The Ultimate Santorini, Greece 5 Day Itinerary & Travel Guide

Published: May 4, 2025

Planning a trip to Santorini? With its whitewashed buildings, stunning sunsets, and dramatic caldera views, this Greek island is a must-visit destination. Whether it’s your first time or a return trip, five days is the sweet spot to soak up the best of Santorini—without feeling rushed. From charming villages to black sand beaches, volcano adventures to wine tasting, here’s the ultimate 5-day itinerary to help you make the most of your time on this iconic Greek island.

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How To Get To Santorini

By Air: Santorini (Thira) Airport (JTR)

Santorini has the largest airport of all the Greek islands, offering direct flights both within Greece and to several major cities across Europe. We were able to fly direct from Santorini to Naples, Italy–super easy! Flying is definitely the quickest and most convenient way to get to (and from) Santorini. Click here to search flights to Santorini.

By Ferry: Port of Athinios

Multiple ferries arrive and depart from Santorini every day, connecting the island with Athens and several other Greek islands. If you’re planning to do some island hopping, chances are you’ll be traveling by ferry, since many Greek islands don’t have airports. Ferryhopper is the best site for checking schedules and booking your ferry tickets–it’s super easy to use. Click here to search the ferry schedules.

One thing to keep in mind: ferries are more affected by weather conditions. Strong winds can sometimes cause delays or cancellations, whereas flights are generally more reliable.

On our recent Greek island adventure, we flew from the U.S. into Athens, then hopped on a quick flight to Milos. After spending five amazing days exploring Milos, we caught a ferry to Santorini, stayed there for a week, and then flew directly from Santorini to Naples, Italy. It was such a fun and easy way to experience multiple islands!

Getting Around: Should You Rent a Car In Santorini?

Deciding whether or not to rent a car in Santorini was something that my husband and I debated for quite a while. In the end, we chose to rent one–but honestly, our car spent more time sitting in the parking than actually being used! Other than driving from the ferry port to our hotel, we only used it a handful of times: once to get to the port of Akrotiri to catch the water taxi, once to visit Kamari Beach and once for a day trip to the villages of Megalochori and Pyrgos. There were several days that the car sat completely unused. Looking back, we easily could have taken taxis or buses to those places, and if I had to do it over again, I probably wouldn’t bother renting a car.

Another thing to think about is parking. We stayed in Imerovigli, and although our hotel didn’t offer private parking, we had no problem finding street parking nearby. But if you are staying in one of the busier towns like Fira or Oia, parking could be a real challenge. In that case, you might be better off sticking to taxis, buses or even renting an ATV for a few days of exploring.

We booked our rental car through Discovercars.com, which made it super easy to compare prices across different rental companies on the island. Our rental company delivered our car directly to the ferry port.

Transportation From Airport or Ferry Port

If you decide not to rent a car, you will need transportation from the airport or ferry terminal to your hotel. You can take a bus, taxi or private transportation. The bus is the cheapest option, but the lines for the buses can be long and you may have to wait awhile if you can’t make it on the first bus. There will be taxis waiting outside but, again, you may. not be able to get one right away. We found that private transportation was the most reliable option. Click here to book private airport or ferry transfers.

Where to Stay in Santorini

The Caldera or The Beaches?

To determine where to stay on the island, the first big choice is whether you want to be on the Caldera side or the beach side of the island.

The Caldera is the iconic part of Santorini — the famous white washed buildings and blue domed churches perched on top of the cliffs overlooking the Aegean Sea. It’s exactly the scene that comes to mind when you picture Santorini. Located on the western side of the island, the Caldera is where you’ll catch those incredible sunsets — and where most of the action (and most of the crowds) are.

On the flip side, the eastern side of the island is where the beaches are located. This area is much quieter and more relaxed than the Caldera. You’ll still find plenty of seaside restaurants and hotels, but with a much more laid-back vibe. If you’re hoping to escape the crowds and enjoy a slower pace, the beach side could be a perfect spot. Just keep in mind–the eastern side of the island gets the morning sunrise, but not the famous Santorini sunsets.

Where To Stay On The Caldera

If you choose to stay on the Caldera side of the island, these are the towns you will choose from:

Fira

Fira is the capital of Santorini and home to the main cruise port. It is also known to have the best night life on the island, with plenty of bars, restaurants and late-night spots to explore. Because it’s such a popular hub, it can get pretty crowded, especially when the cruise ships are in port.

If you want to stay in Fira, Athina Luxury Suites, Astro Palace & Suites, and Enigma Suites are highly rated hotels with sunset views.

