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Find Your Best Weekend

Jim Flynn

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Find Your Best Weekend

Find Your Best Weekend

Jim Flynn

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About Us

A podcast that shares insider information and local tips about properties, restaurants and activities at popular destinations so that you can plan the best weekend possible and avoid common mistakes that could ruin it.A weekend is 2-3 days at most so, you can’t afford to make a mistake on where you stay, where you eat and what you do, there’s just no way to recover in that short time frame. We created BestWeekends to help travelers navigate the vast amounts of information out there and avoid the mistakes that can ruin a weekend. Think of us as your “travel advance team”. We visit each destination, stay in the lodging options, eat in the restaurants, experience the activities and most importantly…talk to the locals. We then present you with the “best” of what we found. We’ll tell you when to go, how to get there, how to get around once you are there, the best lodging choices, the best restaurants and the best activities and who to do them with. We’ll tell you things like where to get the best brunch, the best burger, where to have cocktails, what to do after dinner and much more. We accept no advertising from the places we recommend, so our suggestions are completely unbiased. We seek destinations and properties that are above the norm, not the most expensive, but the most unique that will enhance your experience. You can travel with confidence knowing that we have been there.Podcasts are launched each Friday at 1pm.Music credit: https://audionautix.com

Latest Episodes

Visiting Key West, Florida - What to Do, Where to Eat and Where to Stay

At the southern tip of Florida and only 90 miles from Cuba sits the southern most U.S. city of Key West. Once the base for Caribbean pirates and later home to Ernest Hemingway and Tennessee Williams, Key West also served as the winter White House for President Truman and the inspiration for the drawings of John James Audubon.Inhabitants are a colorful blend of eclectic artists, writers and others just escaping from everyday life. Everyone has a story and they're more than willing to share it with you. No one seems to care about the rest of the world, only about enjoying life every single day. This is Jimmy Buffet's headquarters and the site of the annual Parrot Head convention. Sunshine, tropical breezes, crystal clear water and a never ending party make this an ideal weekend getaway.Where else would you find a restaurant that celebrates Thanksgiving every Thursday night or a town that sponsors bed races down its main street or a place where restaurant owners call the local jail fir...

19 MIN2019 SEP 14
Comments
Visiting Key West, Florida - What to Do, Where to Eat and Where to Stay

Stowe, Vermont - Best Places to Stay, Best Places to Eat and Must Do Activities

Nestled in the valley between the Green Mountains on the west and the Hogback Mountains on the east, lies the picturesque village of Stowe, Vermont. The quintessential Currier & Ives Vermont town with its white church steeple, covered bridge and magnificent mountain views is the perfect weekend getaway. This beautiful town is what everyone envisions Vermont to be like. The smell of fresh grass in summer or wood burning in winter awaken your senses as you approach this so charming Village.While it is called the Ski Capital of the East, renowned for Mount Mansfield's "Front Four", that name belies the truly year-round appeal of the resort. I have enjoyed every season here, the colors more vivid than other places; the green fields of Spring, the colorful wildflowers of Summer, the browns, reds and golds of Fall and the stark whiteness of Winter.The beauty of Stowe has enticed moviemakers over the years as a prime location for films. The Trapp Family Property was the site of the top of ...

17 MIN2019 SEP 7
Comments
Stowe, Vermont - Best Places to Stay, Best Places to Eat and Must Do Activities

Martha's Vineyard - Your Best Weekend on the Island

Most activity revolves around the three primary towns, each of which has a character of its own. Vineyard Haven, the main port into which most of the ferries arrive, sits on the edge of Vineyard Haven Harbor and is home to a collection of shops and restaurants. Oak Bluffs is a kind of honky tonk boardwalk town with gingerbread style homes, a carousel, an arcade, ice cream shops and a waterfront promenade. It has some very good restaurants, is the place for renting boats, kayaks and jet skis and is the nightspot capital of the island. Edgartown is an elegant seaport with narrow streets, beautiful old whaling captain's homes, fashionable boutiques, wonderful restaurants and exceptional accommodations.What makes the island particularly interesting is that its geography changes depending upon where you are on the island. In the west are the cliffs of clay, the north, rocky boulders, the south, small ponds and in the center, dense forests. Visit https://bestweekends.com/seaside-weekends/...

