Your trip itinerary![]()
16 days trip
San Francisco International Airport, Pacific Heights & 57 more
Accommodation
Hotel & Other
Transportation
Car, Train, Trekking, Other
San Francisco International Airport
Day 1
DAY ONE: Saturday - Arrival in San Francisco 4:00pm - Private group taxi pickup from San Francisco International Airport (SFO). Aim to land between roughly 12:30pm and 2:30pm to allow time for immigration (if arriving internationally), baggage, and meeting the driver. Guests arriving outside this window are responsible for their own transfer to the hotel, but I'm happy to help arrange one.
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Pacific Heights
Day 1
Late afternoon - Arrive at our inn in Pacific Heights/Cow Hollow. I'll be waiting to greet you. Head straight up to your private room where your welcome gift is waiting. Refresh and settle in. Evening - We'll meet up for our welcome dinner after having some free time to relax after the flight.
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Mission District
Day 1
Evening - Mission District is home to some of the best Mexican food in the city, thanks to a large and long-established Mexican community. We'll enjoy dinner at a local favorite spot, then take a short walk to explore some of the Mission's iconic murals before heading back to the hotel. Anyone wishing to explore SF nightlife independently is welcome to do so.
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Pacific Heights
Day 1-2
Evening - We'll return to the hotel for the night. DAY TWO: Sunday - Haight-Ashbury, Golden Gate Park & Optional Castro LGBTQ+ History Morning: Free time to grab breakfast and coffee at one of the excellent local spots nearby.
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Haight-Ashbury
Day 2
10:00am - Meet up and to head to the Haight-Ashbury intersection, the legendary counterculture heart of 1960s America and the birthplace of the Summer of Love. We'll walk the historic streets, browse vintage shops, and admire the ornate Victorian architecture the neighborhood is famous for.
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Golden Gate Park
Day 2
Late morning - We'll continue by walking on to Golden Gate Park which is larger than New York's Central Park. Stroll through the gardens, meadows, and hidden groves. Midday - Included picnic lunch in the park.
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Hamon Observation Tower
Day 2
Early afternoon - Next we'll head over to the Hamon Observation Tower at the de Young Museum. Entry is free and we'll get to see 360-degree views of the city, the beautiful park, and the Pacific ocean.
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The Castro
Day 2
Late afternoon (optional) - Castro LGBTQ+ History Walk ($40/€35). Those who wish to join will get a guided walk through the historic Castro District led by a sixth-generation local queer organizer. Tripmates not joining can explore the Castro's independent shops on their own, head back to the hotel, or explore SF independently.
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Pacific Heights
Day 2-3
Evening - We'll return to the hotel for the night. DAY THREE: Monday - Point Reyes Day Trip 8:00am - Depart in the rental car for Point Reyes National Seashore. *Please pack warm layers since coastal Marin County can be foggy, windy, and cool even in July. You can also pack a light breakfast/snacks to bring along if 8am is too early for breakfast. Note: The drive includes very curvy mountain roads; please prepare if you experience motion sickness.
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Cypress Road
Day 3
Morning - We'll drive to the iconic Cypress Tree Trail for a photo stop at the beautiful tree-lined driveway, with a quick coffee/baked goods stop in Point Reyes Station along the way. It's a tiny old railroad town that's become a beloved destination for its bakeries and cheesemakers.
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Chimney Rock Trail Head
Day 3
Late morning - Next we'll go to Chimney Rock Trailhead, which is widely considered the most beautiful easy walk in the park. The path is a wide, mostly level dirt trail that follows the top of a dramatic green bluff, ending at the Elephant Seal Overlook above Drake's Bay, where you can look down over beaches full of sunbathing elephant seal colonies. It's about 1.8 miles round trip and easy for most fitness levels but the only significant walking of the day.
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South Beach Overlook
Day 3
Midday - Drive to South Beach Overlook, where a wooden viewing platform hangs over an 11-mile continuous stretch of wild, crashing Pacific surf. From there, a short paved walk to the Point Reyes Lighthouse observation deck (we'll skip the 300+ steps down to the lighthouse itself, unless tripmates feel up for it) for great views if the summer morning fog has cleared.
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Inverness
Day 3
Lunch - Then we'll drive to Inverness for lunch (own expense) and grab locally sourced deli sandwiches or fresh Tomales Bay oysters, both regional specialties. We'll have a clear view of the S.S. Point Reyes Shipwreck: a rusting fishing boat run aground for decades that's become one of Northern California's most photographed spots.