Firostefani

Just a short walk from Fira, Firostefani has the same stunning Caldera views, sunsets and iconic blue domes– but with a much quieter, more relaxed atmosphere. You’ll still be close to the action without dealing with the heavy crowds or nightlife scene. If you’re looking for a peaceful place to stay with postcard-worthy views, Dana Villas & Infinity Suites, Reverie Santorini and Blue Dolphin Apartments and Suites are some of the top picks in Firostefani.

Imerovigli

Imerovigli (pronounced ih-mere-o-vee-lee) is my personal favorite place to stay in Santorini! Located next to Firostefani, it’s a short, scenic walk to Fira and a perfect mid-point if you’re planning to hike to Oia. Like Firostefani, Imerovigli offers the same jaw-dropping views, stunning sunsets and blue-domed churches– but without the big crowds you’ll find in Fira or Oia. The vibe here is much more relaxed and laid-back, with no busy nightlife scene to worry about. Plus, Imerovigli is home to some of the best sunset-view restaurants on the island. If you’re looking for amazing places to stay, check out Above Blue Suites (where we stayed and loved!), Aqua Luxury Suites, Remezzo Villas and Absolute Bliss— all fantastic choices with incredible sunset views.

Oia

Oia (pronounced EE-UH) is the most famous (and photographed) town in Santorini, known for its cluster pf blue-domed churches and iconic sunset views. It’s also the most crowded and the most expensive of the four Caldera towns. Like Fira, Oia has a lively nightlife scene, but it definitely leans into its Instagram-worthy reputation–you’ll often see lines of people waiting to do photo shoots in front of the famous photo hot spots. It has a total “see and be seen” kind of vibe, with people dressed to the nines. There are also a lot of high end shops and boutiques in Oia. Oia is home to some of Santorini’s most luxurious cave hotels. If you’re looking for a place to stay in Oia, Art Maisons Hotel, Andronis Arcadia, and Sol D’Oro Luxury Suites are all highly rated options.

My Recommendation For Where To Stay On The Caldera

If you want to stay on the Caldera side of Santorini, I highly recommend staying in either Imerovigli or Firostefani. Fira and Oia are beautiful, but they’re also extremely crowded. You can (and should!) still visit those towns but if you want a relaxing and peaceful place to stay –and don’t want crowds of tourists walking past you on your hotel patio, Imerovigli and Firostefani are your best bets.

If nightlife is a big part of your plans, I would suggest staying in Fira rather than Oia. Fira tends to be slightly less crowded and you’re less likely to find yourself waiting in long lines to take photos there. If you stay in Firostefani or Imerovigli, you’re just a short, easy walk into Fira–perfect for enjoying the nightlife without staying in the middle of it.

Most importantly, no matter which village you choose, I highly recommend booking a sunset view hotel on the Caldera. Not all Caldera hotels have direct sunset views, (it all depends on how the property is positioned), so definitely double-check the reviews and look for guest photos of the sunset. Having your own private sunset view from your balcony is honestly priceless–and totally worth the extra cost to avoid the sunset crowds.

Where To Stay In The Beaches of Santorini

If you’re dreaming of a relaxing beachfront vacation, the beach side of Santorini is a great choice. Unlike the caldera towns perched high above the cliffs, the beach towns like Kamari, Perissa, and Perivolos offer a totally different vibe — relaxed, fun, and perfect for those who want to spend their days sunbathing and swimming. These areas are much flatter and easier to walk around, plus you’ll find everything from beachfront hotels to restaurants just steps from the water.

In Kamari, check out Sandblu Hotel, Amara Suites and Strogili Adults Only Hotel. In Perissa, Aqua Blue Hotel, Spiros & Hiroko Hotel and Santo Mangata Boutique Hotel are all gorgeous options with pools and beach access. Istoria Hotel in Perivolos is a romantic, boutique stay with a stunning design — ideal for couples.

If you want a romantic getaway without the crowds–the beaches would be a great fit! These beach towns are more budget-friendly than the Caldera villages and offer easy access to restaurants, beach clubs, and even water taxis to the caldera if you want to explore both sides of the island!

5 Day Santorini Itinerary

Now that we have covered how to get to Santorini and where to stay, let’s dive into the ultimate five day Santorini itinerary!

Itinerary Modifications

For this itinerary, we’ll assume you’re staying in Imerovigli. If you’re staying in a different town, you may need to adjust the plan slightly. Another tip: I highly recommend checking the Santorini cruise port schedule for the dates you’ll be visiting to see how many ships are in port each day. Adjust your itinerary to avoid visiting the Caldera side of the island (particularly the towns of Fira and Oia) on days with the most cruise ships to steer clear of the biggest crowds. Be sure to check out my post on How To Avoid Crowds in Santorini for more info on this.

