Hit The Road!

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It’s no secret that the travel landscape in 2020 looks very different from years past. We’re not jetting off to Europe or the Caribbean this summer, and I suspect many of us will be resurrecting an “old school” summer vacation — the classic road trip.

Luckily, here in New England, that means scenic landscapes, lush forests, and fresh country air — all of which is just what we need after a few months stuck at home. So get ready to pack up your car and explore some hidden gems. Here are our suggestions for some of the best things to see and experience via the open road!


vermont green mountain highway
Misty Green Mountain Byway [Photo Credit: Sam Burriss via Unsplash]

A road-trip through Vermont offers country stores, hiking, fishing, and even an epic cheese-sampling adventure! The Green Mountain Scenic Byway (Route 100) is the perfect route to meander up through the state and has something for every traveler. This 217-mile road goes through the center of Vermont and skirts the edge of the Green Mountains.

colonial house in woodstock vermont

Wind your way through forests, meadows, farmlands, and quintessential New England towns.

[Woodstock, VT- Photo Credit: Craig Tidball via Unsplash]

A northbound road-trip on Route 100 begins with Wilmington, a remote town on the edge of the Green Mountain National Forest. With clear mountainside lakes, this is the perfect spot for swimming, sailing, paddling, and fishing against a stunning backdrop.

Continue upstate onto the Vermont Cheese Trail. There are 50 cheese-makers in Vermont producing more than 150 varieties of cheese (more cheese-per-capita than any other state!) The Vermont Cheese Council has created this handy map of the best spots to sample these delicacies.

[Photo Credit: Kevin Jarrett via Unsplash]

This route takes you through towns like Weston with historic buildings from an era before electricity. Sample fresh cider and doughnuts at the cider mills, and stop to view the roadside waterfalls.

You can follow the route all the way to Canada, but we recommend stopping in Stowe and using it as a home base for the rest of your adventure. This small town is connected to an excellent series of hiking trails through forests, along rivers, and up mountains. Go trout fishing from April-October or take a short scenic drive along Route 108 through the Smuggler’s Notch tree tunnel — one of the best places to view fall foliage in the country!

Best Places to Stay:
Woodstock Inn & Resort – Located halfway between Wilmington and Stowe in the charming town of Woodstock, VT. With farm-fresh cuisine at their four restaurants, Vermont-inspired treatments at their spa, and a myriad of activities from golf to falconry — this is a perfect spot to relax on your Vermont road-trip.

Trapp Family Lodge – With a fascinating Sound of Music backstory, this Austrian-inspired lodge has everything. In the mountains just outside of Stowe it offers a range of accommodations from rooms and suites to villas, and even some pet-friendly options. Three restaurants, a spa, and its own on-site brewery makes this lodge a home-base you won’t want to leave.

New Hampshire

A Peaceful New Hampshire Lake [Photo Credit: Brian Yurasits via Unsplash]

A New Hampshire road-trip is all about the lakes or the mountains.

You can start with the lake district. Lake Winnipesaukee is the state’s largest lake and a perfect home base for your New Hampshire road-trip. At 21 miles long it sits at the foot of the White Mountains and boasts over 250 islands. You can begin by circumnavigating the lake — following the Lake Region Byway, NH-11.

Here you can enjoy activities such as kayaking, boating, sailing, swimming, and fishing (and ice fishing in winter!) Hike the nearby Ossipee range to dry off and get a birds-eye-view.

[Photo Credit: Michael Travis via Unsplash]

If you’re looking for a little more elevation with your adventure, consider heading northwest to the Lost River Gorge where you can explore polar caves. Or head northeast along the Three Rivers Scenic Drive (NH-16). Where you can check out the White Mountain National Forest with its 48 peaks (including the highest in New England, Mount Washington.) Ride the cog railway (or drive the auto road) up Mt Washington, follow well-marked hiking trails to scenic overlooks and waterfalls, and end your days at local restaurants and pubs.

overlooking the top of a mountain in New Hampshire

Enjoy the stunning views, fall colors, and even stop to take a gondola ride.

[Photo Credit: Wendy via Unsplash]

Best Places to Stay:
Wolfeboro Inn – Right on Lake Winnipesaukee, this sprawling New England hotel is in the lake-side town of Wolfeboro. Offering a classic New England Tavern, a small private beach and close proximity to Wolfeboro’s boutiques and galleries, this is your quintessential New England lake-side experience

Wentworth Inn– Nestled in the White Mountains of Jackson, NH, Wentworth is a charming country inn. An idyllic forest setting, farm-to-table dining, and plenty of outdoor activities let you relax, unplug, and unwind.


