Vacationing Smarter

So it feels like a vacation

Joshua Hockett
6 min readJun 29, 2020
Me, 3rd from left. my nuclear family June 19, 2020. Lake Canandaigua

From June 13th to June 21st my family and I took our 3rd annual family vacation road trip up to the Finger Lakes region of upstate NY. Each year we hit a new lake and rent a nice big lake front home that all 9 of us can fit in. We dont go all out exactly but within our means yet at the same time splurge a little as it is our one and only full family vacation which myself (no sig other for me yet) my 3 siblings and their sig others, my folks, my brother in law and my one 3 year old nephew all attend each year for what is now three years in the books. This year was Lake Canandaigua which so far is my favorite of the 3 we have been to.

I am not hear to give you the play by play of how me and my family vacationed exactly. What we did, where we went, when we went, what we ate, drank, etc…it worked for us and we enjoyed it very much. What others have done or would do on the same vacation may differ but that is not right or wrong.

Lookout Point, Finger Lakes Trail

What I do want to highlight and share with others going on vacation in the near or distant future is to take heed of some key tips and tactics we used leading up to and during the trip that in my opinion and also echoed by all on the trip, was the best of the three years so far and one of the best vacations any of us have been on period! Below I will list the tip/tactic and give an example of how this was applied to our trip to show its application.

Plan Early. We had a rental deposit down six months before the trips deadline go or no-go call had to me made which was May 10th. This was rough at first given the COVID19 matters greatly limiting travel and what would be open for us when we got there if we went ahead. Luck had it that WI and NY both went to phase 2 reopening the day we arrived and given that we made the 14 hour drive versus fly, we avoided any airport risks as well. The key was planning early. By getting first dibs on the best places we wanted to consider staying at early assured our hold at the lowest rates.

Wine Flight, Hazlitt’s Winery, Naples NY.

Share the Planning. Do not let yourself try and take on all the logistics on planning a vacation. Share the duties and assign others going on the vacation to take on parts the like doing or are good at doing. We had one or two people head up the lead on the following duties: Daily agenda/itinerary, pick wine tastings and dinners, make RSVP’s, recon the area for activities and events taking place, needed rentals, food and material items checklist. This helped more people take interest, engagement and accountability for the trips activities, collective ideas for what we would do or not do and removed any one person from the burden of planning everything alone.

Inspire Moore Winery

Less is More. I cant stress this point enough. Leave time for nothingness! I think this was critical to our enjoyment all week long. Having time every day to just sit, nap, read, play video games, fish, drink beer, soak up sun, etc… To just enjoy the present momment of being on vacation doing nothing but existing in peace! That is after all why we vacation, to not be busy, to do nothing, to have peace! Leave time for it and bask in it! All too often people plan each day full of activities which makes for a nonstop go-go-go schedule that can leave one burned out and exhausted rather than recharged and restored.

Easy 4 mile loop north of Rushville, NY with lookout point.

Find Balance. Extending off of point 3, you need to gauge your groups vacationing style. Pending where you go and what kind of group you have, base your activities off of that. If your like me and my family, we like getting out and about as much as we do more low key relaxing tasks. We did some nature trails, tubing, I did morning runs, we hit an open market, we did several winetrail tastings, and beer tastings. Yet we also did low key movies each night, home cooked scratch made meals each night, funny family game challenges, and plenty of fishing. If you plan for too much physical, high tempo activity and outdoor adventure, be careful your group is not more of a fishing, napping, movies, video games, and campfire type of crowed and vice versa. Keep a little bit of both in the mix and everyone is happy.

Be Fluid. We had just 1–2 major activities planned for each day as well as several family favorite games at the ready to play as well. We stacked wine tastings in 1 day, beer tastings 1 day and 2 nature hikes on different days from all that. This left plenty of room to move things around if need be for bad weather. Lucky for us we got no rain at all! Now one cannot always plan for this and yes, Mother Nature can sack even the best laid out vacation plans, it happens. If weather does look to be an issue, have a plan B at the ready like hitting up museums, indoor family game day, movie marathons etc. You cant let it rain on your parade, its vacation after all. Being fluid allows you buffer room for when things do not go quite to plan.

There are other tips, tricks, tactics and strategies I could list and others I am sure we did not use that we could have used. But I do know these 5 factors worked for us. The long car ride home and post trip chatter we have all had sense, made it clear that these 5 factors kept coming up at random as to why we enjoyed this trip so much. I felt compelled to jot these down myself for any future domestic and foreign travel I do but also to share with all of you who hopefully, can get back to planning and taking those 2020 family vacations so many of us have not yet been able to take…not yet anyway.

Please note that we practiced all required social distancing guidance throughout the entire duration of our trip. Our rental house was isolated on the lake with considerable wooded space between the next homes. Wine tastings were held either outdoors or at set times for only our group. Masks were worn where required. As you plan your own vacations this summer make sure to abide by and be aware of local measures to stay safe and avoid contracting COVID-19.

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Joshua Hockett
Joshua Hockett

Written by Joshua Hockett

Health and fitness professional by training; food, wine, and travel enthusiast by accident.

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