Greece with Jaelan Davis

Dates

Jun 12–17, 2025

Group Size

10–24 Travelers

Duration

6 days, 5 nights

Activity Level

Exploration

About This Trip

What do you imagine when you picture Greece? Is it island adventures, the Aegean Sea, passionate people, ancient ruins, blue skies, or turquoise waters? When you close your eyes and picture your adventure, know that your imagination is about to become reality. Kalimera and welcome to Greece!
$2,955USD
$3,195USD
Jun 12–17, 2025
6 days
Trip Closed

Meet Your Host

Faceovermatter Getaway!
Faceovermatter Getaway!

Grace and peace! I'm Jaelan, known as Faceovermatter. Over the last 10 years, we've been journeying through life together via social media, this time, let's kick hit up a notch and meet in person at a beautiful location! I am so excited to see the world with you. See you soon!

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Trip Activities

  • Santorini Caldera Hike

  • Santorini Cooking Class

  • Santorini Beach Day

  • Caldera Sailing Day Cruise

Included in Your Trip

  • Double occupancy in 3-star hotels (limited single rooms available)

  • Local guide throughout trip

  • All city transfers

Not Included

  • Flights (except as noted)

  • Food and alcohol (except as noted)

  • Visas and travel insurance

  • Airport transfers

  • Tips & Gratuity

Itinerary

*All durations are approximate

Day 1

Info

Kalimera and welcome to Greece! Please be prepared to meet in the lobby at 5:30pm to depart for your welcome dinner. The dinner reservation time will be finalized closer to your trip date. If you plan on arriving today, we recommend flying into Santorini International Airport (JTR).

dinner

Let's raise a glass together to an exciting trip ahead during your welcome dinner! Tonight's gathering will take place in a local restaurant close to the hotel. Enjoy a delightful 3-course set menu featuring traditional Greek cuisine. Your menu consists of family-style shared starters, a main entree and dessert. Please note that a bottle of water and a glass of wine or a glass of beer are included. Additional beverages can be purchased at the venue. Keep in mind that the menu is subject to change based on the confirmed restaurant.

Kamari Beach (or similar)

Accommodations may vary based on availability or group size, but no matter what, you can expect the same comfort and quality.

Night 1/5

Overnight in Santorini

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Day 2

Info

Begin your day with a satisfying breakfast at the hotel, energizing you for a scenic hike along the coast from Fira to Oia. Take in breathtaking views of the Aegean Sea and the iconic white cliffside homes along the way. After the invigorating trek, explore Oia at your leisure, immersing yourself in its charming streets and enjoying a leisurely lunch on your own at a local taverna. Following your exploration, relax with a private transfer back to the hotel, where you can unwind and reflect on the day's adventures. Spend the remainder of the day at your own pace, whether lounging by the pool or indulging in a soothing spa treatment. Enjoy the tranquility and comfort of your surroundings as you embrace the serenity of Santorini.

breakfast

Breakfast at the hotel is included. Kamari Hotel provides a Greek Continental buffet with a diverse selection including breads, jams, honey, yogurt, milk, croissant, cakes, cereals, seasonal fruits, eggs, cold cuts, bacon and sausage. The specific offerings may vary depending on your confirmed hotel.

Santorini Caldera Hike

5 Hours 30 Mins

Embark on an early morning adventure with a hike along the rim of the volcanic caldera, treating you to some of the most breathtaking views Santorini has to offer. Marvel at the iconic white yposkafa homes nestled on sheer cliffs, surrounded by vineyards and vibrant local flora against the backdrop of clear, turquoise waters. Starting from Fira Village and concluding at Oia Village, this scenic hike spans approximately 6 miles, encompassing varied terrain including sidewalks, cobblestones, gravel, and dirt paths. Be sure to wear comfortable walking shoes and come prepared with a hat, sunscreen, water, and light snacks to stay refreshed along the way. After the hike, enjoy some free time for a quick lunch before being transferred back to your hotel, where you can unwind and reflect on the day's memorable experiences. 6 miles | 1,069 ft | 4 hours | moderate

Kamari Beach (or similar)

Accommodations may vary based on availability or group size, but no matter what, you can expect the same comfort and quality.

Night 2/5

Overnight in Santorini

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Day 3

Info

Savor a delightful morning with a flavorful breakfast spread at your hotel, setting the stage for the day's adventures. Engage in a hands-on cooking class, where expert chefs guide you in crafting traditional Greek dishes, followed by a satisfying lunch featuring your creations. With the afternoon at your disposal, explore Santorini at your leisure, indulging in local delights or simply unwinding by the pool. If you would like, as evening approaches, journey to Oia, renowned for its stunning sunsets over the Aegean Sea. Find a picturesque spot to witness nature's masterpiece.

breakfast

Breakfast at the hotel is included. Kamari Hotel provides a Greek Continental buffet with a diverse selection including breads, jams, honey, yogurt, milk, croissant, cakes, cereals, seasonal fruits, eggs, cold cuts, bacon and sausage. The specific offerings may vary depending on your confirmed hotel.