19 MIN2019 AUG 31
Comments
Martha's Vineyard - Your Best Weekend on the Island

2 Must Visit Luxury Adirondack Properties for Special Occasions

Lake Placid is a charming little hamlet with wonderful shops and restaurants and delightful places to stay. Crystal clear lakes amid the tall pines of the Adirondack Mountains provide great recreational opportunities for all seasons and Whiteface Mountain offers some of the best skiing in the East. The town itself, overlooking Mirror Lake has wonderful shops and restaurants and maintains its small town charm. In this episode we talk about two special occasion luxury properties. So if you're looking for a once in a life-time experience to commemorate an anniversary, birthday or other milestone, you won't want to miss this episode! And checkout https://bestweekends.com/country-weekends/lake-placid-ny/ for additional details after the show.

18 MIN2019 AUG 10
Comments
2 Must Visit Luxury Adirondack Properties for Special Occasions

A Charming Island Worthy Of A Yearly Visit: Nantucket, MA - When to Go, Where to Stay & Where to Eat.

About 30 miles off the coast of Massachusetts sits the magical island of Nantucket, unmatched in its beauty and ability to relax even the most ardent Type A personality. Nantucket has a charm like few other places; cobblestone streets and gas lamps, quaint lanes of cedar shingled cottages and homes surrounded by white fences and adorned with window boxes of colorful flowers. Roses and hydrangeas are everywhere and there are miles of pristine beaches to enjoy. Lighthouses and cliffs, ponds and moors, cranberry bogs and fields of wildflowers make the island the perfect romantic hideaway. Visitors and islanders alike are passionate about their island. Tune into this episode to hear why I return to this island year after year to vacation with my family. And find more information about all the restaurants and lodging mentioned at https://bestweekends.com/seaside-weekends/nantucket-ma/

18 MIN2019 AUG 3
Comments
A Charming Island Worthy Of A Yearly Visit: Nantucket, MA - When to Go, Where to Stay & Where to Eat.

Visiting Napa | Best Winery, B&B, Burger & Restaurant, Plus Must Do Activities

Napa is the largest wine producer in the U.S. and is home to over 400 wineries producing some of the most acclaimed wines in the world. Commercial wine production dates back to the 19th century but premium wine production actually began in the 1960's.Despite its reputation, Napa has retained much of its agrarian origins and remains a small community of people who love the weather, good food and good wine. The scenery is stunning, the weather consistent (70º average temperatures) and the feeling is one of laid back contentment.In this episode, we'll tell you about our favorite wineries, must-do activities, the best places to stay and our top places to eat. Tune in now, and head on over to https://bestweekends.com/country-weekends/napa-ca/ for detailed information about all of the places and activities discussed.

23 MIN2019 JUL 27
Comments
Visiting Napa | Best Winery, B&B, Burger & Restaurant, Plus Must Do Activities

Visiting the Jersey Shore | Where to Stay, What to Do and Where to Eat

In this episode, we chat about the Jersey Shore. It is unfortunate that the image many have of New Jersey is represented by the oil refineries surrounding Newark (Liberty) Airport and the New Jersey Turnpike. In truth, the State's nickname, "The Garden State" more accurately reflects its true nature. While the state is one of the most densely populated in the country, large areas are devoted to vegetable and fruit farming and horse breeding. The northwestern part of the state is mountainous and sparsely populated and the eastern part of the state enjoys some of the most beautiful beaches in the country.The "Jersey Shore" is the area bordering the Atlantic Ocean and stretches from Sandy Hook (about 45 minutes from NYC) down past Atlantic City. Honky Tonk towns like Seaside Heights share the coastline with a revived Asbury Park, sleepy summer towns like Bay Head and Stone Harbor and beautiful year round communities like Spring Lake and Brielle and the gambling mecca of Atlantic City. ...

