Sail in Greece – Santorini (30 May – 6 June 2026)

Description

For our Santorini trip, a member of our crew will take care of provisioning (shopping) and cooking for the group, meaning you’ll no longer need to organize meals collectively as on our usual self-catered trips.  This will give you more time to relax and enjoy the sites and camaraderie on board!

Starting Port City: Paros, Greece

Ending Port City: Paros, Greece

Planned Itinerary

(subject to change, for example due to weather)

Day 1: Saturday — Embarkation in Paros

Embarkation: After 17:00 at Parikia Marina.

• Welcome drinks and safety briefing as the Bare Waves Sailing crew introduces you to your yacht and the exciting Santorini and Cyclades gay sailing adventure ahead
• Evening exploration of Parikia’s charming old town featuring the iconic Panagia Ekatontapiliani church and traditional Cycladic architecture
• Sunset drinks at LGBTQ+ friendly waterfront bars while experiencing Paros’ famous golden hour views

Day 2: Sunday — Paros to Agia Anna, Naxos

• Morning sail to Naxos, the largest and most fertile island of the Cyclades, known for stunning beaches and ancient monuments
• Arrive at Agia Anna Beach, one of Greece’s most beautiful nude beaches with golden sand, crystal-clear waters, and LGBTQ+ friendly atmosphere
• Afternoon anchored near Agia Anna and Agios Prokopios beaches for nude sunbathing, swimming, and socializing with like-minded travelers

Day 3: Monday — Naxos to Amorgos

• Final morning swim at Agia Anna’s clothing-optional shores before departing for the dramatic island of Amorgos
• Afternoon visit to the breathtaking Monastery of Hozoviotissa built into a cliff face 300 meters above the sea
• Local taverna experience featuring authentic Amorgos cuisine and fresh seafood

Day 4: Tuesday — Amorgos to Santorini

• Morning choice between Agia Anna Beach or Kambi Beach on Amorgos for one last nude sunbathing opportunity on this dramatic island
• Sail to world-famous Santorini and anchor at Vlychada Marina, the island’s only proper protected harbor
• Evening exploration of Fira or Oia to experience the legendary Santorini sunset from the caldera edge

Day 5: Wednesday — Santorini Exploration & Night Sail to Ios

• Morning at Vlychada Beach with its dramatic white lunar cliffs and black sand, perfect for nude sunbathing in this unique “moon beach” setting
• Wine tasting at Venetsanos Winery near the marina with breathtaking caldera views and local varietals
• After lunch sail to Ammoudi Bay below Oia (7 nautical miles) for the world’s most famous sunset experience, then sunset sail to Mylopotas Beach, Ios

Day 6: Thursday — Ios Beach & Nightlife Day

• Full day at Mylopotas Beach, Ios’s main beach with lively atmosphere, nude-friendly sections, and proximity to Chora town
• Beach activities including water sports, nude sunbathing, and socializing at one of the Cyclades’ most vibrant beach scenes
• Evening exploration of Ios Chora’s charming alleyways followed by the island’s legendary nightlife scene with bars, clubs, and international party atmosphere

Day 7: Friday — Ios to Paros

• Strategic choice of final morning beach time at Mylopotas Beach or direct sail based on departure timing and weather conditions
• Return journey to Paros by 17:00, enjoying panoramic Cyclades views and reflecting on an incredible week of nude beaches and island adventures
• Farewell celebration dinner at a Parikia waterfront taverna with your new sailing family

Day 8: Saturday — Departure Day

Disembarkation: By 09:00 at Parikia Marina.

• Exchange contact info with your new besties
• Head out to explore the town, or head to the airport for your return journey home with a ton of new memories and connections

Total estimated distance: 123 nautical miles

What’s Included?

Included

Not Included

A fantastic sailboat charter for your entire trip All mooring/marina fees at embarkation and disembarkation ports An incredibly fun and welcoming atmosphere! Dinghy/tender with outboard motor (where available) Expert, qualified skipper(s) Fresh bedding, pillows, and towels Fuel for both sailboat and dinghy/tender Professional cleaning service after your journey Your cabin with selected occupancy Onboard catering

Entry visas or travel immunizations Costs for meals and drinks (we will use a kitty system, managed by our onboard caterer) – see more here Mooring/marina fees at ports of call Pre/post-trip accommodation Shore excursions or entertainment (unless specified as “ticket included” in your trip details) Travel to/from the marina (airfare, transfers, ground transportation) Trip cancellation and international medical insurance (we strongly recommend getting these through a third party)

Special Note About this Trip’s Catering

For this trip, we will still collect a kitty and ask each person to make an initial contribution of €350 upon arrival – we will either top it up along the way if we need, or we will refund any remaining balance at the end to everyone.  The caterer will also be the “minister of finance” and manage the kitty on this trip.  We’ll send a food & drink preferences questionnaire prior to the start of the trip, so we can ensure we stock up on items you like and take any dietary restrictions into consideration.

What’s paid out of the kitty:

• Meals on board (catered) and ashore (3 dinners planned at restaurants ashore*) + supplies for our trip (eg: cleaning items, trash bags, etc.)
• Beer, wine, spirits, water, juice, and soft drinks
• Marina fees for any visits along the way (Saturday and Friday nights in the “home” marina are already included in the trip cost)

What’s not included in the kitty:

• Shore excursions or entertainment
• Personal items not intended for the use of the whole group

Because this trip will now include catering provided by our crew after we had originally planned this as a passenger-provisioned trip, the passenger-provisioned and catered trip provisions in our Terms & Conditions will not apply. Instead, the arrangements outlined on this page will apply specifically to this voyage.

*We plan to enjoy three meals ashore during the trip. If the group prefers a lunch ashore instead of dinner, or if weather or harbor conditions require it, we may adjust the plan accordingly.