Uruguay is small in size but big in spirit—a river-and-ocean country where beach life meets café culture, soccer chants meet symphonic halls, and sunset rituals meet late dinners. Founded in 1726, Montevideo is a capital of rambla strolls, steakhouses, and music, while Punta del Este shines with Atlantic beaches and breezy nights. Westward, Colonia del Sacramento is a UNESCO-listed time capsule with cobblestones, bougainvillea, and candlelit patios.

Expect slow mornings, long lunches, and mate gourds everywhere. Order an asado or a chivito, sample Tannat wine, and learn why Uruguay’s rhythm—candombe—echoes from Barrio Sur on weekends. Safety is generally good; do keep an eye on belongings in busy areas and at beaches. The currency is the Uruguayan peso (UYU), and 10% tipping is customary at restaurants.

This 10-day itinerary balances relaxation and local flavor: beaches and bike rides, winery lunches, padel tennis, soccer nights, and one glorious sunset at Casapueblo. You’ll split time between Montevideo, Punta del Este, and Colonia del Sacramento with sensible travel times and a few insider food stops to keep the vibe unhurried yet delicious.

Montevideo

Montevideo is the heartbeat of Uruguay—a city where the Río de la Plata meets miles of waterfront promenade. Stroll the Rambla at golden hour, explore Ciudad Vieja’s plazas and the grand Teatro Solís, and taste your way through parrillas at the Mercado del Puerto.

• Highlights: Plaza Independencia, Palacio Salvo, Teatro Solís, Mercado del Puerto, Pocitos Beach, Carrasco neighborhood, Estadio Centenario.
• Why go: Culture, soccer, music, and some of the country’s best restaurants—all with a laid-back pace.
• Local tip: Bring a thermos—mate is a lifestyle here, and the Rambla is the city’s living room.

Where to stay: Browse stays on VRBO (Montevideo) or hotels on Hotels.com (Montevideo). Specific picks: Hyatt Centric Montevideo on the Rambla for views and modern design; Sofitel Montevideo Casino Carrasco & Spa for Belle Époque grandeur by the beach; Hotel Iberia for a good-value, central base.

Getting there: Fly into MVD (Carrasco International). Check fares on Trip.com flights or Kiwi.com. From the airport to the city, it’s ~25–35 minutes by car depending on your neighborhood.

Day 1 — Arrival, Rambla sunset, and a classic parrilla

Afternoon: Arrive in Montevideo and check in. Shake off the flight with a slow walk along the Rambla Pocitos—watch joggers, mate drinkers, and kites. Coffee break at historic Café Brasilero (1867) for old-world atmosphere and excellent espresso.

Evening: Dinner at La Pulpería (countertop parrilla; try the ojo de bife and provoleta) or La Perdiz (parrilla plus pastas) in Punta Carretas. Nightcap with live tango and candombe vibes at Bar Fun Fun—an institution where locals actually go.

Day 2 — Bike the city, Old Town tastes, and candombe beats

Morning: Hop on the Montevideo Small Group Bike Tour or E-bike tour with picnic to cover more ground with a local. Expect seaside paths and breezy stops.

Afternoon: Explore Ciudad Vieja: Puerta de la Ciudadela, Plaza Matriz, and the Cathedral. Lunch at Jacinto (chef Lucía Soria’s seasonal plates) or Mercado del Puerto—order morcilla dulce and tira de asado from El Palenque’s sizzling grills.

Evening: If you’re here on a weekend, walk through Barrio Sur to hear candombe drum rehearsals. Otherwise, catch a guided visit or a show at Teatro Solís (19th-century jewel). Late snack: chivito al pan at Bar Arocena in Carrasco—Uruguay’s beloved steak sandwich.

Day 3 — Winery lunch and sports night

Morning: Coffee at Escaramuza (bookstore-café with a garden), then browse the nearby Cordón neighborhood for design shops. If it’s Sunday, add the Tristán Narvaja street market for antiques and street snacks.

Afternoon: Head to the countryside for Pizzorno Winery with Lunch and Wine Tasting—Tannat, gardens, and a lingering meal in a family-run bodega 30–40 minutes from the city.

Evening: Sports time. If in season, catch a fútbol match—Peñarol at Campeón del Siglo, Nacional at Gran Parque Central, or a national-team fixture at Estadio Centenario. Prefer hoops or concerts? Check Antel Arena’s calendar. Pre-game craft beers at Montevideo Beer Company.

Day 4 — Beach morning, padel session, and Pocitos nightlife

Morning: Easy start on Playa Pocitos or Playa Carrasco—calm water, people-watching, and a leisurely swim. Grab medialunas and flat whites at The Lab Coffee or Café Nómade.

