Pescadero is a historic farming and ranching community nestled along the Northern California coast, just north of Santa Cruz and south of Half Moon Bay. It’s a blink-and-you’ll-miss-it town, with a population of less than 650 people and a history stretching back to the 1850s.
During our day trip to Pescadero at the end of March, the first thing that struck me about the area was how unbelievably peaceful it was; Louis Armstrong’s What A Wonderful World definitely popped into my mind on more than one occasion as we drove past rolling green pastures and colorful fields of wildflowers.
Despite being situated just a few miles from the crashing waves of the Pacific—where you can watch whales from the shoreline and gaze upon historic lighthouses—Pescadero is the quintessential pastoral setting, complete with rolling green hills, dilapidated barns and rusty tractors.
It’s a place where you can visit idyllic family-own ranches, twirl through flower fields and pick your own strawberries in the summertime, but also walk barefoot down foggy beaches, collect seashells and scope out secret surf spots.
Rural farmlands and dramatic coastline might seem like a strange combination to those not familiar with Northern California, but it is one I have grown to love deeply since moving to the Bay Area two years ago.
Whether you’re road-tripping down the California coast, looking for a unique excursion during your visit to San Francisco, or are local to the Bay Area, spending one day in Pescadero is a very worthwhile addition to your NorCal bucket list.
Harley Farms Goat Dairy
I have three words for you: SNUGGLE. BABY. GOATS.
That’s exactly what we did during our two hours at Harley Farms Goat Dairy, the first stop during our day trip to Pescadero. We booked one of their 11:00am farm tours, which lasted for 1.5 hours and took us through the edible gardens, pastures, barn and milking room.
The obvious highlight of the morning was seeing the brand new baby goats in the barn! Most of these little guys were just a few weeks old, and we were allowed to scoop them up out of their pens and snuggle them in our arms. Needless to say, I just about DIED from the sheer cuteness of it all.
The baby goats were so playful and curious, trying to nibble on everyone’s clothing, shoes, purses, and fingers. They were absolute little love-bugs and seemed very happy to be held and petted; they kept jumping up against their pens trying to get to us, and wagged their tails like puppies!
I was pleasantly surprised to find that we essentially had as long as we wanted to interact with the babies. The whole group eventually trickled out from the barn into the pasture where the adult goats were grazing, but Derek and I lingered with the babies for quite a while after most of the others had gone.
IMPORTANT: Baby goat season lasts from February through May, and if you want to hold the babies you MUST book one of the tours!
You can absolutely still visit the farm and see the babies without booking a tour, but I do recommend snagging one of the tour spots if you get the chance. Spots are limited and fill up quickly, so be sure to book weeks or even months in advance!
That said, my honest opinion is that certain parts of the tour dragged on a bit; the first 30 minutes were spent sitting in the gardens learning about the history of Pescadero and Harley Farms. Definitely some fun little tidbits of knowledge in there, but ultimately we just wanted to get to the babies
The tour ended in the hayloft, with a tasting of two of the farm’s most popular cheeses: the Honey Lavender Chèvre and the Monet Chèvre, which is adorned with edible wildflowers from the farm’s garden.
Both were divine, but that lavender cheese is the stuff dreams are made of!
Don’t miss the shop, where you can sample even more cheeses with sourdough bread while browsing through farm-fresh dairy products, locally-made honeys and jellies, chocolates, soaps, lotions, and other adorable keepsakes from the farm. They even sell slices of cheesecake made with goats milk!
It is no exaggeration when I say that Harley Farms is one of the most idyllic destinations I have ever had the pleasure of visiting; the only sounds to be heard as you wander through the pastures and gaze upon the surrounding forested hills are chirping birds, bleating goats, and leaves rustling the wind.
Add a fresh loaf of bread, a log of lavender chèvre and a bit of gentle California sunshine to the mix, and you’ve got the ultimate recipe for good vibes and relaxation. Ahhhh.
Lunch at Arcangeli Grocery Co.
Dining at a grocery store? You betcha!
This family-run market and bakery has been a Pescadero institution since it was founded in 1929, and not much has changed during the last 90 years. Come lunchtime, locals and tourists alike line up at the counter to fill their bellies with ridiculously tasty sandwiches and freshly baked loaves of bread.
