top of page

Join us in Greece!

Updated: Aug 19, 2023

Best of Greece September 3rd-17th 2023 (sold out) & September 22nd-October 6th 2023

(Sold Out)

We specialize in tours for adults only. We take you away from your everyday world and the necessary distractions of family life.

Ancient and modern Greece – a land of crumbling ruins and crumbling feta, the sun-bleached cradle of modern civilization. A lot of Grecian itineraries begin with Athens’ historical highlights before skipping quickly off to the Greek Islands, but not this one. We’ve designed a comprehensive tour that includes both- the best of the mainland AND the islands! From the Sanctuary of Apollo at Delphi and the unbelievable monasteries of Meteora, all the way to the olive groves and sandy beaches of the Cyclades islands. Along the way you’ll discover that Greeks are passionate about a few very specific things: good times, good food, and good gossip.

Why you will love this trip!

  • Uncover thousands of years of civilization in Athens with a visit to the world-famous Acropolis and the ancient Agora

  • Get lost in colorful cities filled with natural and ancient treasures as you explore mainland Greece. See where democracy began and how life was lived when Zeus called all the shots. Explore ancient ruins and rituals of the past.

  • Be mesmerized by the magical monasteries of Meteora, an extraordinary site precariously perched on a series of ancient rock pinnacles.

  • Discover the many flavors of Greek cuisine. There's nothing quite like dining on rich and hearty moussaka or grilled lamb and tzatziki in a traditional taverna as Rembetika music floats around you.

  • With its boutique culture, gorgeous beaches and thumping nightlife, the chic isle of Mykonos invites you to embrace your hedonistic side

  • Let the rest of the world melt away as you swim and snorkel in the warm waters of the Aegean Sea.

  • Wander through the charming villages of Syros. When night falls, indulge in delicious seafood dinners in traditional tavernas as Rembetika music floats around you.

  • The sight of a Santorini sunset can turn even the most hardened of souls into a romantic. Walk along the volcanic rim of the island from Thira to Oia, passing through white villages that cling to plunging cliffs.

Now that you are excited let’s get to the details.

For this trip we are doing something unique. You can go on the entire 15 day trip or you can go on either the 8 day mainland portion or the 8 day island portion if your vacation time is limited. PLUS there is a substantial discount for doing the entire 15 day trip.

“I would definitely travel with Penny Pinching Globetrotter again. You doing all the research, planning and coordination makes it a true vacation for me because normally I’m responsible for all that.” Sheryl

Day 1 / Date: SEPTEMBER 3rd 2023 or SEPTEMBER 22nd 2023 Athens Meals included: None Kalimera! Welcome to Greece. Named after the goddess of wisdom, the birthplace of Western civilization, Athens has an amazing array of historic sites to explore; a weighty history that spills out over the modern city, represented most dramatically by the ancient Acropolis. There's much to be seen in the ancient capital of Greece, vibrant and refreshed following the 2004 Olympics, yet still retaining so much visible history.

After the welcome meeting, perhaps head out for some gyros and ouzo with your new travel companions. Special Information Your adventure begins with a welcome meeting at 6pm today – confirm the time and place with reception. If you can't arrange a flight that will arrive in time, you may wish to arrive a day early. We'll be happy to book additional accommodation for you (subject to availability). If you're going to be late, please inform the hotel reception. We'll be collecting your insurance details and next of kin information at this meeting, so please have these on hand.

Accommodation Attalos Hotel (Standard room) or similar

For second trip our hotel for the first night has changed. Please arrive to Arion Athens Hotel as that is where we will be staying.

Day 2 / Date: SEPTEMBER 4th 2023 or SEPTEMBER 23rd 2023 Athens / Thessaloniki Meals included: Breakfast This morning head out to visit the famous Acropolis, one of the Western world's most important historical structures. Start with an ascent to the top of this sacred rock via the towering entrance, the Propylaia. Once inside, encounter the Parthenon – the greatest Doric temple in the ancient world. In the afternoon board a train to cosmopolitan Thessaloniki, the second largest city in Greece. This city especially comes alive in the evening, thanks in part to its large student population, so make sure you hunt down the perfect gyros or some live music.

