Roots Rails & Rambles Roots Rails & Rambles

Istanbul Türkiye, May 2024

ISTANBUL, Türkiye: MAY 25 - JUNE 1, 2024

Istanbul is a city that has been plagued for centuries by an abundance of cliches:
  • The crossroads between East and West!
  • A foot firmly planted in two continents!
  • A magical carpet woven from the threads of antiquity and modernity!
While all those overwrought claims have a ring of truth to them, we have a slightly different perspective on this great city. Your host for this trip, Sarah Ovenden grew up in Istanbul (a few decades ago, but who’s counting?) and while she has deeply-rooted affection and nostalgia for the place, she isn’t swayed by the hyperbole. In 2023, she led a small group back to the city of her youth to explore not only the premier historical and cultural highlights, but also the lesser-known, off-the beaten path gems that lurk around so many corners. We had an amazing time!

The Istanbul of today can appear to be a slightly overwhelming and frenetic beehive, comparable to any modern urban center, but having been built on or around the masterfully-preserved remains of so many centuries of diverse civilizations, the history is inescapably woven into the fabric of even ordinary days. It is a city of stunning architecture from virtually every period of recorded human history, the cultural epicenter of art, music, and literature spanning thousands of years, and provides a fascinating view of the concurrent existence of both the secular and religious lives of its inhabitants.

Yes, we’ll explore the Big Stuff – Aya Sofia, The Blue Mosque, Topkapi Palace, the Hippodrome, the Grand Bazaar – but we’ll also spend time wandering the back streets, sampling the astonishing and delicious array of street foods, criss-crossing the Bosphorus on the ferry, hopping off to explore tea houses, fortresses, street markets, and small fishing villages. We’ll take a day trip out to the fabled Prince’s Islands for a little green respite from the bustling city, and we’ll delve into some of the contrasts between modern and ancient Istanbul.

We’ll draw on the expertise of local historians and guides to ensure that you get the information and context with which to deepen your understanding and enjoyment of this great city, and we’ll leave enough breathing room in the itinerary for surprises, or to circle back to places that deserve a deeper dive. We’ve intentionally paced things a bit differently than most Istanbul tours – we’ll tackle just a few major attractions each day, leaving plenty of opportunities for relaxing with a potent cup of coffee in a shade-covered courtyard, or sampling Turkey’s national drink, raki, on a rooftop overlooking the Golden Horn. For those who may wish to strike out on your own a bit, we’ll help you gain mastery of the transit system and the other tools you may need to do some independent exploring, and for those who wish to get swept up in the adventure within the security of a small group, we’ve got you covered.

Virtually all of your meals are included, we’ll take care of getting your museum tickets, your transportation passes (Istanbul has a massive public transit system of metros, trams, funiculars, and ferries we’ll be using daily), your airport pickup/drop off, and we'll be staying in the lovely Galata's Hotel  in Karakoy -- one of the most lively and interesting neighborhoods along the Bosphorus. All you have to do is get yourself to and from Istanbul, which has a brand new airport with multiple flights daily from the US, Canada and points in Europe.

This trip is very intentionally limited to 12 participants. This gives us the agility with which to move efficiently as a group, dine in smaller, family-owned restaurants and take advantage of the expertise of our local guides – plenty of time for questions and conversation.


Our daily itinerary looks roughly like this, allowing for adjustments based on participants’ interests whenever possible. If you're interested in arriving a day early to adjust to the time zone, we can help with getting you our group rate at our host hotel.

SATURDAY, MAY 25:  Arrive Istanbul International Airport, get picked up by a driver and taken directly to our hotel in the Karaköy neighborhood, steps from the Galata Bridge and the Golden Horn. Depending on arrival times, we’ll have lunch or dinner at one of the neighborhood restaurants and review our schedule for the week. As always, for those who wish to arrive a day early to adjust to the time difference and fend off jet lag, we will happily arrange hotel accommodations at our group rate.

