< Designed Trips

The Trip

Discover the relaxed energy of Puglia, a sun-drenched region along Italy’s heel of the boot. Home to fairytale-like architecture, from conical, dry-stone trulli houses to historic white hilltop towns, and a coastline framed by limestone cliffs and quiet Adriatic inlets, it’s ideal for long summer days spent exploring or seaside. Your adventure begins near the dramatic cliffside village of Polignanno a Mare and the quaint harbor of Monopoli where you’ll discover sea caves and grottos by boat and swim in clear, turquoise water. Visit a local masseria to learn the art of hand-stretching fresh mozzarella and burrata, and stop at a family-run vineyard where iron-rich terra rossa soil produces robust Primitivo wine. Continue the journey south, where the historic coastal town of Otranto will serve as a home base for days of beach hopping and exploration of the honey-colored Baroque city of Lecce. Along the way, indulge in rustic Puglianese cuisine, from hand-shaped orecchiette pasta to daily made burrata and iced almond-flavored espressos. Get ready to eat, sip, and swim your way through one of Italy’s most relaxed and inviting regions!

The Details

Price: 

• From $ per person

Duration:

• 7 nights, 8 days

Inclusions:

• Highly-rated boutique hotels
• Transportation within Italy
• Private & small-group experiences
• Curated destination mini-guide
• Trip preparation & support

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Puglia FAQs

When is the best time to visit Puglia?

The region is best visited during summer months, mid-May through mid-October, when temperatures are warm enough to enjoy the incredible coastline and warm Adriatic sea. 

Where should I fly in and out for this trip?

We recommend flying into Bari International Airport (BRI) and out of Brindisi Airport (BDS) for this trip. Although the trip doesn't include flights, we're happy to help with recommendations of the most cost effective and efficient flights from your home airport.

Does this trip require driving?

We recommend a car rental for this itinerary, as it provides the freedom to explore secluded beaches and more off-the-beaten-path towns at your own pace. However, if you do not want to drive, we can certainly include private transfers instead.

How active & adventurous is this TRIP?

This itinerary is as adventurous as you’d like it to be. Fill your days with coastal hikes, sea cliff jumping and cave swimming, or travel at a relaxed pace and embrace il dolce far niente (the sweetness of doing nothing). The itinerary includes a fair amount of free time, so the choice is entirely up to you.

The Itinerary

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Northern Puglia

• Day 1: Benvenuti in Puglia! Italy’s ‘heel of the boot’ is home to 500 miles of dramatic coastline, with ancient olive groves, historic whitewashed villages, rocky beaches, as well as foods and flavors that are unique to the region. Hop in your rental car and cruise to the countryside where many historic masserias (traditional farms) have been converted into charming boutique and luxury boutique hotels. Check in, drop your bags, and unwind by the pool or stroll through centuries-old olive groves. In the evening, head into one of the nearby whitewashed coastal towns like Fasano or Monopoli to dig into your first Puglianese dinner. Traditionally an agricultural region, local cuisine favors fresh vegetables, wild greens, soft cheeses and hand-shaped pastas, like orecchiette, and local osterias with breezy terraces are abundant. 

 

• Day 2: Wake up to your first frothy Italian cappuccino before heading to the marina in Monopoli. Join a small group and board a boat bound for the famous sea caves of Polignano a Mare. Cruise past sheer limestone cliffs, navigating in and out of sea caves carved into the rock over millennia. Take in views of the whitewashed houses perched high above the water before anchoring in a quiet, secluded cove for a dip in the turquoise Adriatic. Enjoy an onboard aperitivo before heading back to shore for a relaxing afternoon in the sun.

• Day 3: Buongiorno! The morning is free to do whatever feels right. Explore some of the coastline’s rocky calas (coves), with crescent-shaped sandy beaches and crystal clear water, stroll through the historic harbor of Monopoli with fishing boats bobbing in the bay, or lace up your sneakers for a scenic hike through the countryside. In the afternoon, head to a small, family-run farm and winery. Puglia produces 29 DOC wines, but is best known for its bold, full-bodied Primitivo (the same grape as California’s Zinfandel). Learn about the region’s unique microclimate, tour the ancient cellar, and sit down to a guided tasting of red and white wines paired with local snacks. Grab a relaxed dinner in one of the tiny towns nearby, or head into Fasano or Monopoli for a meal by the sea.

 

• Day 4: Rise and shine! Spend the morning relaxing at your hotel on the sand of a nearby beach. After lunch, hop in the car to explore a few of the area’s famous (and hidden), whitewashed villages and hilltop towns. You may want to begin your journey in the UNESCO-listed Alberobello, a town famous for having 1,500 iconic trulli, historic conical shaped dwellings built entirely without mortar. Continue down the road to Locorotondo, a stunning hilltop village overlooking a valley of shimmering olive trees. Or, ask us about smaller towns that are less visited but equally picturesque. As the evening sets in, make your way to a family-owned historic trullo to learn how to prepare some of the food that the region is famous for. With a private chef, you'll prepare pasta dough from scratch, as well as sauce, starter and dessert. Practice rolling, cutting and shaping the region’s most famous pasta shape, orecchiette, before sitting down to a beautiful dinner with vineyard views and a glass of the estate’s own wine.

Southern Puglia

• Day 5: Following a relaxed breakfast, check out of your hotel and hit the road, heading south toward the coastal town of Otranto. On the way, make a stop in the small city of Lecce, nicknamed "Florence of the South" for its extravagant Baroque architecture carved from soft, honey-colored limestone. Meet a local guide for a walk through the historic center, visiting the ancient Roman Amphitheater and Piazza del Duomo while sampling the city’s iconic street food, savory rustico pastries, custard-filled pasticciotto, and iced almond coffee (locally referred to as caffè leccese). After, it’s a short drive to Otranto, a historic port city, originally settled by ancient Greeks. Check into your second boutique hotel and get settled for chapter two of your Puglinese adventure.

