Surprise Vacation 2023 (SOLVED)

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It’s my most favorite time of the year!! SURPRISE VACATION is here and it’s time to put on your detective hats!

Surprise Vacation with www.whatsgabycooking.com (@whatsgabycookin)

For those of you who are new here – let’s start at the beginning. Surprise vacation has been a longstanding Dalkin family tradition since we were kids. It started when I was 9, my sister was 6, and my parents would throw us birthday parties. Now that I’ve thrown a party or two, I know how much work they can be, PLUS add in some screaming and crying children, and it’s an absolutely not for me // and clearly my parents. So my parents decided to do away with the birthday parties and instead they’d plan a surprise vacation for us each year.

So what’s a surprise vacation you ask?

IT’S A SURPRISE. And it’s basically the highlight of my life. I even like it more than my birthday/birth month which is really saying a lot. I’m obsessed. They plan a vacation for us and we get somewhere in the realm of 7-10 clues each year and we have to figure out where we are going. Some years we’ve figured it out, others we are totally surprised.

My sister sometimes figures it out, my husband has been known to do the same… but I’m always, without fail, 100% wrong. I think it’s because I just live for a surprise and love the whole build up.

ANYWAYS… since we were kids, we’ve been getting everyone involved. My tennis coach, friends of friends, parents, professors, you guys!! I mean, it’s basically a puzzle for anyone I know. So I’ll be sharing the clues here as they roll in (roughly one a week) and I’ll just continue to update this post so you don’t have to search high and low for the latest clues. Ready… Clue’s are officially rolling in:

LET’S SOLVE IT THIS YEAR!! Any guesses… comment below!

Clue #1: Lucky #13 – that is all you need.

Clue #2: Evanston, Winnetka, WIlmette, Highland Park and Glencoe – all together now.

Clue #3: LA at birth has the most of these on wood; though there are some nice ones where we are going.

Clue #4: JC Superstar – a US icon for a crazy life; kind of like Smuckers.

Clue #5: Yogi’s picnic buddy rhyming, with than an old midwest gangsters group, with their recent song re-mixed

Clue #6: Termed like a young toddler dump; which then needs something to unlock the alphabet, to then begin…

Clue #7: Something that combines the beauty of Maine and eastern Washington; southern lands in the 1800’s; first rhyming with a past crime.

AND NOW LETS GET INTO THE ANSWERS TO ALL THESE RIDDLES:

Let’s go:

  1. Lucky #13, that’s all you need. Solution: Well, in their alphabet there are only 13 characters….. (Hawaiian characters)
  2. Evanston, Winnetka, WIlmette, Highland Park and Glencoe – all together now Solution: This is referred to as the “North Shore” – which a number of you guessed correctly. Turns out there are 18 areas of the world labeled the North Shore – 13 in the USA (One is on Oahu)
  3. LA at birth has the most of these on wood; though there are some nice ones where we are going. Solution: Great Clue – very proud of this one! It was for the sports buffs, but NOBODY got it. So, LA at birth stands for Lew Alcindor – aka Kareem Abdul Jabbar, who has the most points scored in basketball (which the court in the past has been referred to as on the “wood”). On the island of Oahu there are many Points worth visiting: Laie Point, Kahuku Point, Ka’ena Point….
  4. JC Superstar – a US icon for a crazy life; kind of like Smuckers. Solution: Not so easy here :), JC stands for James Campbell – with Campbell being a US (National) Icon for soup like Smuckers is to jam, crazy life – wild life. Am I sad you are mad at this one – not at bit!! James Campbell National Wildlife Refuge – also on Oahu
  5. Yogi’s picnic buddy rhyming, with than an old midwest gangsters group, with their recent song re-mixed. Solution: Simple – Yogi’s buddy is BooBoo – a rhyme is Lulu. An old midwestern gangster was Al Capone, and the band named “Capone” has a song from 2020 “Oh No”, if you re-mix the letters it is HoNo So together you have Hono and Lulu – Honolulu
  6. Termed like a young toddler dump; which then needs something to unlock the alphabet, to then begin… Solution: Easiest clue of the bunch! Young toddler dump – PooPoo, something to unlock is a Key, and the beginning of the alphabet is an A. Put it all together: Poopookeya – phonetically is Pupukea (a town on Oahu right near where we are staying)
  7. Something that combines the beauty of Maine and eastern Washington; southern lands in the 1800’s; first rhyming with a past crime. Solution: So I had to make the geography a bit off, but the concept is the same: Beauty of Maine – the state tree is the Pine tree, and Eastern Washington (anything east of Seattle is Eastern Washington to me :), is the primary Apple grower for the US. Southern lands in the 1800’s were – Plantations, and the first means “beginning with” a rhyme for a past crime: Stole – which rhymes with Dole. Dole Pineapple Plantation – which of course is on the island of Oahu!!!

