5 Days Santorini, Greece Itinerary
Experience the magic of Santorini with this meticulously planned 5-day itinerary, designed for couples seeking a luxurious and romantic escape. Indulge in breathtaking sunsets, private experiences, and unparalleled views, creating memories to last a lifetime.
Duration
5 days
Budget
$1500-2500
Best Time
The ideal time to visit Santorini is during the shoulder seasons: late April to early June or September to October
Activities
20
Daily Avg
$400/day
Pace
Moderate
Santorini is renowned for its breathtaking sunsets, whitewashed villages clinging to cliffs, and romantic atmosphere. It's a perfect destination for couples seeking a luxurious and unforgettable honeymoon or romantic getaway.
Your itinerary covers 8 of 10 must-have experiences
Iconic Sunset Viewpoint
Day 1: Pre-Sunset Cocktails at a Caldera View Bar
Caldera-View Fine Dining
Day 2: Dinner at Selene Restaurant
Unique Volcanic Beaches
e.g., Red Beach (Kokkini Paralia), Perissa Black Sand Beach
Caldera & Volcano Boat Cruise
Day 1: Pre-Sunset Cocktails at a Caldera View Bar
Ancient Archaeological Sites
Day 2: Private Guided Tour of Akrotiri Archaeological Site
Santorini Wine Tasting Experience
Day 2: Santorini Wine Tasting Tour
Charming Traditional Villages
Day 4: Hike from Fira to Imerovigli
Panoramic Caldera Hiking Trail
Day 1: Pre-Sunset Cocktails at a Caldera View Bar
Local Culinary Delights & Casual Eats
Day 5: Lunch at a Casual Cafe
Chic Cliffside Bars & Nightlife
e.g., Franco's Bar (Fira), PK Cocktail Bar (Fira)
Santorini's cuisine is a delightful blend of fresh seafood, locally grown vegetables, and traditional Greek flavors, often enhanced by the island's volcanic soil which imparts a unique taste. Don't miss the opportunity to savor the local specialties like fava and cherry tomatoes. Many restaurants boast stunning caldera views, adding to the dining experience.
Must-Try Dishes
A creamy dip made from yellow split peas, often served with olive oil, onions, and capers. It's a Santorini staple and a delicious appetizer.
📍 Traditional tavernas throughout the island
Deep-fried tomato balls made with Santorini's unique cherry tomatoes, herbs, and spices. Crispy on the outside and juicy on the inside.
📍 Tavernas and restaurants serving local specialties, especially in Oia and Fira
A rare variety of eggplant grown only in Santorini. Mild and sweet, often grilled or baked.
📍 Restaurants specializing in local produce, often found in the countryside
A fresh, soft goat cheese unique to Santorini. Tangy and creamy, often served with salads or as a spread.
📍 Local markets and tavernas
Food Neighborhoods
Known for upscale restaurants with stunning caldera views and sunset dining.
Known for a wide variety of restaurants, from casual tavernas to fine dining, catering to different budgets.
Known for fresh seafood restaurants right on the water.
Known for traditional tavernas and local specialties, offering a more authentic experience.
Vegetarian options are readily available, especially with dishes like fava, tomato keftedes, and salads. Vegan options may require some inquiry but can be found with dishes focusing on vegetables and legumes. Gluten-free bread and pasta are becoming increasingly common, but it's best to inquire beforehand. Halal options are limited; it's advisable to check with specific restaurants.
Greeks are generally welcoming and hospitable. It's customary to share dishes, especially appetizers. Tipping is appreciated (around 5-10% for good service). Waving down a waiter is acceptable. Don't be afraid to ask for recommendations.
Greek Orthodox Easter
PaschaMost important Greek holiday with midnight services, fireworks, and lamb feasts.
Note: Book 1-2 months ahead for Corfu
🛣️Interesting Detours & Side Trips
- 🚶Private transfer from Santorini Airport (JTR) to your hotel in Oia.$80
2:00 PM - Arrival at Santorini Airport (JTR) & Private Transfer
Upon arrival, a private transfer will escort you to your luxury hotel in Oia. Consider hotels like Katikies Hotel, Andronis Boutique Hotel, or Canaves Oia Suites for stunning caldera views and exceptional service.
