An English Christmas Trip: First Trip Planning Post – How the Trip Came About

Updown Cottage Last Christmas

Updown Cottage Last Christmas

On Christmas Day last year, Mrs. Anglotopia and I were rather despondent. While Christmas is our favorite time of year, it just wasn’t that enjoyable for us. Maybe it was the winter blues, maybe it was the bill for the holiday season but we just didn’t feel like it was a good holiday season. We were also going through our first existential crisis with Anglotopia when we had to pursue legal action against someone who tried to put us out of business (read about that here). On top of this, after watching all the traditional Christmas specials on British TV, we felt rather homesick for the place we would have rather been.

Then it hit us like a lightning bolt.

Why not spend next Christmas in England?

I immediately got in touch with the owners of our favorite Cottage, Updown Cottage in Dorset, to see if it was open for Christmas. It hadn’t been in the past but we wanted to see.

A few hours later we learned that it was indeed free, for the entire holiday season, for 2 1/2 weeks!

Well, decision made then.

We booked Updown Cottage right away and began planning for Christmas 2013 in England. The owners even promised to decorate the cottage for us for Christmas – tree and all!

That was over 6 months ago. A lot has happened since then! We had the trip in the back of our heads, but we had more pressing matters such as the imminent arrival of our second child, Miss Anglotopia and our ongoing legal matter which was thankfully resolved in our favor in March. If it hadn’t worked in our favor, we would have had to cancel the trip as we would have had no way to pay for it. And thankfully after everything was resolved, Anglotopia readers donated enough to cover 2/3 of our legal bills so we were able to keep our plans.

Miss Anglotopia decided to make her appearance a couple weeks early and joined our little family on June 6th. Once the baby haze wore off, it was time to get planning. For reasons that should be self-explanatory, we didn’t want to book airfares and any other accommodation until we were completely sure that Miss Anglotopia had safely arrived. Once she had, we could finally book our tickets!

Deciding on 33 Days

Every time we leave Britain, we wish we could have stayed longer. Various things have always prevented us from long visits. Before it used to be job commitments and family commitments. But now that Anglotopia is our full time job and Britain is basically our livelihood, there was no reason to prevent us from spending a lot of time in England other than cost (pro-tip: American can travel up to six months in Britain without a visa for tourism).

With careful saving, we were able to decide that, really we could spend as much time as we wanted in the UK on our next trip and spend some time there beyond our booking at Updown for the holidays.

We knew we’d have Updown Cottage over the holidays for 2 1/2 weeks, but if we were going to be over there, how about London for a week too? Then we thought that it would be nice to explore somewhere else that we haven’t been for more material for the site. So, we added another week to the end of the trip.

And due to airfare costs being cheaper on certain days around Christmas, we decided on the dates of December 11th to January 13th. A whopping 33 days in Britain!

It would be our longest trip yet.

Now our only worry is leaving our poor dog with relatives for 33 days! He did fine last year when we left him for 17 days so we’re confident he’ll roll with it.

Booking the Plane Ticket

We finally booked our plane tickets a couple weeks ago. We got a pretty good deal. Well sort of. We’re opting to fly with our preferred airline, British Airways. They have two daily flights out of Chicago and we love the experience of stepping into Britain once you board the plane. We’ve always had good service and I have nothing but good things to say.

I felt a little pressure in getting the tickets booked as I’d been tracking the dates for several months and in June there was a small jump in airfares, so I knew I would have to book soon before they went up again. There’s four of us now, so we need to save as much as possible on our tickets.

The biggest increase in cost this time around will be our two year old son, since he’s two and no longer a baby, he has to have his own seat, which costs just a little less than an adult seat. Ouch.

Miss Anglotopia will only be 6 months old in December, so she only needs a cheap lap ticket. Thankfully.

I came across a discount that everyone can use. We’ve posted about it before. British Airways partnered with AARP to offer a special deal to their members. The trick is that you don’t actually need to be a member to use the discount! They don’t even check.