So there you have it!!! Once again I hope I have tortured you relentlessly for the past few weeks, and although a number of you so correctly guessed Hawaii (and Oahu), I applaud you; but feel good that nobody got ALL the clues right. My skill at deception continues for now!!!!

May you all have a wonderful 2023!!!

Papa B, Doctor D, The Clue Master….or just Bruce!!!

Here are our surprise trips from the past… and chances are we can cross those off the list since I don’t think we’d do a repeat. And if you want to read some clues from past trips – click the links below!

  • 2020 + 2021 – skipped because of Covid + ya know, birthing a new baby
  • 2019 – Patagonia
  • 2017 – South Africa + Idaho for a ski week!
  • 2016 – Arizona for a golf/spa week!
  • 2015 – Costa Rica
  • 2014 – Orcas Island + Vancouver + Whistler
  • 2013 – Nat Geo Cruise through Alaska
  • 2012 – Road Trip through France
  • 2011 – Bahamas
  • 2010 – Berlin, Prague, Budapest and Vienna
  • 2009 – Banff, Canada
  • 2008 – none of us can remember where we went this year! whoops 🙂
  • 2007 – Italy
  • 2006 – Turkey
  • 2005 – Greece
  • 2004 – England + Scotland
  • 2003 – Cancun, Mexico
  • 2002 – Hawaii (Big Island)
  • 2001 – Napa / Sonoma
  • 2000 – Los Angeles
  • 1999 – New York
  • 1998 – Washington DC
  • 1997 – Las Vegas
  • 1996 – Texas
  • 1995 – Disney World

106 Comments

  1. Maybe Australia?

    13 treasures of the island of Britain (all in Wales—>New South Wales)

    North Shore is an area of Sydney

  2. Block Island, Rhode Island!!

    -Rhode Island is the 13th state.
    -Towns in the North Shore = Block Island also called New Shoreham
    -I think something with Louisiana and wooden boats? I’ll come back to this one!

  3. Galápagos Islands
    1)Lucky 13 – 13 islands
    2) all the suburbs are located in an area known as North Shore. Galapagos has a north shore
    3)LA at its birth has the most of these on wood. If LA is Louisiana rather than Los Angeles, there are lots of mangroves on the swamp. Galapagos also has mangroves. (if LA, lots of -wood suburbs)

  4. North Shore New Zealand? Works with clue 2 and the time of year at least! Trying to come up with something for 13 — rugby related??

  5. Impressive start!! I have learned so much !
    More clues posting soon, these will help you get a better handle on the first three.

    Some super solutions so far – if you can get them all , a prize awaits!!

    ps – wont say if any are right , might be……‍♂️

    Keep ‘em coming!!
    The Clue Master aka Papa B

  6. North Shore of Oahu

    1) route 13 ?
    2) all suburbs on the north shore, Illinois
    3) surfers or surf boards? Or maybe palm trees?

