Vineyard

Day Trips

Make the most of your day with our curated plans, packed with Vineyard's hidden gems and unique experiences!

day 1
Exploring Historic Center
morning
:

Start your day with a delicious breakfast at a local café known for its homemade pastries and coffee. Afterward, take a stroll through the charming streets of Vineyard, exploring the historic architecture that reflects the town's rich past. Be sure to stop by the local artisan shops to pick up unique souvenirs and gifts.

afternoon
:

Head to the Vineyard Museum to learn about the area's maritime history and cultural heritage through fascinating exhibits. Enjoy a leisurely lunch at a waterfront restaurant, savoring fresh seafood while taking in stunning views of the ocean. After lunch, wander through the nearby parks or take a bike ride along the scenic waterfront paths.

evening
:

As the sun begins to set, join a guided ghost tour that shares the spooky history of Vineyard's oldest buildings. Enjoy a cozy dinner at a farm-to-table restaurant, where you can indulge in locally sourced dishes paired with fine wines. Cap off your evening by attending a live music performance at a local venue, soaking up the vibrant atmosphere.

day 2
Beach and Water Sports
morning
:

Kick off your day with a hearty breakfast at a beachside café, followed by a stroll along the sandy shores of Vineyard Beach. Rent some beach chairs and umbrellas to relax, or dive into the refreshing waters for a swim. If you're feeling adventurous, sign up for a morning paddleboarding session to explore the coastline from a different perspective.

afternoon
:

Savor a picnic lunch on the beach, enjoying the sound of the waves and the warmth of the sun. Afterward, try your hand at windsurfing or kayaking, with rental facilities nearby offering all the gear you need. Spend your afternoon soaking up the sun, building sandcastles, or playing beach volleyball with friends and fellow beachgoers.

evening
:

As the sun sets, enjoy a beachfront dinner at a casual seafood shack, where you can feast on fresh caught fish and lobster rolls. After dinner, take a leisurely walk along the shore, enjoying the sound of the surf and the cool breeze. Finish your evening with a bonfire on the beach, roasting marshmallows and sharing stories under the stars.

day 3
Vineyard Wine Tasting Tour
morning
:

Start your day with a light breakfast at a local bakery, then head out on a guided wine tasting tour of the nearby vineyards. Enjoy the scenic drive through rolling hills and lush grapevines as you learn about the wine-making process. Your first stop will be a family-owned vineyard where you’ll meet the winemaker and sample their award-winning wines.

afternoon
:

After indulging in a delightful tasting, enjoy a gourmet lunch at a vineyard restaurant, featuring dishes that perfectly complement their wines. Continue your tour by visiting two more vineyards, each offering a unique selection of wines and beautiful tasting rooms. Don’t forget to take plenty of photos among the vines and picturesque landscapes.

evening
:

Return to Vineyard and unwind with a casual dinner at a cozy bistro that offers a great selection of local wines. After dinner, join a wine-themed trivia night at a local pub, testing your knowledge and making new friends. Enjoy the lively atmosphere and perhaps win some fun prizes while indulging in more local wines.

day 4
Nature Hikes and Scenic Views
morning
:

Enjoy breakfast at a quaint café before heading out to the nearby hiking trails that offer breathtaking views of the coastline. Choose a beginner-friendly trail that winds through lush forests and leads to stunning lookout points. Keep your eyes peeled for local wildlife and enjoy the serenity of nature as you hike.

afternoon
:

Pack a lunch to enjoy at one of the scenic overlooks, surrounded by beautiful landscapes and the sound of nature. Afterward, embark on a more challenging hike that takes you along the cliffs, providing panoramic views of the ocean below. Take the time to breathe in the fresh air and appreciate the beauty of Vineyard’s natural surroundings.

evening
:

After returning from your hikes, enjoy a hearty dinner at a local steakhouse known for its farm-fresh ingredients. Share stories of your adventures while savoring a glass of wine or craft beer from a nearby brewery. End your evening with a relaxing stroll through a local park, listening to the sounds of the evening and reflecting on the day.

day 5
Cultural Exploration and Arts
morning
:

Begin your day with breakfast at a local diner that serves classic American fare before immersing yourself in Vineyard’s vibrant arts scene. Visit local galleries showcasing the work of talented artists and artisans, each with their own unique style. Engage with the artists and learn about their inspiration and techniques.