Day 1: Arrival & Megalochori

The first day will likely only be a half day due to travel and since you’ll probably be feeling a little exhausted, I have the perfect relaxing afternoon planned! After arriving on the island, pick up your rental car (if you chose to rent a car) and check in to your accommodations.

Explore the Village of Megalochori

Megalochori is one of Santorini’s most charming and authentic Greek villages and is the perfect way to spend a half day in Santorini after a long day of travel! Tucked away from the crowded tourist towns and with its narrow, winding alleys, traditional whitewash houses and beautiful bell towers, you will feel like you are stepping back in time. Spend your leisurely afternoon wandering the streets and courtyards. You will find plenty of cafes and tavernas to grab a bite after your travel day.

For history buffs, you can visit the Lost Atlantis Experience in Megalochori, which is a digital interactive experience.

While in Megalochori, check out the Heart of Santorini which is a heart shape cut out of a rock overlooking the sea. The Heart of Santorini is located on a short trail off of the main road near Venetesanos Winery, and is a great spot to watch the sunset!

Don’t miss a visit to local wineries in Megalochori like Venetesanos Winery and Gavalas Winery where you can sample some of the island’s best wines. Be sure to toast to the first of five fabulous days in Santorini!

Dinner Night 1: Raki Santorini is a great dinner option in Megalochori or check out my recommendations for the Best Sunset View Restaurants in Santorini.

Day 2: Imerovigli to Fira & Sunset Catamaran Cruise

Walk from Imerovigli to Fira

You’ve probably heard about the famous Fira to Oia hike–and yes, it’s every bit as breathtaking as everyone says! (Both by scenery and by exertion!). The full trail stretches 6.5 miles along the Caldera cliffs, taking anywhere from 3 to 4 hours depending on your pace (and how many photo stops you make–trust me, you’ll want a lot!). It’s definitely one of the best ways to get to see all of the epic Caldera views, but it can be a lot to tackle all at once.

Here’s where staying in Imerovigli comes in handy. Since Imerovigli is between Fira and Oia, you can actually break the hike up into two way more relaxed and enjoyable parts. One day, you can do the easy 1.5 mile, mostly downhill walk from Imerovigli to Fira (only about 30-40 minutes), soaking in the gorgeous views without overexerting yourself. Then on another day, you can take on the longer, more adventurous 5 mile hike from Imerovigli to Oia, which is much more doable!

So for day 2, we are going to do the easier of the two parts of the hike from Imerovigli to Fira, which is one of the most beautiful and scenic walks you can take in Santorini. The walk will take you about 30 minutes at a relaxed pace, winding along the edge of the Caldera with breathtaking views of the Aegean Sea the entire way. Along the path, you’ll pass charming blue domed churches and endless photo opportunities of the iconic whitewashed buildings against the deep blue water. It’s a mostly paved, gentle path that’s easy to navigate, but you will still want to wear comfortable shoes and bring a bottle of water if it’s hot.

Once you arrive in Fira, you can explore the many shops in the town center and grab lunch or brunch at Tholoto. After lunch you can either walk or take a taxi back to your hotel in Imerovigli.

Sunset Catamaran Cruise (Volcano & Hot Springs)

For the afternoon and evening of day 2, we’ll book this Sunset Catamaran Cruise that sails past the volcano and Thirassia Island, with a stop for a swim in the Hot Springs and ends with the most epic sunset at sea, complete with a sunset champagne toast! We absolutely loved this tour. The crew was amazing–super friendly and knowledgable–and they kept our glasses and our bellies full. They even prepared a separate gluten free meal for me! It was incredible!

Our pickup was right at the Imerovigli bus stop around 4:00 pm, but you’ll get a confirmation email with your exact pickup time and details. We rode in a comfy sprinter van, picked up a few more passengers along the way before arriving at the dock of Vlychada. The boat holds about 20 people total, and there is an open bar throughout the cruise with wine, beer, soda and water. Prosecco is served with the sunset.

The hot springs weren’t actually hot–they were mild. It is important to wear a black or dark colored bathing suit for swimming in the hot springs–the sulphur will turn lighter colors yellow.

Dinner is served onboard, and you’ll be dropped back off at the same place you were picked up, usually around 9:00 pm.

Bring a lightweight jacket, as it can get cool after the sunsets on the water. Also bring cash to tip your crew!

