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Family Travel Guide - Tips for families on the move

When my Husband suggested Montauk, as in, the beachy tip at the very end of Long Island, for our summer vacation my first reaction was, “That’s too close to home! We can’t go there for vacation.” (We live in Manhattan.)


Then, the beauty of vacationing near home hit me like a ton of bricks: no airport security; no long flight with toddlers; no requirement to stay gone longer than we’d really like - just a perfect family vacation to a place we’ve never been before that is known for being low key!


So, off we went to the perfect vacation rental home, on the perfect family vacation in perfect little Montauk.




Day 1


Ahhh, home sweet home!


We arrived at our amazing, contemporary Montauk vacation rental (that we found on with a sun-drenched deck, huge backyard and children's jungle gym with bikes, ice chest, and other essentials, just before noon. The homeowner met us upon arrival to give us the keys, a tour of the home and tons of advice about the area. It was beautiful. It had tons of room and natural light and was in a great location near everything we had planned.


Meanwhile, my Mom (“Nonna” to my girls) landed at La Guardia and hopped a ride on The Jitney to meet us in Montauk.


Around lunchtime, we drove in to town to pick her up at the bus stop and enjoyed a lovely lunch in the quaint downtown area, sitting outside in the breeze. We finally felt like we were on vacation!


But, it wasn’t long before we realized there’s no time to dally in Montauk! My husband had planned an adventure-packed itinerary so we needed to get started.


Day1.pngMontauk Point Lighthouse, the oldest lighthouse in New York State, was our first destination. The Lighthouse, authorized by the Second Congress, under President George Washington, is still an active aid to navigation today. Our 3-year-old met the minimum height requirement (41” or more) and was allowed to climb to the top with us to check out the view. It was peaceful and amazing all at once.


After all of that hard work climbing up and down the 137 iron steps, we headed over to the gift shop and restaurant for cocktails and milkshakes. 


Later that day, we headed over to Monday night "Concerts on the Green," a free family event sponsored by the chamber of commerce.  A few lawn chairs, some chilled wine and a pizza from the local pizzeria, and we were all set for one of the best nights we've had all year. The band was singing tunes like “Pretty Woman” and kids, young and old, were swinging to the beat. This is how a sunset was mean to be enjoyed. It was like we were in a TV show or a movie, only better - it was real!


After the Littles had their baths, we all snuggled up on the over-sized couches in the living room of our vacation rental and watched Team USA take the gold in Womens’ Gymnastics. Inspired by the win, the Littles attempted their own acrobatics solidifying a "perfect 10" for our first day of vacation!




Day 2


Our second day in Montauk started with everyone slathering on the sunscreen before we headed out to a sun-filled day of activities – mostly on the beach. (Check out my post “A Parent’s Guide to Pool Time on Vacation” for more tips on sun protection). We always make sure all of us are well-coated before we get dressed and leave for the day.


Our first stop was Gin Beach where we took advantage of gorgeous morning and skipped stones. Then we collected sea shells, driftwood and even sea greenery growing on the sand dunes to fill up three glass globes we bought to remember our vacation.  Day2Stables.png


Lunch had us heading over to Navy Beach, a famous restaurant in Montauk where the fresh seafood is really amazing. Its super kid-friendly since they can run around on the beach while you wait for your food, which makes it worth the pricey fare. After lunch, we took a quick nap at our comfy vacation rental, then we were ready for more!


Rita’s Stables was next on the agenda and the perfect place for the Littles to enjoy something right up their alley. It was so fun watching them experience their first saddle rides. It made my mom and I nostalgic for the first time my brother and I rode horseback with my grandparents in Columbus, MS. The petting zoo at Rita’s was a big hit, too. Of course, our littlest wanted to HOLD the animals (not just pet them).


Next up was a quick game of mini-golf at the local Puff & Putt to fill the gap of time between horse riding and our dinner reservation. Note to self: Toddlers don’t play mini golf. It was fun to watch anyway.



One of the best parts about Montauk is that all of the great restaurants you’re dying to visit are family friendly in the early evening hours. We ALL had a great time at Solé East in their beautifully landscaped backyard dining area. All of the money we saved by staying in a vacation rental allowed us to enjoy some restaurants that wouldn’t have otherwise fit in our budget.

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I never get to hit up the Momofuko Milk Bar in NYC so I was determined to visit their Montauk outpost for dessert. We got carry-out to enjoy back at the house around the kitchen table together. 


After spotting two bunnies and four deer (that were on their own family vacation, according to the girls) in the backyard, our elated Littles enjoyed a cool nighttime romp on the jungle gym before bath time put an end to our second day.


Day 3


As early risers, we easily made the 10 am ferry to Block Island, Mass., a place I knew nothing about.


Hubs insisted we bring our bikes so we could all bike around the island together. Once I realized that there was only one ferry a day to and from Block Island, and that both directions take at least an hour, I was a little nervous that this might be an ambitious plan for our multigenerational band of merry travelers.


