If you’re planning a Greece trip and trying to figure out how many days in Santorini you actually need, this is the exact itinerary we’re using for our trip in June.
Our 4-day Santorini itinerary is built around views, slower mornings, a little beach exploring, a wine tour, and a few really special dinners.
Santorini is definitely one of the most popular stops in Greece, so for our first Greece trip, we wanted to include it. This stops helps add a little more of the wow factor with caldera views, Oia, and romantic sunset dinners!
If you want a mix of iconic spots, pool time, good food, and a schedule that still leaves room to relax, this is the route I’d follow.
Why Santorini Is Worth Adding to Your Greece Trip
Santorini is probably the most famous island on a Greece itinerary, and I get why.
It’s less focused on beach days and more about:
- Staying somewhere with a view
- Walking through cliffside towns
- Budgeting for some nicer dinners
- Making time for sunsets
What stood out to me most while planning:
- Most romantic stop on the trip
- One of the best islands for views
- Perfect for a wine tour or catamaran day
- Very different from Milos, Paros, and other Greek islands
It’s definitely more polished and more expensive, but for a few nights, that’s kind of the point!
Where to Stay in Santorini
We’re staying in Imerovigli at Nefeli Homes Adults Only Hotel.
Imerovigli seems like the best middle ground if you want the caldera views without staying directly in Oia, which can often feel overcrowded. Close enough to both the larger cities of Oia and Fira but it is still quieter, more romantic, and less chaotic.
For Santorini specifically, I would not want to stay somewhere just because it’s cheaper if it means giving up the view or location completely. This is one of the islands where your hotel matters more than usual.
I landed on Nefeli Homes after a lot of research for the best balance of price and experience. We booked the Senior Double Room (Cave) because it had that Santorini cave look, a gorgeous caldera view from the balcony, and a private tub as well.
Nefeli Homes- Adults Only hotel in Imerovigli.
Day 1: Arrival + Easy First Night
The first day is intentionally simple.
We’ll be coming from Milos by ferry, so the goal is just to check in, settle in, and not over plan the first afternoon.
Plan:
- Check out in Milos
- Grab a casual brunch
- Ferry from Milos to Santorini (Arrive around 2:15 pm)
- Private transfer to Imerovigli by Welcome Pickups
- The port area is busy, crowded, and not the place I’d want to be trying to figure out a ride after getting off the ferry. For this part of the trip, I’d rather have a transfer booked ahead of time and keep the arrival day easy. We are renting a car for a few days, but I had seen that pickups at the port and the winding drive on the narrow road to/from the port could be stressful.
- Pool time + decompress
- Dinner nearby
We have a 7:00 PM dinner reservation at Aegean, which is only about a 3-minute walk from the hotel.
This is perfect for the first night because we won’t need to deal with driving, taxis, or trying to squeeze in too much right away.
After dinner, I will be keeping it easy with drinks on our own private balcony.
Day 2: Beach Hopping + Oia Dinner
This is our main Santorini exploring day with a rental car.
Santorini is not really known for beaches the way Milos is, but I still wanted to see a few of the unique ones since they are so different from what we’ll see on the other islands.
Must-stop spots:
- Perissa Beach
- Black sand beach
- Good early in the morning before it gets too crowded
- Vlychada Beach
- More relaxed and known for the unique cliffs
- Red Beach
- One of the most recognizable spots in Santorini
The biggest thing here is not trying to make this feel like a Milos beach day. Santorini’s beaches are more of a “see them, enjoy them, then move on” rather than places I’d build the entire trip around.
After the beach stops, we’ll head back to the hotel to shower and relax before dinner.
Dinner plan: Ambrosia in Oia at 8:30 PM.
Day 3: Oia Morning + Ammoudi Lunch + Wine Tour
This is probably the day I’m most excited about outside of our anniversary day.
We’re planning to start in Oia early, which seems like the best way to actually enjoy it before it gets too crowded.
