Exploring Southampton in the Winter



Travel is such an amazing gift to give to your children. Exploring new places, spending quality time together- simply taking a break from the everyday hustle. This is especially true for families who live in big cities like NYC. It is almost as if you can feel the stress drip off- even if it’s just a day or two to escape. But a travel budget is often the last thing we are able to save for, and many families wonder how can they afford to go away beyond the larger yearly planned vacations. That’s why we love to share ideas for local travel- whether it be an overnight stay or a few days. Certainly save your pennies for those tropical or European getaways, but in the meantime plan some time exploring what’s in driving distance from you.

For winter trip ideas, think outside of the box. While some places might be insanely expensive in the summer, prices are considerably lower in the off season.

Example: The Hamptons. 

Although we automatically think of beach houses and extravagant pool parties in the summer, the Hamptons is a beautiful place to unplug and relax in the winter- and at a much more affordable price-tag. We recently stayed at the Southampton Inn in the East End for a peaceful two night retreat. And yes, we still went to the beach.

Southampton Inn





This classic Southampton boutique hotel consists of 90 guestrooms- all with Tempur-Pedic beds (can you say “sleep in?”). In the summer it’s bustling with beach goers, but during the off season it’s a peaceful respite. When we checked in, the reception to a concert in their library was wrapping up. Wine, cheese, and crackers were served as locals enjoyed this Sunday evening event. We were given a room facing the courtyard, and our little one immediately noticed the small play house and slide for her to enjoy.




The Southampton Inn prides itself in its classic decor- in fact it wants to shy away from the trendy Hamptons look that so many places aim for. Owner Dede Gotthelf wants families to feel they’re at home- encouraging children to run around the grounds, enjoy Continental breakfast in the library, and explore the area.


Once settled into the room, I popped a bottle of bubbly and opened up a map of the area to decide on some places for us to explore. Sometimes I already have an itinerary before arriving at a place, and others I play by ear. We decided on seafood for dinner- it was only right being so close to the beach. Rather than looking for a classier sit down restaurant, I perused the map for a potential hole-in-the-wall- ones that often end up being our favorite. In doing this I found Out of the Blue- described as a no frills market and counter-serve restaurant specializing in fresh and smoked seafood.

Out of the Blue





We sat down at a table in the corner with our paper placemats and plastic silverware wrapped in napkins. A nice gentleman walked over and handed us the menus. We opted for appetizers- fried calamari and crab cakes, while the kids ordered mozzarella sticks and chicken fingers from the kids menu. A side of fries and we were ready to dig in.




As predicted, this was exactly what we had in mind. The crabcakes were delicious, the calamari was fresh. Even the fries were seasoned perfectly. Little did we know at the time, but Out of the Blue happens to have a Bronx warehouse location! Out of the Blue purchases from local baymen daily- with seasonal catches such as sea scallops, bay scallops, striped bass, flounder, tuna or monkfish. Their saltwater tanks, with salt water supplied directly from Shinnecock Bay, offer a variety of local de-sanded shellfish, including steamers, clams and oysters. www.ootbseafood.com


Breakfast in the Library





The next morning we walked through the courtyard to the library for breakfast. The Southampton Inn offers continental breakfast to all of its guests. The first morning there was cereal, muffins, bagels, croissants, coffee and tea. Everything was fresh, and I noticed later in the day the breakfast items were replaced with chips, granola, nuts, and graham crackers- something new each day.


Agawam Park







After breakfast we walked over to Agawam Park. Situated on the lake that is named after, there’s a fun playground for kids, a sprawling lawn, and plenty of ducks to watch. Across the street from the park is the Southampton Cultural Center, but being that we were there on a holiday, it was closed. Agawam Park is home to many events throughout the year, including an upcoming Lunar New Year Celebration in February. www.scc-arts.org

Coopers Beach





After the park, we headed back to the hotel and hopped into the car for a short ride to Coopers Beach. Just a few minute drive from the hotel, a note from Dede gave us the fun tip that in the winter you can “peek” through the hedges as you pass by the amazing homes on the way to the beach. Normally what the green hedges would cover in the summer exposed the beautiful homes behind them and it was fun for us to ooh and ahh over our favorites. Normally you can not park at Coopers Beach during the summer season- so there is a shuttle you can take from the hotel. But off season we were able to park and take a walk in the sand.

