos Town can reach 82°F, while at night they dip to 69°F. Cap off your sightseeing on the 27th (Tue) early enough to catch the flight to Barcelona.
Side Trips
Find places to stay Jun 23 — 27:
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Barcelona, Spain — 3 nights

Jewel of the Mediterranean
Barcelona, the country’s second-largest city, is a cosmopolitan urban center known for its throbbing youthful energy and stellar architecture.Basilica de la Sagrada Familia and Barri de Gracia will appeal to history buffs. Museum-lovers will appreciate Casa Vicens and Museu d'Història de Barcelona MUHBA. And it doesn't end there: cast your line with a fishing tour, make a trip to Ciutat Vella, stop by El Born, and take in the spiritual surroundings of Plaça de Sant Felip Neri.
For maps, photos, more things to do, and other tourist information, read our Barcelona trip itinerary site.
You can fly from Naxos Town to Barcelona in 8.5 hours. Alternatively, you can do a combination of ferry and car; or do a combination of ferry and bus. Due to the time zone difference, you'll gain 1 hour traveling from Naxos Town to Barcelona. In June, daily temperatures in Barcelona can reach 79°F, while at night they dip to 66°F. Wrap up your sightseeing on the 30th (Fri) to allow time to fly back home.
Find places to stay Jun 27 — 30:
Highlights from your trip
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Spain travel guide
A colorful country known for its relaxed lifestyle, vibrant nightlife, excellent food, and world-famous folklore and festivals, Spain boasts a huge number of World Heritage Sites and other spectacular places to visit. It also deserves its reputation as a beach vacation destination; the Western edge of the Mediterranean Sea is home to some of the world’s top beaches. But Spain’s geography is so much more than just soft, sandy shores. Its landscapes are as diverse as its people, ranging from lush meadows and snowy mountains to huge marshes and sprawling deserts. The countryside bursts with unspoiled villages of timeless beauty and old-world charm, as well as vast and varied nature preserves.
Greece travel guide
Few places manage to capture the world's imagination quite like Greece, a land of sun-kissed coastlines, tranquil whitewashed villages, lively seaside towns, and well-preserved ancient sites. One of the world's top tourist destinations since ancient times, the country draws nearly 20 million visitors each year. Athens, the birthplace of Western civilization, continues to attract the biggest crowds and serves as a base for exploring the country and its 227 inhabited islands. Away from its cities, Greece features a picturesque countryside of olive groves, vineyards, and tiny settlements nestled against rolling hills and rugged mountain ranges. Explore the old mainland on foot and discover the islands on a guided boat or ferry tour.
Santorini travel guide
Wine Island
Known for dramatic views and romantic sunsets, the island of Santorini draws visitors with its long string of black, white, and red beaches. The largest and most significant of a small group of volcanic islands located just 200 km (120 mi) southeast of Greece's mainland, Santorini boasts just over 15,000 permanent residents. Created by a massive volcanic eruption that likely destroyed a single large island, the archipelago still features an active volcano, which saw its last eruption in the 1950s. The easiest way to explore Santorini's craggy coastline is on foot. Start by visiting the archaeological sites on the island's southwestern side, which offer a chance to discover the area's ancient past with unobstructed views of the famed volcano.
Naxos travel guide
Zeus, the master of all gods from Greek mythology, allegedly grew up in a cave on Naxos, a small but fertile island in the South Aegean Sea. Renowned for its unspoiled beaches and advantageous winds, the island offers excellent conditions for windsurfing and other watersports. Most of the island's western coastline boasts one sandy beach splashed by blue waters rich in marine life--a big draw for amateur scuba divers. The mountainous interior provides a look at the quieter side of the island, featuring a patchwork of lush valleys, quaint villages, and ancient sites. For a change of pace and a bit of modern dining and shopping, visit Hora, the island's biggest city.