Blog Stories Alyssa's Travel Planning Tips

Alyssa’s Travel Planning Tips

By Alyssa Starelli, October 3, 2022

After a busy busy year, and with winter looming, it’s time to start planning winter travel! As a realtor, I’ve been a winter-traveler for nearly 20 years now and despite some bad weather, and maybe a few ferry cancellations, it hasn’t held me back! As a vernacular architecture enthusiast, my search for lodgings is very specific —  I want something specific to the region, preferably historic, and definitely scenic, and I want to try several styles out per trip! With some unusual methods and a decent amount of combing the internet, I’ve been able to find deals on fisherman’s cottages on the pier,  crofter’s shacks with sea views,  estate cottages on the bay, mid-century hotels with skyline views, and a lot of cozy rooms above extra cozy pubs!   These are some of my best tips:

Firstly,  wanna fly someplace but keep it under budget and don’t know where to go? Try the Explore option on! It’ll always quote you the cheapest fare, but then you can go in and adjust to your tastes (flight time, layover, number of stops, or even try for nearby airports which may be more or less expensive).  This is my go to, and I’ve found some stunning deals. Act fast because they disappear! I just lost out on a $650 fare to Yorkshire because I waited 12 hours. Bummer.

I find it ideal to research housing options, museum or castle hours and open days, whether any school holidays are planned for your ideal dates (avoid school holidays at all costs) PRIOR to booking. It gives me an idea of what I’ll pay roughly per night, how much freedom I’ll have to just wing it (or if I should definitely book in advance), if there’s a deal to be had by booking a “home base” for a full week, and if the museums and other tourist sites will be open or not and swamped by over-tired kids and overwhelmed parents.  Case in point – if your whole point is to see a bunch of castles, probably a good idea to make sure they’re open. It’s a real disappointment that so many are closed during winter months, but the ones that are open you usually have almost entirely to yourself (cue Ludlow, Linlithgow, Doune, all of which I toured virtually ALONE!).

Booking accomodation: Sure there’s AirBNB, and there’s, and I use both of those (Genius points are great but sometimes you get the crap room or a raw deal), BUT I also use and click on the pink “bed” symbols to find vacation rentals, hotels, or pubs that might NOT be listed. SUPER TIP: Often vacation rentals won’t be listed at all except maybe on a local small town tourist page. This is how I found an amazing house, on the bay,  in Islay.  It was a mile away and one of the few vacation homes closest to Laphroaig, Ardbeg and Lagavulin distilleries!!  I looked up the local tourist page (, found mention of the Ardtalla Estate and sleuthed out some contact info and emailed the caretaker. I quickly had a handshake deal on three nights in a beautiful home with direct access to the beach. I was to bring cash with me and drop it off to their home on the estate, over my stay.  Now that’s old school TRUST! We came ‘home’ to a beautiful home-made lemon cake and two bags of dried peat to burn (smells incredible!!). It was a stormy weekend, so this was absolutely idyllic way to soak up what life on the Isles is really like.  Many working “estates” in the UK have farm houses that they rent out, so if you see an “ESTATE” on a map, click in and see what they offer!

Example of Pink Bed icons and ESTATES (which might have vacation homes).

Another tip, Cutting the Middle-man OUT:  Find the cottage of your dreams on whatever site you like, there’s hundreds of vacation rentals, or cottages sites. See if the cottage, apartment, hotel, pub inn,  calls itself a specific name and if you can reach them directly via a website they run or especially FACEBOOK. See if they’ll give you a discount for going direct. CAVEAT: You might lose the safety-net of paying through a website that might refund your money by doing this, you might also run the risk of them forgetting your reservation… OR you might get a stellar deal and make friends in the interim.  Story:  I found a delightful fisherman’s cottage in the hamlet of Mousehole on some random cottages site and it had a name, so I went to Facebook and found them directly. I started up a great chat with the family member Ruth, who ran the facebook page and so I booked directly. I felt really safe with her and so wired her some funds  in advance via a web-based payment app (note that I was mentally prepared to find someplace else and eat the cost, if it went awry, that’s traveling!!) When we arrived, her sister had the cottage beautifully set up for us with a Cornish Tea of home-baked scones, clotted cream, and jam. Their darling father dropped a note by inviting us to wander up the hill and hear his well-known, award winning, men’s choir sing at the church and finish up with raucous sea shanties in the pub. The darling neighbor tortoise that lived in the shared yard enjoyed attacking our toes, and all-in-all I can’t think of a booking better experience. If you’re ever heading to Mousehole, Cornwall UK, stay at the TrePen Cottage!

