Chicago, the “Jewel of the Midwest,” known for its deep-dish pizza, jazz music, architecture, and …notorious mobsters. Chicago is the third largest city in the United States. Unlike New York and Los Angeles, you can get a good feel for the city during a weekend getaway. Sometimes called The Windy City (lore says its for its politicians as well as its weather), the city’s entire east side is bordered by Lake Michigan and offers miles of waterfront walking.
Get settled into your accommodations and then head out to dinner at Giordano’s for some famous deep-dish pizza. They have many locations, so look up which is closest to your hotel or evening plans. Gino’s East and Lou Malnati are also local favorites for deep-dish. Save room for pizza dessert!
After dinner, I recommend heading to The Green Mill Cocktail Lounge (4802 N Broadway, Chicago, IL 60640) for a live jazz performance. This uptown lounge was notorious Chicago gangster Al Capone’s old stomping ground.
Saturday: “The Loop”
Start your morning with the Chicago Architecture Foundation’s river cruise (you can start at either of two locations, I recommend starting at 401 N Michigan Ave). This is a cool and enjoyable way to see the city. The river tour guides provide a nutshell of the city’s history in addition to the city’s famous architectural sites. The price is roughly $45, and tours begin every 20 minutes.
After the tour, walk over to Millenium Park to see the much-photographed “Bean.” Millennium Park is located in the heart of the city, and is bordered by many cultural and art institutions. Check out the Tiffany Glass dome in the landmarked Chicago Cultural Center (78 E Washington St.), which was built in 1897 and is open to the public at no charge. Also nearby is the former Marshall Fields Flagship store, which is now a Macy’s (111 N State St). Get a snack and enjoy spectacular views over Millenium Park at Cindy’s (12 S Michigan Ave), located on the 13th floor of the 1893 Chicago Athletic Association Hotel.
Head up to the Old Town/Goldrush neighborhood to catch a 4:00 pm comedy show at The Second City (1616 N Wells St.), which has launched the careers of many celebrity comedians such as Tina Fey, Stephen Colbert, and Bill Murray. After the show, get a happy hour drink and peruse the exquisite furniture offerings at Restoration Hardware, now known as RH (1300 N. Dearborn St.) which is located in an old arts club.
Get some dinner in the Lakeview East neighborhood. Both N. Halsted St and N. Clark St offer a number of great dinner and debauchery locations. N. Halsted is the main strip in Boystown, the historical LGBTQ neighborhood, while N. Clark St, in the Lakeview neighborhood, is geared more towards a younger crowd and Cubs baseball overflow, since it runs south of Wrigley Stadium.
Sunday: Evanston, IL
Start your morning by taking the metrorail to Evanston. Get a coffee and pastry from Hewn Bakery (1733 Central St, Evanston, IL). Spend an hour touring downtown, which has many interesting galleries, small businesses, and museums. Walk over to Northwestern University’s campus, and don’t and forget to check out the waterfront views in the Lakefill section of the campus. After Northwestern, get a two-mile ride to the architectural gem that is Baha’i House of Worship (100 Linden Ave, Wilmette, IL 60091). You can ogle the lace-style details for hours!
For those who do not want to make the roughly one-hour train ride to Evanston, the neighborhood of Ravenswood in Chicago is quaint and offers much to do. It has an old fashioned apothecary. Each fall, Ravenswood sponsors a superb Apple Festival in Lincoln Square. I recommend checking it out if you have a chance.
Cheers to a great weekend in Chicago!
Thank you to Emma, Katrina, Elizabeth, and Jimmy for showing us around your city! Thank you to Meghan and Sarah for exploring with me 🙂
Santa Ynez Valley is a picturesque destination, known for its rolling hills dappled with vineyards, western-style storefronts, and the iconic Danish-style architecture in the town of Solvang. Ronald Reagan, Dolly Parton, and Fess Parker, who played Davy Crocket, have all had homes in this region. Fess Parker loved it so much he even created an inn and vineyard that you can visit today. Pioneers developed the land around a stagecoach stop in the mid 19th century, and much of the feel still has elements of the rustic early settlement. The scenic valley of roughly 20,000 residents is known for its agriculture (mostly wine), horse ranches, and friendly people. It is also the setting for the comedy, Sideways, which I recommend watching! Located just over the mountain range from Santa Barbara and two hours north of Los Angeles. Santa Ynez has many wineries, boutiques, restaurants and galleries to make it a relaxing weekend getaway.
Situated between the sloping hills of the Santa Ynez Mountains and San Rafael Mountains, the Santa Ynez Valley has six charming towns: Solvang, Los Olivos, Santa Ynez, Buellton, Ballard and Los Alamos. All with their own distinct character. But please be warned these are small.
When to go: I would recommend going in the springtime, after the rainy season, when the landscape is lush, green and abundant.