  7. Hawaii?! Honolulu
    #1 Route 13 on the island
    #2 Those suburbs make up the North Shore which is an area on the island
    #3 People send fruit baskets to new parents (birth) which have pineapples on sticks aka Dole Plantation

  8. This is what I think:
    I believe you are going to Egypt. Or
    It can also be Lake Tahoe, Redwood forest, and Yellowstone National Park.

  9. Iceland
    North shores, Fossil Beach

    1. 13 santas of iceland
    2. All those cities are in North shore (North shore is great spot in Iceland to see Norther lights)
    3. Louisiana has town crests painted on drift wood which is a fossil. (Fossil Beach)
    4. Johnny Cash jamming ? Only thing is the Icelandic Johnny Cash or the fact Bjork does a great Johnny cash impression and she is From Iceland
    5. I can’t figure out how the remix of Gangsta Boo’s song though is tied to this. Lol TCFU is a very dirty song. I have new respect for your Dad’s listening choices. Lol

    Previous clue said said picked for Poppy. Iceland Poppy is a flower there.
    You are going in January which is a good time to see the Northern Lights

  10. I had guessed Cook Islands. Now I’m wondering if it might be that plus New Zealand? Or New Guinea. Clue #5 Boo Boo rhyme is CooCoo and a gang could be Burrow which translates to Kookaburra – a bird found in Oceana…

  11. A crazy life is a song by a group from Australia

    Snickers is jam made from grapes and Australia is famous for grapes
    And wine
    Some of the cities listed are in Australia
    It will take 13 hours from L.A to get to Australia probably Brisbane. Woods represents the wilderness that Aussie world is known for. Wllmette is in Australia and Illinois with is connected to president Lincoln because he was from there. The old Midwest gangster group is the Lincolns from Australia.

  12. Well my Iceland guess with explanation for the clues didn’t posts clues didn’t post testing to see if this works ! .

  13. Australia it is lol. 2023 vacation
    Kronos was named 13 lucky best.
    3rd clue – Vegemite song (vegemite is famous in Australia
    4 th clue – LA has Eucalyptus trees so does Australia.
    5th clue- Beattles band remix

  14. Wow! Here goes my stab at this:
    I think you are going to take a cruise to the Virgin Islands on a Princess Cruise.
    Clue 1 – Lucky #13 – that is all you need. Virgin Islands is 13 letters. Love is all you need. Love Boat (Princess Cruise Line)
    Clue 2 – Evanson, Winnetka, Wilmette, Highland Park and Glencoe – all together now. There are 5. The Virgin Islands can also be part of the Windward Islands. There are 4 countries and one territory (5) Chicago is windy as so are the Windward Islands. Maybe there are 5 ports on the trip?
    Clue 3 – LA at birth has the most of these on wood; though there are some nice ones where we are going. If we think LA is Los Angeles then I would guess ships or piers. Los Angeles used to be a big place for ship building. Virgin Islands would also have ships and piers and you would see both if on a cruise.
    Clue 4 – JC Superstar – a US icon for a crazy life; kind of like Smuckers. No idea how this relates. I came up with Johnny Cash but if you use Jesus Christ and think of a different crazy life icon, there are lots of possibilities.
    Clue 5 – Yogi’s picnic buddy rhyming, with than an old midwest gangsters group, with their recent song remixed. Yikes! Boo Boo kind of rhymes with Poipu (but wrong set of islands for my guess) Gangsters, Mafia, Chicago Outfit, South Side Gang….. UNCLE! My brain will now explode. LOL!
    Seriously – I just hope you are going somewhere with SUNSHINE!! Have fun!!

  15. Clue #6 sealed the deal for me! You’re heading to Oahu in North shore Hawaii

    #2 – north shore of Chicago…. Hawaii also has a North shore
    #6 – poo poo, key, a = pupukea … have fun surfing!!

  16. Has to be Australia! Having lived in Seattle and half of Gaby’s family lives there, everyone likes to escape to somewhere warm this time of year (especially after this year’s weather). Plus it needs to be where Poppy can enjoy being a fish since she loves swimming.

