Traveling (Further) South: A Winter Escape
Starfish Point | Cayman Islands
When winter rolls around, I often find myself craving even warmer climates and heading further south to the Caribbean, Mexico, or Central America. From pristine beaches to rich history and vibrant cultures, these destinations have become my go-to spots over the years, and likewise are wonderful winter getaways. With direct flights from cities like Atlanta, Miami, and Charlotte, planning a trip is easier than ever. Here’s a glimpse into some of my favorite spots, personal experiences, and tips for making the most of your time in Latin America and the Caribbean.
Riviera Maya, Mexico
Riviera Maya, Mexico: Sun, Fun, and History
The Riviera Maya is a perfect escape for families, friends, or couples. One of my most memorable trips was with a group of 25—yes, 25 members of my family, siblings, significant others, and the grandkids! We rented Casa Yardena through Tulum Luxury Collection in Soliman Bay just north of Tulum. This stunning beachfront home was ideal for our large crew, offering space, comfort, and privacy all-in-one.
From Soliman Bay, we took day trips to Tulum, where we visited the iconic Mayan ruins. Walking through the ancient site with our group was incredible—the history, the views, and the sense of wonder were unmatched. Make sure to get your tickets ahead of time, and just be prepared for the heat and bring an umbrella or hat for sun protection.
The town of Tulum itself is a mix of Bohemian charm and modern luxury. We explored beachfront cafes, picked up souvenirs at boutique shops, and enjoyed fresh smoothies after a day in the sun at The Papaya Project Beach Club. The Riviera Maya is a place where history, culture, and relaxation come together seamlessly, and I can’t recommend it enough.
Grand Cayman: Snorkeling, Private Rental, Smith Baracadere
Grand Cayman: Secluded Serenity
Grand Cayman is another favorite for its laid-back vibe and pristine beauty. Renting a private home here is the way to go—I loved staying near Smith Barcadere, a charming white sand beach with beautiful water great for the perfect photo op! We chartered a boat out to Starfish Point, where you can see the magical starfish dotting the crystal-clear waters.
For an even more peaceful experience, explore the less-traveled parts of the island. Grand Cayman is ideal for those looking to relax, soak in the sun, and enjoy fresh seafood at local restaurants.
Turks and Caicos: Grace Bay Bliss
Mudjin Harbor
Turks and Caicos holds a special place in my heart. On a past trip, we stayed in a beautiful beachfront home on Grace Bay, next to the iconic Club Med. One of the highlights was renting a catamaran with Viator Tours for the day, where we enjoyed fresh conch ceviche and explored Middle Caicos, including the breathtaking Mudjin Harbor.
Though the island has grown more popular, it’s still a dream destination with its pristine beaches and warm hospitality. Sadly, Daniels Café, one of our favorite local spots in Middle Caicos, is no longer open, but the memories of their fresh catch of the day will always stay with me.
Costa Rica: Diverse Beauty
Costa Rica is a country that feels like it’s always expanding and developing, which brings mixed emotions. The natural beauty is unparalleled, but I hope the charm and authenticity of its smaller towns remain intact.
On my last trip, I landed in San José and took a small jet flight with Sansa Airlines to Quepos before heading to the Southern Pacific Zone. The local jets are an economic alternative, around $120 a ticket and a great option versus the three hour drive down the mountainous terrain to the Pacific Coast (which easily turns to six hours if stuck behind a truck down).The Southern Pacific Zone, stretching from Quepos to Ojocha and even up to Chirrippo, offers everything from lush mountains to jungle rainforest to tranquil beaches.
Dominical is a quaint surfer town that’s still developing but retains its charm—don’t miss a meal at Bar Y Restuarante El Coco, where the whole snapper, fresh ceviche and a batido con leche (fruit smoothie) are must-haves.
For a unique adventure, drive up to Chirripó, Costa Rica’s highest mountain, where you'll find lush cloud forests, pristine rivers and breathtaking panoramic views that make the journey well worth the effort. Chirripó is known for its exotic bird watching and hiking! Many individuals embark on the journey to hike to the peak of Chirripó, an approximately 12-hour trek that rewards adventurers with awe-inspiring views. However, permits are required and tend to sell out quickly, so it’s essential to plan and book well in advance.
Stay at Rio Chirripó Mountain Lodge and enjoy hot and cold river plunges—it’s pure rejuvenation. Just remember, a 4x4 is essential for navigating the mountain roads.
Costa Rica Adventures
Guatemala: A Cultural Gem
Guatemala is a place of vibrant culture and natural beauty. I spent a month exploring this incredible country, starting in Antigua, a stunning colonial city filled with cobblestone streets and historic landmarks. Be sure to visit the Arco de Santa Catalina, an iconic arch with Volcán de Agua as the backdrop, and the ChocoMuseo to learn about Guatemala’s rich cacao history and sample artisanal chocolates.
From Antigua, I traveled to Lake Atitlán, a mystical lake surrounded by volcanoes and charming towns like San Pedro and San Marcos. Each village has its own unique vibe, and exploring them is like stepping into another world.
Exploring Guatemala
Quick Tips for Traveling Further South
Flights: Direct flights to Cancun, Grand Cayman, and Costa Rica are readily available from Atlanta, Miami, and Charlotte.
Best Months: January through March offer perfect weather across these destinations.
Packing Essentials: Don’t forget sun protection, comfortable walking shoes, and a sense of adventure.
Whether you’re exploring Mayan ruins, relaxing on a secluded beach, or enjoying fresh local cuisine, traveling further south during the winter months is the perfect way to escape the cold and embrace the warmth. Keep an eye out for our Further South Story Series as we dive deeper into these incredible destinations!