Where to stay: You can not go wrong staying in any of the villages, although both Solvang and Los Olivos have quaint downtowns that are fun to walk around. There is something to be said for staying in Solvang to avoid the midday crowds. I went on a girls trip, and we were able to actually rent a historical house that was part of Mattei’s Tavern (an original tavern from when it was a stagecoach stop) in Los Olivos!
If you are coming from southern California, I recommend getting dinner en route at Cold Spring Tavern (5995 Stagecoach Rd, Santa Barbara, CA 93105). This mountainside Western saloon, will remind you of the true west. For those who would like to stretch their legs before dinner, there is a one mile hike to the abandoned Knapp’s Castle ( parking can be found roughly at 3880 E Camino Cielo Santa Barbara, CA 93105). It’s a great spot to see the sunset through the stone arches of the original structure. The trail is completely downhill on the way there, so be prepared for the uphill on the way back.
Saturday: Wine tasting
I recommend starting your morning with breakfast at the Corner House Cafe (2902 San Marcos Ave, Los Olivos, CA 93441) in Los Olivos. For those with a sweet tooth, the local favorite God’s Country Provisions Donut Shop sells their donuts in the tower next door on the weekends.
After your breakfast, walk around the small downtown for a little bit before starting your wine tasting with a “chaser” of cupcakes at Saarloos and Sons Winery (2971 Grand Ave, Los Olivos, CA 93441). The family owned winery frequently names and labels their wine after ancestors.. You may get the opportunity to meet snarky, yet family-oriented son #1, Keith, who will share a bit about his elders that he honors in all actions he takes.
We had planned on spending the day wine tasting at different vineyards but ended up spending the whole time at our first stop, Demetria Estates (6701 Foxen Canyon Road, Los Olivos, CA 93441). We packed a picnic to eat outside at Demetria’s which resembles a Greek villa. The Greek-American owners named the vineyard and their daughter after the Greek goddess of harvest, Demeter. We had a local, Raymond (805-757-2342, ~$25/ hour) drive us around and give us the oral history of all the vineyards and the region in general.
After wine tasting we had a suburb dinner on the patio at S.Y. Kitchen (1110 Faraday St, Santa Ynez, CA 93460). They have a great farm to table italian food and cocktails.
For those who aren’t quite ready for the party to end, consider a nightcap at country western, Maverick Saloon (3687 Sagunto St, Santa Ynez, CA 93460).
Sunday: Solvang, a Danish village
Spend Sunday morning walking around the Danish village of Solvang. Danish-American’s moved west in the early 20th century to avoid the long midwestern winters and created this village. Start with a hearty breakfast from Paula’s Pancake House. Enjoy window shopping, the many small boutiques, year round christmas stores, and art galleries. For those with a sweet tooth grab a danish pastry to go!
The rolling hills of Napa Valley have become synonymous with images of culinary excellence and award-winning wine. Much to many Francophiles’ surprise, the area was put on the global wine map when two local vineyards won in a blind taste test at the “Paris Wine Tasting of 1976.” Napa Valley is now best known for its dry red wines, the most popular of which is Cabernet Sauvignon but Merlot, Pinot Noir and even Chardonnay have received high praise. (If you are more interested in vineyards producing white wine, check out the neighboring laid back Sonoma Valley.) I consider the Napa Valley region as the apex of “rural chic” and the culture is still steeped in its agricultural history. Napa Valley is an hour drive north from San Francisco and it makes for a great weekend getaway.
Situated between the sloping hills of the Vaca and Mayacamas mountains, Napa Valley includes five cities: Napa, Yountville, St. Helena, Calistoga, and lesser known American Canyon. The region stretches for over 30 miles from north to south, and be prepared to have up to a 40 minute drive between destinations. Napa Valley can get expensive. Tastings at inexpensive vineyards start at around $35, and seeing multiple vineyards in a day can add up. Please note: I enjoy wine, but I am not a sommelier, so my itinerary is focused on a positive experience rather than as a wine critique! Pace yourself both physically and financially and remember to hydrate, as the area is known for hot temperatures and drinking all day can cause dehydration.
I enjoy watching movies and reading books about a place before I visit. For Napa, I recommend watching movies such as Wine Country, Bottle Shock, or the oldie but goodie, The Parent Trap. A few of Dean Koontz’s novels are set in Napa, but I would recommend The House of Mondavi: The Rise and Fall of an American Wine Dynasty by Julia Flynn Silor.
When to go: I would recommend going in the spring-time, after the rainy season, when the landscape is lush, green and abundant. Autumn and winter are also often good times. I would be wary of going in the summer, as Napa gets very hot and temperatures can go above 100 degrees.
Where to stay: I love staying in downtown Yountville, as it has a quaint downtown and walking around the center is always fun. I have previously stayed at Maison Fleurie, A Four Sisters Inn, and really enjoyed the ambiance.
