< Designed Trips

The Trip

Uncover the beauty of Puglia, a quiet region along Italy’s sun-drenched "heel of the boot" that still feels largely undiscovered. Home to fairytale-like architecture, from conical, dry-stone trulli houses to gleaming white hilltop towns, and a coastline framed by limestone cliffs and quiet Adriatic inlets, it’s a side of Italy unlike anywhere else. Start your adventure in the north exploring dramatic cliffside villages before setting sail from Monopoli to discover coastal sea caves (grottoes) and swim in clear, turquoise waters. 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 and crisp Minutolo wines. Your journey will then take you south, where the historic harbor town of Otranto will serve as a home base for days filled with beach hopping along both the Adriatic and Ionian Seas. Visit Lecce, known as the “Florence of the South,” and tour the city’s honey-colored Baroque streets while tasting local specialties like savory rustico pastries, sweet pasticciotto, and iced almond coffee. Throughout your trip, indulge in rustic Pugliese cooking, from hand-rolled orecchiette pasta to fresh burrata (which was invented right here) and plenty of local wine. Get ready to eat, sip, and swim your way through southern Italy’s best kept secret!

The Details

Price: 

• From $ per person

Duration:

• 7 nights, 8 days

Inclusions:

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

Exclusions:

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

GET STARTED

Puglia FAQs

When is the best time to visit Puglia?

Peak season is July and August, but we highly recommend the shoulder seasons for cooler weather. May to June brings greener landscapes and ideal sightseeing temperatures, while September to October offers warm sea water, local olive and grape harvests, and vibrant food festivals.

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?

Main towns like Bari, Polignano a Mare, and Lecce are easily connected by local trains, but having a rental car (or using private transfers) is highly recommended for this itinerary. Driving is essential for reaching secluded beaches and more off-the-beaten-path sites at your own pace.

How active & adventurous is this TRIP?

This itinerary is as flexible as you’d like it to be. You can take a relaxed pace and embrace “il dolce far niente” (the sweetness of doing nothing), or pack your days with coastal hikes, sea cave swimming, and active exploring.

The Itinerary

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Northern Puglia

• Day 1: Benvenuti in Italia! Welcome to Puglia, the heel of Italy’s boot, celebrated for its 500 miles of dramatic coastline, ancient olive groves, and rich culinary traditions. Pick up your rental car and head toward the countryside surrounding Fasano. Traditionally an agricultural region, many historic masserias (farmsteads) have been converted into charming boutique hotels. Check in, drop your bags, and unwind by the pool or stroll through centuries-old olive trees. In the evening, head into one of the nearby whitewashed towns to wander its quiet alleyways. Historically a region built on rustic farming, local cuisine favors fresh vegetables, wild greens, and hand-rolled pastas over expensive meats. Sit down to your first authentic Pugliese dinner before turning in for a restful night.

 

• Day 2: Wake up in northern Puglia and grab your first Italian cappuccino before heading to the marina in Monopoli. Here, you’ll join a small group and board a boat bound for the famous sea caves of Polignano a Mare. Cruise past sheer limestone cliffs, navigating right up to (and inside) sea caves carved into the rock over millennia. Take in sweeping views of 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 of warm, salty focaccia, taralli, and chilled Prosecco. Head back to shore for a relaxing afternoon and a cozy evening at a local trattoria.

 

• Day 3: Buongiorno! Spend a slow morning exploring the coastline’s rocky calas (coves), or head to Monopoli to wander its historic harbor, lined with blue fishing boats and emerald-windowed homes. If you’re feeling active, lace up your sneakers for a scenic hike through the countryside, looping past ancient groves and iconic, conical trulli (dry-stone dwellings built entirely without mortar). In the afternoon, head inland to a small, family-run farm and winery. Puglia produces 29 DOC wines, but is best known for its bold, full-bodied Primitivo. 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. Return to Fasano for a late-night stroll and relaxed dinner.

 

• Day 4: Rise and shine! After a strong espresso, dive into Puglia’s world-famous dairy traditions at a local masseria. Meet a master cheesemaker and get hands-on experience in every step of the process, learning how milk turns to curd, and trying your hand at stretching and tying fresh mozzarella and creamy burrata (complete with a tasting, of course!). Next, drive into the picturesque Valle d'Itria toward UNESCO-listed Alberobello to marvel at its 1,500 iconic trulli. Continue down the road to Locorotondo, a stunning hilltop village overlooking a valley of shimmering olive trees. Stroll its narrow, flower-filled alleys and grab an afternoon spritz in the sun before returning to your hotel for a peaceful evening.

Southern Puglia

• Day 5: Enjoy a final local coffee, check out, and hit the road heading south toward Otranto. On the way, stop in 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, marveling at 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 (caffè leccese). Afterward, drive down to Otranto, a historic port city originally settled by ancient Greeks. Check into your hotel before spending the rest of the afternoon relaxing at a seaside beach club. For dinner, consider trying Ciceri e Tria, a classic Salento dish of fresh and fried pasta with chickpeas.

 

• Day 6: Start your morning with a strong coffee and a warm cornetto (Italy’s sweet take on the croissant). Today you’ll head out to explore Otranto’s historic sites, first marvel at the astounding 12th-century floor mosaic inside the Otranto Cathedral depicting the "Tree of Life," then walk up to the imposing ramparts of the Aragonese Castle for panoramic sea views. Spend the afternoon exploring nearby natural wonders, like the striking fiery red earth and emerald waters of the Cava di Bauxite quarry, or the ancient ruins near Grotta della Poesia. After a leisurely dinner, end your day with a scoop of fresh seasonal gelato.

 

• Day 7: Grab a cappuccino and sit down to a delicious breakfast before heading out for a day of sun and adventure. Today is dedicated to beach-hopping, a long leisurely lunch, and soaking up the sunshine. One of the things that makes Puglia so special (besides the turquoise sea) is the huge number of beaches, coves, rocky outcrops, grottos and lidos/beach clubs, all of which are primed for sunbathing, swimming and relaxing. We’ll recommend a list of our favorite local beaches for you to discover. After a day of sun and sea, sit down to your final relaxing dinner and raise a glass of primitivo to the memories you’ve made on this trip before tucking in for a good night’s sleep. 

 

• Day 8: Rise and shine to your final morning in the south of bella Italia. Enjoy a relaxed breakfast before packing up and checking out of your hotel. Drop your rental car off at the airport for your flight home.

Pricing & Inclusions

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Boutique

• 4 hotel nights in Northern Puglia: or equivalent
• 3 hotel nights in Southern Puglia:  or equivalent
• ​Small-group boat tour from Monopoli to Polignano a Mare Caves
• Terre di San Vito Wine Tasting
• Dairyman for the day tour
• Lecce History and Street Food Tasting Tour 
• Car Rental, 8 days
• Curated Italy mini-guide
• Trip preparation & support

​Exclusions

• International flights to Italy and home
• 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
• Small-group boat tour from Monopoli to Polignano a Mare Caves
• Terre di San Vito Wine Tasting
• Dairyman for the day tour
• Lecce History and Street Food Tasting Tour 
• Car Rental, 8 days​
• Curated Italy mini-guide
• Trip preparation & support

Exclusions

• International flights to Italy and home
• 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. ​

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Optional upgrades

• Private

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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.