Arcangeli Grocery Co. stocks an impressive selection of Italian and French-style breads (their Artichoke Garlic Herb is the most famous), cheeses, local wines, gourmet condiments and desserts. As were visiting right at lunchtime, we opted for hot sandwiches from their deli.
Derek and I both ordered The Godfather, which can only be described as B – O – M – B. That pesto focaccia bread, mmmmm.
Redwoods and red wine? Talk about a winning—and very quintessentially Californian—combination!
Fortunately for us residents of (and visitors to) the Bay Area, experiencing both is as easy as hopping in the car and making the short drive south to one of California’s most up-and-coming wine regions: the Santa Cruz Mountains.
Drinking wine is something of a local sport here in California; come Saturday and Sunday, everyone flocks to the state’s various wine regions to indulge in locally-sourced libations.
And since moving to the Bay Area nearly 2 years ago, I have been lucky enough to participate in tastings at dozens of California wineries, from the ever-popular Napa and Sonoma to lesser-known wine regions like Livermore and Edna Valley.
But hand-to-heart, one of my absolute favorite wine regions in California is the Santa Cruz Mountains…and not just because it’s located less than 30 minutes from my home in San Jose!
Why Visit the Santa Cruz Mountain Wine Region?
Don’t get me wrong, Napa and Sonoma are AMAZING places to spend a weekend exploring vineyards and sipping high quality wines.
That said, planning a visit definitely requires a bit of foresight; the drive can be a little too long for a day trip from the South Bay Area (especially if drinking is involved!) which means booking a hotel is usually required…and those definitely skew towards the pricey side!
And even though Sonoma is often touted as the more laid-back alternative to Napa, both regions can still have an air of pretentiousness.
So what’s the alternative? If you’re looking for a wine region that is:
In close proximity to the Bay Area (especially San Jose)
Relatively undiscovered among tourists
Completely chilled out, with hardly a whiff of snootiness
Home to multiple award-winning wineries
In a truly GORGEOUS mountainous region of California
…then the Santa Cruz Mountains just might be your dream wine tasting destination!
This mountainous region spans roughly from Half Moon Bay on the north end to Watsonville in the south, though the borders are loosely defined. You can expect the drive to take around 20-30 minutes from San Jose, and roughly an hour from San Francisco (depending on which vineyards you visit).
More than 70 local wineries are interspersed among the redwood-forested hills, each offering their own incredible scenery and signature varietals. Part of what makes this wine region so unique is its multitude of microclimates; because of its mountainous topography, some vineyards are constantly shrouded by cool fog, while others bask in warm sunlight.
Want to sip bright, aromatic Pinot Noirs in the shade of an ancient redwood tree? Or share a bottle of full-bodied Cabernet Sauvignon while overlooking lush green hillsides? Or participate in a guided tasting in a historic, restored wine cellar?
Well I’ve got good news, because there is a winery for every mood in the Santa Cruz Mountains!
And just because this wine region is far less famous than Napa and Sonoma, don’t assume the wine is anything other than amazing. In fact, several of the wineries here are known for their world-class Cabernet Sauvignons, Pinot Noirs, and Chardonnays.
Ridge Vineyards is so much more than just a weekend gathering place for South Bay locals (although it certainly serves that purpose, too!)
During one of my visits to this iconic winery, I was surprised to learn that Ridge’s Cabernet Sauvignon has actually achieved international recognition time and time again, earning titles such as “America’s greatest Cabernet Sauvignon.”
Their Zinfandel was even served at the last state dinner of the Obama administration!
You might expect a winery of Ridge’s caliber to be excessively snooty and pretentious…but you’d be wrong. Their tasting room (open Saturdays & Sundays only) offers tastings that cost just $10, $15, or $25.
However, my recommendation is to purchase a bottle and head to their gorgeous picnic area. Nested amidst the Santa Cruz Mountains at an elevation of 2,300 feet, Ridge Vineyards is the perfect location for soaking in birds-eye views of Silicon Valley (see if you can spot Apple’s iconic “spaceship” campus!).
Located just a few miles down the road from Ridge Vineyards, Picchetti Winery is another local favorite. Originally founded in the 1890s, Picchetti is one of the oldest vineyards in California, and tastings are held in their historic tasting room.
Unlike Ridge – which is set atop a hill – Picchetti is nestled in a valley and surrounded by forested hills. But while you may not get those same panoramic views you’ll find at other Santa Cruz Mountain wineries, you will be treated to a lush green property with a spacious picnic area.