Santorini Cooking Class

3 Hours

A short transfer from the hotel takes you to your test kitchen where you will transform into chefs for the afternoon. Santorini has some of the most amazing local produce and recipes that are unique to the island. In this cooking class, the in-house chef will teach you the secrets of how to cook tasty dishes. This interactive and hands-on experience will bring you closer to the how the locals live and the culinary magic of Santorini. Using the dishes you created with the chefs, the cooking class ends with lunch on premises. Some dishes you may prepare are, tomato dumplings, fava beans (local recipe), tsatziki, Dakos salad (Cretan recipe), Spinach - cheese pie (spanakotyropitakia), Chicken with lavender and myzithra cheese. Final venue and menu to be determined.

lunch

Enjoy the food prepared during the cooking class for lunch together as group. White wine will be served with the meal. The final venue and menu will be determined closer to the date.

Kamari Beach (or similar)

Accommodations may vary based on availability or group size, but no matter what, you can expect the same comfort and quality.

Night 3/5

Overnight in Santorini

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Day 4

Info

Today, immerse yourself in a day of beachside bliss. Accompanied by your local guide, head to the beach where you'll spend the day swimming and soaking up the sun. Following your time at the beach, the rest of the day is yours to enjoy at leisure.

breakfast

Breakfast at the hotel is included. Kamari Hotel provides a Greek Continental buffet with a diverse selection including breads, jams, honey, yogurt, milk, croissant, cakes, cereals, seasonal fruits, eggs, cold cuts, bacon and sausage. The specific offerings may vary depending on your confirmed hotel.

Santorini Beach Day

3 Hours

In the late morning a private coach will transfer you 20-30 minutes to the beach where you will have the afternoon to relax under the sun. There are sun beds for purchase if you wish. Please note today you should pack a bathing suit, towel, sunscreen, glass, hat and cash. Once your time at the beach is complete you will be transferred back to your accommodations for the remainder of the day.

Kamari Beach (or similar)

Accommodations may vary based on availability or group size, but no matter what, you can expect the same comfort and quality.

Night 4/5

Overnight in Santorini

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Day 5

Info

Begin your day with a leisurely breakfast at the hotel, savoring delicious local flavors and fueling up for an unforgettable adventure ahead. After breakfast, embark on an exciting catamaran cruise for the day, where you'll glide across the sparkling waters of the Aegean Sea. A delectable BBQ lunch, carefully prepared to tantalize your taste buds, will be served onboard. After a day of exploration at sea, return to the hotel in the late afternoon for some well-deserved downtime. As evening approaches, gather with fellow travelers for a memorable farewell dinner at a local restaurant.

breakfast

Breakfast at the hotel is included. Kamari Hotel provides a Greek Continental buffet with a diverse selection including breads, jams, honey, yogurt, milk, croissant, cakes, cereals, seasonal fruits, eggs, cold cuts, bacon and sausage. The specific offerings may vary depending on your confirmed hotel.

Caldera Sailing Day Cruise

5 Hours

Enjoy a beautiful day out on the water sailing the Santorini Caldera. This shared cruise includes sailing, swimming and a wonderful meal on board. The yachts includes ample space including hammock style nets on the bow for you to sunbathe and good space in the main cabin for when the sun gets to be too much. The captain will set anchor at a spectacular spot and your crew will prepare a wonderful meal for you. Enjoy the awe inspiring views of the caldera and swim in the Aegean turquoise waters. A BBQ lunch will be served onboard. After your day at sea is complete, you will return to your hotel where you will have free time until your farewell dinner. Please be sure to wear your bathing suits and a cover up and pack a towel, sunscreen, hat and sunglasses in a backpack. Important note: All passengers should have a photo or copy of the passport during the cruise, required by the local port authorities. Please be mindful that this experience is shared with other travelers not on your TrovaTrip.

lunch

Lunch onboard the catamaran cruise is included. Your BBQ lunch includes pork or chicken skewers or grilled vegetables, stuffed vine leaves with rice, tzatziki, greek salad, potato salad and pita bread. Complimentary drinks such as white wine, soft drinks & water will be served. The specific offerings on the final menu may vary.

dinner

Raise a toast to new friendships forged and unforgettable experiences shared at your farewell dinner. Dinner at a local taverna is included. Enjoy a delightful 3-course set menu featuring traditional Greek cuisine. Your menu consists of family-style shared starters, a main entree and dessert. Please note that a bottle of water and a glass of wine or a glass of beer are included. Additional beverages can be purchased at the venue. Keep in mind that the menu is subject to change based on the confirmed restaurant.