- 🚶Hotel is within walking distance of caldera view bars.FREE
3:00 PM - Check-in & Relaxation
Settle into your hotel, unpack, and enjoy the amenities like the infinity pool or private balcony. Take some time to unwind and soak in the stunning caldera views.
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- 🚶Oia Sunset Viewing location is within walking distance from the bar.$40
6:00 PM - Pre-Sunset Cocktails at a Caldera View Bar
Head to a bar like Sun Spirit Bar or 1800-Floga Restaurant for pre-sunset cocktails with panoramic views. Arrive early to secure a prime spot.
Book on Klook - 🚶Dinner location is within walking distance in Oia.$150
7:30 PM - Oia Sunset Viewing & Romantic Dinner
Find a spot to witness the world-famous Oia sunset. Afterwards, enjoy a romantic dinner at Ambrosia Restaurant or Lauda Restaurant, known for their exquisite cuisine and breathtaking views. Book well in advance!
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Oia
Oia is famous for its stunning sunsets, whitewashed buildings, and luxurious accommodations, making it a perfect romantic getaway.
📅 Best Time to Visit
The ideal time to visit Santorini is during the shoulder seasons: late April to early June or September to October. During these months, the weather is pleasant with warm sunshine, crowds are smaller than peak summer, and prices for flights and accommodation are more reasonable. July and August offer hot weather and vibrant nightlife but come with extreme crowds, higher prices, and intense heat. Winter (November-March) is very quiet with many businesses closed, though it offers a unique, serene experience for those seeking solitude.
During the shoulder seasons, Santorini enjoys sunny days and mild evenings. Rainfall is infrequent, and the sea is warm enough for swimming. The weather is perfect for exploring the island and enjoying outdoor activities.
The shoulder seasons (late April to early June or September to October) offer pleasant weather, fewer crowds, and reasonable prices, making them ideal for visiting Santorini.
Be aware of Greek Orthodox Easter, which can significantly impact travel arrangements and availability.
Getting Around
Athens Metro; ferries between islands
Ath.ena Card (Athens)
Book ferry tickets in advance during summer. Athens Metro connects to airport.
Travel
$500-800 (Flights from US East Coast)Accommodation
$500-1000Food
$300-500Activities
$200-500Utilize the efficient and affordable KTEL public bus system for transportation between villages instead of expensive taxis or private transfers. Rent an ATV or scooter for flexibility if comfortable, which can be cheaper than a car.
Eat at local tavernas away from the main tourist hubs of Oia and Fira. Explore villages like Pyrgos, Emporio, or Kamari for more authentic and budget-friendly meals. Consider self-catering some breakfasts or lunches from local markets.
Indulge in a sunset catamaran cruise around the caldera. These often include swimming, snorkeling, and a freshly prepared meal with drinks, offering unparalleled views and a memorable experience.
Treat yourself to a stay in a traditional cave hotel with a private plunge pool and an uninterrupted caldera view. It's a quintessential Santorini experience worth the higher price tag.
Don't limit your exploration to just Fira and Oia. Venture to lesser-known villages like Pyrgos, Emporio, or Megalochori to experience a more authentic side of Santorini, discover charming cafes, and quieter streets.
Try the local Santorini wines, especially Assyrtiko, directly from one of the island's many wineries. They offer unique volcanic terroir and a refreshing taste, often with beautiful vineyard views.
- Wear comfortable walking shoes: Santorini is famous for its steep, cobbled paths and countless stairs. Heels or uncomfortable footwear will make exploring difficult and potentially unsafe.
- Book accommodations and popular activities well in advance: Especially if you want to stay in a caldera-view hotel or take a sunset cruise, bookings fill up months ahead, particularly for peak season.
- Utilize the public bus system (KTEL): It's an efficient and cost-effective way to travel between major villages like Fira, Oia, Pyrgos, and the beaches.
- Protect yourself from the sun: Santorini gets intense sun. Always use high SPF sunscreen, wear a hat, sunglasses, and seek shade during midday hours.