SUNDAY, MAY 26: Let’s knock off a couple of the “bucket list” items! After your first mind-blowing traditional Turkish breakfast (kahvaltı – you’ll learn to love that word) we’ll hop on the tram (within 5 minutes of our hotel) and head over the bridge to Sultanahmet, the area where some of the city’s premier attractions lie. After exploring Aya Sofya, we’ll take a break for lunch then continue on to the Blue Mosque and the Hippodrome, then the Basilica Cistern. A quick tram ride back to our hotel gives us some free time in the afternoon for our first traditional çay evi (tea house) experience, or a sampling of baklava at the city’s largest pastry shop, then we can counter all the antiquity of our morning’s exploration with a visit to the Istanbul Modern, just down the street from our hotel. Our options for dinner are numerous: a traditional fish restaurant, a meyhane, or one of the trendy new restaurants that are sprouting up all over Karaköy.

MONDAY, MAY 27: We’ll beat the crowds and head over the bridge to catch the opening of the legendary Topkapi Palace and spend the morning wandering through the 400 rooms of both the palace and the Harem – OK, maybe not ALL 400 rooms, but we’ll make as big a dent as we can. If we have sufficient energy, we can also tackle the Istanbul Archeology Museum and/ or the Mosaic Museum. We’ll fortify ourselves with lunch at one of the classic Istanbul restaurants of Eminönü, where Sarah can give a tutorial on the art of haggling before heading into the bedlam of the Grand Bazaar. We’ll avoid the main thoroughfares of mass-produced and glitzy tourist kitsch and head into the secluded hans and bedestens – remnants of the original caravansarays – where we’ll have a tutorial on Turkish carpets from one of the bazaar’s most reputable carpet dealers (no pressure at all to buy – he’s just an incredibly knowledgeable and lovely guy).  We’ll have a chance to see the true artistry of Turkish carpets, tiles, copper, textiles, and jewelry. If we’re still vertical, we can take a detour to visit the  Süleymaniye Mosque which, though not always included in the primary mosque attractions, is a stunning example of Ottoman architecture which historians consider one of Istanbul’s most important landmarks. After an afternoon break to catch our breath, we’ll take the underground funicular up the hill to connect with the streetcar to Galatasaray and wander leisurely through the back streets of Beyoğlu down the hill to the Museum of Innocence, the brainchild of one of Turkey’s most esteemed novelists, Nobel laureate, Orhan Pamuk. Dinner could find us either at a traditional meyhane, sampling mezze and raki, or perhaps at one of the rooftop restaurants with commanding views of everything we just explored.

TUESDAY, MAY 28: Let’s take a break from the bustle and congestion of Old Istanbul and poke our way up and down the Bosphorus, using the local commuter ferry service. The dock is practically adjacent to our hotel, and it criss- crosses this strait (NOT a river! Only the tourists call it a river) between the European and Asian sides, with calling points in Üsküdar, Çengelköy, Arnavutköy, Bebek, Emirgan, and Istinye – each a neighborhood/village with its own unique character. The perspective from the water is ideal for understanding the scope of the city and its strategic importance in the many military conflicts it has endured over the centuries, and riding on the upper open-air deck of the ferry, sipping tea and tossing snacks to the swarming seagulls is a really lovely way to spend the better part of a day. We’ll travel under the very first suspension bridge to link Europe and Asia, and along the way get a chance to gawk at everything from the opulent and overly-ornamented summer palaces of the sultans, to the waterfront wooden yalis – some of which have been beautifully restored and some which are crumbling gracefully into the water. We’ll see the fortresses of Rumeli Hisar and Anadolu Hisar (don’t worry – we’ll go back and explore Rumeli Hisar on foot later in the week), and head back along the Asian side, stopping somewhere en route for lunch at a waterside restaurant. Afternoon finds us back at our hotel with time to consider our options for finding some local music for the evening, or perhaps a sunset cruise up the Golden Horn.