Kamari Beach (or similar)

Accommodations may vary based on availability or group size, but no matter what, you can expect the same comfort and quality.

Night 5/5

Overnight in Santorini

Show DetailsHide Details
Day 6

Info

All good things must come to an end, but only until your next adventure! Enjoy a final breakfast and then make your own way onward. If departing directly from the hotel, we recommend flying out of Santorini International Airport (JTR).

breakfast

Breakfast at the hotel is included. Kamari Hotel provides a Greek Continental buffet with a diverse selection including breads, jams, honey, yogurt, milk, croissant, cakes, cereals, seasonal fruits, eggs, cold cuts, bacon and sausage. The specific offerings may vary depending on your confirmed hotel.

Show DetailsHide Details

Physical Activity Level:Exploration

These trips require some movement, but slow and steady is the name of the game. Maybe a mid-length walking tour or at-your-pace sightseeing. No rush.

Cancellation Policy

We get it—life happens. Here's how cancellations work depending on where you're at in the process:

Spot Pending

100% refundable
Not confirmed yet? No worries. You can cancel at any time for a full refund.

Spot Confirmed With 91 or More Days Before Your Trip

Partially refundable + credit towards a future trip
You'll receive a future trip credit for the amount of your down payment (minus a $100 cancellation fee per Traveler). This trip credit is valid for one year from the date it is issued. Additionally, any payments made beyond the original 25% down payment will be refunded to your original form of payment.

Spot Confirmed With 90 or Fewer Days Before Your Trip

Non-refundable
At this point, all payments are non-refundable because your experience is already in motion behind the scenes. By this time, our operating partners will be working with local businesses to secure your accommodations and finalize your activities.

HIGHLY RECOMMENDED: Protect Your Adventure-Invest in Peace of Mind

We strongly encourage purchasing travel insurance with trip cancellation coverage to safeguard your investment. With travel insurance, you're covered in case of unexpected events—from illness to emergencies—that could affect your plans. Life is unpredictable, but your dream trip doesn't have to be.

After booking, you'll receive a personalized recommendation for coverage tailored to your trip. For full details on our cancellation policy, please refer to our Terms & Conditions.

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Reserve your spot with just 25% down, pay in full, or apply for a payment plan at booking. Your dream trip, your way.

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FAQ

Traveling with TrovaTrip

What's it like to travel on a Trova Trip?

Trova Trips are curated group travel experiences designed to help you see the world, meet new people, and connect over shared interests. Each trip is hosted by a community leader you know and trust, and run by professional local Operators who handle the logistics. Expect meaningful experiences, authentic activities, and a like-minded group to share it all with.

What's the difference between the Host, the Operator, and Trova?

Great question! Each plays a key role in bringing your experience to life:

  • The Host is your community leader who brings the group together, fosters connection, and perhaps leads a workshop or two. They're there to bring the vibes, not the logistics. That's the Tour Operator's job.
  • The Operator is the professional travel company that runs the trip on the ground. They handle it all—accommodations, local Guides, activities, and safety. Every Operator we partner with is licensed, insured, and vetted to deliver high-quality group travel.
  • TrovaTrip is the platform who connects it all. We help design the trips, partner with Hosts with Operators, and support you before and during your journey to ensure everything runs smoothly.

In short: The Host brings the vibe, the Operator runs the trip, and we make it all happen. Read more about who does what here.

I'm nervous to book. How can I feel more confident?

First, let us say—it's totally understandable, and you're not alone! Travel can feel intimidating, but we built Trova to take the guesswork out of group travel and earn your trust every step of the way:

    • Every trip is run by licensed Tour Operators with vetted local Guides.
    • Hosts are there to foster connection, meaning you'll arrive solo but never feel alone.
    • Itineraries are clearly outlined so you know what to expect, including activity level, example accommodations, and what's included.
    • Our team is available to support you pre-departure, and Operators—plus your local Guide—are on the ground to assist during the trip. And rest assured, all our Operating partners are trained in crisis management.
    • We always recommend travel insurance for extra peace of mind, whether you're traveling with Trova or solo. It can cover medical issues, lost luggage, or even cancellations.

We know it takes trust to book a trip with new people, and we're here to make sure you feel ready, supported, and excited!”

Can I book solo?

Absolutely! As of 2025, almost 84% of TrovaTrip Travelers go solo. (And yes, we may be a little biased, but we think group travel is one of the best ways to meet new people!) You'll have your own bed and the option to book a private room on most trips. Plus you'll be traveling with others who are just as excited to explore and connect.

What if I need to cancel?