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Pacific Heights
Day 3-4
Afternoon — We'll take the scenic drive back to San Francisco over the Golden Gate Bridge. Early evening — We'll return to the hotel for the night. Take a free evening for independent dinner and rest. DAY FOUR: Tuesday - The Presidio, Palace of Fine Arts, Fisherman's Wharf & North Beach Morning - Free time to grab breakfast nearby before we head out for the day. *Please bring comfortable walking shoes to wear for this day. This is a full walking day with plenty of iconic stops and rest breaks built in.
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Presidio of San Francisco
Day 4
10:00am — First, we'll head to The Presidio which is a former US Army post transformed into a stunning 1,500-acre national park along the Golden Gate. We'll visit the Palace of Fine Arts, originally built for the 1915 Panama-Pacific Exposition and one of San Francisco's most beautiful landmarks. It's a massive Roman-style rotunda surrounded by tranquil lagoons.
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Crissy Field
Day 4
Late morning - We'll walk the flat, scenic dirt path along Crissy Field's waterfront, with the Golden Gate Bridge directly in your sightline the entire way. Continue into Fort Point National Historic Site, tucked directly under the bridge: a Civil War-era brick fortress with dramatic views up at the bridge itself and a perfect spot for photos in front of the bridge.
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Boudin Bakery Cafe
Day 4
Midday - Next we'll go to the waterfront for lunch at Boudin Bakery (own expense), famous for its sourdough bread and clam chowder served in sourdough bowls. Time to explore the on-site shop for things to bring home.
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Fisherman's Wharf
Day 4
Afternoon - We'll take about an hour to explore Fisherman's Wharf which is admittedly the most touristy stretch in the city, but worth a short visit for the barking Pier 39 Sea Lions, the historic tall ships on Hyde Street Pier, and the wonderfully weird Musée Mécanique (a working collection of antique arcade games where you can spend a few quarters and lose an hour).
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North Beach
Day 4
Late afternoon - Then we'll take a short walk to North Beach, San Francisco's Little Italy, and the historic heart of the Beat Generation. We'll walk down Columbus Ave to legendary independent bookstore City Lights Booksellers, founded by beat poet Lawrence Ferlinghetti in 1953. Across the hidden Jack Kerouac Alley sits Vesuvio Cafe where we'll pop in to see the wonderfully preserved 1950s bohemian decor. Stroll through Washington Square Plaza, the neighborhood's central gathering spot with the illuminated spires of Saints Peter and Paul Church rising behind it. Evening (optional) - Group dinner at one of North Beach's excellent local Italian restaurants (own expense). Tripmates can also head back to the hotel or grab dinner elsewhere.
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Pacific Heights
Day 4-5
Evening - Return to the hotel for the night. DAY FIVE: Wednesday - Muir Woods & a Marin County Beach Town 8:00am - Depart for Muir Woods National Monument. *Please pack warm layers since the redwoods and coastal Marin can be foggy and cool. You can pack a light breakfast/snacks too if it's too early for you to eat before we leave. Note: Again the drive includes very curvy mountain roads; please prepare if you experience motion sickness.
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Muir Woods National Monument
Day 5
Morning - We'll walk the main trail which is a completely flat, paved wooden boardwalk winding through the ancient, towering redwood canopy. Our early timing lets us experience the quiet majesty of the forest before midday tour buses arrive. Some of these coast redwoods are over 250 feet tall and 800 years old and walking beneath them is one of California's most humbling experiences. Midday - Then we'll take a scenic drive down Highway 1 to a small favorite beach town of mine that I've been going since childhood summers with my family. I'll reveal the specific location after booking. We'll park and walk along the beach. Lunch - We'll eat at a casual local favorite spot near the beach (own expense).
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Marin Headlands
Day 5
Afternoon - We'll drive back to San Francisco with a scenic stop at Marin Headlands/Hawk Hill Overlook which has the best postcard-perfect cliffside view of the Golden Gate Bridge stretching across the water toward the city skyline.
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Pacific Heights
Day 5-6
Around 4:00pm — We'll return to the hotel for the day and have a free afternoon/evening for independent dinner and rest. SAY SIX: Thursday - Hidden Steps, Salesforce Park, Cable Car & Chinatown at Dusk Morning - Free time to grab breakfast.
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Hidden Garden Steps
Day 6
9:00am - We'll go to the Hidden Steps on 16th Avenue which is a set of intricately mosaiced tile stairs (163 in total) created by neighborhood residents. Climb to the summit at Grandview Park for one of the best panoramic views in the city. Climbing the steps is a workout and anyone who prefers to skip it can hang out at the bottom while we head up. Tripmates who would prefer to skip this activity and sleep in or explore on their own for the morning can meet up with us at the next destination.
