41 days in Spain, Istanbul & Lisbon Itinerary

41 days in Spain, Istanbul & Lisbon Itinerary

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Route & dates

41 days in Spain, Istanbul & Lisbon Itinerary

Start: New York City, United States
Fly:  12 h
1
Madrid, Spain
— 1 night
Train:  45 min
2
Toledo, Spain
— 4 nights
+3
Train + Foot + Train + Fly:  7 h 30 min
3
Istanbul, Turkey
— 14 nights
Fly:  5 h
4
Bilbao, Spain
— 7 nights
Bus:  1 h 15 min
5
San Sebastian - Donostia, Spain
— 5 nights
Fly:  3 h 45 min
6
Madrid, Spain
— 3 nights
Fly:  4 h 15 min
7
Lisbon, Portugal
— 5 nights
Fly:  11 h 15 min
End: New York City, United States

1
night
Madrid, Spain

Madrid ©
Madrid is known for its cultural and artistic heritage, lively nightlife, and a dynamic culinary scene.
Start off your visit on the 2nd (Wed): explore the world behind art at Prado National Museum, then don't miss a visit to Puerta del Sol, and then admire the striking features of Royal Palace of Madrid.

For reviews, ratings, where to stay, and tourist information, refer to the Madrid trip website.

New York City, USA to Madrid is an approximately 12-hour flight. You can also do a combination of bus and flight; or do a combination of train and flight. Traveling from New York City to Madrid, you'll lose 6 hours due to the time zone difference. Expect little chillier evenings in Madrid when traveling from New York City in September, with lows around 59°F. Finish up your sightseeing early on the 3rd (Thu) so you can catch the train to Toledo.

Things to do in Madrid

Museums Historic Sites
Find places to stay Sep 1 — 3:
Highlights from your plan
Prado National Museum ©
Prado National Museum
Royal Palace of Madrid ©
Royal Palace of Madrid
Puerta del Sol ©
Puerta del Sol

4
nights
Toledo, Spain

Toledo ©
Toledo is a World Heritage Site that embodies the complex cultural history of Spain while remaining a forward-moving, modern city.
Step out of Toledo with an excursion to Royal Palace of Aranjuez in Aranjuez--about 40 minutes away. There's much more to do: don't miss a visit to Catedral Primada, examine the collection at Museo del Greco, take in the views from San Martin Bridge, and take in the spiritual surroundings of Monastery of San Juan de los Reyes.

To find ratings, reviews, and other tourist information, use the Toledo trip planner.

Traveling by train from Madrid to Toledo takes an hour. Alternatively, you can drive; or take a bus. September in Toledo sees daily highs of 83°F and lows of 59°F at night. Finish your sightseeing early on the 7th (Mon) so you can travel to Istanbul.

Things to do in Toledo

Historic Sites Museums Neighborhoods

Side Trip

Royal Palace of Aranjuez
Find places to stay Sep 3 — 7:
Highlights from your plan
Catedral Primada ©
Catedral Primada
Casco Historico de Toledo ©
Casco Historico de Toledo

14
nights
Istanbul, Turkey

Istanbul ©
A physical and cultural bridge between Europe and Asia, the transcontinental city of Istanbul serves as a living reminder of the Roman, Byzantine, and Ottoman empires.
Istanbul is known for museums, historic sites, and shopping. Your plan includes some of its best attractions: contemplate in the serene atmosphere at Hagia Sophia Museum / Church (Ayasofya), admire the landmark architecture of Dolmabahce Palace, get engrossed in the history at Topkapi Palace, and take in panoramic vistas at Galata Tower.

To see reviews, photos, other places to visit, and tourist information, read Istanbul road trip planning website.

You can fly from Toledo to Istanbul in 7.5 hours. Alternatively, you can do a combination of train and flight; or drive. You'll lose 2 hours traveling from Toledo to Istanbul due to the time zone difference. While traveling from Toledo, expect a bit cooler days and somewhat warmer nights in Istanbul, ranging from highs of 72°F to lows of 72°F. Finish your sightseeing early on the 21st (Mon) to allow enough time to travel to Bilbao.

Things to do in Istanbul

Historic Sites Parks Museums
Find places to stay Sep 7 — 21:
Highlights from your plan
Hagia Sophia Museum ©
Hagia Sophia Museum
Sultan Ahmed Mosque ©
Sultan Ahmed Mosque
Topkapi Palace ©
Topkapi Palace

7
nights
Bilbao, Spain

A city of stunning architectural and artistic heritage, Bilbao is situated on the banks of the Nervión River.
You'll find plenty of places to visit near Bilbao: San Juan de Gaztelugatxe (in Bermeo), Peninsula of Magdalena (in Santander) and Bodegas Tritium (in Cenicero). There's still lots to do: awaken your taste buds at some of the top wineries in the area, take a stroll through Casco Viejo, admire the masterpieces at Guggenheim Museum Bilbao, and make a trip to Taberna Plaza Nueva.