Another problem we had was that our plane ticket costs were going to be well over $3,000 and all of our bank accounts and credit cards topped out at that limit for spending in a day. How would we pay for our tickets? Well, BA now takes Paypal as a payment option and there’s no limit there. So, we loaded all the money for our plane tickets into Paypal and then paid with Paypal, very smooth and painless.

When we finally did book, we ended up paying $3,127 for the four of us (this is with the AARP discount). Then, the worst thing happened. Literally the next day, airfares dropped a dropped a couple hundred dollars! Oh well, it was too late to get the difference refunded, I’m still happy with the deal we got. A couple hundred dollars wasn’t going to make or break the trip.

So, we’re booked on BA296 out of Chicago on a Boeing 747 in Coach. We always fly out BA296 because it leaves around 8pm so that by the time everyone is settled, we can get some sleep on the overnight flight (hopefully) and arrive in Britain the next morning. Because we’re traveling with a baby, we were able to reserve the bulkhead seats. Since there is four of us, we have the whole row to ourselves along with a bassinet for the baby so we don’t have to worry about making anyone else miserable with our kids on the flight.

Planning for 33 Days

How do you spend more time in England than you’ve ever had before? How do you plan the trip of your dreams? That’s the question I’ll be trying to answer over the next couple months. I’ve pulled out all my guidebooks, maps and iPhone apps to dig into research and find out how to make the most of the trip.

In the coming months, we’ll give you some insight into our trip planning process and also give some information on where we’ll be staying and what we plan to do.

For those interested, here is a rough breakdown of our itinerary:

  • Leaving Chicago December 11th, Arrive in England December 12th.
  • December 12th-December 20th Will be London
  • December 20th-January 6th will be in Shaftesbury, Dorset
  • January 6th-Jannuary 13th will be in the Cotswolds

For those wondering why we’ve opted for such a long trip during the coldest time of year in Britain, we’ll just simply say that we don’t travel to Britain for the weather. And actually, it doesn’t get extremely cold there like it does here in the American Midwest so it should be rather pleasant, albeit a bit wet.

Stay tuned for more updates!

Read More at Anglotopia


  1. avatarPhaedra says

    Great advice and a great time to go! Have a great time on your trip, and I look forward to hearing more of your traveling advice! (I’ve been to England four times now, and will be looking to new adventures there soon!)

  2. avatarKristin says

    Enjoy! I was in England for Christmas two years ago and we thought the weather was fine, albeit one FREEZING day at Hampton Court Palace. It was mostly in the high 40s and dry which is better than home! Definitely check out the carolers in Trafalgar Square at night :) The crowds do get really heavy while Christmas shopping on Regent Street and Oxford Street, especially around Hamleys so if you have a baby carrier that might be a better option than a stroller.

  3. avatar says

    You know far more about this than I, but a lot of local moms and dads rely on this website that you should put on your radar if you don’t know about it already. Perfect for researching indoor, winter activities for young kids around England. It will have lots of suggestions for the ever-popular “soft play” centres around the country, which are a staple for young families here. :)

  4. avatarCynthia says

    For any Anglophile, The British History Podcast, by Jamie, is fascinating. He has an interesting background, and has enriched my trips to Britain a great deal because I know more about what I am looking at. I download him to my iPod and listen while I take my walks.

  5. avatarNora says

    I am envious! Wish I could go. I went to England once for 1 week, and that was not long enough.

  6. avatarR Stickler says

    It seems from the occasional post I get to read of your UK travels, you return to the same areas on your trips. While we’ve been guilty of that ourselves, I think it’s time you ventured further afield, as they say. England may not be a large country by US standards, but there is a lot to see and do beyond London, Dorset and the Cotswolds. Get out there and enjoy some new places!! =)

    • avatar says

      We originally planned to go and explore the North but we decided it was best to wait until we can go in the summer months, it would just be too unpleasant in the winter with two kids under two. We’ve only been to the Cotswolds once, but the location we’ve chosen to stay is on the edge and basically in the heart of England where there is a ton of stuff to do we’ve never done between within a 2-3 hour drive. So, there will be lots of new stuff for us to explore. We’ll be talking about this more in future posts about the trip planning.