One of the coolest things about Picchetti Winery is that it’s connected to the Picchetti Ranch Open Space Preserve, a 300+ acre park that offers 3.7 miles of hiking trails and views of the Stevens Creek Reservoir.
Hike the easy, scenic 1.9 mile Zinfandel Trail (through hillside orchards and woodlands) before circling back to the tasting room for a well-earned bottle of red.
The first time I stepped foot onto the grounds of House Family Vineyards, I could have sworn I had stumbled into a scene from The Hobbit.
In order to reach the tasting room from the small parking area, you must embark on a short and easy quarter-mile walk through the vineyards. After following the compact dirt path through the vines, you’ll arrive to the tasting room: a small, rustic building set atop a flat, wide hill.
Gnarled trees and hanging string lights decorate the space, but it’s the view that will no doubt capture your attention first; from way up here, you can see all of Silicon Valley.
Here’s a fun hypothetical scenario: If you were limited to visiting ONE country for the rest of your life (but could visit as often as you wanted) which country would you choose?
My answer? Mexico, hands-down.
Not only is it a short flight from the U.S. and affordable to visit, it’s just a genuinely spectacular destination – especially for solo female travelers!
Just think about it – Mexico has all of the following (and more):
Sprawling urban cities with world-class museums and restaurants
Rural small towns with vibrant traditions and storied histories
Awe-inspiring ruins and ancient historical sights
Lush jungles teeming with tropical wildlife
Rugged Pacific coastline dotted with laid back beach towns
Turquoise Caribbean waters and sugary white sand beaches
In a single trip to Mexico, you can eat street food in a bustling local market, gaze upon Mayan ruins, cheer with the crowd at a lucha libre or football match, sunbathe on white sand beaches, photograph colorful street murals, hike through the jungle, swim in an ancient cenote, and discover a culture that is rich, warm and enchanting.
Over the years, Mexico has enticed me to visit time and time again, both solo and with others. And honestly, I’ve loved traveling solo in Mexico just as much as I’ve loved visiting with my husband and my friends.
Why Visit Mexico as a Solo Female Traveler?
I truly believe that Mexico is one of the BEST destinations in the world for solo female travelers…especially Americans. It’s definitely one of my personal favorites, anyways.
Why? Well, whenever I’m planning a solo getaway, there are a few priorities that are always at the top of my list.
For one thing, I want a destination that will actually be fun and interesting to visit as a solo female! To me, that means there should be an abundance of activities and experiences that I won’t feel lonely, anxious, or awkward participating in all by myself.
Casual wandering through scenic city streets is always a good option for solo travelers, but I also look for attractions like museums, markets, art galleries, parks, gardens, and walking tours.
And although I’m comfortable enough going out to restaurants by myself for dinner, the more casual dining options there are (like food markets, street food, cafes, and grab-and-go) the better.
Additionally, I like to visit destinations where it’s easy to meet other solo travelers. Even though I’m a mega introvert, I do still get lonely at times while traveling alone. And knowing that I can meet and connect with likeminded ladies (and gents) while abroad is such a welcome thing.
Well surprise surprise, Mexico checks ALL of these boxes.
There are truly an infinite number of reasons to visit Mexico. Whether you want to trek through rainforests and explore mystical ruins, get lost wandering through colorful small towns and villages, or sip fruity cocktails in a hot tub overlooking the sea, you can find it all in Mexico.
The locals are friendly and welcoming, the cuisine is cheap and flavorful, the culture is rich and warm, the atmosphere is spirited and festive, and the sights are stirring and beautiful.
Is it any wonder that travelers like myself end up returning to Mexico again and again and again?
And as an added bonus, Mexico is INSANELY easy to get to as an American traveler.
So many amazing Mexican destinations are within a short nonstop 3 – 6 hour flight from where I live in California…which is much more convenient than traveling across the Atlantic to Europe, or across the Pacific to Asia.
And it’s nice to still be in a similar time zone to my friends and family back home when I’m traveling on my own (anyone who has tried to coordinate a FaceTime session with a loved one while traveling will understand why).
In summary: Mexico offers the perfect combination of adventure, accessibility, and familiarity.
You can visit a vast number of exciting, colorful, and beautiful destinations within Mexico, each with their own cultures, histories, and traditions…without venturing too far from home (I’m speaking to my fellow North Americans here, but I do realize many of my readers are from elsewhere – sorry guys).