Plan:
- Breakfast at Kookoo Bar
- Explore Oia early
- Walk around, shop, and take photos
- Lunch at Ammoudi Fish Tavern
- Return to the hotel to reset and enjoy pool
- Wine tour excursion with dinner and sunset:
Oia is obviously one of the main reasons people go to Santorini, but I do not want to experience it only during the most chaotic sunset window.
That’s why we’re doing it in the morning instead.
For lunch, we have a 12:30 PM reservation at Ammoudi Fish Tavern.
This felt like a good way to experience Ammoudi Bay without trying to combine it with sunset crowds.
After lunch, we’ll head back to the hotel for a quick reset before the wine tour.
Evening plan: 4:00 PM wine tour with dinner and sunset.
This is one of the things I’d book ahead for Santorini. Between the wineries, dinner, and sunset, it feels like a really easy way to enjoy the island without having to plan every detail ourselves.
Add here: link to the exact wine tour once you know which one you want to promote or reference.
Day 4: Anniversary Day
This is our anniversary day, so we’re keeping the plan special but not overly complicated.
The main daytime activity is a catamaran cruise, then we’ll have a slower afternoon before our nice dinner reservation.
Plan:
- 9:30 AM pickup for catamaran cruise
- 5-hour cruise with included food + drinks
- Return to hotel to relax + reset
- Anniversary dinner
This felt like the best way to make the day feel memorable without running around the island all day.
The catamaran cruise gives us the water views and a more fun daytime plan, but we still have time to come back, shower, relax, and not feel rushed before dinner.
Dinner plan: The Athenian House at 7:30 PM.
This is only about a 4-minute walk from the hotel, which is exactly what I wanted for the anniversary dinner.
No long drive. No stressful taxi situation. Just a nice dinner close to where we’re staying.
For this day especially, I’m glad we’re staying in Imerovigli.
Final Morning: Keep It Simple
Our ferry to Paros does not leave until 2:15 PM, so we don’t need to rush out super early.
That said, I still wouldn’t try to cram in a big activity here.
Plan:
- Pack up
- Check out and transfer to the ferry port
- Ferry from Santorini to Paros!
Santorini’s port can be chaotic, so this is one of those days where I’d rather be early and relaxed than trying to squeeze in one more thing.
What I’d Prioritize Most
If you only have a few days in Santorini, this is what I’d focus on:
- Stay somewhere with a view
- Explore Oia early instead of only going at sunset
- Do one bucket list dinner with caldera views
- Book ALL your dinner reservations in advance to avoid waiting for hours at dinner time
- Book a wine tour if you want an easy sunset plan
- Do a catamaran cruise if you want a true Santorini water day
- Leave time for hotel/pool
Santorini feels like the kind of island where you do not want every hour scheduled.
The views and slower moments are a big part of the experience!
Quick Take
Santorini is definitely more expensive and more touristy than some of the other islands on our itinerary, but I still think it’s worth including.
For us, it’s the romantic part of the trip.
Milos is more about beaches and adventure. Paros is more about relaxed island time. Santorini is where we wanted the views, the nicer dinners, the wine tour, and the anniversary feel.
I don’t think you need a full week here, but I do think 3–4 nights is a really good amount of time if you plan it intentionally.
If you’re building out a Greece itinerary, I’d recommend adding Santorini but just make sure you balance it with islands that feel a little more relaxed too.
I go into more detail on our overall Greece itinerary below:
14 Days in Greece: Island-Hopping Milos, Santorini, Paros, and Athens
How to Fly to Greece Using Points (Step by Step Guide)
Milos Greece: 4 Days of Beaches, Boat Tours, & Travel Tips
3 Days in Paros: Beaches, Naousa & Everything Worth Knowing
I’ll Update This After the Trip
We’re heading here soon, so I’ll come back and update this with:
what’s worth skipping
what actually worked
what I’d change
and whether Santorini felt worth the hype.
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