- Carry cash for small purchases: While credit cards are widely accepted, small shops, local tavernas, and some bus tickets might require or prefer cash. ATMs are available in major towns.
- Hydrate constantly: The Mediterranean climate, combined with walking, can lead to dehydration. Always carry a reusable water bottle and refill it frequently.
- Be mindful of the wind: Santorini can be very windy, especially in the evenings or near the caldera edge. Bring a light jacket or scarf, even in summer.
- Enjoy the sunsets responsibly: While iconic, popular sunset spots in Oia and Fira get extremely crowded. Arrive early to secure a good spot or consider a sunset cruise for a different perspective.
- 1Comfortable walking shoes (sandals with good support, sneakers)
- 2High-SPF sunscreen, hat, and sunglasses
- 3Lightweight, breathable clothing (linen, cotton) for warm days
- 4Swimwear and a beach towel
- 5Light jacket or scarf for breezy evenings
- 6Reusable water bottle to stay hydrated
- 7Travel adapter (Type F/C for European outlets)
- 8Small backpack for day excursions
- 9Basic first-aid kit (band-aids for blisters, pain relievers)
- 10Camera and extra memory cards (for endless photo opportunities)
Accommodation (especially caldera-view hotels)
Book 6-12 months in advance for peak season, 3-6 months for shoulder season, due to high demand and limited unique properties.
Flights or ferry tickets to/from Santorini
Book 3-6 months ahead, especially for summer, as prices rise and availability decreases closer to travel dates.
Rental car or ATV/scooter
Book 2-3 months ahead, especially if visiting in peak season, as inventory is limited and ensures better rates.
Sunset catamaran cruise or other boat tours
Book 1-2 months in advance, as popular tours, especially those including sunset or caldera exploration, sell out quickly.
Reservations for popular caldera-view restaurants (Oia/Fira)
Book 2-4 weeks ahead, particularly if you want a table with a prime sunset view.
Airport/Port transfers to your hotel
Arrange 1-2 weeks prior to arrival to ensure a smooth and stress-free transfer, especially if arriving late.
Travel Insurance
Purchase immediately after booking your first trip component to cover unforeseen cancellations, medical emergencies, or lost luggage.
Note: Travel conditions, regulations, and local customs may change. We recommend verifying essential details — such as visa requirements, emergency contacts, and payment options — closer to your travel date.
SIM & Connectivity
SIM Options
📍 Airalo website or app (download before arriving)
📍 Vodafone store at Santorini Airport or in Fira
📍 Cosmote store at Santorini Airport or in Fira
📍 Online booking with delivery to your hotel or airport pickup
Free WiFi is widely available in hotels, cafes, and restaurants, especially in tourist areas like Oia and Fira. The speed can vary, but it's generally sufficient for basic browsing and social media. Public WiFi hotspots are less common.
Useful Apps
Purchase your SIM card or eSIM before arriving in Santorini to save time and hassle. Check the coverage maps of different providers to ensure you get the best signal in the areas you plan to visit. Download offline maps in Google Maps to avoid relying on data when exploring remote areas. Consider purchasing a portable power bank to keep your devices charged, especially when spending long days sightseeing.
Electric Socket Guide
Socket Types
Two round pins (Europlug)
Two round pins + side earth clips (Schuko)
230V
50Hz
Tipping Etiquette
5–10% or round up
Round up to nearest euro
€1 per bag
Tipping is appreciated but not mandatory. Leave change on the table.
Safety & Travel Advisories
Santorini is generally a safe destination. Be aware of petty theft in crowded areas and exercise caution when hiking.
Check official government advisories for the latest safety information, entry requirements, and travel warnings before your trip.
Emergency Numbers
100
166
199
171
112 for all emergencies
Payments
Cash needed on islands and at tavernas
Accepted in cities and tourist areas
Growing in Athens and popular islands
Carry cash for islands and smaller establishments. ATMs available but may charge fees.
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The best time to visit Santorini is during the shoulder seasons (late April to early June and September to October). The weather is pleasant, crowds are smaller, and prices are more reasonable compared to the peak summer months.
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