Boston

Day Trips

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

day 1
Exploring the Historic Center
morning
:

Start your day with a leisurely breakfast in one of Boston's quaint cafes. Afterward, take a stroll around the Market Place and admire the beautiful architecture of the Guildhall and St. Botolph's Church. Capture some pictures and appreciate the historical significance of the town center.

afternoon
:

Continue your exploration by visiting the Boston Guildhall Museum, where you can learn about the town's rich history. For lunch, enjoy some traditional British fare at a local pub, soaking in the atmosphere. As you wander the streets, look for unique shops and local art galleries to discover more about Boston's creative spirit.

evening
:

As evening falls, unwind at a cozy restaurant along the River Witham, where you can enjoy a delightful dinner. Take a relaxing walk along the riverside, enjoying the sound of the flowing water and the ambiance of the twilight sky. End your day with a visit to the local theater for a performance or live music.

day 2
Nature and Parks
morning
:

Begin your day with a visit to the beautiful Witham Way Country Park, where you can enjoy a refreshing morning walk surrounded by nature. The tranquility of the park is perfect for a peaceful start to the day. Take in the lush greenery and maybe even spot some local wildlife.

afternoon
:

After a morning immersed in nature, head to the nearby Boston Cemetery, known for its stunning memorials and historical significance. Pack a picnic to enjoy in the park, or visit a nearby cafe for a tasty lunch. Spend time relaxing or exploring the surrounding gardens.

evening
:

As dusk approaches, visit the local farmers’ market (if available) for fresh produce and artisan goods. Enjoy a farm-to-table dinner at one of Boston's renowned restaurants, where you can sample local cuisine. Conclude your evening with a quiet moment at the park, reflecting on the day.

day 3
Historical Walks
morning
:

Kick off your day with a guided historical walking tour of Boston, where you can learn about its fascinating past. As you walk through the streets, you'll hear tales of the town's development from its medieval origins to the present day. Take your time to capture the beauty of the historical buildings along the route.

afternoon
:

After the tour, visit the Boston History Museum to delve deeper into the local heritage. Enjoy a light lunch at a nearby cafe, then continue your exploration of the museum's exhibits. Don't forget to check out any temporary exhibitions that may be showcasing local artists.

evening
:

For the evening, consider dining at a restaurant that features dishes inspired by Boston's history. After dinner, enjoy an evening stroll around the town center, taking in the illuminated landmarks. If you’re inclined, find a local pub for a nightcap and some traditional live music.

day 4
Local Culture and Arts
morning
:

Spend the morning visiting the Boston Arts Centre, where you can explore local art exhibits and possibly catch a workshop. Engage with artists and learn more about their inspirations and techniques. This is a great way to kickstart your day creatively.

afternoon
:

After a cultural morning, head out to enjoy lunch at one of Boston's artisan cafes known for their unique flavors. Post-lunch, stroll through the local streets to discover more artwork displayed in various spots, including murals and sculptures. Take your time to appreciate the creativity around you.

evening
:

In the evening, attend a local theater performance or art show, immersing yourself in the vibrant arts scene. Afterward, enjoy a dinner at a classy restaurant that features locally sourced ingredients. End your day with a visit to a cozy coffee shop, reflecting on the art and culture you’ve experienced.

day 5
Shopping and Local Cuisine
morning
:

Begin your day with a visit to the town's central market, where you can browse fresh produce, local crafts, and artisanal goods. Enjoy a hearty breakfast at one of the market stalls to fuel up for the day ahead. As you shop, engage with the vendors to learn more about their offerings.

afternoon
:

After shopping, take a break with lunch at a bistro that serves classic British dishes. Continue the culinary journey by exploring food shops selling local delicacies and treats, perfect for souvenirs. Try to immerse yourself in the local flavors and specialties Boston has to offer.

evening
:

For the evening, book a table at one of the town's highly-rated restaurants for a unique dining experience. Pair your meal with a local craft beer or a selection from their wine list. Wind down by exploring the nightlife options, from cozy bars to lively pubs, where you can mingle with locals.

