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11 of the Best Destinations for a Fall Trip

Updated: Aug 19, 2023

Are you ready to plan a Fall Trip?? Fall is one of my favorite times of year to travel. Why??? Most destinations are less crowded, with beautiful weather. Beach destinations still have warm water, teaming with marine life. Mountain destinations have spectacular colors with abundant wildlife preparing for winter. Unless the primary attraction is leaf peeping, the accommodations and airfares are significantly lower than peak season. Here are a few of my favorites fall destinations, both United States and International, mountains and beaches, cities and rural.

Napa Valley, California

One of my favorite places to visit in the Fall is Napa Valley! Visiting wine country at harvest time is so interesting because you can see wine in all stages of production. From the sorting of just picked grapes to fermentation as well as aging in barrels and bottles, there is something going on in every corner of the wineries! Here are a few tips for visiting Napa Valley in the Fall: 🍷Pre- planning improves the quality of your trip to Napa. 🍷 Make reservations for the wineries you really want to visit.🍷Three wineries per day is max for tasting. If your time in Napa is limited, consider a wine tour. 🍷Make reservations for any special restaurants when you book your hotel. Restaurants fill up quickly! 🍷If possible visit on during the week. Weekends are busy.🍷Build non- wine activities into your itinerary including, hiking, biking or hot air ballooning.🍷Plan at least one picnic. Many wineries have beautiful picnic areas. Oakville Grocery & Wine Merchant is a great place to get supplies! Here are some accommodation options from

Hope Town, Bahamas

Looking for an out of the way, relaxed beach destination, consider Elbow Cay, Bahamas. Fall is delightful on this lovely, tropical island with warm days and pleasantly cool nights. The only development on this cay is the delightful settlement of Hope Town. Their history is filled with pirates, British Loyalists, ship building, sponging, and tourism. While the main attraction is the pink tinted beaches, turquoise waters, swaying palm trees and candy colored sunsets, Elbow Cay is a charming place to explore. Home to the famous Hope Town Lighthouse, Hope Town Bahamas is known as the jewel of the Abacos. This quaint, colonial town emanates charm, giving visitors a chance to immerse themselves in both the cultural and natural beauty of the Bahamas. Founded in 1785, Hope Town one of the most beautiful settlements in the Bahamas. The harbor and famous lighthouse are a must see. The candy colored houses are reflective of the island's colonial roots. Motorized vehicles are banned from town, so the streets are a pleasure to walk. There are excellent restaurants, grocery stores, liquor stores, a museum, and interesting gift shops. Part of the Abacos Archipelago of Bahamas Out Islands, Elbow Cay is surrounded by intriguing cays that each have unique character and water sport centric activities. Green Turtle Cay, Man-o-War Cay, and Great Guana Cay are great stops for a day or two of island hopping while staying on Elbow Cay. Elbow Cay is easily accessible via the international airport in Marsh Harbor, the third largest Bahamian city. For great prices on accommodations on Elbow Cay, check out




Glacier National Park, Montana

Glacier National Park is a feast for the outdoor lover. With towering mountains, ancient glaciers, waterfalls, flowering meadows, crystalline lakes, dense forests, and abundant wildlife, Glacier National Park really does have everything you could want from an outdoor vacation. Hiking is one of my favorite things to do in Glacier National Park. For more information, visit my post Day Hikes in Glacier National Park. Don't miss the Huckleberry Cobbler with ice cream at Eddie's Cafe, in the park. For more information on restaurants near Glacier National Park, visit my post The Best Restaurants near Glacier National Park. We stayed at Great Northern Resort, they have several rustic cabins with gas fireplaces. They also offer Rafting Trips on the Flathead River.

