
Private Sailing & Wine Tasting on a Sailboat with a Sommelier
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Quick answer
Is Private Sailing & Wine Tasting on a Sailboat with a Sommelier worth booking?
Private Sailing & Wine Tasting on a Sailboat with a Sommelier is a 5-hour experience in Santorini, Greece, from $858 per person. It scores 45 out of 100 on the Outty Ranking, which we label “Worth a Look”. Cancellation is free up to 24 hours before the start time. Same-day spots are currently showing.
- Outty Ranking
- 45 / 100
- Rating
- Not yet rated
- Duration
- 5 hours
- From
- $858 per person
Experience a one-of-a-kind Santorini sailing tour while sipping some of the island's best wines! Learn about Santorini wines while tasting 6 glasses of different Santorini wines such as Assyrtiko, Nychteri, Vinsanto, and others while sailing through the unique caldera! Choose between a daytime and a sunset cruise. Transfers, drinks and meals are included.
What you get
About this experience
Experience a one-of-a-kind Santorini sailing tour while sipping some of the island's best wines! Learn about Santorini wines while tasting 6 glasses of different Santorini wines such as Assyrtiko, Nychteri, Vinsanto, and others while sailing through the unique caldera! Choose between a daytime and a sunset cruise. Transfers, drinks and meals are included.
What's included
Included
- Towels & Jackets (to be returned to the crew)
- Hotel pickup and drop-off
- Free Wi-Fi on board
- Drinks & Beverages
- Towels and jackets (to be returned after use)
- All Fees and Taxes
- English-speaking certified wine guide/sommelier by WSET
- Use of snorkeling equipment
- Dinner
- Private Sailing cruise on a 44-ft sail boat
- Wine tasting of 6-glasses of Santorini wine
Not included
- Personal expenses
- Gratuities (optional)
What you'll see and do
Vlychada
Time to get onboard and get prepared for our private 5-hour cruise departure from the Vlychada Marina.
15 minutes here
Red Beach
Passing by the most popular beach of the island of Santorini, where you will briefly make a stop to take some pictures of this unique, beautiful and colorful volcanic landscape from the water.
15 minutes here
White Beach
Over passing the beautiful and only accessible by boat white beach, a stunning creation of the massive volcanic eruptions.
On our way you will be able to witness the naturally sculpted on a black rock Indian’s face, before we enter the caldera of Santorini where the picturesque lighthouse is on the top of the cliff on the right. On the left, witness the remaining of an eruption, an island consisting of pumice, the island of Aspronisi.
30 minutes here
Santorini Volcano
This is the time where our sailboat passes between the two volcanoes (Palaia & Nea Kameni) and approaches the sulfuric warm water of the hot springs (warm springs). ps. we do not usually stop there to swim since it is overcrowded and the sulfur can destroy your bathing suit. Moreover, we do not go on the volcano, but we go on the cruise.
Thirassia
Finally you can swim at the calm and crystal clear waters of Thirassia island and enjoy your tasteful meal cooked on board for you having the chance to marvel at the eastward view of the caldera. This will be the time to witness the wonderful Santorini sunset on board.
90 minutes here
Vlychada
After the beautiful sunset, we will head back to the Marina of Vlychada, where your transfer will be waiting for you to drive you back to the same spot you were picked up.
30 minutes here
Santorini
Travel time between attractions is included, however the total tour duration with pickup/drop off will be about 6 hours. * Most of the wine tasting will take place in Thirassia, for safety reasons, however you will have already enjoyed our first 2 wines until we get there. * The tasting includes dry whites, a rose, a dry red & the famous desert Santorini wine (Vinsanto) * Opt for sunset cruise to marvel the sunset on board
120 minutes here
Where it starts and ends
Hotel pickup
Pickup is included for all travelers. Pickup begins about 5 minutes before departure.
Before you book
- Cancellation
- For a full refund, cancel at least 24 hours before the scheduled departure time.
- Languages
- en
- Ticket
- Mobile Only
- Runs on
- Every day
- Group size
- Up to 8 travelers per booking
- Operated by
- Santorini i-Land Tours
Know before you go
- Specialized infant seats are available
- Not recommended for travelers with poor cardiovascular health
- Not recommended for pregnant travelers
- Public transportation options are available nearby
- Suitable for all physical fitness levels
- Travel time between attractions are included in the total tour duration.
- Individuals under the age of 18 are not allowed to consume alcohol under Greek law.
Photos






Good to know
- Duration
- 5 hours
- Free cancellation
- Up to 24h before
- Minimum age to book
- All ages
- Availability
- Bookable today
- Runs on
- Every day
- Price range
- $858 to $1,450
- Hotel pickup
- Included for all travelers
- Booked in 30 days
- 0
- Verdict
- Worth a Look
Who runs this experience
Operated by Santorini i-Land Tours, who run 11 experiences we rank across 2 cities, with an average Outty Ranking of 52.7.
See everything Santorini i-Land Tours runsWhy this scores 45
The Outty Ranking is a weighted composite. Here is how this experience performed on each component.