WEDNESDAY, MAY 29: After everything we saw via the water yesterday, today we’ll get picked up by a chartered van to retrace our steps along the shore road to explore the waterfront neighborhoods of Ortaköy, Arnavutköy, Bebek and Rumeli Hisar. We’ll have a chance to climb around the parapets of the Rumeli Hisar fortress, explore one of Istanbul’s newest museums the Borusan Contemporary, and visit the former home (now a museum) of famous Turkish poet Tevfik Fikret for some stunning views across the Bosphorus, and have a wander through what is consider Istanbul’s most beautiful cemetery, the resting place of many notable Turks from novelists to football players.

THURSDAY, MAY 30: Another ferry jaunt – this time out to the Prince’s Islands – a chain of islands in the Marmara Sea, yet still visible from the city. This is an entirely different environment, one that hosts vacationing families from the city trying to escape the height of the summer heat. We’ll likely bypass the most crowded of the islands and head for the sleepier Heybeliada or Burgazada for a seaside lunch and wander around. The islands are covered in fragrant pine forests and many sheltered coves accessible only by boat. Weather permitting (it may be a little early in the season) we may take a boat taxi to one of the beach clubs for a swim. No gas-powered vehicles are allowed on the islands, so we travel by foot or electric shuttles, while the adventurous among us may want to rent a bike for a ride around the island. 

FRIDAY, MAY 31: Our last full day in the city, we’ll have an opportunity to really immerse ourselves in the Beyoğlu neighborhood, one of the oldest in the city, pre-dating the founding of Constantinople. We’ll have a chance to climb to the top of the Galata Tower for a 360 degree view of the city and many of the landmarks that will now be familiar to you. While Beyoglu’s Istiklal Steet is often touted as one of the city’s prime shopping districts, in reality it has become a congested stretch of international chain stores BUT hidden down the side streets and alleys remain some of the most intriguing “passages” – narrow glass-roofed arcades housing cafes restaurants, used book stores, and antiques – well worth a visit.

Historically, Beyoglu has been host to many foreign embassies, as well as some of the cities landmark hotels – the Pera Palas, the Büyük Londra and others which were the preferred lodging of luminaries disembarking from the Orient Express, notably among them Agatha Christie (who is rumored to have written “Murder on the Orient Express” in Room 411 of the Pera Palas), Ernest Hemingway, and Alfred Hitchcock. These “grand dame” hotels may be getting a little long in the tooth, but having a drink in their slightly over-the-top neo classical ambiance is a great experience. Dinner tonight will likely be at what used to be Rejans, now known as 1924 Istanbul, an almost impossible to find Russian restaurant, founded in, you guessed it, 1924 by Russians fleeing the Bolshevik Revolution. In the 1970s the dining room was presided over by a pair of terrifying Russian sisters who floated like black-clad ghosts in the shadows of the balcony overlooking the dining room and were the stuff of Sarah’s childhood nightmares. But the Chicken Kiev made up for whatever trauma was inflicted upon her. If you wish your final taste in Istanbul to be something authentically Turkish, we can stop for a lahmacun on the way back to the hotel.

SATURDAY, JUNE 1: After breakfast at the hotel, we’ll have arranged private airport transfers to get you back to the airport and on your way to your next adventure.

$4389.00 per person.  Included in your trip fare:
  • 7 nights hotel accommodation, solo-occupancy
  • Private airport pick up and return
  • Local transportation
  • Museum/Attraction entry fees
  • Guide services where we use them
  • Breakfast and at least one other meal each day
Trip fare does not include:
  • Airfare to and from Istanbul (but we're happy to consult about best options)
  • gratuities for hotel staff, tour guides and drivers
  • Within 30 days of deposit, pay your remaining balance of $3889 through our online store.
  • or Contact Sarah at or 802-258-1397 to set up a convenient interest-free monthly credit card draw.
Credit cards (Visa, MC, Amex, Discover) and checks accepted. Payment plans at no additional charge are happily accommodated. Payment plan must be agreed upon and set up within 30 days of sign-up. Deposits, whether paid separately or as part of a full payment up front, are non-refundable. Liability release signature required.

