Curator’s statement
Chartering a boat through the Greek Islands is not just a vacation. It’s an adventure. It offers unparalleled freedom, breathtaking scenery and unforgettable memories. This past summer, I took to the seas for my latest trip to Greece and think it's one of the best ways to see what Greece has to offer. Here, I’ll share my experience, broken down into the key aspects to help you plan for your next trip to Greece!
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How to explore Greece by boat
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Why Chartering a boat for your Greece trip is a great idea
The allure of the Greek Islands lies in their diversity and charm, with each island offering its own unique character. When planning a Greece land itinerary with clients, one of the biggest decision points is how to narrow down which islands to see! Chartering a boat gives you the flexibility to explore many islands and see them at your own pace, away from crowded ferries and bustling ports. Imagine waking up to serene turquoise waters, discovering secluded beaches and docking in quaint fishing villages — all on your own schedule.
Boating allows you to:
Customize your adventure & set your own pace: From island-hopping to relaxing onboard, it’s entirely up to you. You can opt to visit the more remote islands and dock in bays, or focus on the more bustling islands and dock at port so you can enjoy nightlife on the islands. You choose how much or how little time you want to spend on each island.
Reach remote destinations: Many hidden gems are only accessible by sea and are not islands you would necessarily visit on your own (like Rineia)
Enjoy privacy and comfort: Like cruising, the ability to unpack once and not move around frequently is such a luxury and provides great comfort on a trip. Unlike traditional cruising, chartering a boat gives you ultimate privacy.
Types of boats: Choosing the right vessel
When it comes to choosing a boat, there are a few popular options to consider, each with its own advantages:
Sailboats (typically monohull or catamarans): Perfect for those who love the romance of the sea and aren’t in a rush. Sailing adds an element of sport and eco-friendliness to your journey. It’s ideal for experienced sailors or those wanting a relaxed, wind-powered experience. It can be cost-effective as you don't have fuel charges, but it impacts the time you're moving between islands and likely shortens the distance you'll travel.
Motor Yachts: For those seeking luxury and speed, motor yachts are the way to go. Equipped with amenities like spacious cabins, sun decks and sometimes even hot tubs, they’re perfect for a more indulgent experience.
Boats with Stabilizers: If motion sickness is a concern, a boat with stabilizers can make the ride smoother. This is particularly important if you’re traveling with children or people new to boating, especially in Greece!
We opted for a motor yacht with stabilizers. It gave us the perfect balance of speed, comfort and stability for our group and allowed us to see a lot on our weeklong charter.
When to go: Weather & conditions
The prime boating season in Greece aligns with the overall tourism season in the islands, which is June to September. The weather is warm and perfect for swimming. The winds can have a mind of their own though, so you have to take this into account when picking which month you want to travel and which islands. For example, the winds in the Cyclades, known as the Meltemi winds, are usually strongest in the hot summer months of July and August. This doesn't mean they are off limits and your captain and crew will help you navigate a comfortable route, but it is definitely something to be considered!
We chose to travel in late May through the Cyclades, which was the first week of the typical chartering season. We enjoyed warm days (weather in the high 70s) and cooler evenings (high 50s, low 60s). We got very lucky with extremely calm winds. The water was still a bit cold, but we got used to it quickly!
Island routes: Mapping your adventure
The Greek Islands are divided into several groups, each with its own flavor, and each being a great destination for your boating adventure. For most weeklong itineraries, you'll want to focus on just one set of islands to visit, but some clients opt for two-week trips and broaden their path. Your travel advisor, together with your captain can help you decide which is the best for your interests. See a summary of the island groupings below:
Cyclades: Known for iconic whitewashed buildings, vibrant nightlife and picturesque beaches. Must-visits include Mykonos, Paros, Santorini and Milos.
Ionian Islands: Lush and green, with Venetian influences. Highlights include Corfu, Zakynthos and Kefalonia.
Dodecanese: Rich in history and charm. Rhodes and Kos are standout destinations.
Saronic Gulf: Close to Athens, these islands are perfect for shorter trips. Hydra and Aegina are favorites.
Our path: Highlights of the journey
Our itinerary started in Athens, where we stayed for two nights to adjust to the time difference and visit the highlights of Athens. From there, we boarded our home for the next week and took off to explore the Cyclades, visiting 12 islands in total over seven days. We balanced our days between exploring ashore and enjoying the serenity of the open sea. We often anchored in secluded coves for a swim or a leisurely lunch. Here's a highlight of our route:
Aegina: Our first stop from Athens, it's close by in the Saronics and helped us gain our sea legs before sailing off to the further islands. We also did a quick stop in Agkistri, too!
Milos: Our first Cycladic island on the trip - and maybe my favorite. Famous for the Kleftiko caves, and one of the best days on the water.
Kimolos & Folegandros: After Milos, we hit two of the more remote islands. We got to experience some of the more untouched and organic parts of the Cyclades. I really loved Folegandros, and it's becoming more popular as a destination too!
Naxos: One of the bigger, yet quieter islands in the Cyclades, with lush landscapes and incredible local cuisine. Highly recommend a wine and cheese tasting in this stop. On our way to Naxos, we stopped in Schoinoysa, a very remote island, for some hiking and swimming as well.
Paros: The new hot island in the Cyclades. It's a great spot to plan for a meal on land and there's tons of great shopping and beautiful scenery.
Mykonos: Next, it was off to Mykonos for its vibrant nightlife and iconic windmills. On our way, we stopped in Rineia and had the best time with the water toys, like tubing, jet skiing, paddle boarding and foil boarding.
Kythnos: We ended our trip with stops at Syros and Kythnos before heading back to Athens to disembark.
You're probably noticing that Santorini was not on our path. While this island is probably the most popular in the Cyclades, it's one of the furthest away and takes a decent amount of time to get to. For this trip, we opted to spend a few days in Santorini after the boat portion ended instead. But there are a ton of routes that can more easily include Santorini!
Who it’s best for
Chartering a boat in the Greek Islands is a fantastic option for:
Families and multi-gen trips: Kids and parents alike will love swimming, snorkeling and the novelty of life at sea. The convenience of meals and lodging being handled for you is a great luxury with traveling as a family, too!
Groups of Friends: Perfect for creating shared memories, whether celebrating a milestone or simply spending quality time together. This type of trip takes a lot of the headache of group trips out of the equation!
Special Occasions: A unique and luxurious way to mark anniversaries, honeymoons or birthdays.
Final thoughts
Chartering a boat through the Greek Islands is more than just a trip. It’s an experience that stays with you. From the freedom to craft your own adventure to the stunning beauty of the Aegean Sea, it’s a journey I’d recommend to anyone seeking a mix of relaxation, exploration and a touch of luxury.
Reach out to me so that I can help you navigate these decisions. I can match you with the perfect boat and crew, and help you prepare to set sail on one of your most unforgettable vacations yet!
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Travel Advisor
Stephanie Vaughn
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