Afternoon: Book a padel court via popular local apps; clubs in Pocitos and Carrasco rent racquets and balls. Late lunch at Mercado Ferrando (food hall with standout burgers, tacos, and gelato) or plant-forward plates at Café Gourmand.

Evening: Dinner at Francis (seafood and steaks) or Plantado at the Hyatt Centric with river views. Bar-hop in Pocitos (try Negroni for cocktails) or along the Old City’s Sarandí and Bacacay streets for wine bars and live music.

Punta del Este

South America’s summer playground, Punta del Este mixes calm bays (Playa Mansa) with Atlantic surf (Playa Brava). Days are for the beach; nights are for harbor restaurants, open-air bars, and late DJs. Side trips to La Barra and José Ignacio bring dunes, design boutiques, and legendary restaurants.

• Highlights: La Mano sculpture on Playa Brava, Casapueblo in Punta Ballena, Mansa vs. Brava beach hopping, La Barra bridge, José Ignacio lighthouse.
• Why go: Sun, sea, fresh seafood, and that golden-hour glow. Nightlife ranges from mellow wine bars to high-energy clubs.
• Local tip: The Atlantic breeze can be strong—bring a light layer for evenings on the water.

Where to stay: Explore VRBO (Punta del Este) for beachfront apartments near Mansa or houses in La Barra. Compare hotels via Hotels.com (Punta del Este).

Travel from Montevideo: Morning buses take ~2–2.5 hours, around $10–15. Prefer comfort? Book a door-to-door ride with Transfer to Punta del Este from Montevideo.

Day 5 — Montevideo to Punta, toes-in-the-sand afternoon

Morning: Depart Montevideo by bus (~2–2.5 hours) or private transfer. Check into your stay near Playa Mansa for calmer water and sunsets.

Afternoon: Beach time. Rent loungers on Mansa, swim, and nap. Late lunch at Lo de Tere by the port—order corvina a la parrilla or seafood risotto.

Evening: Stroll the yacht harbor and the craft market. Dinner at Isidora in the marina area (local fish, pastas). For nightlife, sip a cocktail at Moby Dick (classic harbor bar) or go high-energy at OVO Nightclub.

Day 6 — Brava surf and Casapueblo’s legendary sunset

Morning: Start with medialunas at Medialunas Calentitas or a healthy bowl at La Linda. Walk to Playa Brava to see La Mano (the iconic “hand” in the sand) and watch surfers.

Afternoon: Lazy lunch in La Barra—Crêpas for buckwheat galettes or fresh ceviche at a seaside spot. Browse design shops and cross the wavy La Barra bridge.

Evening: Time your sunset for Casapueblo in Punta Ballena—buy your Skip-the-Line: Casapueblo Museum Admission Ticket in advance.

Stay for the “Sun Ceremonial” audio and a glass of Tannat as the building turns gold.

Day 7 — José Ignacio day, padel by the beach, and a long dinner

Morning: Optional private tour with a local—custom beaches, art, and photo stops—via Private Have It Your Way Tour in Punta Del Este.

Afternoon: Continue to José Ignacio for dunes and a chic, sleepy village vibe. Book a padel court near La Barra/José Ignacio in the afternoon—many clubs rent gear. Cool off with a dip at Playa Mansa José Ignacio.

Evening: Dinner at La Huella (wood-fired seafood; reserve well ahead) or La Susana for a toes-in-the-sand sunset meal. End with a quiet walk by the lighthouse under huge southern skies.

Colonia del Sacramento

Founded by the Portuguese in 1680, Colonia’s Barrio Histórico is a watercolor of stone lanes, lanterns, and ivy-draped walls. It’s perfect for unrushed mornings, café terraces, and riverfront sunsets over the widest river in the world.

• Highlights: Calle de los Suspiros, the Lighthouse, old city gate, Museo del Azulejo (tiles), riverside Rambla, Plaza Mayor.
• Why go: UNESCO-listed history, boutique eateries, and deeply relaxing vibes—an ideal finale.
• Local tip: Many spots close midweek or between lunch and dinner—plan meals with relaxed timing.

Where to stay: Check VRBO (Colonia del Sacramento) for historic-center homes, or compare hotels on Hotels.com (Colonia del Sacramento).

Travel from Punta del Este: Morning buses via Montevideo to Colonia take ~5.5–6.5 hours total with one change. Plan snacks and a good playlist; the route is smooth and scenic across pampas.

Day 8 — Punta to Colonia, golden-hour streets

Morning: Depart Punta del Este early by bus, connecting in Montevideo (total ~6 hours). Check into your Colonia stay inside or just outside the old town walls.

