Spain and Portugal itinerary Recommendations- 2 weeks

You face a few challenges.

There's so much to see and so many worthwhile places (and your plan has you skipping right past some of Europe's best places), you will be tempted to try and squeeze in too many. 2 weeks is not enough to see the places on your list. Any chance you can extend your trip a bit longer? Every additional day you can manage to extended it would help a lot.

Connections between some places are not efficient. Most notably, getting between Portugal and Spain is surprisingly difficult - flying often makes the most sense. Barcelona, while super-popular, is an outlier - personally I think it's better to think of Barcelona as in a different country (Catalonia) than Spain to help keep it in perspective. IME Barcelona is about as easy to include on a trip to France or Italy as it is on a trip to Spain - something to consider. Fortunately, the high speed train does work well but you'll lose almost a whole day with that connection.

It will be hot in June. Hopefully you can deal with heat.

Other recs: Do not miss the Alhambra (book tickets well in advance). There's a lot more than just "Seville and Madrid", since you're going to be right there, it would be a tragedy to miss Granada, Cordoba, the White Hill Towns. Also Toledo is a gem (just don't do it as a "day trip" which ruins the experience). Too many places to see...

Air B n Bs are too numerous to count. Don't worry about that, you have bigger fish to fry.

Choose fewer locations. Barcelona is the outlier and it is in Northern Spain.
Add Cordoba to Seville as a day trip. Add Toledo and and/or Segovia to Madrid as day trips.

Great graduation gift.
Hmmm.......
Let's focus upon maximizing the potential of creating wonderful travel memories instead of memories about travel.
Land in Lisbon, stay and explore for three days. TRANSFER 1
Travel to Seville, stay and explore for three days. AVE train from Seville to Madrid. TRANSFER 2
Travel to Madrid, stay and explore for three days. AVE train from Madrid to Barcelona. TRANSFER 3
Travel to Barcelona, stay and explore for remainder of trip.

I would fly from Lisbon to Seville to avoid five hours of car travel with a family of four and associated luggage plus drop off fees.
Seville offers ample menu of experiences. In June strive to find a place with a dipping pool and AC. If offered an inside court view room, take it for the benefit of less noise. With family of four we have found short term apartment rental provides additional space, a kitchen and sometimes a clothes a washer. We generally prepare breakfast and save dollars on that meal.
Madrid is one of Europe's largest cities with a relatively compact tourist zone. We are NOT big fans of museums so have trimmed Madrid back to a two day stay (for our travels).
We prefer to take evening trains as the long day of sun shine still provides opportunity for a view of the countryside while not cutting into prime time of site seeing. Second class is ample for train service.
Barcelona is the big menu opportunity BE SURE and take the family to the beach to relax, unwind and be able to say you have dipped your toes into the Med (our teenagers loved this beach time and it helped turn a "trip" into a "vacation")!
TRANSFERS add to travel stress and can suck life out of a trip. Yep, we all have to schelp from place to place, but just eliminating one TRANSFER can help greatly ease a trip dynamics. Please pull out a map and compare the geographic distance you are proposing to cover between Lisbon, Port, Seville, Madrid and Barcelona to a similar distance within the USA. You will get the picture.

Every day you switch hotels becomes an incomplete day in terms of sightseeing. Big moves, and any requiring a flight, will suck up way over half a day. Even short moves by train are costly by the time you deal with hotel check in/out, time spent traveling to and from train stations, and getting acclimated to a new city. And your arrival day, following an overnight flight, is likely to be useless for anything more than wandering around, trying to stay awake.

Therefore, five cities within two weeks is really five cities within nine days plus some scattered hours here and there.

How many nights do you anticipate spending in Europe? A two-week trip is better spent in one of the two countries, rather than both. In two weeks you can hit a few of the great stops in Spain, or you can do a better job of seeing the high spots of Portugal.

If Andalucía remains on the itinerary, I urge you to make this trip as early in June as possible. That area can be miserably hot. Seville's average high in June is 95.5F; the record for June is over 113F. Those statistics are for the period 1981-2010, and I bet the weather is even hotter now.

Along with acraven's good advice, Madrid is often as hot as Andalucia.