Day 3: Hike from Imerovigli to Oia & Kamari Beach

Hike From Imerovigli to Oia

Day 3 kicks off with the epic hike from Imerovigli to Oia. You will want to get an early start for this hike since there’s very little shade along the trail. Ideally, plan to reach Oia around lunchtime to avoid hiking during the hottest part of the day. The hike is about 5 miles and takes around 3 hours–though you’ll probably stop often to snap photos of the jaw-dropping views along the way.

Unlike the easy walk from Imerovigli to Fira on day 2, this is a real hike. There are stretches of dirt and gravel paths, so make sure to wear sneakers and comfortable athletic clothes. (I wore a tennis dress with built-in bike shorts and sneakers–it was perfect!) Most importantly, pack plenty of water. There aren’t many spots to grab a drink along the trail. Don’t forget sunscreen and a hat (bonus for a hat strap–it can get pretty windy!)

If you want to look more polished for photos once you get to Oia, toss a change of clothes into your backpack and do a quick outfit swap when you arrive.

Explore Oia-Santorini’s Most Famous Town

After arriving in Oia, stop for lunch or brunch at Kookoo Bar Restaurant Rooftop, then spend a couple hours exploring Santorini’s most famous town. If you want to see Oia’s top photo spots, be aware that there are usually long lines (an hour or longer) to take pictures at these photo hotspots.

Amoudi Bay is just below Oia and has some great seafood restaurants.

Once you have finished exploring Oia, grab a taxi back to Imerovigli to get ready for an afternoon at the beach!

Kamari Beach

After your morning hike, you will be ready for some relaxation in the afternoon. Pack a beach bag with your snorkel mask, sunscreen, a beach towel and water shoes and head to Kamari Beach. Kamari is a charming beach town, lined with seaside restaurants and shops. The beach itself is full of sunbeds which you can rent or if you buy any food or drinks from the restaurants, they will let you use them for free.

The beach is rocky, so be sure to wear water shoes. Snorkel or float in the water, or just order cocktails on the sunbeds and relax for the rest of the afternoon.

Click here for restaurant recommendations in Kamari.

Day 4: Water Taxi To Red Beach, White Beach and Black Beach

For your fourth day in Santorini, spend the day beach hopping by water taxi. Drive or take a taxi to the port in Akrotiri. If you are driving, put Hotel Akrotiri into your GPS and it will take you to the parking for the port. The hop-on, hop-off water taxi costs 15 euros round trip and takes you to the Red Beach, White Beach and Black Beach. The boats come to the beaches every 30 minutes with the first boat departing from Akrotiri at 10:30am.

Pack cash for sunbed rentals, water shoes, snorkel masks, a towel and sunscreen.

Red Beach

The first stop on the water taxi is the Red Beach, one of Santorini’s most famous and unique beaches. There are no longer sunbeds at the Red Beach, so you will need to sit on a towel. The water taxi will return to this beach every 30 minutes, so whenever you are ready to move on to the next beach, just hop back on the water taxi.

White Beach

The second stop on the water taxi is the White Beach. Named for the towering white cliffs that surround it, the White Beach is only accessible by boat and is truly a unique and must-visit spot on Santorini. The water is crystal clear blue, which is striking against the white cliffs, and perfect for snorkeling. We spent most of our time at the White Beach snorkeling, so be sure to bring your masks. There are sunbeds for rent at the White Beach, but no food or restrooms.

The water taxi will come every 30 minutes, so when you are ready to move on to the next beach, just hop back on.

Black Beach

The last stop on the water taxi is the Black Beach. Like the name suggests, the sand at the black beach is formed from volcanic lava that has broken down into fine black pebbles. The Black Beach is the most organized of the three beaches. There is a restaurant, a bar, restrooms and many sunbeds available to rent.

The Black Beach has sea caves you can snorkel through. Enjoy a delicious lunch and some cocktails at the Black Beach before hopping back on the water taxi to head back to the port at Akrotiri.

Important Note

The water taxi only goes in order of the port of Akrotiri, Red Beach, White Beach, Black Beach, port of Akrotiri. So, you can’t go from the White Beach directly back to the port of Akrotiri, you will have to ride the water taxi to the next beach in order to go back to the port. It takes about 10 minutes to get from each beach on the water taxi.

Dinner at Athenian House

Make dinner reservations in advance for the best Caldera view restaurant in Santorini–Athenian House. Located in Imerovigli, Athenian House has delicious food and stunning sunset views.

Day 5: Perissa Beach and Sunset Wine Tour

Perissa Beach

If you’re looking for a beach day that’s easy, fun and super chill, Perissa Beach is the place to be. It’s one of the most popular beaches in Santorini, known for its soft black sand and gorgeous clear water. You’ll find tons of beach bars, restaurants, and sunbeds, so you can spend the whole day here without a worry. Whether you want to dive into the sea, try some water sports or just kick back with a cocktail in hand, Perissa has you covered.