Private Sailing & Wine Tasting on a Sailboat with a Sommelier: questions travelers ask
Practical detail on this experience, plus the wider planning questions for Santorini.
How much does Private Sailing & Wine Tasting on a Sailboat with a Sommelier cost?
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Prices start at $858 per person. The final price depends on the date, the time slot and the number of travelers, and peak weekends in Santorini usually price higher than midweek mornings. Live pricing and remaining availability are confirmed on the booking screen before you pay.
How long does Private Sailing & Wine Tasting on a Sailboat with a Sommelier take?
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Plan for about 5 hours from start to finish, not counting travel to the meeting point. Most travelers leave another 30 minutes on either side so the rest of the day in Santorini is not rushed.
Is Private Sailing & Wine Tasting on a Sailboat with a Sommelier worth it?
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It holds an Outty Ranking of 45 out of 100, which we label "Worth a Look". That score blends traveler sentiment (0/5 across 0 reviews), the depth of that review evidence, recent booking momentum, value for money against comparable last minute in Santorini, and how flexible the cancellation terms are.
Can I cancel or reschedule Private Sailing & Wine Tasting on a Sailboat with a Sommelier?
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Yes. Cancel free up to 24 hours before the start time for a full refund. Inside that window the booking is non-refundable, and no-shows are not refunded.
Is Private Sailing & Wine Tasting on a Sailboat with a Sommelier suitable for kids and families?
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Yes, all ages are welcome. Families should still weigh the 5-hour running time, and strollers are easier on the earlier, quieter departures.
How far in advance should I book Private Sailing & Wine Tasting on a Sailboat with a Sommelier?
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Around 0 people booked this in the last 30 days, so popular slots go early. Two to three weeks ahead is comfortable in shoulder season, while summer weekends and holidays in Santorini can sell out a month out. Same-day spots do open up when other travelers cancel, so it is worth checking if you are already in town.
What should I bring or wear?
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Bring photo ID, your booking confirmation on your phone, a refillable water bottle and comfortable shoes. Dress for the weather in Santorini and add a light layer if any part of the 5-hour experience runs outdoors or after sunset.
Where does Private Sailing & Wine Tasting on a Sailboat with a Sommelier start and how do I get there?
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The exact meeting point and directions are on your voucher once you book, and they sit in central Santorini within reach of public transport. Arrive 15 minutes early: late arrivals are treated as no-shows by most operators.
What are the best things to do in Santorini?
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On Outty we rank every Santorini experience on the same 0 to 100 scale, and alongside this one the highest scorers right now include Half Day Premium Catamaran Cruise in Santorini including Oia, Private Santorini Tailor Made - Choice of the Guest!, Private Tailor-Made Santorini Land Tour with a Local Driver. The city page groups everything into most popular, highest reviewed, last minute and family-friendly so you can build a day around what actually delivers.
When is the best time to visit Santorini?
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Booking patterns follow the same curve: prices and queues climb in peak weeks, while shoulder season gives you better availability on the top-ranked experiences and more room to change plans.
How many days do you need in Santorini?
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Three full days covers the headline sights without sprinting. A workable rhythm is one anchor experience each morning, such as this one, an unhurried afternoon in a single neighborhood, then a food or nightlife booking in the evening. Five days lets you add a day trip outside the city.
Do I book through Outty or through the operator?
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Outty ranks and explains the experiences, then hands you to Viator to complete the booking with the operator directly. The price is the same as booking on Viator yourself, and Outty earns an affiliate commission on the referral, which is how the rankings stay free to read.
What is included in Private Sailing & Wine Tasting on a Sailboat with a Sommelier?
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Included: Towels & Jackets (to be returned to the crew); Hotel pickup and drop-off; Free Wi-Fi on board; Drinks & Beverages; and Towels and jackets (to be returned after use). Not included: Personal expenses; and Gratuities (optional). Always check the voucher for the final list before you travel.
Does Private Sailing & Wine Tasting on a Sailboat with a Sommelier include hotel pickup?
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Yes, pickup is offered for every traveler from 439 listed pickup locations in and around Santorini. Be ready about 5 minutes before the start time.
What languages is Private Sailing & Wine Tasting on a Sailboat with a Sommelier offered in?
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It runs in English. Pick your language when choosing a date and time, as not every departure runs in every language.
Will I get instant confirmation and a mobile ticket for Private Sailing & Wine Tasting on a Sailboat with a Sommelier?
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Confirmation is sent by the operator after booking, usually within 48 hours; if it is not confirmed you are not charged. Mobile tickets are accepted, so you can show the voucher on your phone.
Is Private Sailing & Wine Tasting on a Sailboat with a Sommelier wheelchair or stroller accessible?
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The operator notes: Specialized infant seats are available; and Not recommended for pregnant travelers. If accessibility is critical, contact the operator after booking to confirm arrangements for your date.
What happens to Private Sailing & Wine Tasting on a Sailboat with a Sommelier if the weather is bad?
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This experience depends on good weather. If it is canceled because of poor weather, you are offered a different date or a full refund.
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