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Salesforce Park
Day 6
Late morning - Next we'll go to the Financial District and ride the free glass gondola up to Salesforce Park which is a lush, elevated 4-acre public botanical rooftop garden weaving directly between city skyscrapers. Midday - We'll have a casual local lunch at one of the independent cafés or eateries beneath the transit center plaza (own expense).
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Dragon Gate San Francisco
Day 6
Afternoon - We'll hop on an historic cable car, one of the last manually operated cable car systems in the world, running since 1873, and ride it to Chinatown's Dragon Gate. San Francisco's Chinatown is the oldest and one of the largest in North America, and it's dense with history and daily life. Explore the produce markets along Stockton and Grant, stop into the tiny Golden Gate Fortune Cookie Factory tucked into Ross Alley to buy warm cookies straight off the press, and watch the mahjong players in Spofford Alley. As dusk hits, the neighborhood completely transforms with red lanterns illuminating the streets. Evening - We'll finish the day with an optional group family-style dinner at one of the local Chinese restaurants (own expense, cost split among the group).
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Pacific Heights
Day 6-7
Night — We'll return to the hotel for the night. DAY SEVEN: Friday - San Francisco to Monterey Morning - We'll have a relaxed free morning to grab breakfast and pack up. 11:00am - Check out and depart for Monterey.
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Moss Landing State Beach
Day 7
Midday - We'll stop at Moss Landing State Beach along the way. There's a scenic viewing point where you can often glimpse wild sea otters and harbor seals in Elkhorn Slough, one of California's largest wetlands and a marine wildlife hotspot. Lunch - We'll stop for lunch at a local favorite restaurant in Moss Landing (own expense). This stretch is famous for fresh seafood, but there will be options for non seafood eaters as well.
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Monterey
Day 7-8
Late afternoon - We'll arrive at our Monterey hotell to check-in, then walk down to historic Cannery Row, the former sardine cannery district immortalized in John Steinbeck's novel of the same name, is now a walkable strip of shops, restaurants, and the world-class Monterey Bay Aquarium. Early evening - As the sun goes down, we'll walk out to the rocky coastline near the Monterey Plaza Hotel to see harbor seals resting on the rocks. Evening - We'll have a casual dinner at a local spot (own expense). Evening - Then we'll return to the hotel for the evening. DAY EIGHT: Saturday - Point Lobos, Carmel & 17-Mile Drive Morning - We'll have a relaxed free morning to enjoy the simple hotel breakfast or eat at one of the local breakfast places.
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Point Lobos State Natural Reserve
Day 8
10:00am - We'll depart for Point Lobos State Natural Reserve, which is one of the most stunning coastal reserves in the world, globally famous for its dramatic, windswept cypress trees, hidden turquoise coves, and abundant marine wildlife. We'll take a walk on the Cypress Grove Trail, a completely flat 0.8-mile loop right along the cliff edges where you can look down into the coves.
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Carmel Gate - 17 Mile Drive
Day 8
Midday - We'll take a drive to Carmel-by-the-Sea, a coastal village of storybook cottages, art galleries, and hidden courtyards. We'll have a relaxed lunch at a local favorite restaurant (own expense). Afternoon — Then we'll drive to the Carmel Gate for the iconic 17-Mile Drive through Pebble Beach. We'll drive the loop slowly from south to north. Because we're doing it in the afternoon, the morning fog should have cleared, giving us brilliant views of The Lone Cypress (perhaps the most photographed tree in North America), the dramatic coastal golf greens of Pebble Beach, and Spanish Bay. Photo stops throughout.
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Monterey
Day 8-9
Evening - We'll return to Monterey for a free evening. DAY NINE: Sunday - Big Sur Drive to Pismo Beach Morning - We'll have a relaxing morning with time to sleep in, have breakfast at the hotel, or grab breakfast at a nearby cafe. 10:45am — We'll check out and head south down coastal Highway 1 along the legendary Big Sur coastline: one of the most dramatic and beautiful coastal drives in the world.
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Bixby Creek Bridge
Day 9
Along the drive - Photo pull-offs at the famous Bixby Creek Bridge (the iconic arched concrete bridge in a thousand car commercials) and the McWay Falls Overlook (an 80-foot waterfall spilling directly onto a pristine cove beach).