Friday: Dinner in Napa
Get a reservation for dinner at Allegria (1026 1st St, Napa, CA), an upscale italian restaurant in a historic bank landmark, built in 1916. Take a stroll through Napa’s downtown after dinner. Please be aware that much of the town shuts down earlier in the evening, since most tourists spend the day sampling wine.
Saturday: Wine tasting
Start your morning with a pastry and coffee from Bouchon Bakery (6528 Washington St, Yountville, CA 94599), in the middle of the quaint downtown section of Yountville.
Drive up to Calistoga, and start your day at Sterling Vineyards (1111 Dunaweal Lane, Calistoga, CA 94515). This has the only aerial tram in Napa Valley and offers cascading views of the area. By the late afternoon, the tram can get hot and crowded, so I recommend starting here.
Next stop is Chateau Montelena Winery (1429 Tubbs Ln, Calistoga, CA 94515) this beautiful 19th century chateau and vineyard was put on the world vintner map when the Chardonnay won the “Judgement of Paris” wine competition in 1976. The movie, Bottle Shock, is a fictionalized depiction of this new world victory!
After visiting two vineyards get a late picnic lunch at V. Sattui (1111 White Ln, St Helena, CA 94574). You can pick up some food from the store and sit outside at many of the park benches. After lunch, you could continue on with winery tours, but I would recommend regrouping at your hotel and window-shopping the quaint shops in downtown Yountville.
For dinner consider the French restaurant, Bouchon Bistro (6534 Washington St, Yountville, CA 94599). For those who are looking to burn through some serious cash, French Laundry (6640 Washington St, Yountville, CA 94599) is a delicious 9 course prefix experience ($310/per person). Located in an unassuming stone farmhouse, this restaurant is repeatedly listed among the top restaurants in the world and received 3 stars in the Michelin guide.
For those who still have the energy, consider an after dinner drink at Restoration Hardware (6725 Washington St, Yountville, CA 94599) which is open until 10:00PM.
Sunday: Hot Air Balloon ride and Oxbow Public Market
For those who are not afraid of heights, start your morning very early with a memorable sunrise hot air balloon ride provided by Napa Valley Balloon, Inc (4086 Byway East, Napa, CA 94558). This could be missed for those who want to sleep in and save some money. Prices run roughly in the low $200’s per guest.
Try a grab and go brunch at Oxbow Public Market (610 1st St, Napa, CA 94559) before heading home for a weekend well spent (in more than one way) in Napa Valley!
This quaint New England harborside city has converted numerous pre-war maritime homes to art galleries, restaurants and bars. Settled in 1623, as Strawbery Banke, Portsmouth sits on the harbor of the Piscataqua River. This among many other New England small cities brings a thriving restaurant scene to walkable historic cities. This is a great long weekend or even day trip from Boston, MA, and is only a one hour drive.
Get settled into your accommodation, I recommend staying in the city center. Once settled, get some dinner from one of the many waterfront seafood restaurants: Old Ferry Landing (10 Ceres St), Surf Portsmouth (99 Bow St Suite 200W) and River House (53 Bow St) all offer great options. After dinner you can see if there is live music at Portsmouth Book and Bar (40 Pleasant St, Portsmouth, NH 03801) which is a bookstore and bar located in 1860 Portsmouth’s old Custom House and Post Office.
I recommend starting your morning with a bike ride around Portsmouth and through New Castle Island. In New Castle take a detour off route 1B down the winding River Street which offers great views of the river and beautiful homes. For those looking to get some more miles in, you can bike all the way to the honky tonk, Hampton Beach and back (round trip is roughly 30 miles of SCENIC east coast greenway). Warning: The bridges into New Castle can be a pain (one has grates on the road and another is a single line of traffic, so you may have to wait.)
In the afternoon, make your way to one of the beaches in Rye, NH. Jenness Beach is a favorite, or if you are trying to get away from people, the river side of Odiorne State Park offers soft sand and few crowds. While in Rye, get some lunch from Ray’s Seafood (1677 Ocean Blvd, Rye, NH 03870).
Walk around the downtown and window shop before dinner. Grab some grub from barrio tacos (319 Vaughan St, Portsmouth, NH 03801). You can build your own tacos here and I recommend a margarita!
Start your morning with brunch from The Friendly Toast (113 Congress Street, Portsmouth, NH 03801). I recommend that you spend the afternoon at Strawbery Banke Museum (14 Hancock St, Portsmouth, NH 03801). Strawberry Banke is the oldest european settlement in New Hampshire. The museum is outdoor and encompasses many buildings which were in use from the 1630’s- 1950’s. Don’t forget to admire the river views and flower garden in Prescott Park which is across the street from the museum area.