To find other places to visit, reviews, more things to do, and tourist information, you can read our Bilbao day trip tool.

Fly from Istanbul to Bilbao in 5 hours. Alternatively, you can drive; or do a combination of bus and train. Due to the time zone difference, you'll gain 2 hours traveling from Istanbul to Bilbao. Traveling from Istanbul in September, you will find days in Bilbao are a bit warmer (78°F), and nights are a bit cooler (58°F). Wrap up your sightseeing on the 28th (Mon) to allow time to take a bus to San Sebastian - Donostia.

Things to do in Bilbao

Parks Nature Zoos & Aquariums

Side Trips

RiojaNatura, Peninsula of Magdalena, Museo de Altamira, San Juan de Gaztelugatxe, Vizcaya Bridge
Find places to stay Sep 21 — 28:
Highlights from your plan
Wine Tours & Tastings
Guggenheim Museum Bilbao ©
Guggenheim Museum Bilbao
Casco Viejo ©
Casco Viejo

5
nights
San Sebastian - Donostia, Spain

As one of the anchoring cities of the beautiful Basque Country, San Sebastián boasts a trendy, cosmopolitan vibe while still harboring a relaxed, coastal charm.
Take a break from San Sebastian - Donostia with a short trip to Palacio Real de Olite in Olite, about 1h 20 min away. Next up on the itinerary: savor the flavors at Food & Drink, take in the awesome beauty at Monte Igueldo, kick back and relax at La Concha Beach, and find your balance on the water with categoryPhrases.alias.some_of_the_best_stand_up_paddleboarding_in_the_area.

For maps, other places to visit, ratings, and other tourist information, use the San Sebastian - Donostia itinerary planning app.

You can take a bus from Bilbao to San Sebastian - Donostia in 1.5 hours. Alternatively, you can drive; or take a train. In September in San Sebastian - Donostia, expect temperatures between 74°F during the day and 60°F at night. Finish up your sightseeing early on the 3rd (Sat) so you can travel to Madrid.

Things to do in San Sebastian - Donostia

Tours Parks Historic Sites

Side Trip

Palacio Real de Olite
Find places to stay Sep 28 — Oct 3:
Highlights from your plan
Wine Tours & Tastings
Food Tours
La Concha Beach ©
La Concha Beach

3
nights
Madrid, Spain

Madrid ©
See some other sides of Madrid: stroll around Parque del Retiro, examine the collection at Museo Nacional Thyssen-Bornemisza, admire the striking features of Estacion de Atocha, and get the lay of the land with Walking tours.

To find where to stay, photos, and tourist information, read Madrid driving holiday tool.

Getting from San Sebastian - Donostia to Madrid by flight takes about 4 hours. Other options: drive; or do a combination of bus and flight. Finish your sightseeing early on the 6th (Tue) to allow enough time to travel to Lisbon.

Things to do in Madrid

Museums Tours Shopping
Find places to stay Oct 3 — 6:
Highlights from your plan
Museo Nacional Thyssen-Bornemisza ©
Museo Nacional Thyssen-Bornemisza
Parque del Retiro ©
Parque del Retiro
Plaza Mayor ©
Plaza Mayor

5
nights
Lisbon, Portugal

Built on seven hills, Lisbon has experienced a renaissance in recent years, making it the cultural star of Portugal.
Explore Lisbon's surroundings by going to Sintra (Quinta da Regaleira & Park and National Palace of Pena). There's still lots to do: don't miss a visit to Belém Tower, take in the exciting artwork at Museu Calouste Gulbenkian, contemplate in the serene atmosphere at Mosteiro dos Jeronimos, and steep yourself in history at Castelo de S. Jorge.

To find other places to visit, maps, photos, and other tourist information, go to the Lisbon trip itinerary builder site.

You can fly from Madrid to Lisbon in 4.5 hours. Alternatively, you can drive; or take a bus. The time zone difference when traveling from Madrid to Lisbon is minus 1 hour. Expect a daytime high around 76°F in October, and nighttime lows around 58°F. Wrap up your sightseeing on the 11th (Sun) to allow time to travel back home.

Things to do in Lisbon

Tours Historic Sites Museums

Side Trip

Sintra
Find places to stay Oct 6 — 11:
Highlights from your plan
Food Tours
Belém Tower ©
Belém Tower
Lisbon Oceanarium ©
Lisbon Oceanarium

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