Included Activities • Athens - Acropolis Archaeological Site Visit with Local Guide Accommodation Le Palace Art Hotel (Standard room) or similar Day 3 / Date: SEPTEMBER 5th 2023 or SEPTEMBER 24th 2023 Thessaloniki Meals included: Breakfast Relax in the splendor of what is regarded as the cultural capital of the country. Walk along the waterfront to the White Tower, take in the Byzantine churches (like the beautifully frescoed Church of Saint Nicholas the Orphan), Ottoman sites and Roman ruins, and appreciate the wonderful views over the gulf. On a clear day you might even catch a glimpse of the home of the gods, Mount Olympus.

The city is undoubtedly the gastronomic capital of Greece and its flavors are unique. For 2,000 years it’s been a melting pot of cultures, with eastern spices, French, Balkan and Mediterranean tastes. Get a taste of the city on an included tastes of Thessaloniki urban adventure where we will seek out the eateries in the area around the agora, where age-old columns and arches brush up against modern apartments and the ancient Rotunda.

Included Activities • Thessaloniki - Tastes of Thessaloniki Urban Adventure Accommodation Le Palace Art Hotel (Standard room) or similar Day 4 / Date: SEPTEMBER 6th 2023 or SEPTEMBER 25th 2023 Kalambaka Meals included: Breakfast Travel by public bus or train to Kalambaka (approximately 3 hours). Upon arrival embark on on a short orientation walk of town, where your leader will point out amenities and help you get your bearings. The rest of the afternoon is free for you to explore the scenic area around Kalambaka and Meteora, where the views are stunning whichever way you look. Having two days here allows you to explore at your own pace, discover the history and legends, witness the incredible views of one of the few World Heritage sites listed under both nature and art at different times of the day, and avoid the crowds. Your leader will have suggestions on hand. In the evening, maybe head to a taverna for dinner and stroll the main square for a taste of local life.

Accommodation Alexiou Hotel (Standard room) or similar

Day 5 / Date: SEPTEMBER 7th 2023 or SEPTEMBER 26th 2023 Meteora / Kalambaka Meals included: Breakfast Climb into the heavens, just like monks have done for centuries, towards ancient monasteries precariously placed atop 400-meter-high rock formations. Meteora is home to 24 14th century monasteries that sit at the top of karst pinnacles, though only six are still occupied. They were once only accessed by rope ladders, but thankfully there are now steps. The cliff faces also feature caves where hermits lived an even simpler life than those in the teetering monasteries. The monasteries, which used to be supplied by rope and pulley systems, house wood carvings, frescoes, paintings, and one even features the skulls of the first founders. You’ll enjoy some great views back over the town. The area makes for incredibly dramatic photos – multi-color streaked rock, bright green forest, and the pale terracotta of the monastery roofs against the Grecian sky. The mists that can surround the pinnacles make the constructions seem like they’re floating in the air. Hawks drift on the valley thermals looking for prey, and black-frocked priests shuffle silently around. Included Activities • Meteora - Monastery Visits Special Information A strict dress code applies when entering any of the monasteries. No bare shoulders or knees are permitted, and women must wear skirts. It is possible to borrow a long skirt at the door if you don't have one. Please also note that today will involve a fair bit of walking with many steep stairs, so it is recommended you wear comfortable shoes. Accommodation Alexiou Hotel (Standard room) or similar