  17. I think you’re going to the island of Oahu in Hawaii! Here’s what I have so far:

    Clue #1: Lucky #13 – that is all you need.
    – The Hawaiian alphabet has 13 letters, so “that’s all you need” where you are going!

    Clue #2: Evanston, Winnetka, WIlmette, Highland Park and Glencoe – all together now.
    – All suburbs north of Chicago, which “all together” form the North Shore, a part of Hawaii.

    Clue #3: LA at birth has the most of these on wood; though there are some nice ones where we are going.
    – BEACH-wood Canyon is a community of LA that contained what is the original Hollywood sign (LA at birth); therefore, “these” refers to “beach” which there are a lot of nice ones in Hawaii!

    Clue #4: JC Superstar – a US icon for a crazy life; kind of like Smuckers.
    – Still working on this one – will get back to you if I can figure it out!

    Clue #5: Yogi’s picnic buddy rhyming, with than an old midwest gangsters group, with their recent song re-mixed
    – Yogi’s picnic buddy is Boo-Boo which rhymes with LULU; Old midwestern gangsters group is the MAFia; a recent song release might be called a drop; another word for drop might be fall. Together = Lulumafu Falls!

    Clue #6: Termed like a young toddler dump; which then needs something to unlock the alphabet, to then begin…
    – A young toddler would a call dump a poopoo (PUPU), something to unlock is a KEY, and the alphabet, to then begin = A ; putting this together = Pupukea!

    Clue #7: Something that combines the beauty of Maine and eastern Washington; southern lands in the 1800s; first rhyming with a past crime
    – Maine is known for its pine, eastern Washington is known for its apple – combine them to get = Pineapple. Southern lands in the 1800s = Plantations; stealing is a crime – in the past = stole which rhymes with DOLE (first indicates that it goes at the start of the clue); putting this together = Dole Pineapple Plantation!

    Sounds like a fantastic trip! Hope you all have an amazing time!

    1. Incredible! I want you on my team if I have have a puzzle/riddle to solve! Thanks for breaking down all the explanations too!

    2. I think you are right about location, but clue three I have more for HollyWOOD (eucalyptus in HI is so beautiful) and so are the stars.
      Clue four, Jesus Christ Superstar, huge musical, as is Spam-a-lot. Spam is an iconic Hawaiian food!

    3. For Clue #6, we call appetizers PUPUs in Hawaii so perhaps that’s the connection?

    4. Joyce – Still scrolling but I want to congratulate you on getting 4 clues correct!!! So far that is the most 🙂
      Papa B

  18. OREGON!

    I was a paralegal for an attorney who graduated from Wllimet college. Her family has owned a ‘jammery’ forever. The jam is all natural produced on site at the ‘fam.’

    Fingers crossed

  19. Before the answers come out, I had to update my last set of guesses with an attempt at Clue #4 even if I’m completely off!

    Clue #4: JC Superstar – a US icon for a crazy life; kind of like Smuckers.
    Jesus Christ Superstar is a famous MUSICAL (and specifically ROCK opera), which may be a descriptor for this “US icon for a crazy life”. A musical US icon may be Elvis Presley. Kind of like Smuckers = jam. One Elvis Presley jam (song) is called Rock-A-Hula, which also happens to be a luau dinner show in Hawaii!

    I’m sure some of the other guesses are at least partly or totally wrong too, but I love a good puzzle and have been playing along with Surprise Vacation for the past few years! Looking forward to Bruce’s explanations and hoping for partial credit 🙂

    1. Congratulations Joyce you have the most correct answers!!!! Still only 4 right, but that is more than half, and I am VERY impressed!!!!!! Great start and finish, weak in the middle…(those were clearly the toughest)
      Nice work, next year you must get them all! You now know how my deviant clue mind works 🙂
      Bruce

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