But even if you’re not from North America, Mexico is well worth the time and money it takes to travel there. It’s also a destination where you can easily get by without speaking the local language, although knowing a bit of basic Spanish will always help.
Places to Visit in Mexico as a Solo Female Traveler
1. Mexico City
Ah, San Jose. Surrounded (and overshadowed) on all sides by travel magazine-worthy destinations like San Francisco, Yosemite and Napa…you never really stood a chance, did you?
Sure, you’re the tech capital of the nation and a popular jumping off point for all sorts of California adventures…but how can you compete with iconic San Francisco and wine country to the north, wild mountain ranges to the east, and stunning stretches of coastline to the south and west?
Honestly, I do understand how many people could feel this way about San Jose…but not me.
Photo via Visit San Jose
San Jose is the 10th largest city in the United States and the largest in Northern California (yes, bigger than San Francisco).
It was founded by the Spanish in 1777, and is now considered to be one of the most affluent cities in California, a hub of technological innovation, and the heartbeat of Silicon Valley.
Nestled in a valley surrounded by grassy hills, San Jose has a typical Mediterranean climate (meaning generally mild weather, dry summers, and wet winters). With nearly 300 sunny days per year, I truly think San Jose has some of the nicest weather in all of the United States.
Why Visit San Jose, California?
I don’t want to paint a misleading picture – San Jose is no San Francisco.
Although it’s actually the larger city, San Jose is much less dense than San Francisco, giving it a more suburban feel in many areas.
It doesn’t have a strong existing tourism presence, an abundance of time-tested itineraries, or a long list of “must see” attractions on TripAdvisor. You won’t find any sights as iconic as the Painted Ladies or as grand as the Golden Gate Bridge here in San Jose.
No, San Jose is still far under the tourism radar…so what DOES this city have to offer visitors?
San Jose is incredibly diverse, with large populations of Mexican, Vietnamese, Chinese, Korean, Indian and other immigrants. It’s a true melting pot of cultures, which visitors can experience through the vibrant food sceneand abundant multicultural events.
The city also has a growingcraft beer presence, and is in close proximity to what Conde Nast labeled as one of “the best wine regions to visit in 2019” (the Santa Cruz Mountains).
Simply put, San Jose is up-and-coming. It’s a city with interesting stories to be told, beautiful sights to be seen, and incredible food, wine and beer to be enjoyed.
As someone who is not native to San Jose but has lived here for nearly two years, I like to think I have a unique blended insider/outsider perspective. With that said, here’s my take on how to spend one perfect day in San Jose, California:
9:00AM: The Breakfast Club at Midtown
Red. Velvet. Pancakes. Need I say more?
…Okay, I should probably say more! And here it is: if I could recommend just one place for breakfast or brunch in the San Jose area, it would hands-down be The Breakfast Club at Midtown!
And while their red velvet pancakes (topped with cream cheese drizzle, powdered sugar, whipped cream and chocolate chips) are the absolute BOMB, the rest of their menu is pretty dang amazing, too.
I’m a big fan of their Benedicts (they have a whopping ten varieties to choose from), but they also offer an impressive selection of scrambles, omelettes, and Mexican-inspired breakfast dishes. (Breakfast nachos? Sign me up!)
Oh, and did I mention their crepes, waffles, French toasts, mimosas, spiked coffees, and INSANE Bloody Marys and other cocktails? Just trust me on this one, guys – I KNOW my breakfast & brunch joints, and this is a good one. The best one, in fact!
(Insider tip: Arrive early in order to avoid – or at least minimize – the inevitable long wait for a table.)
10:00AM: Municipal Rose Garden
After breakfast, hop in the car and drive just a mile up the road towards San Jose’s Rose Garden neighborhood.
Rose Garden is easily my favorite neighborhood in the city, and it’s easy to see why as you drive through the quiet residential streets. Historic homes dating back to the 1800s with beautifully manicured lawns are the norm here, as are towering palms that sway in the breeze.
The highlight of the area – and the destination that you’re heading for – is the San Jose Municipal Rose Garden, which has been named “America’s Best Rose Garden.”
This 5.5-acre garden features an expansive grassy lawn and more than 3,500 perfectly planted rose shrubs. It’s a gorgeous (and fragrant!) space for strolling and snapping some photos, especially if you happen to be visiting during the springtime.