Afternoon: Light lunch at Lentas Maravillas (garden terrace and homemade cakes) or Charco Bistro on the river. Wander Plaza Mayor, the city gate, and Calle de los Suspiros for photos.

Evening: Dinner at Buen Suspiro (Uruguayan cheeses, charcuterie, and Tannat in a stone cellar). Post-dinner stroll to the riverfront for stargazing—Colonia’s night skies can surprise you.

Day 9 — Slow Colonia: lighthouse views, beach hour, and wine bar

Morning: Climb the Lighthouse for panoramic views, then visit the tile museum (Museo del Azulejo). Coffee at Café del Muelle facing the water.

Afternoon: Rent bikes and follow the coast to Playa Ferrando for a quiet swim and siesta among eucalyptus. Late lunch back in town—try grilled fish or a hearty chivito at a plaza-side bistro.

Evening: Sunset near Bastión del Carmen. Dinner at Charco Bistro (river catch, seasonal sides). Nightcap at a wine bar in the historic quarter—ask for small producers and Tannat recommendations.

Day 10 — Lazy morning and departure

Morning: Breakfast on a leafy patio; pick up ceramics or leather goods from local artisans. Final photos under the jacarandas if in bloom.

Afternoon: Bus to Montevideo Airport via the Tres Cruces terminal (plan ~3–3.5 hours with connection; build in a generous buffer). Check flight options and times on Trip.com or Kiwi.com. If you prefer a seamless ride from Colonia, hire a private car locally and allow ~2.5–3 hours to MVD depending on traffic.

Extra Montevideo options if you want more guided time

Prefer a deep-dive with a private guide? These well-reviewed tours focus on history, architecture, and hidden corners. They fit nicely on Day 2 or Day 4, or on an added night in Montevideo:

• Private Walking Tour in Montevideo

Dining and coffee cheat sheet

• Montevideo: Jacinto (seasonal; Ciudad Vieja), La Pulpería (parrilla), La Perdiz (classic), Mercado del Puerto (grill hall), Francis (seafood), Plantado (Rambla views), Café Brasilero and Escaramuza (coffee).
• Punta del Este & nearby: Lo de Tere (harbor), Isidora (port-side), Medialunas Calentitas (breakfast), La Linda (bakery), Crêpas (La Barra), La Huella and La Susana (José Ignacio), Moby Dick and OVO (nightlife).
• Colonia del Sacramento: Charco Bistro (riverfront), Buen Suspiro (cheese & Tannat), Lentas Maravillas (cakes and light fare), Café del Muelle (coffee with a view).

Sports, concerts, and padel—how to weave them in

• Watching sports: Check fixtures for Peñarol, Nacional, and Estadio Centenario; for basketball or major concerts, browse Antel Arena’s schedule. Arrive early and bring cash for stadium snacks.
• Padel tennis: Book courts via local apps—clubs around Pocitos, Carrasco, La Barra, and José Ignacio rent gear. Early mornings or late afternoons are best on hot days.
• Live music: Teatro Solís hosts classical and contemporary shows; smaller bars in Ciudad Vieja and Parque Rodó program jazz, rock, and candombe year-round.

Accommodation quick-links by city

• Montevideo stays: VRBO | Hotels.com (Specific: Hyatt Centric Montevideo, Sofitel Montevideo Casino Carrasco & Spa, Hotel Iberia)
• Punta del Este stays: VRBO | Hotels.com
• Colonia del Sacramento stays: VRBO | Hotels.com

Transport quick-links

• International flights to MVD: Trip.com | Kiwi.com
• Montevideo ↔ Punta del Este private ride: Viator transfer (about 2 hours, door-to-door)

Included Viator activities in this itinerary:

• Montevideo Small Group Bike Tour or E-bike tour with picnic
• Pizzorno Winery with Lunch and Wine Tasting
• Transfer to Punta del Este from Montevideo
• Skip-the-Line Casapueblo Museum Admission Ticket
• Private Have It Your Way Tour in Punta Del Este
• Optional add-on in Montevideo: Private Walking Tour in Montevideo

Budget note (61/100): Expect mid-range pricing with a few well-placed splurges. Mix parrillas and bistros with market food halls; in Punta, book some lunches over dinners to catch sea views without nightclub markups.

Summary: This 10-day Uruguay plan leans into relaxation—sunny beaches, slow meals, wine-country afternoons, padel sessions, and music-filled nights—paired with a few can’t-miss icons like Casapueblo and Colonia’s cobblestones. It’s a gentle rhythm: live like a local in Montevideo, drift along the Atlantic in Punta, and savor river sunsets in Colonia before flying home with sand still in your shoes.