How to plan, pack, style, and wear summer looks on a boat and while roaming Greek islands
Thoughts on Sailing
Sailing is for everyone who is up for adventure, freedom, distant horizons, and magnificent seascapes.
Even though I’ve been sailing in style for the last 10 years, I still feel this thrilling sensation of exploring the unknown and expecting the unexpected when going on a boat. But hey, as they say, true sailors are defined by the storms they had to endure and not by the mere sailing experience itself, right?! ⛵💨
So, while the weather conditions are always the top priority, my mind is more often than not tormented by what outfits to pack for the trip (besides my life vest of course), which comes immediately after as the second-ranking issue in terms of importance. 😁
How should I style for the life afloat with its remote anchorages and secluded bays where we usually throw private DJ parties or organize candle-lit dinners? What should I wear when browsing adorable little villages or when roaming ancient Greek ruins? How about swimming, diving, and sunbathing on board? 😱
OMG, so many daunting style issues to resolve! For me, the way you dress affects your experience when traveling places because the choice of outfits helps me blend in, feel the rhythm of the place and be in perfect harmony with the setting. Basically, the right outfit makes me absorb the environment to the fullest!
Sporades Islands in Greece
So when we headed to the archipelago of the Sporades in the Aegean Sea, I was on a mission to enhance my cruising life with outfits that are in sync with the lush pine flora, the stunning mountains, the turquoise sea, and the white houses.
Sporades islands consist of about 135 islands and islets, but the larger and most important of these are Skiathos, Skopelos, and Alonissos. They lie along the coast of Thessaly and offer some of the best sailings in the Mediterranean or Greece at its best! 🏝
Packing done! ✅
Planning: Based on previous experience, I knew I needed to plan beach outfits for swimming, casual looks for hanging and helping onboard, party clothes for the unfailing events, glam combos for the port towns.
Packing: Having digitized my clothes, here is how I efficiently packed ready-to-wear outfits, not separate pieces that can’t be combined in my baggage. I created a hashtag #Sporades-sailing on La Koketa app and tagged all my outfits accordingly so I can easily review, edit and access them!
Sailing Itinerary in Detail
First stop:
Our crew embarked on this voyage from the port of Volos, which is an important industrial center situated between Athens and Thessaloniki and serves as the first step to the Sporades islands.
herefore, I needed a summery city-style outfit to get me in the mood of sailing life, while at the same time making me feel casually glam when strolling the shopping streets and the long strip with the marina on one side and a line-up of cafes and tavernas on the other.
Second stop:
The bay of Volos is huge and looks like an enormous ring shielded by land from all sides, which meant we needed to anchor in a quiet bay near Milina port on the mainland before actually reaching the first and most popular island of the Sporades archipelago, Skiathos.
Since we were a flotilla of five vessels including a “party catamaran”, the plan was to raft up boats next to each other so we could have a welcome party. Sailors know that this rendezvous with friends could be a tricky maneuver that requires excellent skippers and crew to position, anchor, and tie the boats together.
Based on my substantial style experience, I chose a sporty outfit in neon colors for the first section of the trip to feel comfy and available for fixing fenders, mixing drinks, and/or pulling ropes. 😊
Third stop:
Skiathos town is absolutely beautiful because it combines buzzing waterfront bars and tavernas, vibrant pedestrian cobbled streets with cute boutiques and local delis, archaeological sites, and the best sandy beaches in Greece to top it all off.
Needless to say, as soon as we moored the boat on the pier, we eagerly plunged into exploring the timeless beauty of Bourtzi peninsula with the small Venetian Castle, enjoyed the sunset by the Agios Nikolaos church on top of the main town, hit the shopping streets and ended in a taverna by the port before the cocktail bar. 🍹
Such social events certainly require the proper attire, so I sported a maxi knit dress and flat sandals that are perfect for climbing slopes in style. I forgot my straw hat but corrected the mistake right away when shopping for souvenirs. 👒
Fourth stop:
Getting into the rhythm of cruising life also entails some mental and physical prep-up because true sailors know that you practically marry your crew (yeah, that’s right, you all should be dancing to the same tune). 😊
On the next stop, we were literally planning to dance away the birthday of an all-important crew member, which of course demanded anchoring in a secluded bay on Skopelos island instead of in the main town (boat raft up and party all night, you know). 🥳
Naturally, I put on my party outfit and got this party started in style even before getting to the destination! As you might expect, the occasion called for dancing shoes, bright colors, and the mandatory outerwear for chilly evenings onboard.
Fifth stop:
Skopelos town is definitely worth visiting, but we decided to save the sea trip around the island and approached it on scooters from Neo Klima through magnificent pine forests and mountains opening glorious views of the coastline.
I decided to wear a printed silk set and platform sandals for browsing Skopelos town, which is truly fascinating with the whitewashed houses draped with bougainvillea flowers and clinging on a steep hill that overlooks the harbor. 🌺
On the next morning, we visited the Agios Ioannis Church, which is set atop an impossibly steep ridge and is more famous as the setting for the Mama Mia musical. The church is 100 meters above sea level with an astounding view from the terrace, but the climb was tricky and called for comfy shoes and breezy clothes to endure the workout and the heat.
Sixth stop:
Alonissos is a sustainable island and some of its areas are off-limits to help preserve the Mediterranean monk seal. Before going on the sailing trip, reports of seal attacks came to our attention and we decided to be extra careful when and if swimming in the vicinity. Unfortunately, the only seal we encountered had decided to lounge peacefully in the dinghy of our neighbors. 😁
We moored in the harbor village of Patitiri and took an exploratory stroll around the settlement in bold florals because as you know the right outfit helps you blend in the vivid environment flawlessly and graciously.
The main event, however, was our visit to the capital Chora on the next morning. It was ruined in an earthquake in 1965 and later rebuilt and revived with galleries, tavernas, and the quaint limestone houses with blue shutters.
We come across donkeys still used as the main mode of transporting supplies around the narrow streets. We enjoyed the amazing views from the top of the island in colorful sporty outfits to do justice to the vibrant environment.
Seventh stop:
After so much partying and sightseeing, it was time we head back to Skiathos and revel in a quiet candle-lit dinner tenderly cooked on our wonderful in-built boat grill.
We chose Maratha Beach to spend some quality time with the crew. We indulged in swimming, sunbathing, grilling, and lost ourselves in profoundly sweet conversations over delicious homemade food. As expected, the choice of attire was beach casual to honor the intimate occasion.
Final stop:
The final day of our trip delighted us with high winds. It offered an enjoyable sailing experience with around 30 degrees heeling all the way to Volos.
The crew was more than happy with the favorable wind conditions and we safely arrived at our final destination with the sea horizons reflected in our eyes and the beauty of the places we discovered imprinted in our hearts. 🌊⛵
Ultimately, I couldn’t help it, but sport a maxi floral dress for our final dinner in Volos to end the seafaring voyage on a high fashion note. 👗
For more ideas on how to combine summer outfits and how to pack efficiently, read our blog.
Make sure you follow our fashion adventures on social media.