5 Seaside Getaways to take this summer from Boston, while safely Social Distancing:
Cape Cod, MA
No matter where you are coming from, Bostonians always call it “the Cape.” Cape Cod is known for beautiful beaches along its 400 miles of shoreline. My favorite beaches are the ones along the Cape Cod National Seashore, especially Cahoon Hollow Beach in Wellfleet on the Lower Cape. While the surf is rough, there are lifeguards on duty, a parking lot, and The Beachcomber, one of the best beach bars/restaurants in America. For family fun, you may want to try one of the more tranquil beaches on the bay side of The Cape. I have always enjoyed the Cape’s great bike trails, such as the Cape Cod Rail Trail, which runs from Yarmouth to Wellfleet or Shining Sea Bike Trail in Falmouth. For a scenic ride, take route 6A or “Old Kings Highway” (just to remind you are in New England) from Bourne to Provincetown, a distance of about 65 miles.
One of the many charming New England seaside cities, I love biking from historic and vibrant Portsmouth, NH along scenic Route 1A, also known as Ocean Boulevard, to the honky tonk locale of Hampton Beach and back. The whole New Hampshire shoreline is less than 20 miles long, and is worth a drive. Portsmouth has a few well-preserved museums dating back to the early colonial days of the 17th century. Portsmouth is surprisingly lively considering it’s in low-key New Hampshire. The downtown has many restaurants, bars, galleries and street performers.
This quaint New England seaside city has converted numerous pre-war maritime warehouses to art galleries, restaurants and bars. This among other coastal state capitals is a walkable historic city that now has many breweries and is flush with colonial history. I love shopping in the quaint city center, biking down to the lighthouse and grabbing a lobster roll from the food truck.
The North Shore city of Gloucester is known as a fishing port and it’s the setting for the book and subsequent movie The Perfect Storm. In fact, The Crow’s Nest dive bar is still located in downtown Gloucester. I enjoy a beach day at Good Harbor Beach. For cyclists, the Essex Scenic Route is a beautiful bike route through seaside Essex, Gloucester, and Rockport.
This charming small city is also located on the North Shore. The stately brick Federal-style houses and the brightly- colored wooden houses come right out to the edge of the sidewalk, attesting to the early history of Newburyport, before cars were prevalent. The Essex County Superior Courthouse, designed by Charles Bulfinch and built in 1805, is a beautiful brick Federal-style building overlooking a pond. In the downtown waterfront area are many interesting shops and restaurants.
San Luis Obispo (or SLO for short), is a small city in California’s Central Coast. SLO’s location makes it a popular and manageable weekend getaway for Los Angelenos and San Franciscans alike, as it’s 3 hours from LA and 3.5 hours from San Francisco. SLO was originally developed around the Mission San Luis Obispo de Tolosa, a 300 year old Spanish mission with a museum. It is known for its rich history and as the location of Cal Poly SLO, but is a Central Coast gem that can be enjoyed at any age!
Accomodations: Definitely the most iconic stay would be in the eccentric pink Madonna Inn (100 Madonna Rd), it seems like a hotel that you would find in Las Vegas 30 years ago… You can also find accommodations on airbnb or booking.com.
If you are able to arrive a little early, Wolff Vineyards stays open for sunset views. Otherwise arrive and check into your accommodations and get settled.
Hike the Bishop’s Peak, which takes about two hours.
Enjoy a well-deserved brunch at Mint + Craft (848 Monterey St); they have small outdoor seating in a pedestrian alley.
After brunch relax at Avila Beach. Avila Beach paddleboard and other sports offers first come first serve kayaks and paddleboards. If you remain for sunset, Pierfront (480 Front St, Avila Beach, CA 93424) Mr. Rick’s (404 Front St, Avila Beach, CA 93424) and Ocean Grill (268 Front St, Avila Beach, CA 93424) offer great sunset views. For those who are not beach goers, the Paso Robles region offers an abundance of wineries that you can check out.
Get dinner at Novo (726 Higuera St), the restaurant is walking distance to all the bars downtown. They have a beautiful tiered outdoor seating, which overlooks the San Luis Obispo Creek. You can hear the faint sound of the stream and birds while dining. It’s dining in a real life upscale rainforest cafe! Try to get a reservation for outdoor seating in advance.
Start your meandering day off with brunch at Luna Red (1023 Chorro St), they have a peaceful outdoor patio seating. The restaurant is located next to the Mission San Luis Obispo de Toloso, which is worth an hour to check out. Spend the rest of your time window shopping the quaint downtown, don’t forget to walk down the infamous bubblegum alley.
Head back home after a relaxing weekend getaway in SLO!
The Santa Cruz Mountains are dappled with houses among wooded forest. This is what I picture Marin County, thirty years ago before it was turned over by tech yuppies looking for a rustic home. The “Mountain Folk” as my friend who lives there adoringly calls herself and her neighbors, are friendly and remind you of a bygone era of early California settlers. The Santa Cruz Mountains are great to slow down and enjoy the serene nature that California has to offer. One hour and a half south of San Francisco, this is a great day trip retreat from the hustle and bustle of the city.
