Clearwater Beach, Wyndham Grand Clearwater Beach | St. Petersburg, FL
Considered America’s #1 beach, Clearwater Beach, with its sugary sand and warm waters all year long, makes it a popular winter escape. The Wyndham Grand Clearwater Beach resort, with views of the Gulf of Mexico and the Intracoastal Waterway, is a great spot for those looking for more than a day visit. The resort features Pallavi Spa and multiple onsite restaurants.
Fun for kids: The resort is partnered with Clearwater Marine Aquarium and also features six aquatic-themed guest rooms with bunk beds, including the iconic Winter the Dolphin and other marine life.
The closest airport is St Petersburg-Clearwater International Airport which is just a 12-minute drive to Clearwater Beach.
Mokapu Beach, Andaz Maui at Wailea Resort | Wailea, Hawaii
Mokapu Beach located at the Wailea Resort Complex is a sandy beach popular for swimming, snorkeling, and sunbathing. An exotic spot for winter vacations that is far from home at right at home at the same time. With no passport needed for American citizens, you can have an exotic beach vacation while feeling right at home.
The Andaz Maui at Wailea Resort is happily situated on 15 acres of Maui beachfront, featuring three cascading infinity pools, one lagoon pool, a full-service spa with a private adults-only pool, and two highly acclaimed restaurants. The three-bedroom Ilikai Villas are perfect for family stays. The closest airport is Kahului (OGG) Airport, approximately 25 minutes drive to the resort complex.
Fun for kids: Join an island advocate on a walking tour of the resort to learn about hidden gems and their relationship with Hawaiian culture.
Rio Grande Beach, Wyndham Rio Mar Resort | Rio Grande, Puerto Rico
This long golden sand beach with crystal clear water is perfect for snorkeling, swimming, and water sports. The Wyndham Grand Rio Mar Puerto Rico Golf & Beach Resort is a beachfront resort located very close to El Yunque rainforest, the only US National Park rainforest, for family eco-adventures. If you love nature and the beach, you’ll feel like you’ve hit the jackpot here with the mixture of nature, sun, and surf all on a secluded beach.
The resort features family rooms, some with bunk beds, three pools, and a full roster of activities and endless dining options. The closest airport is San Juan, approximately a 30-45 minute drive to the resort.
Fun for kids: Insert squeal and picture iguana feeding! This resort offers some great activities, including hair braiding, pool volleyball, Latin dance classes, and complimentary s’mores by the fire pit on the weekends.
Related: Puerto Rico Is Calling & Here’s Why You Should Take the Kids
Grace Bay Beach, Beaches Turks & Caicos | Providenciales
Internationally renowned and voted the best beach in the world, Grace Bay Beach, with its turquoise-colored water, is exceptional. Twelve miles of white sand beach and crystal clear water on the northern coast of the island of Providenciales. You can even see baby stingrays swimming along the shore if you are lucky. The luxurious Beaches Turks & Caicos, an ultra-all-inclusive resort, is the ultimate place to stay. With included activities like scuba diving, snorkeling, glass bottom boat tours, sunset tours, and catamaran tours, the resort features five villages with architecture and ambiance of Italy, France, the Caribbean, and Key West. You’ll find 21 gourmet restaurants, 10 pools, and something for everyone.
The closest airport is Providenciales International Airport, approximately 20 minutes drive from the resort.
Fun for kids: There is so much to do here, including a 45,000-square-foot waterpark. There is a club for all ages and stages, including Sesame Street® characters, an Xbox Play Lounge, and a sizzlin’ teen disco.
Seven Mile Beach, Camana Bay, Grand Cayman
Seven Mile Beach is a long crescent of coral-sand beach on the western end of Grand Cayman Island. The beach is open to the public and you can walk along the full length regardless of where you are staying. Several restaurants, beach bars, and calm waters make this a great stop, even if you are staying elsewhere on the island. The newly built Camana Bay area, with upscale shops and open spaces, is a popular spot to relax or participate in activities like parasailing. Whether you are looking for relaxation or adventure, you’ll find it here.
If you want to stay along the beach, The Westin Grand Cayman Seven Mile Beach Resort & Spa is a prime oceanfront location. The whole family will enjoy the freshwater pool and swim-up bar when you are not at the beach. If a walk on the beach is not enough exercise, you’ll be happy to know the fitness center here is open 24 hours. You can check out their onsite dining or wander the beach and follow your nose for meals.
The closest airport is Owen Roberts International Airport, approximately 8 minutes to Seven Mile Beach.
Fun for kids: Stingray bay and the sandbar are close to this resort and always a hit.
Cayo Ensenachos Beach, Iberostar Selections Ensenachos | Cuba
Playa Ensenachos is one of the most beautiful beaches in Cuba and is located on a secluded lush island. Powdery white sand and crystal-clear turquoise waters combined with calm and shallow water make this a great spot for families.
The Iberostar Selection Ensenachos is an all-inclusive hotel that’s great for couples and families. The resort has an adults-only section and family programming, making it an excellent spot for multi-gen travel or groups. If you want to put your kids to the kids club and then relax in the adults-only section for a few hours, this is the place to do it.
The closest airport is Abel Santamaría Airport, followed by a 2-hour drive to the resort.
Fun for kids: A wide selection of water activities, a mini disco, Star Camp for children ages 4-12, and a splash park in the kids’ area.
Aunt Lydia’s Cove | Cape Cod, Massachusetts
Cape Cod is known for its beautiful beaches, and Aunt Lydia’s Cove, located in Chatham, is a great spot to visit in winter, to spot the gray seals at low tide. The waters here are protected. Another great spot is the private beach at Chatham Bars Inn, a beloved destination for family getaways, offering a wide range of children’s activities all year round, including lobstering, clamming, fly fishing, whale watching, white shark expeditions, and more. The hotel has an eight-acre farm where guests can forage for their own fruits and vegetables and then have them cooked for dinner.
The closest airport is Cape Cod Gateway Airport, approximately 30 minutes from Chatham.
Fun for the kids: The activities here are off the beaten path and include farm visits, clamming excursions, and whale watching.
Bean Hollow State Beach| Half Moon Bay, California
If you are looking for something a little different, Bean Hollow State Beach is a great spot for whale watching in Half Moon Bay. This beach is also very close to the Pigeon Point Lighthouse, built in 1871 to guide ships on California’s Pacific coast; at 116 ft, it is the tallest lighthouse on the West Coast.
Surrounded by hiking trails and a dark sky preserve, explore during the day and stargaze at night. Whether you’re looking for a relaxing coastal escape or an active getaway to learn about the area, the HI Pigeon Point Lighthouse Hostel offers vacation-rental-style accommodations for up to 15 people.
The closest hotel is San Francisco International Airport, approximately 1-hour drive from the property.
Fun for kids: onsite tide pools, harbor seals watching, and a secluded beach.
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