day 6
Family Fun Day
morning
:

Start your family-friendly day with breakfast at a charming cafe, then head to the Boston Bowl for some fun bowling time. Engage in some friendly competition and enjoy the relaxed atmosphere. This will set a joyful tone for the rest of the day.

afternoon
:

After bowling, visit the local soft play area or family attraction, providing plenty of entertainment for kids and adults alike. Grab lunch at a family-friendly restaurant offering a variety of options that cater to different tastes. Spend the afternoon enjoying games and activities suitable for the whole family.

evening
:

As evening approaches, consider a family dinner at a restaurant with a kids' menu and activities to keep the little ones entertained. Enjoy some post-dinner gelato or dessert from a nearby shop. End your day with a walk in the park, letting the children run around as you relax.

day 7
Adventure and Exploration
morning
:

Get ready for a day of adventure by starting with breakfast at a cozy café before heading out to explore Boston's surrounding countryside. Opt for a scenic walk or bike ride along the picturesque Witham Way. The morning is perfect for enjoying fresh air and nature.

afternoon
:

After exploring the countryside, have lunch at a quaint village pub along your route. Afterward, visit a nearby park or nature reserve for some outdoor activities, such as bird watching or hiking. Discover the local flora and fauna while enjoying a leisurely afternoon.

evening
:

For the evening, return to Boston and indulge in a hearty dinner at a restaurant specializing in locally sourced ingredients. Share stories of your adventures over a meal with friends or family. Wrap up your day with a star-gazing session at a local park, soaking in the peaceful atmosphere.

day 8
Festivals and Events
morning
:

If your visit coincides with one of Boston's local festivals or events, kickstart your day by attending the opening activities after a quick breakfast. Immerse yourself in the local culture through performances, stalls, and demonstrations unique to the occasion. Engage with locals to fully enjoy the vibe of the celebration.

afternoon
:

Savor lunch from various food stalls at the festival, trying out traditional bites and specialties. Enjoy the afternoon engaging with the entertainment options available, including music, dance, and arts and crafts. Take your time exploring the offerings and participating in different activities.

evening
:

As evening settles in, find a good spot to enjoy live performances or fireworks if the festival includes them. Celebrate the evening with a festive dinner at a local restaurant that embraces the spirit of the event, featuring special dishes. Conclude your day by joining the buzzing crowd back at the festival, dancing the night away.

day 9
Relaxation and Rejuvenation
morning
:

Begin your day with a healthy breakfast at a cafe that emphasizes fresh ingredients, followed by a visit to a local spa or wellness center. Take part in a yoga or meditation session to rejuvenate your mind and body. This peaceful activity will help set a calm tone for your day.

afternoon
:

After your wellness morning, treat yourself to a light lunch before visiting a nearby garden or park for a serene afternoon picnic. Enjoy the beauty of your surroundings and take time to read or simply relax while taking in the fresh air. You may also wish to explore a local bookstore for some leisurely shopping.

evening
:

For the evening, enjoy a nourishing dinner at a restaurant that specializes in health-conscious meals. After dinner, take a leisurely stroll around the town to reflect on your day and relax. End your day with a calming herbal tea at a cozy cafe, preparing for a restful night.

day 10
Last Day Exploration
morning
:

On your last day, savor a farewell breakfast at a favorite cafe, reminiscing about your journey in Boston. Take one final stroll around the town to revisit any spots you loved or missed. Capture this moment with photos as a cherished memory.

afternoon
:

Indulge in a relaxed lunch while soaking in the final sights and sounds of the town. Spend the afternoon at any last attractions you wish to see, perhaps doing some last-minute shopping for souvenirs. Make sure to enjoy every last moment before your departure.

evening
:

As evening approaches, have a leisurely dinner at a local restaurant, celebrating the end of your trip with a special meal. Take the time to reflect on your experiences in Boston and savor your favorite moments. Conclude your journey by creating a vision board of your favorite photos and memories from your visit.

Discover Boston

Read more in our Boston 2025 Travel Guide.

Boston Travel Guide