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I love to travel, so I'm always happy to pack my bags, whether it's for work, play or family obligation. And I'm always planning the next trip!
My favorite family vacations involve multiple generations, with lots of people coming and going, and possibly a pet or two. In thinking about my ideal family vacation, I realized that it's actually multiple trips. And it's not just being a travel-lover, it's because I want to include everyone!
Although we don't have children, my husband (Chief) and I are lucky to have a lot of family. Both sets of our parents are divorced, with three out of the four remarried to our wonderful step-parents. Combined we have six siblings, three of whom have spouses and children. With nieces, nephews, cousins, aunts, uncles, and my very active 94 year old grandfather (look out ladies, he pinches, no really), we're well into double digits when tabulating how many bedrooms the rental house needs to have!
With so many people, it's impossible to find a one-size fits all solution, but since this is a fantasty I'm going to plan enough vacation to satisfy everyone! Here are a few vacations that Chief and I would love to host, with open invitations to our families to join us:
August on Cape Cod
A giant house on the beach in Falmouth, with weathered shingles and dormer windows. Six or eight bedrooms, including a dorm style room in the attic where the pre-teen cousins all sleep. There's also a partially enclosed porch, for sunset and fireworks watching.
The back yard has a crooked clothesline, covered with faded red and white striped towels that are perpetually damp, plus mismatched, sandy bathing suits.
Every night the grownups sip icy white wine spritzers and light beers, while the kids play tag and get bitten by mosquitos. We eat lobster so often that we (almost) get tired of it.
September in Sicily with a side trip to Lepcis Magna
I'm half Sicilian on my dad's side. A few years ago he, my stepmom and brother went to Sicily, and it was a magical trip. (Well, magic and terrifying, if you factor in the part about Italians driving on steep mountain roads!)
Their pictures and stories, plus the lure of seeing my "heritage" put this island on my Must See list. Then I did some research and found out that you can rent a villa, on a cliff, with a pool overlooking the Mediterranean. Count me in!
Activities on this trip to Sicily include taking photos, visits to archeological sites, and incessant imbibing of:
- vodka tonics with fresh lemon
- olives
- fresh seafood
- fresh pasta
- wine
- arancini
We also charter a disturbingly rickety, but ultimately safe, private plane, and visit the Roman ruins of Lepcis Magna in Libya, because heck, we're practically there anyway. The return trip is made possibly the by the pilot distracting handsomeness, and a well-appreciated flask of Limoncello.
Who's with us on this trip? It's a grown up excersion that definitely includes the extended Italian side of my family, including all of the aunts, uncles and cousins -- but probably not the nieces and nephews. You don't have to be old enough to drink in Italy, but it helps.
October in Hawaii
If you're sensing a sea-side theme, you're right. And what's not to love? Soft ocean breezes, delicious seafood, relaxing beaches -- all things that Hawaii does better than almost anywhere else, because it's all done with Aloha and umbrella drinks. *Sigh.
Chief and I start this trip with just the two of us in Honolulu for a week, enjoying the uniquely Waikiki combination of a city vacation at the beach. We stay at our favorite boutique hotel, the New Otani, and eat as much ahi poke as we can stuff into our heads.
From there we island hop to Kauai, and rent a villa on a beach of silky, white sand, where we are joined by the West Coast part of the family (mainly Chief's people). In a show of unity, we all take surf lessons in the relative seclusion of our private beach, and are put to shame by the quickly acquired skills of my youngest brother-in-law.
Your Turn!
I could keep going for all 12 months of the year, but you get the idea. If you are also a travel dreamer, remember to enter the “Do What You Love” Sweepstakes, for a chance to win your own ultimate family vacation. I was selected for this sponsorship by the Clever Girls Collective, which endorses Blog With Integrity, as I do.



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