Day 6 / Date: SEPTEMBER 8th 2023 or SEPTEMBER 27th 2023 Delphi Meals included: Breakfast Travel by private transfer to Delphi (approximately 4 hours). Located on the slopes of Mt Parnassos, by a valley of cypress and olive trees, this modern town and ancient ruins overlooks the Gulf of Corinth. The ancient Greeks regarded Delphi as the center of the world (legend says that Zeus sent two eagles flying from opposite ends of the world and they crossed paths over Delphi), and today it’s one of the country's most inspiring and memorable archaeological sites. On arrival, your leader will take you on an orientation walk of the cliffside town of Delphi. Then, make the most of your afternoon by visiting the ancient site of Delphi. Here you’ll find the famous sanctuaries of Apollo and Athena, which contain numerous monuments, temples, a well-preserved theater, and the impressive reconstructed Athenian Treasury. The site was also home to the Delphic oracle, said to have spoken for Apollo himself – she sat on a chasm, inhaling vapors from the Earth and entering a trance-like state, her cryptic answers to questions translated by priests. There’s also a mountain-top stadium, which was used for the Pythian Games (an Olympic Games precursor), held every four years as early as 586 BC.

Included Activities • Delphi - Archaeological Site & Museum Accommodation Hotel Varanos (Standard room) or similar Day 7 / Date: SEPTEMBER 9th 2023 or SEPTEMBER 28th 2023 Athens Meals included: Breakfast Travel back to Athens today by bus, arriving in the late afternoon (approximately 3,5 hours). Shop for the perfect souvenir at the Monastiraki flea market or take a relaxing stroll through the Greek national gardens. If you haven’t already, check out the Temple of Olympian Zeus or the Tomb of the Unknown Soldier to watch the changing of the guard. While in the neighborhood explore the excellent Museum of Athens, Syntagma square with the Parliament building, and the Panathinaiko Stadium which housed the first Olympic games in 1896.

Included Activities • Athens - Markets, Ruins & Ancient Athens Urban Adventure

Accommodation for first trip Attalos Hotel (Standard room) or similar

For second trip Apollo Hotel in Athens (Standard room) or similar

Day 8 / Date: SEPTEMBER 10th 2023 or SEPTEMBER 29th 2023 Athens Meals included: Breakfast Today you have time to explore Athens on your own. Perhaps check out the renowned changing of the guard at Syntagma (Parliament) Square. Or take this as an opportunity to rest up for the next leg of the trip.

For those leaving us, enjoy your trip home. If you are continuing on to the island portion of the trip see below. Note if you are doing both trips for the full 15 days then Day 8 above and Day 1 below are the same day.


Day 1 / Date: SEPTEMBER 10th 2023 or SEPTEMBER 29th 2023 Athens Meals included: None For those just joining us Welcome to Greece. As there's not much time to explore Athens on this trip before you head out to the islands, arriving a few days early is recommended. Highlights include the renowned changing of the guard at Syntagma (Parliament) Square, the National Gardens, the Temple of Olympian Zeus, the original Olympic Stadium and of course the Acropolis, where you can enter the Pantheon and enjoy fabulous views over the city. Maybe join an Urban Adventure day trip, such as 'Taste of Athens' or 'Markets, Ruins and Ancient Athens'. You could also take a day trip to the Peloponnese peninsula via ancient Epidavros and the orinthian canal. After the welcome meeting, perhaps head out for some gyros and ouzo with your new travel companions. Special Information Your adventure begins with a welcome meeting at 6 pm today – confirm the time and place with reception. If you can't arrange a flight that will arrive in time, you may wish to arrive a day early. We'll be happy to book additional accommodation for you (subject to availability). If you're going to be late, please inform the hotel reception. We'll be collecting your insurance details and next of kin information at this meeting, so please have these on hand. When traveling around Athens please be aware that we have had reports of travelers being pickpocketed on public transport, especially the metro. Please be careful with your valuables while traveling on the metro or the bus.

