Planning a trip: timing for tickets, hotels, venues

I work my flight plans first, and the rooms come later. And I often will get my first and last nights arranged on front end.

With a Chromebook and the internet, you can easily make room arrangements on the fly--a day ahead. I never know where I'll be going places I want to stay a day or more and don't want to stick to a set schedule.

I travel to Europe with airline miles so I usually end up booking flights 9-12 months ahead of time. Even then I haven't always been able to get my first choice of hotels. If accommodations are limited on Lindisfarne, I would check cancellation policies and book for the time that I expect to be there even before I have my flights, if it's possible to cancel/change without penalty.

Hope you have a great birthday!

If your dates are flexible, then check both air and hotel prices before you buy. There can be a big difference in prices from one day to the next. For hotel prices, some travel sites like Expedia will show you room prices for a specific hotel over a period of up to about a month. It wouldn't hurt to check two or three hotels in your price range to get a feel for the best priced dates. For air prices, there are also a number of web sites. Google has two, Google flights and Google ITA Matrix. They can also show the best prices over a range of dates. As for when to buy, I'm not aware of any rule. If you have the patience to periodically check prices, sometimes you can get lucky and catch a quick sale. The downside of buying too early is that if your plans change, then you could lose money on the air tickets.

Once I booked flights and then planned my itinerary and found that because of one or two dates during the period, it was a real pain in the neck to fit my plans into my forced time frame. Since then, I've always planned my itinerary first, especially including hotels for critical dates (local festivals, holidays), and then bought my flights. On the other hand, traveling solo, I have different considerations . . . my flights are usually a smaller part of the budget than accommodations, for example.

This is your birthday, the retreat is the most important event for you, so clarify that booking first. Be sure you have availability there, and the b & b, then start looking at plane tickets and work with your dates. But you don't want to buy plane tickets first and afterwards find out your retreat is already booked up with a big group.
I'd start looking at plane tickets now. American Airlines had some very reasonable flights for May a few seeks ago--higher in June though.

I do a lot of back and forth to see what dates might offer cheaper flights and hotels, and the best direction to go if I'm adding a short intra Europe flight to another city (has to be non-stop and less than $150 is my criteria) and once I get the right combo and feel there's plenty of choices for hotels I first purchase the flight(s)--got to get there--then I select hotels. I'd been travelling in mid to late May but this year it was cheaper to go to Amsterdam in the 3rd week of April and I just booked a couple of weeks ago.