Photo via Visit San Jose
You likely won’t need more than 30 minutes or so here, but I’d recommend budgeting a bit of extra time for leisurely exploring around the neighborhood.
(…or holding an impromptu photoshoot in the gardens. It happens!)
11:00AM: Winchester Mystery House
I’m not particularly superstitious; in fact, if anything, I’m a bit of sceptic.
But there’s no denying that there’s something a bit unsettling about the infamous Winchester mansion!
The legend behind the sprawling 161-room Victorian estate goes something like this: After the tragic death of her husband, Sarah Winchester – heiress to the successful Winchester rifle fortune – believed that she was being haunted by the victims of her deceased husband’s rifles.
A psychic told the widow that the only way to seek refuge from the angry spirits was to drive them away with the sounds of drills and hammers. So, she purchased an old farmhouse and began renovating it…24 hours a day, for the next 38 years.
By the time Sarah died in 1922, the Winchester estate had become a maze of confusing hallways, slanted floors, stairways that led into the ceiling, and doors and windows leading to nowhere.
Whether it was the Winchester rifle ghosts (as Sarah believed) or just the strange and unusual layout, both Derek and I felt dizzy, disoriented, and on-edge during our tour of the mansion.
We booked the standard Mansion Tour, which is $39 for adults and lasts just over 1 hour. Tours are held every 20 minutes, beginning at 9:20am.
Although there is a good chance you will be able to walk up and purchase a ticket at the window, I do recommend booking in advance online if there’s a specific entry time you..
Enchanting stone corridors illuminated by string lights, intimate tapas bars tucked away down narrow alleyways, bustling plazas flanked by imposing Gothic cathedrals, whimsical Gaudi architecture…
Ah, Barcelona! Could you possibly be any more charming?
I’m not sure what I loved most about this vibrant city – the elegant, cosmopolitan streets; the incredible gastronomy (Paella! Jamón ibérico! Tapas! Pinxos! Sangria! Cava!); the dramatic medieval architecture; the bohemian cafes and art galleries; or the balmy air and sun-drenched beaches.
To summarize, Barcelona was everything I tend to love about traveling in Europe…with the bonus of the city’s unique Catalan flair.
Speaking of, Barcelona is the capital of Catalonia, an autonomous community in Spain’s northeastern corner. Catalonia’s history stretches back to the Middle Ages, and today the region still retains its rich culture, long-standing traditions, and fierce sense of independence.
My husband Derek and I were lucky enough to spend four days in Barcelona this past October, and to say we loved it would be an understatement!
Barcelona is a large, complex and diverse city with plenty to offer its visitors. I have no doubt that we only just scratched the surface during our few days in the city – that said, below are the sights and activities that I personally consider to be the best things to do in Barcelona!
The way I’ve structured this guide is as follows:
If you’re just looking for a quick and dirty checklist, check out the “overview” section.
If you want to learn more about the sights, read tips for visiting, hear about our personal experiences, and see photos, then keep scrolling!
Overview: Best Things to Do in Barcelona
Pont del Bisbé
Basilica de Santa Maria Del Mar
Basilica de Santa Maria del Pí
Els Quatre Gats
Palau de la Música Catalana
La Sagrada Familia
Casa Mila (La Pedrera)
Beaches + Port Vell
Parc de la Ciutadella
Arc de Triomf
1. Explore the Gothic Quarter By Foot
Barcelona’s Gothic Quarter perfectly captures the essence of Old World Europe’s charm and beauty.
This neighborhood is the historic heart of Barcelona, and is home to mysterious alleyways, pointed medieval arches, and majestic cathedrals with soaring spires and haunting gargoyles.
Meandering the streets of the Gothic Quarter left me spellbound and dreaming of ages long gone, though to be fair, modern-day Barcelona is completely captivating all on its own.
Cozy cafes tucked down narrow streets and trendy tapas bars with heavy pours of sangria and wine are the norm in this vibrant neighborhood.
It’s sensory overload in the best possible way: church bells tolling and cyclists wizzing past; visitors snapping photos of historic plazas and edgy street art; enticing smells wafting out of bakeries and open-air food markets.
The Barcelona Cathedralis hands-down the main attraction, and with very good reason. The outside alone is striking, but it was the inside that sealed the deal and stole my heart for good.
Soaring ceilings, imposing stone columns, powerful organ music, and breezy courtyards flanked by swaying palms and flickering candles await those who venture inside this medieval masterpiece.