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Cambria
Day 9
Midday - We'll stop for a break and have lunch (own expense) in Cambria. This is a charming small coastal town roughly halfway between Big Sur and Pismo. This will break up the drive and give everyone a chance to eat, stretch their legs, and use the restroom.
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Pismo Beach
Day 9-10
Afternoon - Then we'll drive the final hour to Pismo Beach. We'll arrive at our beachfront motel in the late afternoon and take free time to relax and refresh. Evening - We'll meet up again and walk directly from the hotel to the Pismo Beach Pier and Boardwalk to watch the sunset over the Pacific. Then we can eat a casual dinner at a nearby restaurant (own expense). Night - We'll return to the hotel for the rest of the night. DAY TEN: Monday - Optional Shell Beach Bluffs & Sunset at Oceano Dunes Morning - We'll have a free morning to sleep in and grab breakfast at one of the local spots nearby. The activities this day will be optional to join and alternatively tripmates can stay at the hotel or relax on the beach.
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Shell Beach Bluff Trail
Day 10
Late morning (optional) - We'll drive to Shell Beach Bluffs for an easy walk along the paved trail along the grassy cliff edges overlooking ocean tidepools and dramatic coastline. It's a great spot for a morning walk and amazing views.
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Pismo Beach
Day 10
Midday to afternoon - Those who joined the morning walk will return to the hotel for free time to relax on the beach steps from your door, rest in your room, or grab lunch at one of the nearby local restaurants.
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Oceano Dunes State Vehicular Recreation Area
Day 10
Late afternoon (optional) - Those who wish to join will drive to Oceano Dunes State Beach which is one of the only beaches in California where vehicles can drive on the sand, and home to some of the largest coastal dunes in the state. We'll park and take a long, easy walk along the pedestrian boardwalk to catch the sun setting over the massive sand dunes.
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Pismo Beach
Day 10-11
Evening - We'll return to the hotel for the night. DAY ELEVEN: Tuesday - Pismo to Los Angeles via Santa Barbara & Malibu Morning - Free time to have breakfast nearby and prepare to leave. 10:00am - We'll check out and drive south past rugged ranch land and ocean bluffs toward Santa Barbara.
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Santa Barbara
Day 11
Midday - First we'll stop at the historic Santa Barbara County Courthouse. It's a stunning Spanish Colonial Revival building that's considered one of the most beautiful public buildings in America. Explore the architecture and gardens, then take the elevator up the clock tower for a free spectacular 360-degree view of Santa Barbara's iconic red-tile roofs and the ocean. Lunch - Next we'll have lunch at a local favorite restaurant near Stearns Wharf (own expense). We'll walk down the pier before we depart.
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Malibu
Day 11
Afternoon - We'll drive down the Pacific Coast Highway to Malibu and stop at Zuma Beach for time on the sand. It's one of Southern California's longest and most beautiful public beaches that can be great for watching surfers or relaxing on the sand. Evening - We'll have dinner in Malibu (own expense), timing our departure to avoid LA's worst rush hour traffic.
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Los Angeles
Day 11-12
Around 8:30–9:00pm - We'll arrive at our LA house and check in. DAY TWELVE: Wednesday - Hollywood Sign, Griffith Observatory & Hollywood Boulevard 7:00am - This morning will be an early departure. We'll stop at a local favorite café first for coffee and breakfast (own expense).
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Lake Hollywood Park
Day 12
Morning - We'll drive to Lake Hollywood Park which is hands down the best spot for photos with the Hollywood Sign (the famous 1923 landmark that started as an advertisement for a housing development and became the icon of the American film industry).
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Griffith Observatory
Day 12
Late morning - Next, we'll drive up to Griffith Observatory. It has free entry and some of the most beautiful views of the entire LA basin. The observatory itself is a stunning Art Deco building perched on Mount Hollywood and remains a working astronomy center.
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Universal Studios Hollywood
Day 12
Midday (optional) - Universal Studios Hollywood (check the Universal website for current pricing). Tripmates can spend the day at either the full theme park or take the classic Studio Tour. If everyone in the group wants to go, I'll join. Otherwise, tripmates not going can get lunch (own expense) and visit Hollywood Forever Cemetery which is a working cemetery and a beautiful outdoor space where many famous figures from Hollywood's golden age are buried. Late afternoon - We'll regroup and pick up any tripmates who went to Universal Studios.
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Hollywood
Day 12
Late Afternoon - We'll park and take a walk down Hollywood Boulevard to see TCL Chinese Theatre (with its famous handprint and footprint courtyard of movie stars) and The Walk of Fame. Evening - We'll go for dinner at a local favorite restaurant in the Hollywood area (own expense).