The Berkshire Mountains, Massachusetts

The Berkshires are a region in Western Massachusetts and northwest Connecticut best known for its serene mountain vistas, lush forests, clear blue lakes and quaint towns like Stockbridge and Lenox Massachusetts. In the summer cultural events at places like Tanglewood and Jacob's Pillow attract crowds from New York City and Boston, making it an ideal place to visit in the quieter Fall months. The cool days and crisp evenings beckon you to hike the numerous trails, pick apples and explore villages straight from a Norman Rockwell painting in the waning days of Fall. One of my favorite trips to the Berkshires included several Fall days at Kripalu Center for Yoga and Health. It is the prefect place to unwind, recharge and recommit to healthy life practices. If you are looking for more traditional accommodations, check out the low prices for the Berkshires on

Crete, Greece

Crete is the largest island in Greece and the second largest in the Mediterranean. It is the largest and southern most island in the Aegean Sea. We love the Mediterranean Holiday vibe on this diverse island. We love the affordability, the food, the people, the natural beauty and the history. Recently we made our was the 7th visit to Greece. Greece is the first place we traveled internationally to as a couple nearly 40 years ago. In May/June of 2019, we spent a month in Greece, including 2 delightful weeks in a small apartment overlooking the port on Hydra. We followed that same recipe for success in July of 2021 by renting a small apartment over looking the new port in Chania, Crete. The only downside is the crowds, which is why I recommend visiting Crete in the Fall when the crowds are less and the weather more temperate. Are you ready to book a trip to Crete, check out for great options. We found these delightful budget friendly places to stay through them: ELOUNDA HEIGHTS HOTEL ON CRETE, IKAROS ART HOTEL ON CRETE and SEA & TOWN GETAWAY ON CRETE.

British Virgin Islands

The British Virgin Islands are a magical archipelago of coral and volcanic islands that are very lightly developed. While Road Town on Tortola is a bustling hub of commerce, transportation and tourism, walking around Great Harbour on Jost Van Dyke transports you back to the days of pirates. The steady trade winds blow through, making these islands a mecca for sailors. Divers and snorkelers come from all over to explore the enchantment of their pristine reefs. I first came to these islands in 2009, on a Windstar Cruise. I fell in love with the untouched beaches, abundant sea life, lively beach bars and relaxed, casual ambience. After several additional visits, CaptK and I bought a 43 foot Motor Catamaran through the Moorings Yacht Ownership program. Now we enjoy these islands several times a year. My most favorite time to visit is November, the air has a cooler drier feel to it and the water is wonderfully warm. Even with dozens of visits, I still have a list of things I have not seen, restaurants I have not tried yet and activities I want to try. If you would like more information on the British Virgin Islands, check out my blog post, Seven Day BVI Cruising Itinerary, 23 BVI Photos to Inspire You to Plan a Trip, Best Restaurants in the British Virgin Islands.

Essential Online Links For Booking Your Trip to the British Virgin Islands

Logistics: There is one international airport in the British Virgin Islands. You can also fly into St. Thomas USVI and take a ferry to Road Town, Tortola. :

Taxis are available throughout the islands. Private Transfers are available from both airports: Private Arrival Transfer from EIS Airport to Tortola, Private Ground Transfers, St. Thomas, Ferry Schedules are available at, Water Taxi transfers are available through Dolphin Water Taxi

Top-rated British Virgin Islands tours and experiences:

Conch Island Snorkel Tour: Contact Kelly at or Whatsapp at 281 496-0961

Top places to stay in British Virgin Islands: Scrub Island Resort, Spa & Marina (Tortola - Luxury) ***Wyndham Tortola BVI Lambert Beach Resort (Tortola - Budget Friendly, ) *** Sebastian's on the Beach Hotel (Tortola - Budget Friendly) ***Rosewood Little Dix Bay Virgin Gorda (Virgin Gorda - Luxury, )***Saba Rock Resort ( North Sound - Luxury,) *** Anegada Beach Resort (Anegada -Budget Friendly, )

My favorite Guidebook for Bareboating in the British Virgin Islands: The Cruising Guide to the Virgin Islands

My favorite Guidebook for the British Virgin Islands: Top 10 US & British Virgin Islands

My favorite Novel about the Caribbean: The Embarrassment Of Mangoes

Don’t forget to pack: water shoes*** underwater camera*** HD mask ***reef safe sunscreen.