For those who joined us on the land portion today is a free day and you are not required to attend the meeting. Accommodation for first trip Attalos Hotel (Standard room) or similar

For second trip Apollo Hotel in Athens (Standard room) or similar

Day 2 / Date: SEPTEMBER 11th 2023 or SEPTEMBER 30th 2023 Syros Meals included: Breakfast Today travel by metro to the port of Piraeus, then catch a relaxing scenic ferry to Syros (approximately 4 hours). In the heart of the Cyclades, Syros offers a rare opportunity to see the islands as the Greeks do. One of the Aegean's most underrated islands, the island features typical whitewashed houses, farms,terraced fields, and gorgeous sandy beaches. Your leader will take you on a wander through the main town of Ermoupolis, home to well preserved neoclassical mansions and 19th-century tenement blocks. Syros is also home to delicious sweets. Stop at a family run traditional loukoumi workshop where you will be shown the procedure of how these multi-colored fruit-flavored jellies (also called Greek Delight) and chalvadopita (hazelnut, almond or honey-filled wafers) are made - make sure you try some of them. You'll have plenty of time to explore tomorrow, so perhaps kick up your feet at a waterfront cafe and watch the setting sun turn the houses pink.

Included Activities • Syros - Loukoumia Workshop Visit Accommodation Hotel Archontissa (Standard room) or similar Day 3 / Date: SEPTEMBER 12th 2023 or OCTOBER 1st 2023 Syros Meals included: Dinner Take a walk through the fortress-like town of Ano Syros, which offers great views of the Aegean Sea. Wander the narrow alleyways, pass handmade-souvenir shops and keep an ear open for traditional Rembetiko music floating out of the family-run tavernas. Enjoy free time to further explore Syros at your own pace. Discover abandoned windmills, ancient ruins and charming villages on a network of stone-paved tracks that crisscross the island. Perhaps head to the various archaeological sites on the island, or you might prefer to simply hole up on a beach for the afternoon. Outside of Ermoupolis are many small tranquil coves, while the most popular beaches are on the southern side of the island. While some are sandy and others pebbly, all boast crystal clear waters for swimming in. In the evening, take taxis to a taverna to a remotely located village in the rugged northern part of the island to sample delicious local specialities during an included meal, all while watching the sun set over the Aegean Sea. Included Activities • Syros - Ano Syros Walk • Syros - Sunset Dinner Accommodation Hotel Archontissa (Standard room) or similar

Day 4 / Date: SEPTEMBER 13th 2023 or OCTOBER 2nd 2023 Mykonos Meals included: Dinner Today board a two-hour ferry to Mykonos, a beautiful island named in honor of Apollo's grandson. Mykonos is legendary both in ancient and modern times. Known in ancient Greek mythology as the battlefield where Zeus fought the Gigantes, today the island is best known for its decadence, style, and nightlife. Join your leader for a walk through the maze-like old town and be captivated by the quintessential Greek Isles vista of squat white houses brightly juxtaposed against the cerulean sea. Browse the chic galleries and boutiques, follow flower-lined paths past age-old churches and tiny restaurants to secluded, sandy beaches, and spend the afternoon soaking up the rays and splashing in the water. As the sun sets, join the group for a picnic dinner of local specialties. Your leader will know the ideal spot to sit back and enjoy an Aegean sunset. Included Activities • Mykonos - Wine & Finger Food Special Information Please note that our hotel in Mykonos has a variety of rooms in different shapes, sizes, and with different views. Some rooms front the pool, others have a private terrace or even a view, and yet others have none of the above. Group members will be allocated rooms according to availability, and rooms will most certainly differ from one another. Accommodation Aegean Hotel (Standard room) or similar

