Small Group
Greek Islands Multi-Active
Endless charms of the Cyclades
7 Days, 6 Nights
Maximum Group Size
16
Activity Level:
B&R Activity Levels
Priced per person from
$9,795 USD
Single Supplement: $3,055 USD
Jan
Feb
Mar
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Dec
Carbon Neutral Trip
Hop through the Cyclades—Greece’s chicest island cluster—where whitewashed villages, hidden beaches, and seaside trails promise daily doses of postcard envy. Pedal and hike ancient paths, sail turquoise waters, and indulge sumptuously in local flavours. Embrace leisurely island rhythms and mingle with our local friends—just try not to gloat when you get back home, and yours ask how your trip went.
With over 4,000 islands in Greece waiting to be discovered, we've spent years exploring and have chosen five of our favourites to share with you.
Preview the itinerary
No two trips are ever the same, but this will give you a taste of what your journey will be like.
Day 1
We'll meet in Santorini for a volcanic hike then cruise to the lesser-known picturesque island of Folegandros to explore Cycladic architecture. This evening, we’ll head into town for a casual walk around the charming village. After showing you our favourite spot to watch the sunset, we’ll indulge in a traditional dinner at a restaurant overlooking the cliffs.
Activity:
5 km (3 mi.) hike along the caldera on a volcanic trail | Elevation gain: 132 m (433 ft.)
Optional hike on Folegandros
Day 2
Enjoy the slow pace of island life today as we spend time out on the coast, snorkelling and swimming in its aquamarine waters. This evening, tour Kastro Citadel before exploring the town on your own for dinner.
Activity:
Snorkelling and speed boating around Folegandros
Day 3
Set out on a hike along the Folegandros coast with occasional stops to explore village delights. After a seaside lunch, we'll head across the sea destined for the island of Sifnos to unwind. This evening, indulge at a cocktail party before we sit down for dinner at the hotel.
Activity:
7 km (4 mi.) coastal hike | Elevation gain: 168 m (551 ft.)
Day 4
From Apollonia, we’ll begin our hike along a beautiful route to Artemonas. Then, we'll meet our local friends on a farm for a 'slow food' cooking experience using traditional culinary techniques. Later, spend time relaxing at the pool before we head to a local seaside taverna for dinner.
Activity:
7 km (4 mi) hike to Apollonia | Elevation gain: 238 m (780 ft.)
Day 5
After a ferry ride to the island of Paros, we’ll head to the start of our walk in Lefkès, a restored Parian village full of narrow streets and churches. Walk along an ancient Ottoman-era trail ending in Prodromos, then we’ll pause for a seaside lunch. We’re then off to Naoussa, where we’ll have time to enjoy some shopping before we regroup for a fabulous dinner.
Activity:
4 km (2 mi.) easy going hike from Lefkes to Prodromos | Elevation gain: 35 m (117 ft.)
Optional hike | 2 km (1 mi.)
Day 6
Hop on our private boat to head to the neighbouring island of Naxos for a day of biking. On two wheels, discover another surprising island full of Byzantine churches and Hellenistic sights. For our final evening, we’ll explore an organic family-run farm and enjoy a farm-to-table experience hosted by the family.
Activity:
23 km (14 mi.) ride from Filoti to Kalantos | Elevation gain: 295 m (970 ft.)
Day 7
Although our journey has ended, the memories are yours to keep. We'll say farewell for now then depart for onward travels.
Rendezvous
Airport City: Santorini
Trip Start: Katikies Garden Hotel
Time: 8:30am
Farewell
Airport City: Paros
Trip End: Paros National Airport
Time: in time for your flight
* Itineraries are subject to change. Please confirm exact Trip Start and Trip End locations upon booking.
Featured stays
Anemi Hotel
Location: Folegandros Island, Greece
Elies Resorts Sifnos
Location: Sifnos, Greece
Parocks Luxury Hotel & Spa
Location: Paros, Greece
Dates & availability
Dates
Price
per person, double occupancy
Join
Join a group of up to 16 like-minded travellers.
Privatize
8+ people
Pricing depends on group size
Detailed Itinerary
Uniquely tailored for each date
Can't find your dates?
Get in touch to craft a Bespoke itinerary or request an additional date to Privatize.
What's included
Accommodation & dining
All breakfasts, lunches and dinners as indicated on the itinerary.
All accommodation as indicated on the itinerary.
Thoughtfully selected local wines, beers, cocktails or non-alcoholic beverages with all meals.
Active essentials
Use of two lightweight, telescoping walking sticks and a reusable B&R water bottle.
Choice of bike as appropriate for terrain (see below), equipped with handlebar bag and helmet.
Use of a smartphone with downloaded GPS routes provided via RideWithGPS.
Guided services & gratuities
Services of B&R guide(s).
All special events, private tours, guest experts and entrance fees.
All gratuities for baggage, porters and hotel services.
Transportation & logistics
Transportation from rendezvous to farewell, including ferry rides from Santorini to Folegandros, Folegandros to Sifnos and Sinfos to Paros.
Baggage transportation.
Access to the B&R support van every step of the way.
What's Not Included: International flights, travel protection, gratuity for your B&R guides.
This trip is carbon neutral. Learn more about our Sustainability commitment.
Experience Designer
Good to know
Terrain
The Greek islands offer diverse terrain, which can be rocky and hilly. Please be comfortable hiking and biking in these conditions and choose your bike selection accordingly.
Food
We'll embrace the local dining traditions by enjoying most of our lunches family-style.
Air conditioning
The hotels are equipped with air conditioning, though the temperatures may not be as cool as typical North American standards.
Why choose a Small Group trip?
An Effortless Journey
Our expert Experience Designers are perfectionists, using first-hand knowledge of routes, restaurants and hotels to create an unforgettable experience. This means all the planning is taken care of for you. All you need to do is enjoy.
Active Exploration
From emerging destinations to iconic sights, B&R trips show you the world in a new way on our expertly developed cycling, walking and hiking routes. Travelling through historic villages and romantic vineyards and up to striking viewpoints, our routes offer a variety of challenges for every activity level.
Friends for Life
Your fellow travellers are as passionate and curious about the world as you are, which means the conversations and laughs will be as free flowing as your drink of choice. Don't be surprised if your group starts planning a reunion before the trip is done.
Room for Surprises
We love a plan, but we adore a spontaneous moment even more. Whether it’s an impromptu al fresco meal or a moon-lit musical performance, our advice is to expect the unexpected.
Speak to an Expert