Family trips are way easier than you think

Ruth Mendes with her family enjoying a foliage stroll at the Hill-Stead Museum in Farmington. Photo credit: Rebecca Wilhite

Ruth Mendes is a wife and mami of four kids, a blogger, a digital marketing communication professional, and a black belt in taekwondo. She’s always loved a good adventure and truly believes that it’s possible to enjoy travel with kids, grandparents, and extended family.

With fifteen years of family travel experience under my belt, including a multitude of intergenerational and extended family trips, I’ve learned to be creative in my search for the perfect family-friendly destination and accommodation. Prior to having children, my husband and I loved luxury travel. We honeymooned in Hawaii and spent two weeks in a mix of vacation rentals and oceanfront luxury suites.

Our first extended-family trip staying in a vacation home was in 2001 when we visited Santo Domingo, Dominican Republic, with my parents, siblings, and their significant others for my grandmother’s 90th birthday celebration. We rented a place in the colonial district of the capital city that provided room to spread out, cook, and reconnect. This experience of shared expenses and access to a full living space opened up a new world of extended family travel that enabled us to travel more often as our family grew.

Growing up in a Dominican family in the United States, vacations consisted of trips back home to the island, or road trips where my mother got up early and cooked a big pot of moro, a one-pot rice dish consisting of rice and beans, the perfect road trip meal, as we hit the beach, mountains or city. The memories that are filling my heart in the midst of a pandemic season of stillness include train trips to NYC with mom friends and little girls, beach time on Martha’s Vineyard with large groups of extended friends and family, and ski trips to beautiful mountains in three-floor ski homes filled with amazing food, family, and laughter.

Intergenerational trips with my parents have been a staple in our kids’ upbringing and something that we look forward to post-pandemic. Has this pandemic left you with a longing for experiences that fill your soul with joy? Let me share some of our favorite destinations and activities for large family travel that will inspire you to call the grandparents, siblings, and friends to plan your next family getaway.

Amelia Island, FL

With its uncrowded and pristine beaches, Amelia Island is the ideal multigenerational family vacation destination. With 13 miles of beaches, sand dunes, pools, splash pads, diverse seafood selection, and amazing sunsets and sunrises, there is something to keep everyone in the family happy. We traveled to Amelia Island with my parents, and one of our most memorable experiences was looking for and finding shark teeth in the crashing waves.

The author’s kids playing in the surf on the beach while looking for shark teeth in Amelia Island, FL. Photo credit: Ruth Mendes

The east side of Amelia Island offers a variety of beachfront and near beachfront homes, as well as homes with beachfront access. If you need to take a break from the sun, head over to Fort Clinch State Park to enjoy walking trails and the historic fort. If you’re into nautical history, a visit to the Maritime Museum is a must. If time permits, a trip to nearby Cumberland Island, Georgia, to see the wild horses should be next on your agenda. To learn more about the area, finish up your trip with a boat tour on the Amelia Island River Cruise.

Block Island, RI

Block Island is a New England hidden gem that is worth the ferry ride necessary to get there. You can get to Block Island via boat or plane, but most people, like our family, choose to visit via the Block Island Ferry. We have day tripped with friends and have taken the car ferry while spending a week eating, drinking, and exploring this little piece of paradise.

Due to its location just steps from the ferry in Old Harbor, Ballard’s is usually the first stop when arriving on Block Island. Ballard’s has a private beach with lounge chair and umbrella rentals, an outdoor bar, beach volleyball, live music, and beach food and drink service. Our kids love body surfing and jumping off the pier dock nearby.

Jumping off the pier on Block Island while watching the ferries arrive. Photo credit: Ruth Mendes

Rhode Island is known for a hot lobster roll, which is my absolute favorite way to enjoy lobster. At 200 feet above sea level, Mohegan Bluffs is the perfect place to enjoy the views, fly kites, and watch the boats go by. Fellow lighthouse enthusiasts will find that the small island provides many opportunities to take short hikes to secluded and picturesque lighthouses. Our family loves securing a home near the Mohegan Bluffs, which provide the perfect mix of privacy and accessibility to biking and activities.

Martha’s Vineyard, MA

Our family has been spending time on Martha’s Vineyard (MV) for years regardless of the season, which is part of why we love it so much. Nothing says summer like extended family and friend time in Oak Bluffs and the surrounding towns on the island. Beyond its reputation as the summer playground for those Black and bougie, Martha’s Vineyard is a location steeped in Black history, art, and culture, and historically, a safe haven created by Black families when they were prohibited from visiting other Cape Cod beaches.

Today, it is a destination where ours and many other Black families connect with extended family, friends, college classmates, line brothers and sisters, and others that we haven’t seen all year long. While it’s easy to visit MV and find yourself overscheduled, overdressed, and having to impress others, our family has made it our goal to experience a more laid-back MV annual experience. To me, summer on MV is about makeup-free beach time, boogie boarding, sunbathing, sitting in circles with loved ones on the Inkwell Beach, South Beach or Menemsha Beach at sunset while enjoying seafood, and meals packed in coolers while dancing to 90’s music.

The Mendes children bidding farewell to the island as the ferry departs from Martha’s Vineyard. Photo credit: Ruth Mendes.

The Vineyard, as it’s referred to by many, is also one of my favorite locations to walk the beach at low tide looking for sea glass. No trip to MV would be complete without taking a spin on the oldest platform carousel in America, Flying Horses Carousel, where you can win a free ride if you get the bronze ring. Then, take a stroll through the gingerbread houses at the Oak Bluffs Methodist Revival camp, visit the cliffs at Aquinnah, and while there, explore the Gay Head Lighthouse.

If you visit in mid-September, you can attend the annual Aquinnah Wampanaog Pow Wow, hosted by the Wampanoag Tribe of Gay Head (Aquinnah), which features Native American storytelling, artisans, crafts, drumming, and dancing. Don’t leave the island without a late-night visit to Backdoor Donuts for hot donuts and apple fritters.

Renting a house with in-laws or friends and packing your groceries in a cooler from the mainland makes this little piece of paradise accessible to just about anyone looking for a nearby getaway. We limit our eating out to take-out seafood from local fish markets, which we enjoy at sunset on a beach. Our favorites are The Net Result in Vineyard Haven and Larsen’s Fish Market in Chilmark.

The travel memories that we’ve created with our family and friends have been instrumental in our parenting journey. I hope that you’ve been inspired to plan your next family getaway and that you personally experience some of these remarkable destinations.

Follow Ruth on Instagram: @havekiddoswilltravel and Twitter: @havekiddoswill