DAY 1: Santorini
Hotel: Maryloujohn Villas Studios & Apartments
Basic but cute apartment-style hotel in Oia. If you are traveling on a budget but want to be close to the action, this is a great option. It’s walkable to everything in town. The views from the property are beautiful and the rooms have kitchenettes if you need to cook a safe or more affordable meal, which is super convenient.
Had such a great meal here. Our waitress was super knowledgeable and helped us navigate the menu. She double checked dishes and came back to give me all the info I needed. The dolmas (stuff grape leaves) were the best I’ve ever had!
Breakfast: Terpsi N Oia
Adorable little breakfast spot in Oia with the most impressive views from the upstairs seating area. Loved coming here for coffee and an omelet in the mornings.
Lunch: Venetsanos Winery
This winery is a must visit! We did a wine tasting with a lunch pairing and I was not expecting much, but they even had gluten-free bread and every course was so impressive and yummy. The views were unreal. There are a few wineries around here (see Santo below) but this one was incredible. It was my favorite place we went in Santorini!
Dinner: Ammoudi Fish Tavern
Unique waterfront restaurant down in the bay. We ordered fresh fish and a Greek salad. Try to make a reservation on the earlier side (before sunset) to get one of the better tables that are right on the water with views of the red clay cliffs.
Sightseeing: Santo Wines
The most well known winery in Santorini. There weren’t a ton of gluten-free options to eat, but the wine was wonderful and the views were jaw dropping!
Hotel: Caldera Premium Villas
On day 3, we moved to a nicer hotel as we we’re about to be celebrating something special. This place is a gem. Cave-style hotel rooms with jaw dropping views. The best part is that this spot is not as pricey as the surrounding hotels with the exact same views. Continental breakfast was safe and sufficient. We loved our stay!
Delicious breakfast on the walking street of Oia. It’s across the street from the water but still has nice, uninterrupted views of the ocean. Ordered a big omelet that was spot on.
Small but cute restaurant in Oia with a quaint rooftop terrace. Allergens are marked on the menu and staff was knowledgeable. There’s only a few tables on the rooftop so try to make a reservation before going.
Fine dining in Imerovigli— we went here for our engagement dinner and had a spectacular night. The restaurant sits next to an infinity pool overlooking the stunning views of the ocean. There were plenty of gluten-free dishes and the waiter was extremely knowledgeable. A good option if you are looking for that high end fine dining option but very very pricey.
We explored the village of Imerovigli! There are so many beautiful lookouts and photo-worthy spots. You can also hike Skaros Rock if you are there earlier in the day.
Lunch: Pitogyros Traditional Grill House – Gyros, souvlaki, kebab.
The most delicious little kebab spot in Oia. Came back twice to get kebab skewers and halloumi. Always a long line—it’s a town favorite!
Dinner: NAOS Oia Restaurant – Bar
Very trendy rooftop restaurant. The staff was super knowledgeable about allergies and helped us order. The atmosphere was beautiful and I highly recommend going at sunset. You need a recommendation well in advance.
We stopped for cocktails to enjoy the stunning views from the terrace!
We visited the Windmill of Oia! Oia is the cutest little walking town with tons of shops and views to take in. The windmills are sitting at the tip of the island, so it is a beautiful spot to walk around and explore.
DAY 5: Mykonos
Hotel: Petinos Hotel
Nice hotel with a great pool and helpful staff. It’s not super central to much, but the hotel is right on the water and it was easy to get around. We rented ATVs to explore the island and were only a few minutes from Mykonos town.
Dinner: Soho Roc House
Beautiful beach club with a restaurant on the water. The staff is super knowledgeable about allergies and could alter dishes as needed. Make a reservation beforehand as guest policies on the restaurant change from time to time.
Lunch: Kastro’s Restaurant
We stumbled on this restaurant after seeing that they had private balcony tables jutting out over the water! We ordered a few appetizers like the grilled cheese and the sea bass ceviche and of course, some rose to top it off. It was one of the most memorable meals I’ve ever had!
Dinner: Anios Mediterranean Cuisine
Chic beachfront restaurant on a nice boardwalk of beach clubs restaurants and bars. Had the most delicious wild mushroom risotto.
Cocktails: Negrita Bar Mykonos
This is a cocktails-only bar but such a cute place to take a break and relax for a bit. The tables are right on the ocean in the little Venice part of town. So nice to have a cocktail and listen to the waves crash.
We rented ATVs and explored Little Venice! This is one of the easiest ways to get around the island.
Breakfast: Petinos Hotel
The breakfast is buffet style but the eggs and meats were fully separated from the grain area.
Very sceney but worth it. We reserved a day bed here one day and then had dinner here another night. Make reservations as early as possible as it stays booked. There are some gluten-free marked items on the menu, like these wagyu lettuce wraps, and the staff is really helpful.
Cocktails: Caprice Bar Mykonos
Perfect spot to watch the sunset. This place doubles as a restaurant and a lovely bar at night. We only went for drinks but plan to get there early as it is pretty famous. The tables are right on the water.
Lunch: Petinos Hotel
After much celebrating, we opted for a pool day at the hotel. I ordered halloumi— which was definitely a win.
Our dinner was wonderful and the restaurant is really cool. Recommend booking a table at sunset. The experience in each area is different (i.e. booking a daybed by the beach vs. coming for dinner), so it was a totally different vibe even though it was our second time here. We ordered grilled cheeses, fish, and finished with this delicious mousse. It was the perfect way to end a trip of a lifetime.
Cocktails: Principote Μύκονος
Super chic and fun day club. Make a reservation for a day bed or table reservation well in advance. Menu is full of fresh fish and plenty of great cocktails and wine. Expect a party environment.