 

• Day 6: An espresso doppio will fuel your morning as you dive into Puglia’s world-famous dairy traditions at a local masseria. Meet a master cheesemaker for hands-on experience in every step of the production process, learning how milk turns to curd, and trying your hand at stretching and tying fresh mozzarella and creamy burrata before sitting down to taste the freshest cheese you may ever eat. Spend the afternoon exploring nearby natural wonders, like the emerald waters of the Cava di Bauxite quarry, or the ancient ruins near Grotta della Poesia, or head into Otranto to visit the 12th century Cathedral or the Aragonese Castle with panoramic sea views. After a leisurely dinner, end your day with a scoop of gelato made with fruits that are fresh and in-season.

 

• Day 7: Your final full day in the relaxed region of Puglia is dedicated to hopping from one beach to the next, soaking up the sunshine and sitting down to a long, leisurely lunch. With the entire day free, pick and choose between the dozens of beaches, coves, rocky outcrops, grottos and lidos/beach clubs, all of which are primed for sunbathing, swimming and relaxing (included in your destination Mini Guide). After a day of sun and sea, sit down to your final dinner and raise a glass of big, bold primitivo to the memories you’ve made over the past week before tucking in for a good night’s sleep. 

 

• Day 8: Rise and shine to your final morning in southern Italy. Enjoy a cozy breakfast before packing up and checking out of your hotel. Drop off your rental car at the airport and step on the plane for your flight home… or to another Italian or European destination. 

Pricing & Inclusions

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Boutique

• 4 hotel nights in Northern Puglia: or equivalent
• 3 hotel nights in Southern Puglia:  or equivalent
• 8-day car rental 
• ​Small-group boat tour from Monopoli to Polignano a Mare caves
• Tour and tasting at family winery
• Private cooking class in an ancient trullo
• History and street food tour of Lecce
• Dairy visit with hands-on mozzarella & burrata workshop and tasting
• Curated Italy mini-guide
• Trip preparation & support

​Exclusions

• International flights to/from Italy 
• Meals & activities not listed above
• Travel insurance

Boutique Pricing

• From $ per person

​*Pricing based on double occupancy and may vary depending on travel dates and total number of travelers. ​

Luxury Boutique

• 4 hotel nights in Northern Puglia: or equivalent
• 3 hotel nights in Southern Puglia:  or equivalent
• 8-day car rental 
• ​Small-group boat tour from Monopoli to Polignano a Mare caves
• Tour and tasting at family winery
• Private cooking class in an ancient trullo
• History and street food tour of Lecce
• Dairy visit with hands-on mozzarella & burrata workshop and tasting
• Curated Italy mini-guide
• Trip preparation & support

Exclusions

• International flights to/from Italy 
• Meals & activities not listed above
• Travel insurance

Luxury Boutique Pricing

• From $ per person

*Pricing based on double occupancy and may vary depending on travel dates and total number of travelers. ​

Luxury

• 4 hotel nights in Northern Puglia: or equivalent
• 3 hotel nights in Southern Puglia:  or equivalent
• 8-day car rental 
• ​Small-group boat tour from Monopoli to Polignano a Mare caves
• Tour and tasting at family winery
• Private cooking class in an ancient trullo
• History and street food tour of Lecce
• Dairy visit with hands-on mozzarella & burrata workshop and tasting
• Curated Italy mini-guide
• Trip preparation & support

​Exclusions

• International flights to/from Italy 
• Meals & activities not listed above
• Travel insurance

Luxury Pricing

• From $ per person

​*Pricing based on double occupancy and may vary depending on travel dates and total number of travelers. ​

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Optional activities

• Private boat tour of Polignano a Mare caves 
• Olive oil mill tasting and tour

• Group kayak excursion from Otranto
• Otranto historic walking tour

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​This Designed Trip was developed based on our personal travels, with local contacts, favorite hotels and authentic activities that we've experienced first-hand.
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Ready to Get Started?

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FAQs

​WHAT IS A DESIGNED TRIP?

A Designed Trip is a pre-designed travel plan based on our personal, first-hand travel experiences in each destination. As they are pre-designed, our Designed Trips have been created as a turnkey travel option and can be booked and delivered in as little as one week. ​

CAN I MAKE ANY CHANGES TO A DESIGNED TRIP?

Absolutely! Pre-designed doesn’t mean there isn’t any flexibility. Whether you want to shorten or lengthen your trip, switch out a destination or change an activity, let us know. If, however, you want a trip built around your specific desires, a Custom Trip might be more appropriate. We can help you decide, so get in touch.

​HOW LONG DOES THE PROCESS TAKE?

Once you’ve selected your Designed Trip and chosen between a Boutique, Luxury Boutique or Luxury experience, your trip can be booked and delivered in as little as one week. If you would like to make some changes to your trip, such as including an alternative activity, shortening or lengthening your trip, then this can take a bit longer.

HOW DO I KNOW HOW MUCH MY DESIGNED TRIP WILL COST?

Once you have decided on your Designed Trip, your dates, and any adjustments we will provide a personalized itinerary and pricing for your trip. We have included base pricing on each Designed Trip page to give you an idea as to what the final cost might be, but prices can fluctuate depending on time of year and any personalization. Get in touch and we can help.

If you have any other questions, feel free to check out more FAQs or send us an email.