The Rocky Maine Coast [Photo Credit: Liz Picurro]

If a rugged, yet charming coastline is more your road-trip cup of tea then we suggest heading even further north to Maine. Maine’s mid-coast US Route 1 heads through peninsulas and pine forests, meandering along rugged cliffs and through Victorian fishing villages. Utilize this route to see a number of Maine’s 65 historical lighthouses or to sample every lobster roll you can find at the harbor-side cafes.

Many of Maine’s lighthouses date back to the heyday of shipping in the late 18th century. Starting with the most famous Cape Neddick lighthouse just over the New Hampshire border. Continue along to Bar Harbor and try to see them all!

[Photo Credit: Frank Mckenna via Unsplash]

This stunning coastal route offers classic seaside views with fjord-like bays, steep cliffs, and islands claimed by sea lions. Start at the very south of the state in York, then cruise along the coast stopping in quaint towns like Portland, Waldoboro, Rockland, and Kennebunkport — all of which boast delicious seafood, historic buildings, and cozy atmospheres.

Also known as the Lobster Trail, Route 1 takes you past the best lobster shacks in the country. You can see the lobster coming straight off the boat and into the restaurant!

[Photo Credit: Karl Magnuson via Unsplash]

As you continue north you’ll merge with the Schoodic National Scenic Byway. It passes through the mainland section of Acadia, and you can enjoy lobster boats, wooden piers, lighthouses, and wildlife. Consider staying in one or two different towns overnight to go on sailing, whale watching, or puffin spotting tours.

Best Places to Stay:
Captain Lord Mansion– This incredibly charming B&B in Kennebunkport is a perfect stop on your way up Route 1. Luxurious rooms, an intimate spa, and extensive gardens await you in this quiet historic gem. Still only steps from Kennebunkport’s activities and attractions.

Samoset Resort – A sprawling oceanfront Resort in Rockport is the perfect northern stop. The newly renovated resort boasts ocean views, luxurious rooms, and plenty of activities around the nearby Penobscot Bay. Relax by the pool, get active at their sports facilities or head out into the bay for a lobster tour; this resort has a little something for every type of adventure.

A quintessential New England road-trip is certainly good for the soul. Whether you’re excited to get out into the stretches of forest and enjoy the fresh air or you’re ready to go antiquing in all the country stores and little towns along the way, a road-trip through Vermont, New Hampshire or Maine is a perfect way to spend a long weekend or weeks-long vacation. Let us know when you’re ready to start planning!

California Dreamin’

Long-time clients Linda and Fred had a conference in San Francisco and wanted to extend their stay by adding a quick road trip down the coast with some friends. I helped them plot out an “escape” that included a little bit of everything (from food/wine, to Pacific beaches, wildlife and scenery) and it sounds like it was a hit!

Hi Ann – now that I have a few minutes wanted to give you some more details. The trip was absolutely fantastic.  Paso Robles is a beautiful town. Usually we are not big fans of riding in the car but the scenery from SF to Paso was just beautiful — lots of farms and hills.  We had lunch in a small restaurant called Berry Hill Bistro (great Paninis  and good wine.)  Walked around for a short time (wish we had more) but wanted to get to Hearst Castle before it closed and wanted to see the sunset on the Pacific.  The Castle was amazing with spectacular views.


Checked into the Pelican Inn — what a wonderful place, right on the ocean — we made it in time to watch the sunset and it was breathtaking.  We were still full from lunch so we enjoyed the complimentary wine, veggies, cheese tray and dessert.  The room was beautiful with a gas fireplace. It was really nice to relax in front of the fire after the hustle and bustle of  San Francisco. Had our complimentary breakfast, walked along the beach, and on to Monterey.


We stopped along the way to see the elephant seals and then went to Big Sur (Julie Pfeiffer Burns State Park, which was recommended by someone in SF) it was beautiful and then we stopped at Nepenthe for lunch ( extraordinary views of Pacific and mountains) which I highly recommend. It is supposed to be beautiful at sunset.


The hotel in Monterey (Monterey Plaza Hotel and Spa) was perfect — overlooking the harbor  with the seals and otters frolicking in Monterey Bay right outside our room.  We had dinner in the hotel and the next day we explored Monterey in the AM and then Carmel in the afternoon. We had breakfast every morning on our hotel balcony overlooking the bay. The hotel was fabulous! I had been told we might be able to see whales in Monterey Bay (one thing I wanted to see was whales) It looked like it wasn’t going to happen but we woke the morning we were leaving and I overheard some people talking about seeing something big in the harbor. I jumped into my clothes, grabbed the binoculars (provided in every room) and ran downstairs.  There they were  3 whales spouting and breaching in the harbor.  I was in awe.