25 MIN2019 JUL 20
Comments
Visiting the Jersey Shore | Where to Stay, What to Do and Where to Eat

Tips for a weekend in Savannah, Georgia | Where to Stay What to Eat & What to Do

Just two hours south of Charleston, Savannah seems years apart from its neighbor to the north in their leap into the 21st century. While Charleston has charged into the new millennium, Savannah seems content to walk there, at its own pace. A stroll down its main street reveals store signs that haven't changed in 50 years. And the locals are quite happy with the state of things. Nevertheless, Savannah's quiet dignity and welcoming hospitality make it an ideal choice for a weekend getaway.Georgia's "first city" may just be one of the country's most beautiful towns. Founded in 1733 by James Oglethorpe on the banks of the Savannah River, the city was planned with a series of orderly grids around 24 squares. The squares today are delightful parks with benches, fountains, flowers and stately oaks dripping with Spanish moss. The parks are surrounded by magnificent, restored mansions reflecting a variety of architectural styles from the 18th and 19th centuries. There's even a section in one...

19 MIN2019 JUL 13
Comments
Tips for a weekend in Savannah, Georgia | Where to Stay What to Eat & What to Do

Visiting Charlottesville VA | Where to Stay, What to Do & Where to Eat

Deb Smith & Jim Flynn discuss the best resorts, restaurants & activities that will turn a weekend stay in Charlottesville, VA into a best weekend! Nestled in the shadows of the Blue Ridge Mountains, Charlottesville, Virginia is a largely undiscovered destination for weekend travel, yet offers everything you would want for an enjoyable getaway; great accommodations and dining and plenty of interesting things to do. Charlottesville is best known as the home of the University of Virginia and Thomas Jefferson's beloved Monticello and while a visit to Monticello is worth the trip alone, Charlottesville is so much more than just that.Two other presidents, Madison and Monroe had homes here that are major tourist attractions and this city of 45,000 residents has a vibrant music scene, wonderful art galleries, ACC college sports, nationally recognized wineries, terrific shops and cafes in a Downtown Pedestrian Mall, great golf courses and a host of other indoor and outdoor recreational activ...

15 MIN2019 JUN 29
Comments
Visiting Charlottesville VA | Where to Stay, What to Do & Where to Eat

Visiting the Hamptons | Where to Stay, What to Do & Where to Eat

Deb Smith & Jim Flynn discuss the best hotels, restaurants & activities that will turn a weekend stay in the Hamptons into a best weekend!The Hamptons is a popular destination, but before the crowded summer months or after the crowds have returned to New York City, the Hamptons offer a wonderful weekend retreat of pristine beaches, quaint shops, antique stores, wineries, top rated restaurants and plenty of things to do to occupy your time.There is a Hamptons personality to fit just about any mood. Tony East Hampton offers upscale shops like Tiffany and Ralph Lauren, Sag Harbor is a charming waterfront village, Montauk is a laid back and casual beach town and the North Fork evokes thoughts of the California wine country.Listen now to hear all the insider tips for a spectacular weekend in the Hamptons. For additional information, visit https://bestweekends.com/seaside-weekends/the-hamptons-ny/

19 MIN2019 JUN 22
Comments
Visiting the Hamptons | Where to Stay, What to Do & Where to Eat

Latest Episodes

Visiting Key West, Florida - What to Do, Where to Eat and Where to Stay

At the southern tip of Florida and only 90 miles from Cuba sits the southern most U.S. city of Key West. Once the base for Caribbean pirates and later home to Ernest Hemingway and Tennessee Williams, Key West also served as the winter White House for President Truman and the inspiration for the drawings of John James Audubon.Inhabitants are a colorful blend of eclectic artists, writers and others just escaping from everyday life. Everyone has a story and they're more than willing to share it with you. No one seems to care about the rest of the world, only about enjoying life every single day. This is Jimmy Buffet's headquarters and the site of the annual Parrot Head convention. Sunshine, tropical breezes, crystal clear water and a never ending party make this an ideal weekend getaway.Where else would you find a restaurant that celebrates Thanksgiving every Thursday night or a town that sponsors bed races down its main street or a place where restaurant owners call the local jail fir...

19 MIN2019 SEP 14
Comments
Visiting Key West, Florida - What to Do, Where to Eat and Where to Stay

Stowe, Vermont - Best Places to Stay, Best Places to Eat and Must Do Activities

Nestled in the valley between the Green Mountains on the west and the Hogback Mountains on the east, lies the picturesque village of Stowe, Vermont. The quintessential Currier & Ives Vermont town with its white church steeple, covered bridge and magnificent mountain views is the perfect weekend getaway. This beautiful town is what everyone envisions Vermont to be like. The smell of fresh grass in summer or wood burning in winter awaken your senses as you approach this so charming Village.While it is called the Ski Capital of the East, renowned for Mount Mansfield's "Front Four", that name belies the truly year-round appeal of the resort. I have enjoyed every season here, the colors more vivid than other places; the green fields of Spring, the colorful wildflowers of Summer, the browns, reds and golds of Fall and the stark whiteness of Winter.The beauty of Stowe has enticed moviemakers over the years as a prime location for films. The Trapp Family Property was the site of the top of ...