Getting there: Continue on 17 from Los Gatos, CA then continue onto Summit Road and a right onto Soquel San Jose Rd.
Start your morning by getting a coffee and a homemade treat from the female owned Casalegno’s Country Store (3 Laurel Glen Rd, Soquel, CA 95073). It has been around since 1929 and is a great stop for a coffee on your drive through the redwoods of Soquel en route to…
Spend a few hours hiking the Forest of Nisene Marks State Park (Aptos Creek Rd, Aptos, CA 95003) which offers over 40 miles of hiking trails through 10,223 acres of wildlife. There are so many variations and amount of time you could spend here, you can check out more information here. With so much land, expect to not see many crowds.
After hiking, drive down to Capitola Village and get a well deserved brunch from Zelda’s (203 Esplanade, Capitola, CA) which overlooks the brightly colored guest suites of the Capitola Venetian and Soquel Canal. Spend an hour looking around the small downtown area. There is a beautiful and brief (10 minute) pedestrian walk along the Soquel Creek.
For those who prefer a leisurely day you could end here, but for those who would like a little more adventure, you can check out some the Wine Trail. MJA Winery Tasting Room, Wargin Winery (5015 Soquel Dr, Soquel, CA 95073), and Alfaro Vineyard Winery (420 Hames Rd, Watsonville, CA 95076) will not disappoint.
Cap your wine off with some BBQ from the family-owned and delicious Aptos St BBQ (8059 Aptos St, Aptos, CA 95003), they often have live Blues Music playing. Try the tri-tip and my personal favorite, pulled pork sandwich! Those who want brisket, beware that it sells out quickly. Cheers to a relaxing day in the Santa Cruz Mountains.
A huge thank you to Lolo and Ivan for showing me around their beautiful town!
Carmel-by-the-Sea is a small beach city on the Monterey Peninsula, two hours south of San Francisco. Historically a Bohemian artists village, Carmel-by-the-Sea has been home to many famous people such as Doris Day, John Madden, Ansel Adams, and John Steinbeck. Clint Eastwood was not only a resident, he was elected Mayor of Carmel. The picturesque city of less than 4,000 residents features unique homes including many cottages with minute detailing valued in the millions because of the location. One house which we viewed was decorated with heart-shaped cut-outs decorating the picket fence, the shingles, and gracefully furbishing the interior decorative trim. The luscious gardens rolled into each other in everflowing bloom.
Timing: We happened to visit Carmel during the Concours d’Elegance (“Competition of Elegance”), an annual event in which illustrious cars are displayed and judged. The event provided an interesting car (and people) watching all around town. My brother, a gearhead, was definitely jealous, I could tell the color of a car but I knew nothing about make or model. The Concours is normally the second week in August.
Addresses: Please note that much of Carmel is a grid system, so most businesses use cross streets instead of a number.
When I explore a new neighborhood I enjoy exercise, learning about the local culture, and then taking time to replenish and often indulge in some food and drink. Here is how to spend one day in the picturesque Carmel, California:
Start your morning at the Carmel Mission Basilica. This is the final resting place of St.Junípero Serra, who founded the first 9 of the 21 Spanish missions in California. You won’t need more than an hour to enjoy this peaceful and well kept historic site. The mission boasts housing the first library of California which started with only 30 volumes in 1778. Those first books and accompanying Franciscan sherpa’s came north from Mexico City’s San Fernando Apostolic College. Many of the original books are far older than the mission itself, having been printed in Spain, probably in the early 18th century and travelled to Mexico and then on to the mission in what was then called “Alta California”.
After learning about California’s rich mission history of “El Camino Real” (English: “The Royal Road”), enjoy brunch at the nearby Mission Ranch Restaurant. Despite the name the farm is unaffiliated with the mission itself. The restored farmhouse serves as a restaurant and inn. Clint Eastwood owns the 22 acre estate that has views of Point Lobos State Nature Reserve, the Pacific Ocean and the Santa Lucia Mountains. On Sunday’s Mission Ranch offers a jazz brunch. Make sure to take a stroll on the property to see the sheep grazing. If the weather permits, try to sit outside.
Burn off your brunch with a walk along the coastal trail between Carmel River State Beach and Carmel Beach. This should be less than two miles, but feel free to turn back at any point. This is also a great car ride. This seaside walk passes many historic houses, don’t miss any of the beautiful detailing on the houses, for modern lovers there is a Frank Lloyd Wright original. The houses mostly remind me of childhood fairytales with abundant beds of flowers, whimsical architecture, and ornate detailing.
