- 1:30pm – Take the ’22-minute’ (yes, literally…) flight to Santorini from Athens
- 3:30pm – Arrive in Santorini and take a EUR 20 taxi to Hotel Kavalari in Fira (don’t bother with the bus!)
- 4:00pm – Spend some time walking through the village of Fira. There are dozens of local shops, street vendors, etc. Grab a Gyro (1.5EUR) and then a smoothie or cocktail at Tropical featuring a stunning caldera view…you are officially in paradise! Quick Tip: When you are in Fira, or virtually abroad anywhere, we recommend using Foursquare (rather than Yelp) for reviews of local hot spots. That’s how we discovered the majority of the bars / restaurants.
- 5:00pm – Take the 10-minute Gondola ride down to the Old Port (old fisherman town / cruise ship launch site). You can actually ride a donkey down the winding dirt path, but in this heat, we skipped it!
- 7:00pm – It’s nearly show-time (e.g. the famous Santorini sunset in Oia!). Take a 20 minute taxi north to the town of Oia and find a perfect spot to watch the sunset. This is hard because in summer, be ready for it to be crowded with tourists snapping photos! If you arrive early, you can sit and have a cocktail at one of the many bars that overlook the Cliffside and blue-domed cathedrals that give you a picturesque view of the sunset while you sit and enjoy an appetizer.
- 8:00pm – Head back (via taxi) to the hotel in Fira and get ready for dinner.
- 9:00pm – We had dinner at the Argo Restaurant in Fira. Wine is cheap in Santorini (not quite up to our Napa Valley standard), but we split a bottle of white and shared the seafood platter. (80 Euro). We found the Greek cuisine not drastically different from that of Turkey (nor other Mediterranean coastal countries), where it’s hard to go wrong with seafood, various kebabs, pita, feta, hummus as appetizer staples, etc.
- 10:00pm – Several bustling bars filled with international tourists to check out. We recommend Tropical, Highlander, Tango, etc. Can’t go wrong by just walking around the town and enter the one playing your favorite music!
- 9:00am – Rent an ATV (~$40 p/day) and put on sunscreen. Get ready to explore the island! There are a number of small companies in Fira offering daily ATV or Scooter rental. We had our hotel call on our behalf to organize a pick-up near the Ambassador hotel.
- 10:00am – Drive south along the magnificent Cliffside in Santorini to reach the southern tip of the island where you will find Αρχαίο Ακρωτήρι Θήρας (Akrotiri Prehistoric Town). We aren’t history buffs, but spending an hour here to see this 4,000 year old pre-historic village is fascinating! It’s an entire, underground city that has been impressively preserved for centuries.
- 11:30am – Head west to make a brief stop at the Red Beach. We wanted to cross this destination off of our list, but if you don’t have that much time, this is one you could skip. It’s a long (somewhat challenging) walk to actually get to the actual beach, and despite the uniqueness of the red sand and rock, was quite dirty when we arrived!
- 12:30pm – Hop on the ATV and head to JoJo’s Beach Bar (quite possibly the swankiest beach bar in Santorni) in Perivolos Beach to relax (or party, if it’s Sunday). Grab a cabana on the beach and order your favorite cocktail as you take in some sun overlooking the Sea of Crete. If you walk into the actual resort, they feature a full-service bar / outdoor pool that offers a sexy, lounge-like atmosphere. However, you can hear the music from your beach cabana making for an excellent opportunity to relax.
- 3:30pm – Get back on the ATV and head to Megalochori, a traditional village in Santorini. The village is very walkable through its many alleyways and features a few shops and restaurants.
- 4:00pm – Head to Santo Winery (hands-down, one of our favorite places in the world, and let us add: a fantastic destination wedding location). Santo Winery is situated on what feels like the “top of the world.” If you grab a seat (virtually anywhere), you will be mesmerized by magnificent, 360-degree panoramic views of the Santorini Cliffside, Volcano, Aegean Sea and there will likely be 1-2 weddings occurring. We recommend doing a cheese plate and splitting a wine flight here, and if you can stay long enough, wait for the sunset…absolutely unforgettable!
- 8:30pm – Grab cocktails or after-dinner coffee at Franco’s, a quirky bar with a caldera view and nice cocktails that interestingly enough features loud, classical music.
- 8:00am – Wake up, hop on the ATV, and zoom to Oia again. As you ride through the winding Cliffside, you’ll see a spectacular sunrise on the Eastern side of the caldera.
- 9:00am – Once you arrive in Oia, grab a coffee in the cute town (no tourists at this time, yet!). There are at least three of the blue-domed cathedrals here that you can photograph.
- 10:30am – Head back to return the ATV and take the bus to the Main Port (Athinios) where all the ferry and commercial boats arrive. It’s approximately a 2-hour ferry ride on “SeaJets” to Mykonos.
(We recommend buying your ticket in the town of Fira the day before your trip as prices are quite standard. Santorini to Mykonos was around [65 EUR]. The boat ride is really nothing more than a straight-shot through open sea, so we decided to skip the 5-hour upcoming ferry from Mykonos to Athens and booked the 120 EUR flight directly to Athens instead, to save time.)