17 MIN2019 SEP 7
Comments
Stowe, Vermont - Best Places to Stay, Best Places to Eat and Must Do Activities

Martha's Vineyard - Your Best Weekend on the Island

Most activity revolves around the three primary towns, each of which has a character of its own. Vineyard Haven, the main port into which most of the ferries arrive, sits on the edge of Vineyard Haven Harbor and is home to a collection of shops and restaurants. Oak Bluffs is a kind of honky tonk boardwalk town with gingerbread style homes, a carousel, an arcade, ice cream shops and a waterfront promenade. It has some very good restaurants, is the place for renting boats, kayaks and jet skis and is the nightspot capital of the island. Edgartown is an elegant seaport with narrow streets, beautiful old whaling captain's homes, fashionable boutiques, wonderful restaurants and exceptional accommodations.What makes the island particularly interesting is that its geography changes depending upon where you are on the island. In the west are the cliffs of clay, the north, rocky boulders, the south, small ponds and in the center, dense forests. Visit https://bestweekends.com/seaside-weekends/...

19 MIN2019 AUG 31
Comments
Martha's Vineyard - Your Best Weekend on the Island

2 Must Visit Luxury Adirondack Properties for Special Occasions

Lake Placid is a charming little hamlet with wonderful shops and restaurants and delightful places to stay. Crystal clear lakes amid the tall pines of the Adirondack Mountains provide great recreational opportunities for all seasons and Whiteface Mountain offers some of the best skiing in the East. The town itself, overlooking Mirror Lake has wonderful shops and restaurants and maintains its small town charm. In this episode we talk about two special occasion luxury properties. So if you're looking for a once in a life-time experience to commemorate an anniversary, birthday or other milestone, you won't want to miss this episode! And checkout https://bestweekends.com/country-weekends/lake-placid-ny/ for additional details after the show.

18 MIN2019 AUG 10
Comments
2 Must Visit Luxury Adirondack Properties for Special Occasions

A Charming Island Worthy Of A Yearly Visit: Nantucket, MA - When to Go, Where to Stay & Where to Eat.

About 30 miles off the coast of Massachusetts sits the magical island of Nantucket, unmatched in its beauty and ability to relax even the most ardent Type A personality. Nantucket has a charm like few other places; cobblestone streets and gas lamps, quaint lanes of cedar shingled cottages and homes surrounded by white fences and adorned with window boxes of colorful flowers. Roses and hydrangeas are everywhere and there are miles of pristine beaches to enjoy. Lighthouses and cliffs, ponds and moors, cranberry bogs and fields of wildflowers make the island the perfect romantic hideaway. Visitors and islanders alike are passionate about their island. Tune into this episode to hear why I return to this island year after year to vacation with my family. And find more information about all the restaurants and lodging mentioned at https://bestweekends.com/seaside-weekends/nantucket-ma/

18 MIN2019 AUG 3
Comments
A Charming Island Worthy Of A Yearly Visit: Nantucket, MA - When to Go, Where to Stay & Where to Eat.

Visiting Napa | Best Winery, B&B, Burger & Restaurant, Plus Must Do Activities

Napa is the largest wine producer in the U.S. and is home to over 400 wineries producing some of the most acclaimed wines in the world. Commercial wine production dates back to the 19th century but premium wine production actually began in the 1960's.Despite its reputation, Napa has retained much of its agrarian origins and remains a small community of people who love the weather, good food and good wine. The scenery is stunning, the weather consistent (70º average temperatures) and the feeling is one of laid back contentment.In this episode, we'll tell you about our favorite wineries, must-do activities, the best places to stay and our top places to eat. Tune in now, and head on over to https://bestweekends.com/country-weekends/napa-ca/ for detailed information about all of the places and activities discussed.