We left and went to Henry Cowell State Park to see the Redwoods. They were beyond my expectations.  We had time before our flight so we headed back to SF for what we hoped would be a walk across the  Golden Gate bridge however it was jam packed and we couldn’t get close.  We still had time so we backtracked to Half Moon Bay which was where you were going to have us stay if we were staying an extra day.  Beautiful trip there — fabulous views of the Pacific.  We found a restaurant on the beach  where we sat for 3 hours enjoying a fire pit  outside and having a very leisurely dinner waiting for the sunset.  We even met a woman from RI who had been in CA for 40 years. We enjoyed our last sunset over the Pacific and headed back to SF for our trip home.

So, again, thank you for  your help and expertise in another trip of a lifetime. The weather was perfect and we thoroughly enjoyed everything in and out of San Francisco. It was perfect.



A gold-medal-winning weekend

Our good friends Dean and Laura recently marked their 30th wedding anniversary, and asked us if we’d like to come along for a weekend in Lake Placid to celebrate. Didn’t take long to say yes to that!  Despite growing up in New York, and spending lots of time in Burlington, VT, I had never been to the NY side of Lake Champlain, the Adirondacks, etc. and I have to say that this trip was a major revelation to me.  It is absolutely gorgeous up there!


We drove about five hours from Rhode Island, heading west into Massachusetts and then taking a sharp northern turn at Albany, past Saratoga, Glens Falls and Lake George, before arriving in the lovely little town of Lake Placid. It’s hard to imagine that this was the site of two Olympic Games (1932 and 1980) as I have no idea where they put everyone. The town itself basically consists of one main street overlooking Mirror Lake, and then a series of gorgeous homes (and a couple of lodges) built around the edges of Lake Placid.

We stayed at the High Peaks Resort, which has an ideal location in the center of town, walkable to everything. Our rooms were spacious, the lake view was fantastic, and the onsite restaurant/bar was very welcoming after a long drive.  There was a major wrestling tournament going on in town while we were there, and our hotel was hosting both a wedding and a military retreat of some kind, but it never felt crowded or busy. In fact, the common theme for the whole weekend was “it’s so quiet and peaceful up here!”


On Saturday, we started with a two-mile walk around the lake, and then indulged in a decadent breakfast at the Breakfast Club. We were lucky enough to be there the day that the boat tours at Lake Placid Marina started up for the summer, so we were the very first passengers of the season. The tour was about a 90-minute ride around the lake in a pontoon boat, with commentary about the “Camps” along the shore (kind of like calling the Newport Mansions “Cottages”) and the history of the area.


Afterwards, we visited the Lake Placid Olympic Ski Jumping Complex, and rode the elevator 25 stories up to the top of the jump to take in the view.


After a lunch overlooking the lake, we window-shopped down Main Street and then hopped back in the car to go check out the nearby Whiteface Lodge (definitely worth a return visit, to stay in one of their luxurious suites, or just dine at KANU).  Our evening started with some fabulous cocktails and charcuterie at the Lake Placid Lodge, where we lingered for a while, watching the boats on the lake, and then we had a late dinner at The Cottage, a cozy little lakeside restaurant that’s part of the Mirror Lake Inn. I really could not imagine a more perfect day!


Sunday morning we took another walk around the lake (trying to work off all those decadent meals) and then checked out and headed back towards Rhode Island. Along the way, we made a detour to Fort Ticonderoga, and a scenic drive around Lake George.  Despite some serious traffic in Massachusetts, we were home by dinner time.


If you go:

–          You can do it in a weekend, like we did, but one extra day would really have been better.

–          May is the “shoulder season” and we lucked out with very nice weather, and the opening of the boat tours, but there probably would have been more to do if we came later into the summer. Or in the winter, when we could have tried the toboggan chute onto frozen Mirror Lake!

–          If you’re really into the Olympic experience, take a look at the “Olympic Passport”, which gets you discounted admission to a whole host of exhibits and activities.

–          There are a range of accommodations right in town, from mom and pop motels, to branded chain hotels, and more luxurious resorts/inns. The High Peaks was perfect for us, but the Mirror Lake Inn about a block away would be great for a romantic getaway and the two five-star lodges on Lake Placid (Whiteface and Lake Placid) are now firmly on my bucket list.



