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This sample price: priced within the past 7 days for arrival on 8/17/2025, departure from New York City NYC (All Airports) (NY), US. Choose your own departure city, cabin type and dates.
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This is a suggested independent itinerary that you customize. Please select the best flights, hotels, trains, activities, transportation and number of nights in each destination to fit your needs.
Two dynamic European cities are combined here into one unforgettable vacation visiting Portugal and Spain. Begin in Lisbon (the capital of Portugal; set on the banks of the Tagus river with an ancient medieval fort) then, catch a flight to Madrid (with an undeniable energy; famous museums, fabulous shopping and nightlife).
What Makes Tripmasters Vacation Packages Different? Unique, fully custom approach to vacation planning Choose your preferred flight cabin class Select up to 14 nights in each city during your stay Pick from a wide selection of accommodation types (hotels, apartments, B&Bs, Guesthouses, and more) Add transfers, activities and experiences, and more services to enhance your vacation Live phone and chat support
This 6 night sample itinerary includes:
Flight into Lisbon and out of Madrid
Hotel for 3 nights in Lisbon
Flight from Lisbon to Madrid
Hotel for 3 nights in Madrid
Price history for this itinerary (past 7 days):
From Boston BOS (MA), US for 6 nights
1359.88 * incl.tax
From Chicago CHI (All Airports)(IL), US for 10 nights
1637.77 * incl.tax
From New York City NYC (All Airports) (NY), US for 6 nights
991.79 * incl.tax
From Orlando MCO (FL), US for 6 nights
1387.03 * incl.tax
From San Francisco SFO (CA), US for 6 nights
1140.54 * incl.tax
From Washington WAS (All Airports)(DC), US for 6 nights
Lisbon, a dazzling city stretching along the Tagus river, makes an enchanting European capital. Its nucleus, an ancient fortress, is now circled by neighborhoods drenched with medieval charm. Handcrafts - from embroidery to leatherwork - are peddled right on the streets. At night, yellow electric tramcars continue to wind their way up and down the hills to the sound of traditional Fado songs. Ample opportunities exist for seeing popular celebrations, for shopping, and for enjoying the nightlife along the riverbank.
Visit Alfama, Baixa and Chiado, Se de Lisboa, Sao Roque Church, Mosteiro dos Jeronimos, Torre de Belem, Discoveries Monument, Museu Nacional dos Coches, Parque das Nacos, Elevador de Santa Justa, Tram 28 and so much more!
3 nights in Madrid
In the last few years, Madrid has gained the reputation of being one of Europe's most active and attractive cities for its nightlife and cultural activities. Capital of Spain since 1562, Madrid's museums host, among others, Dalis, Miros and Picasso's Guernica. Madrid is a city of great contrasts: the Old City, the Madrid of the Hapsburgs, the Royal Palace, the Puerta de Alcala, the Retiro Park. At night, the city changes gears with its famous Madrid nightlife. The city's endless energy is hard to resist, and its sociable style invites you to jump right in.
Visit Palacio Real, Plaza Mayor, Prado Museum, Puerta del Sol, Puerta de Alcala, Plaza de Cibeles, Gran Via, Madrid Cathedral, Thyssen-Bornemisza and Reina Sofia Museums and so much more!
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Lisbon Hotels (226 total)
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Madrid Hotels (202 total)
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Tours in Lisbon (1151 total)
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Tours in Madrid (751 total)
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Package Map Picture
Portugal
Thousands of years of history are on full display in vibrant <b>Portugal</b>, fast becoming one of the most popular tourist destinations in western Europe. Each region of Portugal offers something unique to the traveler, like unparalleled beaches and resorts in the Algarve; rolling plains that lead to mountains in the Alentejo; delicious food and drink in the Minho and the Douro River Valley; and of course the country's bustling capital, Lisbon, which boasts the best of everything that Portugal has to offer, from restaurants to historical landmarks.
<b>Spain</b> is one of the most popular countries in the world for tourists, and the experiences you can have while on vacation here can be just as varied as you are. The best way to experience Spanish life today is to visit one of its largest cities, such as Madrid, the country`s capital; Barcelona, its second city; and provincial capitals such as Seville and Valencia. Andalucia, the epicenter of Moorish rule in Spain, is known for its beautiful landmarks such as the UNESCO World Heritage Site, the Alhambra. The north of the country features such varying experiences as Catholic pilgrimages in Galicia, skiing in the Pyrenees, and immersing yourself in the culture of the gorgeous Basque Country. For beach vacations, Spain is tops, from the Costa del Sol to the Balearic islands of Ibiza and Mallorca to the Canary Islands.
The package rates displayed are your total price per person based on Double Occupancy and your Arrival Date and Number of Nights selected.
You can change details after selecting your travel date.
*Sample prices on display include ALL taxes & fuel surcharges... read more
close [x] * Sample prices displayed include international and domestic airline tickets as per itinerary and ALL airline-related taxes and fuel surcharges and are per person, based on double occupancy, and are dynamic in nature. Prices do not include insurance or delivery charges which are optional and customizable by the traveler. The airfare portion of the itinerary price is based on economy class, midweek departure. Prices do not include fees for carry on or checked baggage which can add additional fees per ticket on a roundtrip flight based on carrier charges. It also does not include any entrance fees or visa fees that may be charged at international airports. Some cities may charge local taxes that can only be collected by hotel at destination.
Prices were accurate at the time we posted them. Sample prices were for a specific travel date and specific departure airport, as indicated. Your prices will vary according to departure cities and travel dates. We do not control prices (airlines and hotel reservation systems do). Prices may change dynamically and at times significantly numerous times during any given day.
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Lisbon and Madrid by Air
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Lisbon
Lisbon, a dazzling city stretching along the Tagus river, makes an enchanting European capital. Its nucleus, an ancient fortress, is now circled by neighborhoods drenched with medieval charm. Handcrafts - from embroidery to leatherwork - are peddled right on the streets. At night, yellow electric tramcars continue to wind their way up and down the hills to the sound of traditional Fado songs. Ample opportunities exist for seeing popular celebrations, for shopping, and for enjoying the nightlife along the riverbank.
Visit Alfama, Baixa and Chiado, Se de Lisboa, Sao Roque Church, Mosteiro dos Jeronimos, Torre de Belem, Discoveries Monument, Museu Nacional dos Coches, Parque das Nacos, Elevador de Santa Justa, Tram 28 and so much more!
In the last few years, Madrid has gained the reputation of being one of Europe's most active and attractive cities for its nightlife and cultural activities. Capital of Spain since 1562, Madrid's museums host, among others, Dalis, Miros and Picasso's Guernica. Madrid is a city of great contrasts: the Old City, the Madrid of the Hapsburgs, the Royal Palace, the Puerta de Alcala, the Retiro Park. At night, the city changes gears with its famous Madrid nightlife. The city's endless energy is hard to resist, and its sociable style invites you to jump right in.
Visit Palacio Real, Plaza Mayor, Prado Museum, Puerta del Sol, Puerta de Alcala, Plaza de Cibeles, Gran Via, Madrid Cathedral, Thyssen-Bornemisza and Reina Sofia Museums and so much more!