afternoon
:

After lunch at a nearby café, join a pottery or painting workshop at a local art studio, where you can unleash your creativity. Spend your afternoon creating your masterpiece under the guidance of experienced instructors. This hands-on experience will give you a deeper appreciation for the artistic talents present in Vineyard.

evening
:

In the evening, attend a local theater production or live performance at one of Vineyard's charming venues, showcasing local talent. After the show, head to a nearby restaurant for dinner, enjoying dishes inspired by both local and international cuisines. Conclude the night at a cozy coffee shop, sipping on artisan brews while discussing the day's artistic adventures.

day 6
Family Fun and Adventure
morning
:

Start your family adventure with breakfast at a pancake house that offers a variety of toppings and flavors for everyone's taste. Afterward, head to a local amusement park or adventure center where the kids can enjoy thrilling rides and games. Participate in fun family activities like mini-golf or go-kart racing for some friendly competition.

afternoon
:

Enjoy a picnic lunch in a nearby park, complete with all your favorite snacks and treats. After lunch, visit a local aquarium or nature center to learn about the local marine life and ecosystems. Engage in interactive exhibits that will entertain and educate both kids and adults alike.

evening
:

Wrap up your day with a family-friendly dinner at a restaurant that offers a kids' menu and fun activities. After dinner, take a stroll around the park, letting the kids play on the playground or join in on some outdoor games. End your day with a movie night at a local theater, catching the latest family blockbuster together.

day 7
Local Markets and Culinary Delights
morning
:

Begin your day with a visit to the local farmer's market, where you can sample fresh produce and artisanal goods. Enjoy breakfast from one of the food stalls that feature local specialties, such as breakfast burritos or smoothies. Take your time exploring the market, meeting local vendors, and picking up ingredients for a later cooking class.

afternoon
:

Attend a cooking class in the afternoon, where a local chef will guide you in preparing dishes using the fresh ingredients you collected at the market. Engage in hands-on cooking while learning about the culinary traditions of the region. After the class, enjoy the delicious meal you've created together with fellow participants.

evening
:

Conclude your culinary journey with a dinner reservation at a highly-rated restaurant that specializes in seasonal and locally sourced dishes. Savor an exquisite multi-course meal, experiencing the best of Vineyard's culinary scene. Finish the night with dessert at a charming ice cream parlor, sampling unique flavors inspired by local ingredients.

day 8
Historical Landmarks and Insights
morning
:

Start your day with coffee and pastries at a historic café before setting out to explore Vineyard’s significant landmarks. Visit the town’s oldest structures, learning about their historical significance and the stories behind them. Stop by the visitor center to gather maps and recommendations for a self-guided walking tour.

afternoon
:

After lunch at a local eatery, continue your exploration by visiting historical sites such as old lighthouses and museums that highlight the region's maritime history. Take guided tours that bring the past to life, sharing fascinating tales of Vineyard’s early settlers and their adventures. Capture photographs of these beautiful landmarks to remember your journey.

evening
:

Wrap up your day with dinner at a restaurant that offers historical ambiance, perhaps in a restored building that reflects the town's history. Engage with locals and share your experiences of the day while enjoying traditional dishes. End your evening by attending a local lecture or storytelling event that dives deeper into the town's rich history and culture.

day 9
Relaxation and Spa Day
morning
:

Indulge in a leisurely breakfast at a cozy café, enjoying fresh pastries and specialty coffees to kick off your relaxation day. Afterward, head to a local spa for a morning of pampering, starting with a rejuvenating massage or facial treatment. Take your time to unwind in the spa's tranquil environment, soaking in the peaceful atmosphere.

afternoon
:

Continue your day of relaxation with a healthy lunch at a nearby wellness café, offering light and nutritious options. Afterward, participate in a yoga class that focuses on mindfulness and relaxation, helping you to center yourself. Spend some time lounging by the hotel pool or taking a quiet walk on the beach to soak up the calming surroundings.

evening
:

For dinner, opt for a calming setting at a restaurant known for its serene ambiance and delicious healthy cuisine. After your meal, enjoy a peaceful evening stroll along the beach or in a nearby garden, reflecting on your day of self-care. Conclude your relaxation retreat with a soothing herbal tea before heading back to your accommodations.

Discover Vineyard

Read more in our Vineyard 2025 Travel Guide.

Vineyard Travel Guide