California Dreamin’

Not sure if you got the memo, but California was BIG this year! I had easily half a dozen clients ask for California coast road trips this summer, and I was more than happy to oblige:) There’s so much to see and do in that stretch of coast from San Francisco to L.A. that it can be tailored to anyone’s specific tastes and interests. Here’s a trip report from Kevin and Sue, whose trip happened to coincide with the August earthquake in Napa:

Hi Ann.  We had a terrific time on our California vacation!  

We did experience the earthquake, but it luckily ended up being—exactly as you put it—just a good travel story.  The “funny” part of it was my wife Sue’s initial reaction.  We were in bed, as the quake happened just before 3:30 in the morning. Sue’s first words as the bed started shaking moderately were, “Kevin, what are you doing?”—said in a slightly annoyed tone!  I sat up and said, in a surprisingly calm voice, “I’m not doing anything, and I’m pretty sure this is an earthquake.”  The shaking lasted for what seemed like about 15-20 seconds.  I do feel bad for the folks up in Napa who experienced the brunt of it, but as far as we could tell, San Francisco itself suffered no damage at all.

The Jet Blue flights were good both ways.  I think they are my favorite domestic airline at this point.  We also enjoyed excellent weather during the trip.  It seemed like every day was a mix of sun and clouds, temperatures during the day in the low 70s, cooling to about 59/60 at night, and no rain.

Kevin Grady 2

The Prescott Hotel in San Francisco was fine for our purposes—good central location, clean accommodations, friendly and helpful staff, comfortable bed, plus continental breakfast and a daily cocktail hour included.  (We only took advantage of the cocktail hour one day because we were out and about so much).  It is an older building and some of the furnishings are a little dated, but we were content there. I would rate it overall as about a 3.8 or 3.9 out of 5 stars.  Sue and I both loved the city of San Francisco.  It felt a lot like Boston to us, except for all the steep hills there!  One thing we learned is that the famed cable cars are not at all useful on summer weekends.  Lines to get on a cable car during the weekend ranged from about 30 minutes to 2 hours!   

Kevin Grady 1

We enjoyed Fisherman’s Wharf; Alcatraz was great; we took an enjoyable Segway tour; walked down Lombard Street (it was not as pretty as it apparently is in the Spring, but it was still cool), went across the Golden Gate Bridge a couple of times, had lunch one day in Sausalito; and walked through Muir Woods.  We absolutely would go back!  Here are a few restaurants we liked—Scoma’s (seafood at Fisherman’s Wharf), Jeanne D’arc (good reasonably priced prix fixe French food including a soufflé—but it’s a small and very quirky setting–located in  the basement of a hotel and decorated like a cross between a castle and a church); and Ristorante Milano (very small neighborhood Italian restaurant, with excellent homemade pastas including lasagna and gnocchi).

We very much enjoyed the drive south to Monterey!  The Jeep worked out fine.  We loved our accommodations at the Monterey Plaza Hotel & Spa.  The room and bed were very comfortable; we had a great view of the ocean right below (including sea otters frolicking); and the staff were all friendly and helpful!  The spa there was excellent—we took advantage of the two rooftop hot tubs each day and each of us had a massage on the last day!  The restaurant in the hotel had good food and a first class ocean view.  I would rate the hotel overall about a 4.3 or 4.4 out of 5. 

Kevin Grady 3

We enjoyed the Monterey Aquarium; we went horseback riding on the beach; we walked around Carmel and had a drink at Clint Eastwood’s Mission Ranch (he apparently shows up a lot and plays the piano there, but we did not see him that day); we loved the 17-mile drive at Pebble Beach and then the drive down to Big Sur (had lunch on the way at a restaurant called Rocky Point—good food (not exceptional but good) and just an outstanding/fantastic view, where we saw a number of whales from our table!)


Kevin Grady 4

Bottom line—our trip was an unqualified success!  We are very glad we went; we would do it again; and we would recommend it to anyone!

Thanks again for your help putting it together, Ann!!

Maybe it’s time to think about planning the NEXT vacation!!!





You provided excellent guidance for us. I appreciated that you really had us think about what was most important to us when we were selecting the right cruise – and not to totally focus on what other people had to say. THANK YOU for helping to make this a memorable trip for our family! It really was a trip of a lifetime!

Clare and Mark (family cruise to Alaska)

The level of service we experienced was out of this world (and we did NOT make it easy on Ann). We weren’t quite sure where we wanted to go, when we would be able to go, or what “vibe” we were going for. After asking us some key questions (what we liked, didn’t like, why, etc.) Ann helped us narrow down our trip details and planned the honeymoon of our dreams. She helped book some of our excursions, answered some emergency questions while abroad and was always available/willing to help. I think it’s safe to say we won’t be using anyone else for future travel planning – Ann is a rockstar!

Carli (Italy and Spain)