Making the Most of Your Hawaii Trip via Land and Sea

Hawaii’s natural beauty and cultural richness pull in throngs of travelers all year long. Even during a summer slowdown, Hawaii sees thousands of visitors, counting 199,760 tourists in 2022 from Japan alone. In a regular season, Hawaii can receive up to 1.6 million visitors in total.

This Pacific archipelago is home to incredible sights and is a particular favorite for sailors and regular tourists alike. In this article, we discuss how to immerse yourself in Hawaii’s treasures through both road trip adventures and exhilarating yacht journeys.

Unveiling Hawaii by land

Many tourists frequent public transportation despite the additional challenges of plotting the route system and bus schedule and competing for a spot against other commuters. However, contrary to popular belief, a rental car is best for saving time, energy, and even money when traveling by land.

The key is in how you choose and use the rental car. Instead of renting at popular but expensive tourist spots like Waikiki, you can choose from the car rentals at Honolulu Airport. The rentals can be booked online to secure the lowest rates before the high season starts. Additionally, you can search the website later to rebook at any lower rate available. This gives you a choice to rent your dream vehicle, whether that’s a convertible for an open-air feeling or a Wrangler or SUV for a sportier ride.

Once you have your ideal rental car, you can craft your itinerary and embark on your adventure. Take advantage of the flexibility of driving your own vehicle. For instance, a 10-minute detour along the Farrington Highway will bring you to Mokule’ia Beach, where you can enjoy solitude alongside lucent, turquoise waters. Such discoveries will round out your trip and count among the most memorable moments of your vacation.

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Credit: Daniel Ramirez under license CC BY-SA 4.0. No changes were made to the image.

Navigating Hawaii’s aquatic wonders

Many people would be happy to end their Hawaiian vacation with a road trip — not realizing that the full potential of a rental car is unlocked only when you use the vehicle to travel to the coastline and begin the sea part of your adventure. For instance, you can drive back to Oahu’s windward shore after thoroughly exploring the islands by land. Here, you can rent different watercraft near Kaneohe Bay, from sailboats to even kayaks, to reach the Kaneohe Sandbar. Extending approximately a mile in width and three miles in length, this submerged sandbar is a hidden gem that’s only accessible when you allow yourself to travel Hawaii via land and sea.

Credit: California Cow under license CC BY-SA 4.0. No changes were made to the image.

For beginners, sailing is often best done during the summer, when the islands experience warm, stable weather conditions around 30°C (around 86°F) and consistent trade winds. However, Hawaii is still a viable sailing destination during the winter months. The trade winds may be less predictable, but you can enjoy quieter anchorages and fewer crowds. Some areas, like the Big Island’s Kona coast, also experience more sheltered conditions, making winter sailing more manageable.

Credit: Chloekwak under license CC BY-SA 4.0. No changes were made to the image.


Otherwise, it may be best to skip the solo sailboats and kayaks and immediately opt for a reputable yacht charter company from November to April. Experienced captains are familiar with local conditions and can provide insights into the best anchorages and snorkeling spots during these colder months.


For the ultimate maritime adventure, you can consider a yacht charter vacation any time of the year. A yacht charter in Honolulu will allow you to explore the coastline and even cruise the windward neighbor islands of Molokai, Lanai, and Maui. You can visit Waikiki Beach and Pearl Harbor by car, then make your way to Turtle Canyon by yacht and enjoy the once-in-a-lifetime experience of swimming alongside green sea turtles, reef fish, and pods of dolphins. By the end of your trip, you can sail your way back to land, where your rental car will be waiting to bring you to Honolulu Airport, thus ending your Hawaii trip safe and sound.

Does this sound like an exciting experience? To seamlessly blend land and sea exploration in Hawaii, charter a yacht with us today at The Windward Islands Cruising Company. Our 20-year expertise ensures a smooth sailing experience, allowing you to confidently uncover the island’s hidden gems for an unbeatable Hawaii trip.

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