So those are likely my best tips for creating a great vacation. Other random tips include: searching for accomodation with parking if you’re renting a car; booking your first and last night at a hotel near the airport and asking for late check out to deal with jet lag and or late day flights; booking flights so you arrive relatively near the time you’re able to check in —  spending several jetlagged hours wandering the cold,  dark streets of Reykjavik taught me this, the REALLY HARD WAY —  I was so jetlagged and tired that I couldn’t remember the code to my suit case locks for a day (my coat was in there!! Brrr); Always try the local breakfast option at hotels, even(or especially) if it’s fish (mmm Arbroath Smokies) or haggis! It’s a great way to try something new and get a real taste of the locality, plus great protein!; Do not brush your teeth with tap water in Cuba, ask me how I know….(cry); If you’re an Oregonian, salt water is actually salty (we Oregonians wouldn’t know this because we only go in up to our ankles here….), bring water because rum in a coconut does not kill sea-water thirst, I’m serious, ask Robinson Crusoe. haha.  That’s about it for now!

Happy Vacation Planning!


Alyssa Starelli

Broker | OR

A Portland native, Alyssa started her real estate career in the chaotic market of 2005, and quickly realized she reveled in matching particular clients with their perfect home, no matter how unusual. She then began specializing in mid-century properties - both Modern and Modest. More recently, she has included what she calls "Period-Perfect" homes to her repertoire. Her goal in this is to seek out those hard-to-find, unremodeled original homes of all eras. When I started in real estate, I realized there was a market for ranch homes, from Mid-Century Modern to the more modest Daylight Ranch, but few REALTORS® willing to service it. I started highlighting these 'Picks of the Week' on my website, introducing enthusiasts to the full gamut of midcentury houses of Portland. In 2006, I founded the Mid-Century Modern League in order to educate the public about the importance of preserving these gems. Today I continue to focus on Mid-Mod, but have added vintage, mostly unremodeled houses of earlier eras, which I call 'Period-Perfect', because they have interest to clients and are under-serviced too. Frankly, I enjoy seeking out any unusual or original elements a client might be interested in, it's a challenge to rise to." As Founder of the Mid-century Modern League, Alyssa is considered an authority in the local mid-century architecture scene, and is especially proud to include the Editors of Atomic Ranch Magazine in her past-client list. Often quoted in news and radio, she has been able to bring additional interest to her business, listings, and client's homes - many of which have been featured in magazines such as Atomic Ranch, Oregon Home, The Oregonian and also included on several local home tours. With a background in marketing, and an eye for the unique, Alyssa really enjoys buying and selling properties whose interesting features may be overlooked by other realtors, even (or especially) if those features aren't mentioned in the listing. As a hobby, Alyssa has issued herself a challenge to walk every residential street of Portland proper and document the best architecture specimens of each neighborhood. There are about 3500 square miles of Portland, and it's a big feat. By the time she finishes, she will have seen every house in Portland with her own eyes! You can follow her walks on her blog Portland-by-Foot. When off duty, you can find Alyssa at estate sales, honky tonks, her friend's cattle ranch, or seeking out ghost towns, roadtripping to the Oregon high-desert. A music fanatic and semi-retired booker/manager, Alyssa is heavily immersed in the western swing, old-school country, and rockabilly music scene, and you'll often find her out at shows, dancing, maybe even sharing her favorites on the radio. Alyssa Starelli 503-888-1362
Read More
  • T: 503-888-1362
  • F: 503-961-8224

You might also enjoy

Hello, its Julia!

Julia Robertson

Let me re-introduce myself. Hello, I’m Julia! Real Estate Broker in Oregon, Washington and Utah. I’ve...


Aryne + Dulcinea

THE LRR SPRING NEWSLETTER IS HERE! Check out Living Room Realty’s Spring newsletter full of stories,...

Just Listed! Rose City Park Jewel Box!

The Twin Team

3325 NE 73rd Ave Portland, Oregon 97213 Redesigned, reimagined and restored to perfection! This sweet sized...


Aryne + Dulcinea