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Los Angeles
Day 12-13
Night - We'll return to the house for the night. DAY THIRTEEN: Thursday - Venice, Abbot Kinney & Santa Monica Sunset Morning - We'll enjoy free time to sleep in and have breakfast nearby, or make breakfast in the kitchen we're sharing.
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Venice Canals
Day 13
Late morning - We'll start the day with a stop at the Venice Canals: a hidden network of narrow waterways with arching bridges and charming beach cottages, built in 1905 to mimic Venice, Italy. It's a magical, quiet corner most first-time visitors miss entirely.
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Venice Beach Boardwalk
Day 13
Midday - We'll park and walk to the famous Venice Boardwalk. It's one of LA's great people-watching stretches, filled with skaters, street performers, artists, and a decidedly countercultural energy. Walk the boardwalk, head out to the pier, or people watch. Lunch - We'll eat at a local restaurant (own expense). Afternoon - Next, we'll explore the shops and design boutiques along Abbot Kinney Boulevard: Venice's chicest street and one of LA's coolest shopping strips.
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Santa Monica
Day 13
Late afternoon - Afterwards we'll go to Santa Monica, park, and walk to the gorgeous beach. We'll spend time on the pier, on the sand and stay long enough to catch the sun setting over the iconic Santa Monica Pier.
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Los Angeles
Day 13-14
Evening - We'll return to the house and have a free evening. Tripmates can cook at the house or grab food from nearby restaurants. DAY FOURTEEN - Friday - Optional Getty Museum & Beverly Hills This is a fully optional day and tripmates can join or take a free day to explore independently, hit one of LA's incredible beaches, or simply relax at the house.
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The Getty
Day 14
9:30am (optional) - We'll depart for the Getty Museum which is one of the world's great art museums, with a stunning modernist campus by architect Richard Meier perched on a Brentwood hilltop. Free entry; we'll split the cost of parking for this optional activity.
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Beverly Hills
Day 14
Midday (optional) - After the museum we'll drive to Beverly Hills where we'll park and walk around to see the famous shops along Rodeo Drive. Tripmates can do some shopping if they wish. Lunch - We'll eat at a Beverly Hills café (own expense).
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Los Angeles
Day 14-15
Late afternoon — We'll return to the house for the day. Evening — Free evening to relax or explore independently. DAY FIFTEEN: Saturday - Downtown LA, Grand Central Market, Little Tokyo & Arts District Morning - Free time to make breakfast or grab it at a nearby cafe. 10:00am — We'll depart later in the morning to avoid the worst of the morning traffic and drive to Downtown LA and park in a garage. We'll explore the rest on foot.
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The Broad
Day 15
Late morning - Visit The Broad Museum with free entry to one of LA's most exciting contemporary art collections (housed in a striking honeycomb building designed by Diller Scofidio + Renfro). Across the street, you can see the historic Angels Flight Railway: a 1901 funicular that runs 298 feet up Bunker Hill. Optional quick rides are available for $1.50/€1.30.
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Grand Central Market
Day 15
Midday - We'll stop for lunch at the historic Grand Central Market (own expense). It's an incredible food hall that's been operating since 1917, with dozens of vendors serving everything from Mexican tortas to Thai boat noodles to specialty coffee.
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Little Tokyo
Day 15
Afternoon - Next we'll walk to Little Tokyo. It's one of only three official Japantowns remaining in the United States. Tripmates can walk down Japanese Village Plaza and explore the shops and neighborhood.
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Arts District
Day 15
Late afternoon - Then we'll visit the Arts District which is DTLA's most creative neighborhood, filled with murals, breweries, galleries, and independent shops in converted warehouses. Early evening - We'll have dinner at a local restaurant in the Arts District (own expense), timed to avoid the worst commuter traffic leaving downtown.
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Los Angeles
Day 15-16
Around 7:30pm - We'll go back to the house for the night. Tripmates wishing to explore LA's nightlife independently are welcome to stay out, but you'll be responsible for your own rideshare back. DAY SIXTEEN: Sunday - Departure Morning - We'll have free time to pack up and get ready to leave. 10:00am - We'll check out and I'll drive everyone to LAX airport for flights home. I recommend booking flights departing between 1:00pm and 6:00pm to allow for a relaxed morning and comfortable transit time (LA traffic to LAX can be unpredictable). Tripmates flying out of a different LA-area airport (Burbank, Long Beach, Ontario) or leaving on a different day can be helped with alternative arrangements at their own expense, just let me know your plans in advance.

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