      • avatarJanet says

        I’m sure you will enjoy your trip next Winter. Remember though that December and January are the darkest months of the year (can be pretty dark by 4pm in December) and the countryside just isn’t as inviting as it is in the Spring and Summer months. It still has its charms though. Cold hard frosts and mists in the hedgerows and all that. At least you’ll get a different perspective coming over in the Winter.

  7. avatar says

    BRAVO!! I love your planning, and the taking of bolder steps to see yourselves in your dreamland. I am sure England will be magical at the holidays, but I am also sure the kids will help keep it real. Thanks for the updates.

  8. avatarbJ says

    The run up to Christmas in London is exciting, ice skating at Somerset House (great backdrop), Hyde Park’s magical Winter Wonderland with Christmas village, kids rides, food and a st. nick grotto, Christmas lights on Oxford/Regent Street, Panto shows, various Christmas tree lightings, Christmas markets, mince pies with tea….oh

  9. avatarKaryn says

    Your trip sounds great. I am planning a trip to London in 2014 with about 6 friends and was wondering if you knew of any web sites that rent vacation homes as there will be so many of us we thought this would be nicer then a hotel. Thanks for any help.

    • avatar says

      Yes! This is something we were going to talk about in our next post but we booked our London flat with London Connection. Booked with them before and we have nothing but nice things to say. You’ll definitely save money booking a flat versus a hotel. Here’s their website:

  10. avatarDenise says

    I remember when we started going over to the UK……20 years ago. We could go for 3 weeks for around $1800 & we would travel first class by train to several cities.. Every time we book a trip now, the time spent there gets shorter & shorter because of the expense..
    We are trying to pull a trip together for mid October. (we tried swapping a time share for the first time but no luck on that yet) Still looking at the fares which are now running at $1000.. I think our first trip it was $395. It is very depressing. So Jonathan, your tips are very welcome in my book. Thank you. I think Christmas in the UK is a great idea. I will enjoy hearing about your plans.

  11. avatar says

    I’m a creature of habit when it comes to our visits to England, too. I love the Cotswolds and have been several time but I vowed that when we went to England in Sept 2014, I was not going to be lured back. So, instead, one of our destinations is Devon for a week (in particular Dartmoor ) which we’ve only been to twice :) It is a stunning area and we love letterboxing so it’s a perfect fit. AND Dartmoor is the perfect foul weather destination. The moors are surreal and the mistier and foggier the day, the better. We’re tacking on trips to Cornwall (where we’ve never been) when the weather is sunny, since it’s so “close” to Dartmoor.

    Most of our stay will revolve around Kent as that is where my husband’s family lives. With our trip next September we’re doing something we’ve never done and that’s to let self-catering accommodations when we visit the family. It was swell to bunk at their lovely home in the village of Matfield (for FREE) but they’ve since moved to smaller quarters so we’re getting our own “home” for the two weeks we’ll be in that area. We’re hoping to do several day trips from Matfield – up to Cambridge – maybe over to Suffolk and who knows where else. The advantages of being American when looking for day trips is that we’re not put off by a two- or three-hour drive out (my husband the Englishman has been in America for close to ten-years so he’s gotten used to driving a fair distance to visit a place and then driving back home).

    I’m mostly keen on villages and the beautiful estates and gardens (don’t leave home with out an NT membership) and we love the B-roads.

    I’m delighted that you go into such detail about your planning and we’re you’re staying and what you hope to do. Thanks for taking the time. There is no such thing as too much detail when it comes to travel plans. And yes! I would sit for five hours watching your family holiday videos and photos!

    Have a wonderful trip and a very Merry Christmas in England! (You can read about our travel plans here: No worries if you don’t want to include the link to my blog post – just thought you and Mrs Anglotopia would enjoy another Anglophile’s vacation dreams).