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First Trip to Spain: 11 Days

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Hello! I am looking for some expert feedback to help with our first trip to Spain. I am very excited but looking for some help and feedback with my itinerary. My boyfriend and I want to take full advantage of beach and sightseeing. But also want this to be a relaxing and exciting adventure. We don't like jumping around and feeling pressured at all times. With that said, that's why I'm looking for help with our 11 day trip to Spain.

First- I have not booked the flights yet. But will be doing so in the next week and a half. I am currently looking into flying from US to Madrid and flying out of Barcelona. We'd prefer for Barcelona to be the last city and fly out of, but I can open to changing this.

Madrid-San Sebastian and San Sebastian-Barcelona​. It feels pretty scrunched already. I really hate losing about 11 hours traveling by train from city to city. I considered flights. But I feel using a train would be a little more simple. But if people have had experiences using flights and found that this is best for travel between I would reconsider. We can also take the AVE which is a 3 hour fast train between Barcelona to Madrid. That would require changing the layout of the trip. We are really interested in getting some beach time and enjoying the Spanish during our visit.

I would love to see San Sebastian, but feel it's quite out of the way between the two cities. Plus we are going in September during the boat races and right before the film festival.

I'm sure we can fit in at least 1-2 small day trip in each city as it stands. Any recommendations on quick cities to go see would be great.

9-Sep USA TO MAD Tuesday Day
(Depart from Spain airport around 9AM)

MAD: 3 Full Days, 3 full nights
9-Sep MAD Tuesday Night
10-Sep MAD Wednesday Day
10-Sep MAD Wednesday Night
11-Sep MAD Thursday Day
11-Sep MAD Thursday Night

Train MAD to SS Friday until 1PM SS: 1 Half Day

San S: 3 Days, 4 nights
12-Sep SS Friday Day
12-Sep SS Friday Night
13-Sep SS Saturday Day
13-Sep SS Saturday Night
14-Sep SS Sunday Day
14-Sep SS Sunday Night
15-Sep SS Monday Day
15-Sep SS Monday Night

Train to Barcelona Tuesday until 1PM BC: 1 Half Day

BARCELONA: 3 Days, 4 Nights
16-Sep BC Tuesday Night

17-Sep BC Wednesday Day
17-Sep BC Wednesday Night
18-Sep BC Thursday Day
18-Sep BC Thursday Night
19-Sep BC Friday Day
19-Sep BC Friday Night
20-Sep BC Saturday Morning

Depart BC to US

Thank you to anyone to provides any help!!

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