Full transparency, however: Although the Barcelona Cathedral was constructed in the early-1300s, the iconic Neo-Gothic facade was added in the late-1800s. For me, this knowledge didn’t affect the magic or majesty of the cathedral whatsoever; I was utterly blown away by the intricacies and ornate details.
Located just behind the cathedral is another of Barcelona’s most noteworthy sights: the Pont del Bisbé, a Neo-Gothic bridge that stretches across the stone alleyway and stops pedestrians in their tracks.
The bridge is truly like something out a fairytale; it’s easy to picture a medieval maiden swooning amidst the arches and columns, while a forbidden love calls out to her from below.
Another favorite church in Barcelona’s Gothic Quarter is the Basilica de Santa Maria Del Mar. The stained glass windows are absolutely gorgeous! (I also feel that it’s worth noting that you can get some BOMB gelato from the shops surrounding this basilica…just saying.)
What else shouldn’t you miss in the Gothic Quarter?
Basilica de Santa Maria del Pí: 15th-century Gothic church (there is a small admission to enter, €4.50 for adults)
Els Quatre Gats: Cafe that served as a popular meeting spot for Catalan modernist artists (including Gaudi and Picasso) during the 1890s
Picasso Museum: Houses one of the most complete collections of works by Spanish artist Pablo Picasso
Palau de la Música Catalana: Historic concert hall designed in the Catalan modernist style; it is known for its incredible colors and design details
Placa Reial: A beautiful and lively square surrounded by cafes, restaurants, and nightclubs; the square itself contains a large fountain and is filled with swaying palms and wrought-iron benches
2. Be Enchanted by El Born
While the Gothic Quarter is best described as “dramatic” and “medieval,” the nearby neighborhood of El Born is elegant, artistic and trendy. Both neighborhoods are equally walkable, though Derek and I both favored strolling through El Born a bit more.
Twinkling string lights lined many of the narrow stone alleyways, giving them an air of whimsy and wonder. All sorts of electric shops, art galleries, and boutiques had their doors propped open, encouraging visitors to wander on in.
El Born is a superb neighborhood for drinking and dining, from the hipster cafes to the trendy cocktail bars to the dimly lit taverns. I highly recommend grabbing dinner here at least once – there are dozens of options for enjoying..
Located less than one hour away from Barcelona by train or car is one of Spain’s most charming and relaxed seaside escapes: Sitges, a sunny resort town with a population of less than 30,000 people and a history stretching further back than the Middle Ages.
Derek and I spent three blissful nights in Sitges during our weeklong trip to Spain last October. Truth be told, I had never even heard of Sitges before planning this trip, and likely never would have booked a stay there were it not for the fact that our good friends invited us to attend their wedding there!
Bonus wedding photos – how GORGEOUS was our friends’ Spanish villa wedding?!
But this coastal town – lovingly nicknamed the Saint-Tropez of Spain – swept us off our feet and charmed its way into our hearts. In fact, I dare say I loved it just as much as the drastically more popular Barcelona!
Maybe it was the whitewashed Mediterranean buildings accented with cobalt blue doorways and dusty gold arches, or the breezy seaside promenade line with swaying palm trees and al fresco restaurants.
Perhaps it was the many sidewalk cafes and cozy taverns tucked away down narrow alleyways, or the pleasant sea breeze and gentle sunshine that found us even in the maze of cobblestone streets.
Most likely, it was all of the above. In more ways than one, Sitges reminded me of Trogir, another European seaside treasure known for its charm, beauty, history, good weather, and excellent seafood.
In any case, Sitges is a destination that I would highly recommend to any traveler looking to get a taste of Spain’s charming coastal towns and cities.
Things to Do in Sitges, Spain
Explore Sitges on Foot
Sitges is a near-perfect example of a “walking city.” It’s small, easy to navigate, and ridiculously scenic.
If you want to maximize your sightseeing in Sitges, there are three main areas I recommend prioritizing:
The promenade: The place to see and be seen! Strolling up and down this waterfront boulevard is a local pastime, and one of the best ways to scope out Sitges’s world famous beaches.
The narrow streets behind the Church of St. Bartomeu: My favorite area for aimless wandering! The streets here are winding, hilly, and off-limits to motorized vehicles. Meander through the maze of scenic alleyways while keeping an eye out for whimsical details like colorful plaques and tiles, elegant arches, and windowsills lined with buckets of flowers.
