Family reunions on Monhegan Island offer a special magic

Family Reunion spots on the East Coast

Want to host a reunion on the East coast?

Try Key West, the Outer Banks, Stowe or a sailboat!

Key West Conch Cottage

Clara hosts a family reunion for 29 in Key West When my client Clara first arrived at her conch cottage court with her family of 29, she admits that she was skeptical.   But this cozy cluster of cottages, smack in the heart of Old Town Key West, just a block off of busy Duval, provided the perfect balance of solitude and buzzing activity.

Solitude?   In 5 small cottages, all centered around a private pool and garden, they were able to prepare dinners, each making a dish from their own kitchenette and then gathering in the orchid-adorned garden to share lavish dinners.    Tucked away from the bushels of town and other vacationers, their group of 29 were sequestered in this oasis where they visited away lazy afternoons.

Near the buzz?    Yes, just outside the cottages’ gate was lively Key West with water sports for her teenage grandkids, bars and music for her 20-somethings, golf for her son-in-laws, shopping and museums.

And the grand finale was a toes-in-the-sand dinner for her large clan at the Southernmost House.

Outer Banks gathering

Rambling beach houses are not unique to North Carolina’s Outer Banks but there’s something about those wide open beaches.   You have long picnic tables laid with newspaper, crab mallots and platters of corn on the cob… cousin races down the sand dunes of Jockey’s Ridge… outdoor nightly theater shows at the Lost Colony (when my kids were little, we used to call this the “mosquito matinee” but it’s a tradition all by itself)…and watching the sun set over the Sound.

Here’s a good site to find spawling family homes.    Imagine your own family here:

Perfect family reunion spot in Outer Banks NC

Monhegan Island in Maine

Reunion at the Monhegan Island beach barn in MaineMaybe Monhegan Island doesn’t get top scores for “easy to get to” – it’s off of Midcoast Maine, accessible only by ferry from Port Clyde or Boothbay Harbor and not particularly close to any airports.

But once you’re there, Monhegan is an ideal family bonding spot.

Island traditions are deeply carved into everyday life – you jump off the dock when your family members or guests leave on the daily ferry… regulars spend many winter days dreaming of their first homemade rootbeer ice cream float made at the island’s own brewery… and everyone gathers, every night, for magnificent sunsets.

And the most special tradition of them all?  Hand-created moss-and-mini-pine-cone fairy houses.   Read about them here:  Summer with the Fairies on Monhegan.

Check out the big beach barns at Brackett Rentals, like Jenny’s “Cottage” here, and find one perfect for your clan.

Winter reunion at Stowe

If dogsledding and horse-drawn sleigh rides, cookie decorating and story time by the fireplace sound like activities your extended family would love, then head up to Stowe and the Von Trapp Family Lodge. 

In the winter, there’s also a brilliant network of cross county ski trails that culminate in a rustic cabin at the peak where you can warmup with homemade soups and hot chocolate in mid-ski.  And of course, there’s the entire Stowe Ski mountain with lessons and ski clubs and gondola-accessed restaurants.

They call is “a little of Austria, a lot of Vermont” and while you may love the Austrian architecture of the old inn, there are newer villa set ups with as many as 3 bedrooms so families can have plenty of room to sleep, cook and share meals, and hang out between the countless mountain activities.

Boat-n-breakfast Reunions

Is your family a bunch of water fanatics?

Or would you love to use your family reunion time for the whole group to learn a new skill?

Charter a sailboat on the Chesapeake bay and you can sail up to Havre de Grace for a crab-picking feast, or stop at Thomas Point Shoal Lighthouse for a tour.

Pull up to an island for a cookout, or grab a slip at one of the waterfront watering holes for sundowner drinks and live music.

Most of all, make memories, just you and your family, on your own vessel.  (Captains can be hired for extra fee – cooks too!)

Here’s a 45’er that sleeps 8called Wild Heart and you can charter her for a 3-day weekend for $3500.

Charter a boat on the Chesapeake for your next family reunion

Contact Rare Finds Travel today 

to make your next family reunion one that you all will never forget!

(609)923-0304 or

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