23 MIN2019 JUL 27
Comments
Visiting Napa | Best Winery, B&B, Burger & Restaurant, Plus Must Do Activities

Visiting the Jersey Shore | Where to Stay, What to Do and Where to Eat

In this episode, we chat about the Jersey Shore. It is unfortunate that the image many have of New Jersey is represented by the oil refineries surrounding Newark (Liberty) Airport and the New Jersey Turnpike. In truth, the State's nickname, "The Garden State" more accurately reflects its true nature. While the state is one of the most densely populated in the country, large areas are devoted to vegetable and fruit farming and horse breeding. The northwestern part of the state is mountainous and sparsely populated and the eastern part of the state enjoys some of the most beautiful beaches in the country.The "Jersey Shore" is the area bordering the Atlantic Ocean and stretches from Sandy Hook (about 45 minutes from NYC) down past Atlantic City. Honky Tonk towns like Seaside Heights share the coastline with a revived Asbury Park, sleepy summer towns like Bay Head and Stone Harbor and beautiful year round communities like Spring Lake and Brielle and the gambling mecca of Atlantic City. ...

25 MIN2019 JUL 20
Comments
Visiting the Jersey Shore | Where to Stay, What to Do and Where to Eat

Tips for a weekend in Savannah, Georgia | Where to Stay What to Eat & What to Do

Just two hours south of Charleston, Savannah seems years apart from its neighbor to the north in their leap into the 21st century. While Charleston has charged into the new millennium, Savannah seems content to walk there, at its own pace. A stroll down its main street reveals store signs that haven't changed in 50 years. And the locals are quite happy with the state of things. Nevertheless, Savannah's quiet dignity and welcoming hospitality make it an ideal choice for a weekend getaway.Georgia's "first city" may just be one of the country's most beautiful towns. Founded in 1733 by James Oglethorpe on the banks of the Savannah River, the city was planned with a series of orderly grids around 24 squares. The squares today are delightful parks with benches, fountains, flowers and stately oaks dripping with Spanish moss. The parks are surrounded by magnificent, restored mansions reflecting a variety of architectural styles from the 18th and 19th centuries. There's even a section in one...

19 MIN2019 JUL 13
Comments
Tips for a weekend in Savannah, Georgia | Where to Stay What to Eat & What to Do

Visiting Charlottesville VA | Where to Stay, What to Do & Where to Eat

Deb Smith & Jim Flynn discuss the best resorts, restaurants & activities that will turn a weekend stay in Charlottesville, VA into a best weekend! Nestled in the shadows of the Blue Ridge Mountains, Charlottesville, Virginia is a largely undiscovered destination for weekend travel, yet offers everything you would want for an enjoyable getaway; great accommodations and dining and plenty of interesting things to do. Charlottesville is best known as the home of the University of Virginia and Thomas Jefferson's beloved Monticello and while a visit to Monticello is worth the trip alone, Charlottesville is so much more than just that.Two other presidents, Madison and Monroe had homes here that are major tourist attractions and this city of 45,000 residents has a vibrant music scene, wonderful art galleries, ACC college sports, nationally recognized wineries, terrific shops and cafes in a Downtown Pedestrian Mall, great golf courses and a host of other indoor and outdoor recreational activ...

15 MIN2019 JUN 29
Comments
Visiting Charlottesville VA | Where to Stay, What to Do & Where to Eat

Visiting the Hamptons | Where to Stay, What to Do & Where to Eat

Deb Smith & Jim Flynn discuss the best hotels, restaurants & activities that will turn a weekend stay in the Hamptons into a best weekend!The Hamptons is a popular destination, but before the crowded summer months or after the crowds have returned to New York City, the Hamptons offer a wonderful weekend retreat of pristine beaches, quaint shops, antique stores, wineries, top rated restaurants and plenty of things to do to occupy your time.There is a Hamptons personality to fit just about any mood. Tony East Hampton offers upscale shops like Tiffany and Ralph Lauren, Sag Harbor is a charming waterfront village, Montauk is a laid back and casual beach town and the North Fork evokes thoughts of the California wine country.Listen now to hear all the insider tips for a spectacular weekend in the Hamptons. For additional information, visit https://bestweekends.com/seaside-weekends/the-hamptons-ny/

19 MIN2019 JUN 22
Comments
Visiting the Hamptons | Where to Stay, What to Do & Where to Eat
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