Drive or walk back into the downtown of Carmel. Enjoy walking through the shopping district, with many boutiques and smaller locally owned businesses. Carmel-by-the-Sea’s downtown is an outpost for specialty stores: tasting rooms of local Monterey County vineyards, cheese shops, and small bakeries and restaurants. Established in 1899, The Carmel Bakery (Ocean Avenue, Suite 203), is the oldest commercial building in the town. The original owner even lived in an apartment above the bakery! There is a reason this small bakery has been in business for over 100 years: it offers delicious pastries and suburb sandwiches daily.
Rub elbows with various vintners while sampling local wines at one of the small tasting rooms. Most of the shops, like most of Carmel-by-the-Sea, are dog friendly. Three tasting rooms that will not disappoint are: Albatross Ridge Tasting Room (Dolores Street between Ocean and 6th Avenue), Caraccioli Cellars (7393 Dolores Street), or Scheid Vineyard Tasting Rooms (San Carlos Street and 7th Avenue). My favorite is the combined art gallery and tasting room, Scratch Wines Tasting Room (Dolores between Ocean and 7th Avenue). It is female-owner by a UCLA alumni, my alma mater! There is also The Cheese Shop (Ocean and Juniper), with its fun selection of cheeses, olives, and wine. For those who would like to sit down in a quaint lunch spot, Tuckbox (Dolores Street between Ocean and 7th Avenue), housed in a 1927 cottage offers tea and snacks.
I usually am exhausted at this point in the day, so I would recommend relaxing at your accommodation or down at the beach.
Spend about an hour and a half before dinner to enjoy a joy ride on the famous 17 Mile Road. While the entrance ticket seems like a rip off; the houses are extravagant, the sunset views are magnificent, and it hosts the ‘golf capital of the world’, Pebble Beach. On this path is the well-esteemed Pebble Beach Resorts which has hosted the U.S. Open six times. Pebble Beach Resorts has a small visitor center, which is worth the visit to learn the history of the iconic golf course. I would recommend getting a sunset drink at one of Pebble Beach’s sundrenched restaurants that offer outdoor seating: The Bench or Stillwater Cafe. At both, you should expect steep prices and affluent clientele.
For dinner there are many options: Forge in the Forest (Junipero Street and 5th Avenue); order tapas and enjoy live music at Terry’s Lounge at Cypress Inn (Lincoln St and 7th Avenue); if you enjoy farm-to-table asian fusion with a piano bar, Affina (6th and San Carlos Street) is the place to go. Both Treehouse Cafe and Vesuvius offer rooftop dining. Treehouse offers a global menu while Vesuvius (owned by Chef Pepe, who owns the Carmel Bakery) has great italian fare.
While Carmel is not known for their nightlife, you could venture to get a cocktail at one of the rooftop lounges: Vesuvius or Starlight Rooftop Lounge (6th Ave), or get some live music at Barmel which sometimes turns into a dance party.
The rolling green hills are decorated with honey-colored limestone houses with stone shingled roofs. Each village seems quintessentially British with a local pub and tea shops downtown.
With the industrial revolution and the development of cotton this region saw a major economic decline and many people left the countryside for the city. Now it’s a favorite seasonal get-away for Londoners and tourists in the mood for manor house nostalgia.
Getting in: We rented a car from Robinson Gross (Tredington Park, Tredington, Shipston-on-Stour CV36 4RN, United Kingdom) just outside of Moreton-on-Marsh. If you plan ahead and give them ample notice, they offer reasonably priced-rides to the train station. We took the train from Gatwick Airport (directly to the right when you exit arrivals) to Reading and transferred to a second train heading to Moreton-on Marsh. You can also take the train to Oxford and transfer from there.
Accommodations: We wanted to stay in a charming older inn, and we had a car and could stay in a town that wasn’t a transportation hub. We chose The Lion Inn, (37 North Street, Winchcombe, Cheltenham) which proved to be a good home base after a day of trekking and exploring nearby villages.
Day 1: Enjoy a meal at your Inn or local gastropub. After a few hours of navigating the train system or driving in from London, get settled into your lodging. We stayed at the Lions Inn in Winchcombe and enjoyed our first meal at their delightful gastropub. We enjoyed a nightcap in front of their roaring fire. To celebrate your arrival and initiate your adventure, I recommend getting dinner at your local Inn, or a local village favorite that is within walking distance. This way you can still get up early the next morning and start exploring.
Day 2: Hike, Explore Broadway Hike, Explore Hailes Abbey, Broadway and Chipping Campden:
I like to get some exercise in before each adventure. Start your morning off by hiking either Cleeve Hill or Broadway Tower. If you choose Broadway Tower don’t bother paying the 5 pounds to go the three flights up, you have an equally beautiful cascading view from the hilltop. After getting your hike in, feel free to go about your day in your hiking clothing, the area is very sporty. Check out Hailes Abbey, Chipping Campden and Broadway. Hailes Abbey (Hailes, Cheltenham GL54 5PB, United Kingdom) embodies the reminiscent ruins of a 13th century abbey. The heritage site includes a free audio guide and an intact church showcasing medieval paintings. It also offers a great place to picnic or take a leisurely stroll. Next up on the itinerary is Broadway. I loved Broadway, with its expansive center and many shops and tea parlours.