It was a rather warm winter day, so it was lovely to stand at the water’s edge and take in the Atlantic Ocean without all of the beach goers around. There were a few people sitting in their cars enjoying the view, and a family with their dog exploring the sand. www.tripadvisor.com



We returned to the room for a quick lunch. To save, we packed sandwiches and Luis’s delicious shrimp ceviche that we also brought to enjoy. There was a small fridge in the room, but we opted to keep everything in our cooler to make packing back up easier. Before heading back out, we let the kids release some energy in the playroom located downstairs at the other end of the hotel. There were plenty of kitchen sets, trucks, blocks, and video games for the kids to play with. The playroom is located right next to one of their venue spaces- perfect for a fun childcare option at weddings.


Duck Walk Vineyards





After lunch we hopped back in the car and drove just ten minutes away to Duck Walk Vineyards. Located right where the Hamptons Wine Trail begins, this is the perfect place to stop and squeeze in a mini “date” when you’re with the kids. They hung out at the long picnic tables inside as we enjoyed some wine tasting. $8 bucks gets you five wines to taste and they did an awesome job at figuring out what wines we would enjoy. www.duckwalk.com

Southampton Historical Museum





After the vineyard, we stopped at the grounds of the museum on the way back into town. The actual museum itself is closed while they renovate thanks to a grant that they received, but you can still walk around and see 12 historic buildings, including a school house, an 1825 barn, and 19th century paint store.  www.southamptonhistoricalmuseum.org

Conscience Point




Lastly we drove to Conscience Point, the location where English Settlers from Lynn Massachusetts first landed in Southampton in June of 1640. Me being Italian and Irish with some English decent, and my children being half Dominican with Geronimo as their last name, it was a great teaching moment and my oldest completely understood the history. She even wanted to ‘Larp’ (Live Action Role Play) and reenact what might have happened as they docked and found land. I always try to squeeze in some history into our explorations, and the fact that my girl’s enjoy it makes me incredibly happy. www.fws.gov

Dinner at Union Cantina





After a full day of exploring the town, we headed back to the room to get ready for dinner. We had reservations at Union Cantina, a Mexican restaurant with updated Mexican dishes just a few minutes away. This rustic chic restaurant features plenty of pretty white lights strung both outside and in, with a patio and full tequila bar. A big basket of chips and salsa were placed on the table by our lovely waitress as we decided what we wanted to order.




I opted for the Deconstructed Enchilada with Skirt Steak. While I am all for keeping a classic as is, this dish was delicious. Layered with three tostadas instead of the usual tortilla, the flavors were on point. The kids opted to share quesadillas while my husband enjoyed his Snapper. We sipped on ice cold cold Margaritas and somehow managed to make room to share the delicious warm churros with chocolate sauce that came with the kid’s menu. www.unioncantina.net

After such a yummy meal, we went back to the room to relax in that insanely comfortable King size bed. The kids pulled out the sofabed and jumped in- and  before I knew it, we were knocked out.


Check Out




Before check out, we enjoyed another peaceful breakfast in the library. The Southampton Inn’s website reads, “As a guest of the Southampton Inn, you are always welcome to arrive as early as you like on your check-in date and depart as late as you wish on your checkout date. Although guestroom check-in is at 4:00pm and checkout is at 11:00am, we encourage all of our guests to come early, stay late, and utilize all of the amenities that we have to offer–effectively turning your one or two night stay into a two or three day getaway in Southampton.”

This was so nice to not feel the pressure of rushing to check out.  But alas, it was time to head back to reality so we loaded up the car and headed home. There was plenty more we wanted to come back and explore, so we will definitely be back. For more information on The Southampton Inn, visit www.southamptoninn.com.



Additional Places To Visit




Whether your budget is large or small, planning little weekend or midweek getaways to explore local towns is the perfect way to spend time with your family. Decide on your budget, figure out lodging, and then plan your adventure accordingly. Many cultural institutions are free or low cost, and exploring outdoors is always a free to low cost option. Pack your own meals if you don’t have a large food budget, and look for reviews on cheap eats in the area. Do as much research on an area you’d like- you can always plan to return to see even more.

Happy Travels!







We received some accommodations to facilitate this post. As always, opinions and ideas are our own.


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