Bring your water shoes, snorkel masks, sunscreen, towels and some cash!

Sunset Wine Tour

After your relaxing beach day, we will end day 5 with a Sunset Wine Tour. A wine tour is the ultimate way to wrap up your time in Santorini. After days of exploring whitewashed villages, lounging on colorful beaches, and eating way too much feta (no regrets), spending your final full day sipping wine and watching the sunset feels like pure magic.

We booked a small-group tour that hit three different wineries, each one with its own vibe and incredible views. The best part? You don’t have to worry about driving — they pick you up and drop you off, so you can fully relax and enjoy every last sip.

First stop: a cozy, family-run winery, Estate Argyros, where we got a crash course in Santorini’s wild, volcanic grape-growing style. (Fun fact: the vines are trained in little baskets to protect them from the island’s crazy winds!) We sampled Assyrtiko wines and even a sweet Vinsanto and learned that most of the wines made in Santorini are white.

Next we headed to a cave winery, and it honestly felt like stepping back in time. The tasting room was built right into the volcanic rock with rows of old barrels tucked into the walls. The vibe was cozy and rustic.

Finally, the grand finale — Santo Wines. We arrived just in time for sunset. They set us up with a beautiful wine flight and a table overlooking the Caldera cliffs, just as the sun started to set. I don’t think I’ve ever seen a sunset so ridiculously beautiful — and paired with a crisp glass of Assyrtiko, it was absolute perfection.

Honestly, ending our Santorini trip with a sunset wine tour felt like the perfect “cheers” to an amazing vacation. If you’re planning your itinerary, save this for your last full day — you’ll thank yourself later.

Pro Tip: Bring a light jacket (it cools down fast after sunset).

Click here to book your sunset wine tour!

Alternatives & Substitutions

There are so many things to do in Santorini that it is impossible to fit them all into five days! Here are some alternatives that you can substitute for any of the activities on our itinerary:

Volcano Tour

The sunset catamaran cruise we did on day 2 does not actually stop at the volcano itself. If you want to be able to walk out onto the volcano, consider this volcano tour.

Akrotiri Archaeological Site

History lovers will enjoy visiting the Akrotiri Archaeological Site and exploring the ruins.

Town of Pyrgos

The charming town of Pyrgos in Santorini is full of winding alleys, stone houses, blue-domed churches and flower covered balconies. It is stereotypical postcard Greece, but with a much more chill vibe than the Caldera!

Perivolos Beach

Perivolos Beach is another fabulous black sand beach in Santorini, with restaurants, bars and waterspouts options available.

Greek Wedding Show

If you’re looking for a unique and super fun night out, check out the Greek Wedding Show. It’s an interactive theater experience, where you actually become part of a traditional Greek wedding celebration. There’s singing, dancing, plate smashing (yes, really!), and lots of audience participation. You’ll get to taste local wine and maze during the show, too. It’s a mix of storytelling, live music and full-on Greek party vibes–perfect if you want something memorable and different from your typical dinner night.

Santorini Cooking Class

Take a cooking class inside a Santorini cave house!

Santorini Kayak Tours

Kayak tours in Santorini are very popular. The guided tours will take through several sea caves and along the Santorini coastline.

ATV Tours

Another popular tour in Santorini is the ATV tours. The tour takes you through Perissa Beach, Megalochori and the Emporio Venetian Castle.

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@postcardsfromcarrie Santorini’s hop on, hop off water taxi was one of our favorite activities in Santorini. 🇬🇷 There is no website for the water taxi and we found it difficult to find any information on it online. We heard about it from other visitors 🇬🇷 Since there is no address, type “Hotel Akrotiri” in to your GPS and that will take you right to the port. 🇬🇷 Be sure to bring cash if you want to rent sunbeds beds at the beaches 🇬🇷 The beaches are rocky so wear water shoes 🇬🇷 Bring snorkel masks to explore the sea caves at the white beach and black beach 🇬🇷 Highly recommend adding this to your Santorini trip itinerary 🇬🇷 A great thing to do to avoid the Caldera crowds on busy cruise ship port days 🇬🇷 Have you been on the water taxi before? Save this and follow for more ⬇️ #santorinigreece🇬🇷 #santorini #greekislands #greece🇬🇷 #greecetiktok #greecetravel #beach #watertaxi #travel #traveltiktok #exploregreece ♬ Tropical Summer Vibes - Netuno Music

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