We had high tea and snacks at Tisanes Tea Room (Cotswold House, 21 The Green, Broadway WR12 7AA, United Kingdom), which was affordable and low key. Two of the grand hotels: The Lygon Arms and The Horse and the Hound, offer great options for a more upscale high tea experience. Spend an hour or so strolling through the town’s various shops. Don’t forget to snap a photo in front of the iconic red telephone booth. Next stop on the village itinerary is Chipping Campden, which is a fifteen minute car ride. For those on foot, it is a five mile walk.
You can also saunter down to Broad Campden and back up, which provides a quaint respite. The walk is decorated with some iconic thatched roof houses. Once back in Chipping Campden, I recommend getting dinner at The Huxley (High St., Chipping Campden, United Kingdom) in the middle of the village center. Check out if they have a live music event, and in good weather,eat outdoors and get a feel for the village and its people. If you are in the mood for a nightcap at the end of your day, I recommend a visit to Hollow Bottom Beer Garden (Guiting Power, Cheltenham GL54 5UX) for a refreshing local brew from among the many beers on tap.
Day 3: Sudeley Castle, Lower Slaughter, Borton-on-the-water, and Stow-on-the-Wold:
Start your morning by exploring Sudeley Castle (Website,10:00AM-4:00PM, ~17pounds). Get your fill of centuries worth of English history! Next head over to Lower Slaughter. En route to Lower Slaughter, drive through small and underwhelming Upper Slaughter, which is not worth the stop. Once parked in Lower Slaughter, walk around the town and enjoy the beautiful running mill and attached cafe. We had the luxury of arriving just as they were putting some scones into the oven! After walking around Lower Slaughter, follow the 1.5 miles path to the left of the river to walk to the neighboring town of Bourton-on-the-water.
Bourton-on-the-water is absolutely beautiful, but does cater more to tourism. The village is known as “the Venice of the Cotswolds”. Enjoy a leisurely lunch and window shopping in Bourton-on-the-water, like the name entails a river runs through it. I loved just walking over the various bridges downtown. Take the leisurely walk back to your car and end your day in Stow-on-Wold.
In Stow on the Wold, walk around the center of town, which is more “bustling” than the others. The multipurpose St Edward’s Hall is a library, tourist office and museum. If it peaks your interest, check out the English Civil War artwork on the second floor. The building was built in 1878 from unclaimed funds at the local bank. Don’t miss the medieval St. Edward’s Church.
End your day with dinner at Porch House (1 Digbeth St, Stow-on-the-Wold, Cheltenham GL54 1BN, United Kingdom), publicizing itself as the oldest Inn in England. On their hearth, they have witches’ blessings engraved in the 1700s fireplace. Most of the area has fresh local produce and a seasonal menu. When I was there they had butternut squash risotto, it was amazing!
Day 4: Daylesford, Woodstock and Blenheim Palace, and local favorite Falkland Arms:
Start your morning off with brunch at Daylesford Organic Farm (Daylesford, Kingham, Moreton-in-Marsh GL56 0YG, United Kingdom) in Gloucestershire. In the United States we have John Deere farm equipment, in England they have JCB, started by Joseph Cyril Bamford in 1945. Anthony Bamford, succeeding his father as the current owner of JCB, was appointed a Lord in 2013. He is also a collector of antique Ferraris and other luxury cars. The Daylesford Organic Farm was started by his wife, Carole. This upscale farmstand is a must see, as it represents a positive outcome of a recent tourism movement in the Cotswolds: sleek, clean, and new. Focusing on organic farming and clothing, this farmstand is the definition of country chic. Spend some time walking around the farmhouse and shops. Those who prefer to be pampered can get a massage at the spa.
Spend the rest of the day at Blenheim Palace. It has a quirky place in history in that on November 30, 1874, Jennie Churchill was attending a party here when she began to go into labor and gave birth to Winston (what a surprise to the guests and the Churchills alike).
Blenheim Palace is the only English palace that is not in royal rule at this time; those “nonroyals” include Winston Churchill, Consuelo Vanderbilt, and Princess Diana before she married Prince Charles.
I highly recommend the audio guide to enhance your Blenheim Palace visit. Grab a snack and a coffee from the cafe to sustain you through this expansive tour.
After spending the day at the luxurious Blenheim Palace and garden, enjoy a meal in the Village of Woodstock. I recommend the Black Prince (2 Manor Rd, Woodstock OX20 1XJ, United Kingdom), which has elevated pub food and a beautiful riverside dining area.
