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September - 7 Couples 10 days - Itinerary Advice

I'm planning a 60th birthday vacation for my best friend - we will have 6 -8 couples and 10 days.
I know we can't see it all with a group of this size so looking for advice.
We definitely want to spend time in Libson, Evora (Wine region) and some beach time.
After reviewing several forum strings - this is what I'm thinking, please provide your feedback and suggestions:

Day 1: Arrive in Lisbon - recover from jetlag and get our bearings
Day 2: Lisbon RS Walking Tours / Sightseeing
Day 3: Lisbon more sightseeing
Day 4: Lisbon morning, then travel to Sintra (either Uber or Train)
Day 5: Sightsee Sintra, take in sunset at Praia da Adraga (Beach time)
Day 6: Day trip to Cascais from Sintra (Beach time)
Day 7: Take train from Sintra to Evora
Day 8: Evora - wine tasting
Day 9: Travel back to Lisbon for one last day
Day 10: Travel home

I'd love to see Porto/Douro Valley and Algarve - but I feel with a group of this size it would be way to much moving around and too stressful! Please provide all suggestions.

Posted by
6813 posts

I think Sintra works great as a day trip. It's super-easy to take the train there (and back). Uber?!
Not sure it's a great "beach time" location or overnight stop.

Planning for such a large group may be tricky. Have you - and all your companions - been to Europe much/at all before?

Posted by
2545 posts

Organizing an international trip for 6-8 couples requires packing Valium.

Posted by
8913 posts

I think you could do something similar to what the Rick Steves Tours often do for the time in cities. Spend part of the time each day with an organized outing, walking tour,etc and leave the rest of the day as free time for couple to choose how to spend their time themselves. Meet up for a group dinner.

It can challenging to match the interests of just one other person when trip planning. For 14 others, you will be wise to leave big chunks of free time so each can sort it out for themselves.