We arrived at Delray Beach city marina after an early morning running of a Gauntlet of bridges from our North Palm Beach anchorage. During this stretch, we started noticing the transformation of boat sizes and houses. We are no longer seeing typical houses with cabin cruisers but Mansions with Yachts docked in front. My definition of a yacht is a boat that requires a hired crew to manage.

Delray Beach was named “Most Fun Small Town in the USA” by Rand McNally and USA Today – and it’s easy to see why. Nestled between Boynton Beach and Boca Raton, Delray Beach is famous for its lively main street, inviting beach weather, thriving arts scene, and interesting culture that stretches back centuries.

By day, this ocean-side community of 75,000 still has the feel of a small beach town, complete with bronzed surfers and plenty of Lululemon and lobster-print pants. But at night, boisterous crowds are drawn to the promenade of bars, restaurants, and shops along palm-lined Atlantic Avenue like gulls to a school of herring.

So priority number 1; toes in the sand! The great thing about being on Atlantic Ave is that everything is walkable. In just a few minutes we went from an energetic restaurant scene to the serenity of waves crashing the shore. Lounge chairs and umbrellas are available to rent so you can sit back, and relax and an attendant will assist you.

Delray Beach has no shortage of things to keep you occupied until Happy Hour, it’s what Claudia counts down her hours for. Happy Hour is every hour on the beach but most restaurants and bars up and down Atlantic Ave are going to offer discounted bites and libations from 4-7 pm. Not too far away from our boat, we went for Margarita Mondays at Hawkers for their famous spicy Mojitos & Mexican Street Corn but ended up staying for dinner for their Taiwanese street food – Soup Dumplings and Singapore noodles.

No trip to Delray Beach is complete without spending some time down on Atlantic Ave. The next day, we strolled down this trendy, pedestrian-friendly street, lined with shops, boutiques, restaurants, art galleries, and more. We started our day with a delicious cup of joe from one of the many cafes. Then walked by the famous haunted Colonial Hotel. Then browse the unique stores for souvenirs, shoes, jewelry, and ended our day seeing the mighty 100 ft tall Christmas tree and delicious Poke Bowls at the downtown Delray Market.

Back on our boat, we opened the doors to the cockpit to listen in on the conversation the palm trees are having with the breeze. Until that moment, we had never heard of Delray Beach and didn’t think that this small village by the sea would steal a little piece of our hearts but we’re so glad that it did.