London, England

London is an amazing city. There are iconic landmarks to experience in person. You will also find world class shopping, secret spots, live performances and hidden gems. Filled with museums, castles and iconic buildings, a walk around London is a walk through history. England ruled the world hundreds of years and during that time, stocked her museums with artifacts from around the world. It takes days to see the best of London museums. I try to visit a new museum each time I visit. If you are a first timer to London, put the British Museum at the top of your must see list. While England's cuisine often gets a bad rap, London’s restaurants are ethically diverse and significantly improved in recent years making it a must-visit for the foodies. In the Fall ,the crowds are less making exploring museums and getting restaurant reservations much easier. Fall also means the return of "Footie"(British Football or as we call it in the States, soccer). Stop into any pub on a Fall weekend and you can experience the Fans cheering, singing and toasting their favorite football clubs. Even better, you can get tickets to experience the sport live. London a multiple teams, each with their own stadium, so you have many options to catch a game live. Looking for moderately priced accommodations in London, check out

Alabama/Florida Gulf Coast

From Gulf Shores, AL to Apalachicola, FL there are 232 miles of stunning beaches that are easily accessible from most mid-west, mid-atlantic, and southern states. Beautiful beach towns like Perdido Key, Navarre Beach, Grayton Beach, Mexico Beach, and Port St. Joe; as well as bigger cities like Pensacola, Destin, and Panama City perch on the edge of the crystalline Gulf of Mexico. There is something for everyone on this gorgeous stretch of the sugar white beach. There are five major reasons to jump in the car and head south. It's less crowded than the summer season, the weather is pleasant with highs in the 70's, the accommodation prices are lower, it is generally family oriented, there is lots to do besides the beach. Here are some of my favorite places to stay along the Gulf Coast: Phoenix X, Perdido Key, Alabama, Turquoise Place, Orange Beach, Alabama, Summerchase, Orange Beach, Alabama, Phoenix West, Orange Beach, Alabama,

Lake Maggiore, Italy

Just 90 minutes from Milan, is the idyllic Italian Lakes Region. Nestled in the foothills of the Alps, on the border of Italy and Switzerland, sits Lake Maggiorie, the largest of the Italian lakes. Lake Maggiore and the towns along its shores have long been the playground and inspiration for artists, authors, politicians and celebrities. This alpine lake area is temperate year round, allowing for lush gardens and landscape. During our September visit, Lake Maggiorie was blissfully uncrowded and the accommodation prices were very reasonable. We were only able to spend 24 hours soaking all this area has to offer. We wished we planned for a longer stay. Ready to plan your trip check out these places to stay: Regina Palace on and Stresa Accommodations on

Smokey Mountains National Park

The Smokey Mountains are the southeastern section of the Appalachian Mountains, which traverse from Georgia to Maine. The Smokey Mountains start in Georgia and run along the Tennessee/North Carolina border. They are called the Smokey Mountains because of the natural fog that is frequently seen around the higher peaks. They are home to Smokey Mountain National Park and the Blue Ridge Parkway. During our time in Chattanooga , CaptK and I were able to explore the verdant forests that make up much of the area. As part of our explorations, we visited places like the kitschy but fun Gatlinburg and artsy, culinary delight, Asheville. We drove across Smokey Mountain National park, from Tennessee to North Carolina, as well as driving the Blue Ride Parkway from South Carolina to North Carolina. Fall is truly the best time to visit this area, when the hardwood forest is wearing her fall colors. These mountains are not the soaring majestic peaks of the Rockies or the Alps. These are softer, quieter, nurturing ecosystems that are home to the hard wood forest at the lower levels, and evergreen forests in the higher levels. Hiking, rafting, camping, kayaking or tubing are the best ways to explore the wonders of these mountains. For more information visiting the Smokey Mountains go to my posts Oysters, in Chattanooga and Chattanooga Hiking.

The Florida Keys

In the Fall of 2020, we loaded up the inflatable paddle board and inflatable kayak and headed out on a road trip to the Florida Keys. It had been 30 years since we visited the Keys and we were not sure what we would find. We were in search of "Old Florida," outdoor activities, and minimal crowds. What we found wowed and amazed us. We left planning our return trip. NO, we didn't go to Key West or Duval Street, but I do have a list of things to do in Key West when we visit, next time. YES, the sunsets are still some of the most beautiful you will ever see. Don't forget to pack your Reef Safe Sunscreen, HD Snorkel Mask and Sunhat. If you need more gear for the tropics, check out my Amazon Store. For more information on visiting the Florida Keys, check out my blog post Exploring the Natural Beauty of the Florida Keys and The Best Things I Ate in the Florida Keys.

Do you have a favorite place you like to visit in the fall? Please leave it in the comments section, so we can all add it to our fall travel must visit list.

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