Itinerary Help - Should we book ahead or "wing-it"?

I'm in the final stages of planning a 24-day trip to Portugal that starts next week. I planned my route in advance and booked all my rooms (no aribnb's) in Jan-Feb. That's what I'm most comfortable with and I'm picky about where I stay. Even so, some of the most recommended hotels were already fully booked. I'm renting a car for 10 days to visit the eastern part of the country, which is more sparsely populated. I'm not going to the south at all.

You need to get a guide book or 2 and figure out what most interest you. I'm using new Lonely Planet, Rick Steves, DK Eyewitness country guide books and a 5-year old Michelin Green guide too. Lonely Planet is the most comprehensive, listing sights and activities for just about everywhere, but only very brief descriptions are doesn't rate them. They have recs for eating and sleeping, usually with a range of prices from budget to splurge. There are also suggested routes for multi-day visits to each area of the country. DK is helpful in getting an idea of what might fit your interests and very colorful. They include "eat & sleep" recs, but they are brief and feel like "tokens" to say their guides are "inclusive." Michelin does a good job of describing the sights. It also ranks both towns and individual sights by star (0-3). Michelin's Green books are only for sights. They have a Red series for food, drinks and sleeps which is comprehensive (no idea if they include AirBnb). RS is an excellent step-by-step guide for the first-time tourist, like how to get from the airport to the town center, how to use local transportation, and self-guided tours for top sights and city walks and includes multi-day itineraries. The major drawback is that it omits huge swaths of the country and some towns and sights even in the parts that it covers. I have the RS and LP as ebooks. Michelin in paper is the one I would travel with - light-weight and easy to reference on the go.

Where you fly into depends on where you want to go. If you want to visit the Algarve, you'd fly into Faro. Otherwise either Porto or Lisbon. It's about a 3-hour train trip between them, so you could do a loop from Lisbon or a zig-zag one-way route.

You are more likely to get useful advice if you provide descriptions of your interests, budget, and goals for your trip. I could spend a month in Lisbon alone and not get bored, but I am a huge Portugal fan.
I suggest that you fly from London to Porto. Start your trip in northern Portugal and work your way south, with a plan to fly out of Lisbon at the end of your visit. Rick's Portugal guide is good for Porto and Lisbon, the LP guide is better for other parts of Portugal. You certainly can "wing it" that time of year, I did so last year at that time, but you will need to be flexible regarding lodging. A rental car is not necessary in the north, but it is nice to have for exploring rural areas. Cities and towns throughout Portugal have good public transportation links, and parking in the cities is difficult and expensive.

3) Perhaps starting north (Porto airport) and do some grape harvest at Douro. The season for grape harvest is from beg-mid September till more or less 10th October. See this link:

http://en.roteirododouro.com/activities/grape-harvest

1) If you want to attend the grape hasvest, definitely book a night or two. Otherwise, even with the increase of tourism, I think you would be able to adjust things when you arrive. But I suggest you have a list of places to stay, so you can book 2 or 3 nights before you arrive to some place. Also suggest booking the nights before your flight whan you have to leave.

2)Heading to SE Asia - Yes, Lisbon is the best option.

I second what captvic4 said.

So long as you are willing to be flexible with your accommodations then you can wing it to a large degree.

As someone who has been traveling for the past 5 months (and also from Seattle), I can tell you that sometimes you strike gold and sometimes you don't when you wing it.

A positive attitude and knowing that sometimes "it's just for one night" can get you through a lot.

We are heading to Portugal from Israel next week. Flexibility is allowing us to stop for an extended layover in Budapest for 3 days which is cheaper than a direct flight from Tel Aviv to Porto. That doesn't always happen but it's proof that winging it can work to your advantage sometimes.

Good luck and please give teh PNW my best.

Thanks everyone! We ended up booking into Lisbon, then booking to Bangkok 29 nights later....very exciting! Love all your comments and advice - thanks!

Tracy