We understand that life happens. Our cancellation policy is designed to provide flexibility while balancing the logistics of group travel:

  • Spot pending100% refundable. Not confirmed yet? No worries. You can cancel at any time for a full refund.
  • Spot confirmed with 91 or more days before your tripPartially refundable + credit towards a future trip. You'll receive a future trip credit for the amount of your down payment (minus a $100 cancellation fee per Traveler). This trip credit is valid for one year from the date it is issued. Additionally, any payments made beyond the original 25% down payment will be refunded to your original form of payment. 
  • Spot confirmed with 90 days or fewer before your tripNon-refundable. At this point, all payments are non-refundable because your experience is already in motion behind the scenes. By this time, our operating partners will be working with local businesses to secure your accommodations and finalize your activities.

HIGHLY RECOMMENDED: Protect Your Adventure–Invest in Peace of Mind
We strongly encourage purchasing travel insurance with trip cancellation coverage to safeguard your investment. With travel insurance, you're covered in case of unexpected events–from illness to emergencies–that could affect your plans. Life is unpredictable, but your dream trip doesn't have to be.

After booking, you'll receive a personalized recommendation for coverage tailored to your trip. For full details on our cancellation policy, please refer to our Terms & Conditions.

What's included in the trip cost?

Most trips include accommodations, daily activities, ground transportation, some meals, and a dedicated local Guide. Because Travelers are coming from all around the world, flights to and from your destination are not included. Each trip page breaks it all down for you.

Will I have free time?

Yes! While we pack in incredible experiences, most itineraries include built-in free time so you can relax, wander, or check out personal must-sees.

What do the activity levels mean?

Every trip has a physical Activity Level from 1 to 5 so you can find the right fit for your travel style:

  • Level 1 – Relax + Unwind: Minimal movement (spa days, beach lounging, local markets)
  • Level 2 – Low-Key Movement: Light, easy-paced activity (snorkeling, boat tours, gentle hikes)
  • Level 3 – Moderate Activity: Ready to move (multi-day hikes, skiing, camping)
  • Level 4 – Get Your Heart Rate Up: More intense movement (long hikes, biking, active days)
  • Level 5 – Extreme Adventure: High-adrenaline travel (challenging hikes, dives, technical climbs – experience may be required)

You'll find the Activity Level clearly listed on each trip page, and a more in-depth explanation of each level here.

Who can I contact with more questions?

Our support team is here to help! Visit trovatrip.com/company/contact-us to reach out. You can expect to hear back within 2 business days, but probably sooner—our Trova elves are pretty speedy!

Accommodations

What does "or similar" mean next to the accommodations?

When we say “or similar,” it means the hotel listed is an example of what you can expect—not always the exact spot you'll be staying. Sometimes Operators adjust accommodations due to seasonal availability or group size. But rest assured: the quality and comfort will match what's shown.

Why would the accommodations change from time of booking?

Flexibility allows Operators to choose the best-fit accommodations closer to your trip—based on availability, logistics, and what works best for the group (like the number of Travelers and room configurations). This ensures a smooth experience without sacrificing comfort or quality.

Finalized hotel info is typically shared about 30 days before departure in your Traveler Portal, along with your final itinerary.

Trip Operations & Compliance

Who actually runs my trip, and how does Trova keep things safe?

Your trip is operated by licensed, certified Tour Operators who manage all trip logistics and safety—from accommodations and local Guides and day-to-day logistics. All trips comply with local legal and regulatory standards. We vet each Operating partner carefully so you can travel with confidence.

Who do I talk to if I have questions about safety or compliance?

If you have any questions about safety protocols or trip compliance, reach out to us at safety@trovatrip.com. We're here to help.

General Travel Questions

Do I need any documentation to travel?

It depends on where you're headed. Though it is not a universal requirement, many countries require that your passport be valid for at least six months beyond your arrival date. This ensures Travelers have sufficient time to return home even if their visas are extended or if unexpected circumstances arise. 

Some destinations may also require a visa. Check our visa page to consult your country's travel resources.

Do I need any vaccines?

It's always best to check with your healthcare provider or a travel doctor before your trip. You can also visit the CDC website (or your local government's travel health resource) for destination-specific vaccine guidance. Health and safety first!

Are flights included in the trip cost?

Because our Hosts and Travelers are coming from all around the world, flights to and from your destination are not included. Some trips include internal flights (like a short domestic hop), and those details will always be listed on the trip page if applicable.

Can you accommodate my dietary needs?

We’ll do our very best! Our Operators aim to accommodate dietary restrictions, though availability varies by destination. For example, some places offer plenty of vegan and vegetarian choices, while others might be quite limited. The earlier you let us know—through your trip form or by contacting our support team—the better we can prepare. Once you arrive, be sure to remind your local Guide about any allergies or restrictions so they can help you enjoy your meals safely and comfortably.