u/Kid-wolf

My girlfriend and I will be in Santorini for 4 nights in early October and are deciding between a semi-private sunset catamaran and renting a small self-drive boat from Ammoudi.

For anyone who's done either/both:

Which experience would you recommend?

How difficult is it to operate a small boat with zero boating experience?

Is it easy enough after the safety briefing, or would you recommend a captain?

Looking for a romantic, relaxed experience for two, not a party boat. Thanks!

My girlfriend and I will be in Santorini for 4 nights in early October and are deciding between a semi-private sunset catamaran and renting a small self-drive boat from Ammoudi.

For anyone who's done either/both:

Which experience would you recommend?

How difficult is it to operate a small boat with zero boating experience?

Is it easy enough after the safety briefing, or would you recommend a captain?

Looking for a romantic, relaxed experience for two, not a party boat. Thanks!

My girlfriend and I will be in Santorini for 4 nights (7–11 October). For those who have visited around this time:

How is Santorini in early October in terms of crowds, restaurants and overall atmosphere? Does it still like everything is still open and enjoyable, or are things starting to close?

Also, is a sunset catamaran cruise worth doing in our case?

A few days earlier we'll be doing a full day Kleftiko boat tour in Milos, and in Santorini we're staying in Imerovigli with a private Caldera view accommodation with an outdoor hot tub.

Would you still do the sunset cruise, or would you skip it and spend that time exploring Oia and maybe doing a sunset wine tour or doing something else all together in the Oia region? We've earmarked an entire day for Oia.

Would especially love to hear from anyone who's done both Kleftiko in Milos and a Santorini sunset cruise.

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My girlfriend and I will be in Santorini for 4 nights (7–11 October). For those who have visited around this time:

How is Santorini in early October in terms of crowds, restaurants and overall atmosphere? Does it still like everything is still open and enjoyable, or are things starting to close?

Also, is a sunset catamaran cruise worth doing in our case?

A few days earlier we'll be doing a full day Kleftiko boat tour in Milos, and in Santorini we're staying in Imerovigli with a private Caldera view accommodation with an outdoor hot tub.

Would you still do the sunset cruise, or would you skip it and spend that time exploring Oia and maybe doing a sunset wine tour or doing something else all together in the Oia region? We've earmarked an entire day for Oia.

Would especially love to hear from anyone who's done both Kleftiko in Milos and a Santorini sunset cruise.

I’ll be in Greece in October and am deciding between:

FLIGHT: Olympic Air: Athens 7:20 AM to Milos 8:00 AM

FERRY: Athens 7:40 AM to Milos 11:10 AM

I’ll have 3 nights in Milos, followed by 4 nights in Santorini, with a ferry from Milos to Santorini already planned.

My Milos itinerary is fairly relaxed, so I don't necessarily need the extra 3 hours, but it would make my first day in Milos a lot more relaxed. However, I'm wondering whether the ferry experience itself is worth choosing over the flight: Aegean views, sitting on deck, arriving at Milos by sea, etc.

For those who've done both: would you take the flight or ferry in this situation, and why?

I’m traveling to Greece in early October and will be spending time in both Milos and Santorini. I’m planning to propose to my girlfriend in either of the two places and I’m currently torn between two options:

•Skaros Rock / the Skaros trail in Santorini at sunset

•Sarakiniko in Milos, potentially around sunrise

I’m looking for a stunning, dramatic backdrop and ideally somewhere that doesn't feel extremely crowded. The actual proposal would be private, with just a photographer and no decorations or setup.

For those who have been to both, which would you choose for a proposal? Would love to hear from anyone who has actually proposed or had engagement photos taken at either location.

Are there any other locations in either Milos or Santorini that beat the above options?