Day 5 / Date: SEPTEMBER 14th 2023 OCTOBER 3rd 2023 Delos / Mykonos Meals included: Breakfast This morning you will take a half-day trip out to the nearby island of Delos. One of the most important archaeological and mythological sites in the Greek Islands, a sacred area that was once the political and religious center of the Aegean, Delos is considered to be the birthplace of Apollo and Artemis. A living museum, the wealthy built mansions in the town that developed around Apollo’s sanctuary, decorating them with luxurious frescoes, mosaics and statues. The island is overflowing with archaeological finds like the Terrace of the Lions and the Sacred Precinct, with many more still being uncovered. Later on today you might like to head to one of Mykonos' many beaches, which are some of the nicest in Europe. Take a short bus ride to the pumping Paradise or Super Paradise beach bars, or perhaps find a quieter spot to relax along the beautiful coastline. You could also check out the 19th-century House of Lena or the Aegean Maritime Museum in town. This evening you could make your way to the village of Ano Mera and seek out a tavern for a seafood dinner or perhaps wander down to Little Venice, where colorful balconies hang precariously over the sea.

Included Activities • Delos - Day Trip to the Island of Delos • Delos - Archaeological Site Accommodation Aegean Hotel (Standard room) or similar Day 6 / Date: SEPTEMBER 15th 2023 or OCTOBER 4th 2023

Santorini Meals included: Breakfast Take another ferry and arrive on the spectacular southern island of Santorini (approximately 3 hours). Renowned for its amazing natural beauty, Santorini is one of Europe's tourist hot spots, the home of the iconic image of the Greek islands – whitewashed, blue-domed buildings clinging to the cliff face with sparkling water in the background. Discover the hilltop ruins of Ancient Thira and its fascinating Prehistoric Museum, as well as the archaeological site of Akrotiri, a Minoan Bronze Age settlement that gives an insight into how the people here lived before the eruption. Check out the range of restaurants and shops in the island's capital, interchangeably called Thira or Fira. This afternoon head to one of Santorini's volcanic beaches and enjoy a hot springs. Be sure to try some of the island’s delicious food – the nutrient-filled volcanic soil makes the ingredients grown here full of flavor. Included Activities • Santorini - Volcano & Hot Springs Half Day Trip (by boat) Special Information Please note that our accommodation is located in the village of Karterados. It is a walk of approximately 20 minutes into Santorini's main town of Thira, or alternatively there are frequent bus departures from the bus stop right beside the hotel. Accommodation Pelican Hotel in Santorini (Standard room) or similar

Day 7 / Date: SEPTEMBER 16th 2023 or OCTOBER 5th 2023 Santorini Meals included: Breakfast In 1500 BC a volcanic eruption sank the center of Santorini, forming one of the most significant geological formations on the planet – the awe-inspiring caldera. The spectacular natural beauty of this caldera is what makes Santorini such a special place. Today take an excursion along the crater rim, starting in Thira town and walking through little villages all the way to Oia, passing steep cliff faces and experiencing breathtaking views along the way. If you have time, you might also like to take a half-day trip to the island's volcano and hot springs in the center of the lagoon. Or perhaps visit one of the island’s wineries – the vines here are cultivated in a very unusual way, with the plants being pruned to form a low basket shape that sits on top of the volcanic soil to protect the grapes from strong winds. On the last evening of your adventure, rub shoulders with friendly locals in packed pubs and cafes, sipping a cocktail as you witness a magnificent Santorini sunset.

Included Activities • Santorini - Caldera Rim Hike to Oia

  • Special Information-Please note that the hike along the caldera usually takes approximately 3-5 hours / 12 km, and the surface varies between gravel and loose volcanic scree. There are multiple uphill and downhill sections, and there are no shade and no toilet facilities along the way. Please speak to your leader for more details if you have any concerns. As an alternative to the hike you can take the bus to Oia instead, and meet up with the rest of the group there.

Accommodation Pelican Hotel in Santorini (Standard room) or similer

Day 8 / Date: SEPTEMBER 17th 2023 or OCTOBER 6th 2023 Santorini Meals included: Breakfast Today your Greek Islands adventure comes to an end. There are no activities planned and you are able to depart the accommodation at any time. You might want to extend your stay to see all Santorini has to offer. We are happy to book additional accommodation, subject to availability. Please inquire at the time of booking.