St. Augustine, the oldest European settlement in the United States, was founded by the Spanish explorer Pedro Menendez de Aviles in 1565. It was originally called La Florida (“Land of Flowers”) by Spanish explorer Juan Ponce de Leon, who claimed the land in the name of Spain on March 27, 1513. The Land of Flowers still seems to fit this beautiful old area of Florida.
Growing up in America’s northeastern seaboard, I recall someone jokingly referring to Florida as “a sunny place for shady people”and I avoided the state for other southern destinations such as New Orleans, Savannah or Charleston, with rich culture and history and comparably warm climates. Yet, St. Augustine, Florida has been on my American bucket list for a number of years and now I finally got to see it. It was worth the wait as I found the city to be charming, historic, full of good restaurants and genuinely friendly, welcoming people. Here is a brief weekend itinerary for anyone interested in visiting.
When to go:
Living in New York City, I would highly recommend going during our cold months (January, February, or March) when you want to get out. The summers in Florida are too hot and humid for me. So anytime from December-March is ideal. I had the luck of visiting during a festival called “Lincolnville Porchfest” which is a grassroots neighborhood festival featuring local artists at different porches in the Lincolnville section of St. Augustine over President’s Day weekend.
Get settled into your accommodations and go out for dinner either at one of the many seafood places along Avenida Menendez with views of the Matanzas River, or go over the Bridge of Lions and try one of the popular restaurants on A1A Beach Boulevard. Having just arrived in St. Augustine, I chose Sunset Grille, arriving at the peak of Friday Night Happy Hour. I admit that I chose the Sunset Grille based solely on the name and the proximity to St. Augustine Beach, which is across the street. Unfortunately, there are no ocean views due to tall buildings and a berm being in the way. While the Sunset Grille had no romantic sunset views, it had a really lively Happy Hour attended by friendly, ebullient locals who were celebrating the end of the work week and the beginning of the weekend. In sum, while the food was okay, and there are no sunset views, the Sunset Grille is a fun place to kick off the weekend.
Drive over to the St. Augustine’s Amphitheater Farmer’s Market (1340C A1A S). Open Saturday 8:30-12:30pm.
Late morning: Window shopping Aviles St and St Georges St (both of which cater to tourism), check out the Cathedral, the main square, and the gardens at the LIghtner Museum.
Try to get a table outdoors and enjoy a healthy brunch at the Floridian Restaurant.
Afternoon: take a tour of Flagler College (74 King St, historical tours are offered at 10:00AM and 2:00PM and last about an hour). This elegant college campus was formerly the Ponce De Leon Hotel, built in the late 1800s as a winter resort by Henry Morrison Flagler with the interior designed by Louis C. Tiffany. Flagler was an industrialist, railroad pioneer and oil magnate. The school store doubles as the ticket office and the college students who run the store also serve as the tour guides, so the school store/ticket office is closed from 10-11 AM and 2-3 PM while the tours are going on. Try to get tickets ahead of time because in high season they sell out. The engaging tour guides are very knowledgeable and humorous.
We stayed at an airbnb in the historic Lincolnville neighborhood near downtown St. Augustine during porchfest, so we walked around Lincolnville and enjoyed the music and banter with the neighbors. Lincolnville is an historic black neighborhood where Martin Luther King, Jr., spoke and stayed over during the Civil Rights Movement.
Get a happy hour drink at San Sebastian Winery (157 King St, Monday-Saturday, 10 AM – 6PM and Sunday, 11 AM – 6PM). San Sebastian Winery is in Henry Flagler’s East Coast Railway Building. They have complimentary tours and wine-tasting starting every 20 to 25 minutes. The highlight was making it to the rooftop bar that offers live music most nights.
The charming restaurant called Preserved (102 Bridge St) is housed in a renovated Victorian house. If possible try to get seating outside on the patio. They serve locally sourced ingredients at this southern restaurant.
Brunch at Maple Street Biscuit Company or Blue Hen Cafe.
Spend an hour checking out the beautiful Mission of Nombre de Dios (Saturday 9:00AM- 5:00PM, Sunday 12-4:00PM) and the great cross. The beautiful mission and its grounds present a nice place to enjoy a morning stroll.
Get a coffee fix from Crucial Coffee Cafe before heading to the Castillo de San Marcos National Monument (9:00 AM – 5:00 PM) They do cannon reenactments on the top level. Try to sit close to where the cannon, so you can hear the history lesson, but you may want to block your ears for a moment as the cannon is fired.
For Sunday night dinner, I highly recommend that you try the large Columbia Restaurant. Call ahead for reservations. This old-time restaurant has been in the same family for over 100 years. The wait-staff, ambiance and food are phenomenal. I recommend the sangria, paella and the salad. In my group, we ordered varied entrees, did some sharing and found the food to be consistently excellent.