Wondering how to plan a trip, and not sure where to start? You’re not alone!
For experienced travelers, booking flights and throwing together an itinerary is second nature. But I remember the first time I planned a trip all on my own, I was kiiiiind of a nervous wreck.
Sure, I was excited as hell for my first independent travel experience. But I had ZERO clue how to efficiently create an itinerary, search for flights, find places to stay, or figure out transportation. Needless to say, I second-guessed myself at every turn.
But, not anymore! All these years later, and I’m something of a trip-planning pro (…I did have a brief stint as a travel agent back in 2016, after all!)
I receive dozens and dozens of emails and messages from soon-to-be travelers, and I thought it would helpful to create a detailed guide for anxious first timers (or even experienced travelers who happen to love checklists and helpful tidbits – I like them too).
I crammed as much knowledge and as many resources as possible into this “How to Plan a Trip” guide. I hope you’ll find it helpful, but as always, drop any questions in the comments section and I’ll do my best to answer them!
(Short on time? You can find a condensed list of my favorite travel resources here.)
1. Pick a Destination
Researching and choosing a travel destination is by far one of the most exciting parts of planning a trip.
At this point in time, the whole world is your oyster. You can go anywhere, and do anything!
Then again, the world is a pretty damn big places, so it’s good to have a strategy for narrowing down your options.
Here are some methods for picking a travel destination:
Seek inspiration. One of my favorite resources for finding travel inspiration is The Travel Book by Lonely Planet. It features brief overviews of EVERY SINGLE COUNTRY in the world along with some seriously stunning photos. I’ve wasted away many hours flipping through this book! I also like browsing Pinterest and Reddit for travel photos and itineraries. And of course I follow many travel bloggers on Instagram and Bloglovin‘!
Choose the destination that’s cheapest to fly to. Open to going anywhere in the world? Save yourself some serious money by simply booking the least expensive flight you can find! Sign up for a service like Scott’s Cheap Flights, which sends you airfare deals from your local airports. You can also use the Explore tool on Kayak to shop around for cheap flights to anywhere.
Build a bucket list. Sometimes when I’m browsing online and stumble across a new destination or interesting attraction, I’ll jot it down in the notes section of my iPhone. I keep a “local” bucket list (filled with all sorts of destinations near where I live in California) as well as a global bucket list. It can be easy to forget what originally caught your eye about a city or country, so having some notes handy when it comes time to book a trip can help with your decision.
Pssst – I own all 3 of these coffee table books, and they’re amazing for finding travel inspiration!
2. Decide How Long Your Trip Should Be
Four days? A week? Two weeks? A month?
There’s no right or wrong answers when it comes to the length or your trip, but typically this decision will come down to a few factors:
Vacation time. How much of it do you have? How much of it do you want to spend on this trip?
Travel time to the destination. In general, the further away you’re traveling, the longer your trip should be. If your destination is only a three-hour flight away, you can definitely spend just a few days there and get your money’s worth. If you’re spending 20 hours on a plane, however, you’ll likely want a full week (better yet, two) at the minimum in order for the travel time to be worth it.
Time needed to enjoy the destination. Countries come in all sizes, and the time needed to “properly” explore China vs. Costa Rica (for example) would be drastically different. It’s true that you’ll likely never see everything a country has to offer, no matter how much time you have. But if you’re visiting a large destination, or one that really fascinates you on a deep level, it’s smart to budget more time.
Monetary budget. Generally speaking, the longer your trip, the more you’ll spend. Which brings us to…
3. Set Your Budget
Some people may prefer to set their budget earlier in the process; for example, even before deciding on the destination or length of trip. And this probably makes sense if you’re on a very strict or limited budget.
For example, if you know that you absolutely cannot spend more than $1,000 total, then it’s smart to make that decision first, and then look for destinations that fit into your budget (either because they have a low cost of living, or because they’re cheap to fly to).
But personally, I tend to already have a dream destination in mind, and then build my budget around the airfare and average destination costs.
Street food = cheap!
For example, if I’ve picked Mexico (which is a short flight away, as well as a relatively cheap destination) I will set a much lower budget than if I had picked Germany, which costs more money to fly to, on top of being a more expensive country.
Again, if you know that you have a limited budget, it makes sense to rule out unaffordable destinations right off the bat. But if you have a bit of wiggle room, it makes sense to be flexible in your budgeting based on the location.