“Travelling can be so rewarding but so confusing as well. My trip with Penny Pinching Globetrotter took the confusion away and let me relax and enjoy every moment of my trip. They took care of every aspect of the itinerary so I didn't have to worry about planning days or dealing with difficult situations. I highly recommend Penny Pinching Globetrotters and look forward to traveling with them in the near future!” Pam


Full 15 day trip- The cost for the entire 15 day trip is $3,860 per person sharing a twin room, a savings of $740 over booking each portion separately. Booking priority will be given to those booking the entire trip. Solo and want a single room? Add $865

7 night land trip-The cost for the land portion only is $2,075. Traveling solo and want a single room? Add $410

7 night island trip-The cost of the island portion only is $2,525 Traveling solo and want a single room? Add $455

Add a night at the start or end of the trip? Add $130 per person

Add airport transfer upon arrival or departure? Add $85 per person each way (flight details must be provided 60 days before departure)

A deposit of $750 per person is due to secure your spot.

Payment schedule is as follows:

9/26/22 25% of remaining balance

2/1/23 25% of remaining balance

5/15/23 final balance due

I accept PayPal, Venmo or I can send an invoice that you can pay with a credit card or ACH but there is a 3.5% fee for the invoice.

My PayPal is and I ask that you please select sending to a friend or someone you trust so a fee is not deducted or add 4% to cover the fee.

My Venmo is Melissa-nance-19

Or if you want an invoice please just let me know. Note there is a 3.5% fee.

Please note proof of current COVID vaccination is required and one will be expected to adhere to any local mask mandates in the areas we are traveling.

Travel insurance is required for all travelers.

AIRFARE is not included.

Travel insurance is required for all travelers. We use and recommend World Nomads. Over 70 or want an additional quote? Check out Insure My Trip.

World Nomads provides travel insurance for travelers in over 100 countries. As an affiliate, we receive a fee when you get a quote from World Nomads using this link. We do not represent World Nomads. This is information only and not a recommendation to buy travel insurance.

Our cancellation policy is as follows:

Should you cancel no more than 30 days after making your deposit you get a 100% refund minus a $150 admin fee.

Should you cancel between 30 days of booking to 180 days before the trip you will get a 50% refund minus the $150 admin fee.

Once we are within 180 days of the trip starting there are no refunds.

Note-should you find someone to fill your spot I can transfer your balance to them minus the $150 fee. Should you become sick or have other issues it’s highly likely the required travel insurance would kick in and reimburse you so be sure and check with your provider.

“The hosts Melissa and Wade are great! They were very prepared and were able to answer all questions and met all of the group's needs throughout the trip.” -Tammy

Things to Note:

  • Please be aware that some of the Greek Islands are hilly and mountainous which means lots of steps that are an inherent feature of the landscape. There may be times when you will need to lift your luggage and carry it up and down stairs and/or inclines. Also, stone streets can become very slippery when wet. Some people may find Greece's topography very demanding.

  • As accommodations on this trip is twin-share, single travelers will share a room with another traveler of the same sex. If you’d prefer not to share, a single room supplement is available at an additional charge. Please ask your travel consultant for more details. Also, hotels in Europe often don't have double beds, but rather two single beds that can be pushed together.

  • The primary means of transportation in the Greek Islands is by public ferry. These ferries are large car ferries that transport hundreds of people, along with cars and trucks. There are no reserved seats and passengers are free to walk around the ferry freely. Luggage is stored in a designated area on the car deck and is not accessible while the ferry is moving.

Greece has been on my to go-to list for almost 6 years so I am excited to finally get to visit and hope you will join us! Please note that there are only 10 spots on this trip. As all of our trips so far have sold out I recommend you act quickly.

If you have any questions please don't hesitate to reach out to us at

Hope you can join us!

Melissa & Wade

3,193 views1 comment

Recent Posts

See All

1 Comment

What a fantastic adventure filled itinerar.

bottom of page