Hubs and the oldest Little had a great time biking all over the island, shopping, eating and hitting up yet another petting zoo. Nonna, Littler, our friend and myself had a less fun day after a series of near fatal biking accidents. Ok, maybe I’m being a tad dramatic. But there was more than one accident and there was blood. And it was mine. Enough said.




We did manage to get ourselves to the Old Town area of Block Island, where Littlest promptly put herself up for sale for fear we might put her on the


back of  another bicycle.


Leaving Block Island was more enjoyable as it included cocktails on the dock and a chance to watch real fishermen cleaning their catch of the day while we waited to board the ferry.


Not a moment too soon, Hubs had arranged for a little vacation romance on our final night!


My husband definitely knows how to plan a date! We indulged at the hottest dinner spot in town, Byron at Surf Lodge and had the best table there. Afterwards, we pretended we were slightly younger than we are and headed to Rushmeyers Electric Eel Bar for Comedy Night with Seth Herzog where we laughed and recovered from the day’s adventures. Perhaps Hubs read my post, "Rest, Relaxation & Romance" about spending quality couple time during a family vacation.


Day 4


After a lazy morning with the girls, Hubs surprised us all with the perfect souvenir t-shirts on our last day. In no time, we were packed and ready to hit the road. Montauk: The End!


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Diana Heather writes at She is also the Chief Mom, both at home to her two girls and at You can follow Diana on Twitter @ParentingsATrip.


Family vacations are usually busy with activities, sightseeing and more. But, another big component of vacationing in the summer in my family is spending time at the pool.



One of the reasons we love vacation rentals so much is because we can have our own private pool. With two small children, privacy is a big advantage. A hotel pool or public pool, for instance, doesn’t offer us the same unique opportunities to play with our kids freely without the worry of getting in the way of other guests. Mostly though, having a private pool is the safest way for us to keep an eye on the Littles while giving us some time for R&R.



Girls in Grandaddy's Pool summer 2011.jpgAny parent can attest lazy pool days aren’t quite as lazy once you have kids. If you’ve ever chased your toddler around a pool trying to rub her down with sunscreen, then you know what I’m talking about. However, Hubs and I both agree we have a lot more fun by the pool now that we have the Littles and there’s nothing we would trade that for.



We have also learned that a little structure can go a long way, so we fill our day with a good mix of games and break times to make sure the Littles don’t get too tired or lose interest. 



One of our favorite pool time activities is encouraging playful physical challenges like, “who can jump into the water the farthest” or “kick your legs like a froggy.” We’ve found this helps them develop new swimming skills and keeps them entertained. 



We also try to bring along a few pool accessories if there’s room in our suitcases. Inflatable items that pack flat are the best and luckily for us, Hubs has big lungs! If we’re road-tripping and have more room, we are huge fans of the PuddleJumper® floatation device. 



Also, even though they may fight the notion of getting out of the pool, we always make it a point to take a few small breaks throughout the day. Grabbing some shade under an umbrella or even going inside for a light snack keeps the Littles energized and ready for more summer fun! Plus, even though the kidlets may be full of pool water, we always make sure to keep them hydrated with actual water or a drink with electrolytes. Pool water, sun and hours of activity can easily dehydrate all of us.



Another thing that’s very important to me is sun protection. I grew up on the Gulf Coast of Mississippi and both of my young parents have already had skin cancer spots removed; so I’m a little OCD on the sunscreen front.



Whether we’re playing at a pool or hiking in the mountains, we always pack plenty of sunscreen on our summer vacations since UV exposure is greatest from May-August in the United States.



The Environmental Working Group (EWG) offers an in-depth Sunscreen Guide that keeps parents up-to-date on all the latest guidelines and includes an extensive list of every sunscreen on the market with the EWG’s ranking of each one.


Here are some other good Sunscreen 101 tips:


  • Only use products labeled “Broad Spectrum,” meaning they protect against both harmful UVA rays and sunburn-causing UVB rays
  • You should apply sunscreen every 2 hours and more often if you’re exposed to extreme water or sports activity. Do not let higher SPF numbers give you a false sense as to how long the sun protection will last
  • Be generous in your applications. The recommended amount for an adult body is about the size of a shot-glass and a teaspoon for your face. Obviously this should be less for children, but make sure they’re adequately covered
  • Nothing provides better sunscreen than covering up with a long-sleeved shirt and hat. You can even add SPF to clothes or buy them with SPF already built in. To make your own, wash tightly woven cotton clothes in a UPF rinse, which can raise the SPF value up to a level of SPF 30.




When you travel with your family, how much time do you spend by the pool?


Have fun splashing into summer on your vacation this year! 


Khloe swimming.jpg



Diana Heather writes at She is also the Chief Mom, both at home to her two girls and at You can follow Diana on Twitter @ParentingsATrip.