Calimera

Day Trips

Make the most of your day with our curated plans, packed with Calimera's hidden gems and unique experiences!

day 1
Arrival and Village Stroll
morning
:

Enjoy a cappuccino and fresh pastry at a local pasticceria as you absorb the gentle morning light on Calimera’s stone buildings. Wander through narrow streets and admire vibrant bougainvillea cascading from balconies. Feel the authentic pace of village life in small piazzas and corner shops.

afternoon
:

Visit the Casa Museo Antonio Jasionowski to learn about the local Arbëreshë heritage and traditions. Stroll to a nearby olive oil mill to witness centuries-old milling techniques and sample freshly pressed oil. Pause at a family-run café for a light lunch of focaccia with olive oil and fresh tomatoes.

evening
:

Savor your first dinner at a charming osteria featuring regional dishes like orecchiette alle cime di rapa paired with a local Negroamaro. Join villagers in the main piazza for an evening passeggiata among lantern-lit arches. End your night with a scoop of creamy gelato as church bells chime softly.

day 2
Olive Grove Exploration
morning
:

Set out early to wander through centuries-old olive groves on the rolling Salento hills. Join a local producer for a hands-on tasting of different olive varieties while learning traditional harvesting methods. Breathe in the crisp country air and photograph sunlit gnarled trunks.

afternoon
:

Enjoy a farmhouse lunch of fresh burrata, grilled vegetables and homemade bread alongside a tasting of extra-virgin olive oil. Participate in an interactive olive-picking workshop or press your own mini bottle to take home. Relax under shaded pergolas with views of endless silver-green leaves.

evening
:

Experience an intimate farm-to-table dinner amid lantern-lit tables in an old masseria courtyard. Delight in slow-cooked lamb and seasonal vegetables paired with a robust Primitivo. Listen to local musicians playing pizzica as the fireflies appear around the fields.

day 3
Baroque Lecce Excursion
morning
:

Take a short train ride to Lecce and begin with breakfast in a historic piazza flanked by Baroque façades. Join a walking tour to marvel at ornate columns, carved stone balconies and the grand Basilica di Santa Croce. Capture close-up shots of cherubs and floral motifs in the morning light.

afternoon
:

Stop at a traditional pasticceria for pasticciotto and espresso before visiting the Roman amphitheater beneath Piazza Sant’Oronzo. Spend time exploring artisan workshops specializing in papier-mâché and goldsmithing. Savor a pizza rustica in a hidden courtyard café.

evening
:

Return to Calimera and dine at a trattoria featuring Lecce’s local specialties, such as rustico leccese. Sample a glass of local rosé while sharing stories with fellow travelers. Stroll home beneath softly illuminated alleyways lined with tangerine-hued buildings.

day 4
Torre dell'Orso Coastal Adventure
morning
:

Drive to Torre dell’Orso and start the day swimming in the turquoise Adriatic waters framed by limestone cliffs. Relax on the golden sand beach and spot the twin sea stacks known as Le Due Sorelle just offshore. Sip a fresh fruit smoothie from a beach kiosk.

afternoon
:

Rent a paddleboard or kayak to navigate hidden coves and grottoes along the rugged coastline. Pack a picnic of local cheeses, olives and tomatoes from a seaside deli. Lounge under a parasol with views of sailboats drifting on the horizon.

evening
:

Stay for sunset at a laid-back seafood trattoria overlooking the sea and feast on grilled prawns and spaghetti alle vongole. Toast to the day with a cold birra artigianale as the sky shifts to rose and gold. Conclude with a beach bonfire gathering if available, listening to the gentle lapping waves.

day 5
Gallipoli and Sea Kayaking
morning
:

Head to the historic island town of Gallipoli, entering through the ancient aragonese bridge as fishermen unload their catch. Begin with a cappuccino on a terrace overlooking the marina and watch fishing boats return. Explore the Baroque old town’s labyrinthine streets with colorful balconies.

afternoon
:

Join a guided sea kayaking tour around Gallipoli’s limestone promontories and secluded bays. Stop on a remote beach for a handcrafted sandwich of local capocollo and ricotta salata. Swim in crystalline coves before returning to the harbor.

evening
:

Dine on pan-fried fish specialties at a waterfront ristorante as seagulls circle overhead. Pair your meal with a crisp white Verdeca from a neighboring vineyard. End the evening with a stroll along the ramparts to admire the sparkling lights reflected on the water.

day 6
Otranto Cultural Discovery
morning
:

Travel east to Otranto and begin at the imposing Castello Aragonese overlooking the Adriatic. Wander through the medieval ramparts and enjoy sweeping sea views. Sample a sfogliatella at a local pastry shop for a sweet start.

afternoon
:

Visit the Cathedral to marvel at Europe’s largest mosaic floor, depicting biblical and mythological scenes. Have lunch in a shady piazza where you can taste scapece fish and local marinated vegetables. Explore artisanal shops selling coral jewelry and hand-painted ceramics.

evening
:

Watch the sunset from the city walls as you sip a glass of Lizzano rosé. Dine on fresh octopus stew at a family-run trattoria in the old town. Conclude with a moonlit walk along the beach, listening to waves crash gently against rocky cliffs.

day 7
Salento Wine and Cuisine Immersion
morning
:

Join a guided tour of a historic Salento winery nestled among olive trees and vineyards. Learn about indigenous grape varieties like Negroamaro and Primitivo, and taste wines paired with local cheeses. Bask in panoramic vineyard views under the warm sun.

afternoon
:

Return to Calimera for a cooking class where you knead orecchiette by hand and prepare a traditional ragù. Savor the fruits of your labor alongside crisp salads and freshly baked bread. Gain insight into family recipes passed down through generations.

evening
:

Attend a convivial multi-course dinner showcasing the dishes you helped prepare, accompanied by regional wines. Engage in lively conversation with your hosts about Puglian culture and folklore. Experience a spontaneous folk dance performance to end the evening on a high note.

day 8
Historic Hilltown Road Trip
morning
:

Embark on a scenic drive through Salento’s hinterland to explore charming hilltop villages like Martano and Scorrano. Stop for espresso in a venerable piazza surrounded by limestone houses. Photograph medieval towers and ancient dry-stone walls.

afternoon
:

Continue to Corigliano d’Otranto, visiting its Renaissance castle and botanical garden. Enjoy a rustic lunch at a countryside trattoria serving pasta with wild herbs and local pecorino. Browse markets for olive wood crafts and handwoven textiles.

evening
:

Return to Calimera and dine at a small family-run enoteca offering regional charcuterie boards. Sample artisan salumi and the local cellino cheese. Conclude with a nightcap of limoncello on a terrace under a star-filled sky.

day 9
Porto Cesareo Beach Retreat
morning
:

Travel to Porto Cesareo and spend the morning snorkeling in the protected marine reserve teeming with colorful fish. Rent a sun lounger and umbrella on the powdery white sand. Grab a granita al limone at a beachfront kiosk to cool off.

afternoon
:

Charter a small boat for a coastal cruise around panoramic cliffs and hidden sea caves. Drop anchor for a swim at Punta Prosciutto’s crystalline waters and enjoy a picnic of fresh seafood salads. Relax on deck as the captain shares stories of local maritime traditions.

evening
:

Dine at a seaside pizzeria offering wood-fired focaccia topped with seasonal vegetables and fresh mozzarella. Pair your meal with a chilled glass of rosato from a neighboring estate. Watch the sun dip below the sea and enjoy live acoustic music on the shore.

day 10
Farewell Feast and Reflection
morning
:

Sleep in and enjoy a leisurely late breakfast at your favorite Calimera café. Reflect on your journey with a fresh pastry and espresso while people-watching in the main piazza. Purchase last-minute olive oil or handmade souvenirs from local vendors.

afternoon
:

Take a final stroll through ancient olive groves or revisit a hidden chapel on the town’s outskirts for quiet contemplation. Share a festive lunch of grilled vegetables, cured meats and local cheeses with newfound friends. Toast to memories made with a glass of sparkling Falanghina.

evening
:

Host or join a farewell dinner in a masseria courtyard lit by lanterns and candles. Delight in a multi-course Puglian feast featuring pasta, seafood and sweet almond cake for dessert. Cap the evening with heartfelt goodbyes as traditional music drifts through the warm summer air.

Discover Calimera

Read more in our Calimera 2025 Travel Guide.

Calimera Travel Guide