Since the advent of Covid-19, and its impact upon travel, we feel purchasing travel insurance has gone from wise precaution to fiscal necessity. Going forward, we are strongly suggesting that all patrons  carry trip insurance that provides, at a minimum, coverage for the following:
  • Cancellation for Covid-19 illness
  • Trip Cancellation
  • Trip Interruption
  • Cancel for Medical Reasons
  • Medical Coverage for Covid-19 (often included under Emergency Medical Care)
  • Emergency medical care
  • Medical Evacuation
After doing extensive research, we feel a product such as AXA USA Assistance Silver or Nationwide Essential provides robust coverage for all those items at a very fair price. Both of those products (and many more) can be purchased through our affiliate, Squaremouth. Because travel insurance is such a highly personalized product, when you click on the link and are directed to the Squaremouth landing page and the "Compare and Buy Travel Insurance" calculator, you’ll have to enter your own demographic information – age, state of residence etc. -- after which you'll be presented with a number of options to consider. Among them will be the AXA and the Nationwide products. You are certainly not limited to those two products  – we are merely outlining the elements of coverage that we are requiring going forward and a convenient way to access them. If you purchase the policy through that link to Squaremouth it does not cost you anything more than purchasing the product directly from the vendor, but we receive a small commission. 

Our customers are extremely important to us, and when travel disruptions occur, we are committed to working with you to minimize the financial impact. In the event that you need to cancel a trip for whatever reason, we will work with you to try and find a buyer for the space you are needing to give up. Often this works out well for all: the person needing to cancel recovers most, if not all, of their investment, and a person who might have been on a waiting list gets to go on the trip - however, there are no guarantees.

We understand that the new realities of travel are such that we need to be more flexible than ever before. We are also an extremely small business with many fixed costs that can't always be recovered if a trip needs to be postponed or cancelled due to health and safety concerns. We will be completely transparent if a scheduled trip looks like it needs to be adjusted in any way that might impact your enjoyment of the experience. Please read through our cancellation policy carefully and feel free to reach out to us with any questions or concerns.

Cancellation policy: Deposits, whether paid separately or as part of a full payment up front, are non-refundable. Outside of deposit and credit card fees, full refund will be given up until 90 days prior to start of trip. 50% refund 60-89 days. No refund less than 60 days prior to start of trip. Reservations are fully transferable to another person.The payment of a deposit or any part or full payment for a reservation shall constitute consent to all the provisions contained herein.

Roots, Rails and Rambles shall not be held responsible for property loss or damage and/or any damages resulting from illness, personal injuries or death which may be sustained by reason of, or while engaged on, any trip or tour whether due to the ownership, maintenance, use, operation or control of any vehicle, hotel, common carrier or any other conveyance used in carrying out these tours. We can assume no liability due to any cause whatsoever whether caused by failure or delay or other irregularity, acts or omissions occurring during a tour under which the means of transportation or other service thereby is offered or supplied by owners, operators or public carriers for whom Roots, Rails and Rambles acts only as agent. Roots, Rails and Rambles reserves the right (at its discretion) to alter or omit any part of the itinerary, or change any reservation, feature and/or means of conveyance without notice or for any reason whatsoever and without allowance or refund and with extra costs, if any, resulting therefrom paid by the passengers. We reserve the right to cancel any tour prior to departure, in which case payment will be refunded without further obligation on our part. Roots, Rails and Rambles shall not be responsible for any injury to person (whether or not resulting in death) or damage to property.

Baggage is at the owner's risk entirely. The transportation companies concerned are not to be held responsible for any act, omission or event during the time passengers are not aboard their carriers or conveyances. The passenger contract in use by the carriers concerned (when issued) shall constitute the sole contract between the transportation companies and the purchaser of these tours and/or passage. By accepting the ticket the passenger also agrees to its terms and conditions. By forwarding of deposit, the passenger certifies that he/she does not have any mental, physical or other condition or disability that would create a hazard for him/herself or other passengers. Roots, Rails and Rambles reserves the right to cancel or withdraw any person as a member of the tour at any time. Roots, Rails and Rambles management reserves the right to refuse service to anyone whom it considers incompatible with the best interests of its services or its guests.