My wife and I just did your trip minus Barcelona in April. We flew into Porto, then flew to Madrid, took the high speed train to Seville, and then flew to Lisbon. 4 nights in each city except 3 in Seville. There are no good options for public transportation between Portugal and Spain. The fastest, easiest, and cheapest way is flying. If we could have changed anything we would have done 3 nights in Porto and 4 or more nights in Seville. Madrid has the most energy I've ever felt from a city. It's on all night long there. Your young adults might love it there. Adding in Barcelona sounds like too much travel. That's two additional travel days. 15 nights was not enough for us to see enough in 4 cities.

Thanks to all for your suggestions! Keep them coming! You have given me a lot to think about.. We may just concentrate on visiting Spain this time. Graduation is not until mid June, so most likely we will be traveling right around that timeframe and I know it will be hot. We have done tours in the past but too much time is spent at Museums and Churches, which my kids are not very fond of after seeing one. I will check out Rick Steve's travel videos for Spain and his books this weekend to try and narrow it down. :) Really looking forward to this family trip :)
Thanks again!

I think your children would enjoy the Aqueduct and Alcazar in Seville as a day trip from Madrid and the Royal Palace in Madrid.

The aqueduct to which Cala refers is in Segovia. There are alcazars in both Segovia and Seville, so I won't presume to say which of those is being especially recommended.

Limiting the trip to Spain is a good idea, because it will reduce the amount of time spent in transit. Spain is very large and full of great destinations, so you'll still have to be really selective.

Five cities in two countries in two weeks is just spreading yourself too thin. Stick to Spain this time with the classic fortnight.

Day
1. ARRIVE Madrid (4N)
2. Madrid
3. Day to Toledo
4. Day to Segovia, or more Madrid
5. Train to Seville (4N)
6. Seville
7. Day to Cordoba for the Mezquita
8. Seville
9. Train to Granada (2N)
10. Visit the Alhambra
11. Fly to Barcelona (4N)
12. Barcelona
13. Barcelona
14. Barcelona
15. DEPART Barcelona

If you only stick to Spain.......
Set your airfare search engines to fly to Seville. Doing so will mean flying to Madrid and changing planes, but offers the following advantages:
1) we have found the added cost to be minimal and in the same range of taking a train
2) you are already at the airport and simply making a connecting flight
3) the same day of a long travel day you arrive at a destination to which you do not have to back track
So fly to Seville and spend "x" days
On the morning of your last day in Seville rise early and take the AVE TRAIN to Cordoba and hop off for a day visit. Do your research on where to store your luggage. At the end of the day hop back on an AVE and travel onto Madrid arriving in the evening.
In Madrid stay for "x" days and plan a daytrip
From Madrid take the AVE to Barcelona where you will complete your journey.
So you are now making only TWO transfers: one from Seville to Madrid and a second from Madrid to Barcelona. You have essentially added another day to enjoy your journey.
If it were me I would do the following:
Three days in Seville
One day in Cordoba
two days in Madrid
one day trip while in Madrid
Remaining time in Barcelona with two day trips and at least 1/2 a day at the beach.
What you will obtain is experiencing three different cultures in Spain.
Old Andalusia via Seville/Cordoba
Vibrant Madrid mixing old and new
Barcelona which is a culture, even a nation, of it's own offering a mixture of old, new, hip and slow along with a beach and mountains.
The best advise we can provide..........
From day one force your USA tummy clock to adjust to local eating habits. Doing so creates a great opportunity to experience more of the local culture, forces you to learn the value of participating in late evening activities and adds wonderful memories to your journey.
It will be hot so start hydrating the day prior to your journey and stay hydrated during trip. We take siestas as co peting among throngs of hot sweaty tourists during the heat of the day is no fun. Take a break, avoid the heat and stay out later when the sun sets.
Keep an eye out for sidewalk cafes where the owner has watered the pavers in front of his place as doing so quickly releases the heat from the stones and creates a cooler seating environment. Also, seek exterior tables adjacent to the restaurant wall where a windon well maybe relasing cooler air from the cellar.

Well I'm not a fan of hot weather, so I'd suggest skipping Madrid and Andalucia, opting instead for the Costa Brava - Barcelona, Valencia, and 2-3 days in the Pyrenees. Barcelona's sights easily fill a week, especially with the day trip choices.