But how do you actually set your travel budget?
Essentially, you just figure out how much you’re able to comfortably spend, and then force your expenses to fit into that budget. Easy, right?
It can be helpful to think in terms of dollars per day; for instance, if you have $2,000 available to spend (not including flight costs) and want to travel for 10 days, you know that you can spend $200 per day on accommodations + food + activities, etc.
Having this estimate handy can help you make decisions about hotels and activities later in the planning process.
4. Start Researching Flights & Dates
Super important rule: flights should ALWAYS be the first thing you book.
Airline prices and availability are much more volatile than hotel or activity prices and availability.
If you a book a flight, and then discover that the hotel room you liked is no longer available, there’s still a good chance you can find someplace to stay that will meet your needs and fall within your budget.
But what if you already booked your hotels, only to find that the flight you were looking at has doubled in price? Or is no longer available at all? Or is significantly cheaper the day before or after you had planned to start your trip?
You’ll also need to know your arrival and departure schedule in order to build your itinerary.
For instance, factors such as whether your flight arrives in the morning or evening may determine how much time you spend in your arrival city before moving on to the next destination.
Here are some variables to consider while researching dates and flight routes:
When can you comfortably take time away from work or school?
What season do you want to travel in? What will the weather be like in your destination at that time?
Do you want to travel during high season (typically the best weather, but most expensive prices) or low season (fewer tourists and lower costs, but may have poor weather or other inconveniences)?
I personally like using Kayak to search for flights, but I always book directly with the airline. Why? If something happens (like a delay, cancellation, or missed flight) third party vendors will be less equipped to help you than the actual airline.
Once you’ve locked down your dates and identified a flight you’re happy with, I still recommend creating a rough itinerary before actually booking your flights. Which brings us to…
5. Create Your Itinerary
At this stage, I like to make a list of all potential cities, sights, and activities within my destination that interest me. A Word document or the notes section on your phone is a good place to make this list. I’ve even used PowerPoint if I want to include images in my notes.
…this list is usually WAY too long.
If you have a week to explore a country, you’re not going to fit visits to 5 different cities in. You’re just not! Narrow down your list to the 2 cities that interest you the most.
If your trip is longer, scale up the number of destinations accordingly; for instance, in 2 weeks you could reasonably visit 4 (or possibly 5) cities.
Some personal rules of thumb:
2 days per city at an absolute minimum
For major cities (like Paris), double that number
3 days is my sweet spot for most mid-sized cities
Avoid single-night stays…even for small towns. It’s just too much of a hassle with checking in and out of hotels; no time to actually relax!
Factors to help you narrow down your list and choose which cities to visit:
Travel accessibility and time between cities (if one city is a 9-hour bus ride away, and another city is a 1-hour shuttle ride, I’d almost always pick the second city)
Things to do in each city; what interests you the most?
Accommodation availability in each city
And here’s something most guide books probably won’t tell you: there is no such thing as a must-see city or attraction.
Seriously! It’s all relative.
If your dream is to bicycle around the French countryside exploring small villages and tasting local wines, and the thought of walking through city streets and touring art museums sounds like hell, why would you spend any of your precious time in Paris during your week in France?
I know, it sounds like a sin to skip a city as great as Paris…but honestly, I believe it’s worse to skip those destinations that set your imagination on fire and fill you with excitement, in favor of someone else’s “must see.”
I mean…Paris IS pretty great though!
I don’t believe in skipping touristic sights just for the sake of going off the beaten path (truthfully, popular sights are usually popular for a good reason) but if they truly don’t speak to you, follow your heart.
…Sorry, that was a bit of tangent! But here’s where I’m going with that: I know it’s hard fitting everything you want to see into your itinerary. For me, it’s usually more than hard – it’s impossible!
My advice: Accept the fact that you can’t see it all, choose the places that excite you or interest you the most, and trust that you’ll have such an amazing time visiting those places, that you won’t even think about the places you had to cut.
It’s the truth, I promise.
6. Start Booking!
Once you’ve settled on an itinerary you’re happy with, it’s time to lock it all into place by finally booking your flights, accommodations, activities, and any other transportation.
Book Your Flights
This is always a super exciting moment for me, because no matter what happens next…there’s no turning back now, you’re going on your trip!
Book Your Accommodation
After securing flights, accommodation is always the next thing I book.