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If it’s been years since you’ve seen Aunt Sally in the flesh, you’re probably thinking of ways to make up for lost time by planning the best family reunion ever. With all the hustle and bustle of downtown Edgartown and the Vineyard’s many attractions, you certainly have options — but having too many great choices can be a bit daunting, too. Don’t worry — we’ve come up with a few tips for planning an unforgettable family reunion on Martha’s Vineyard.

 

Family reunion on the coast of Martha's Vineyard.
Photo: Massachusetts Office of Tourism / Flickr CC BY-ND 2.0.

 

Pick an Attraction to Anchor Your Reunion

Consider the size of your group and their interests. If you’re bringing a large crew, rent a private charter on Mad Max to conquer the high seas, or a enjoy a Cape Poge over-sand tour on the other island, Chappaquiddick.

 

If your group is a little on the small side, take an afternoon stroll through beautiful meadowlands at the Polly Hill Arboretum in West Tisbury, or get on the green for a family golf day. Kids coming on the trip? Take a spin on the Flying Horses Carousel in Oak Bluffs or let loose at one of the Vineyard’s gorgeous beaches.

 

Plan the Menu

You probably shouldn’t let Aunt Sally go hungry during  your family reunion on Martha’s Vineyard.  The crew can enjoy an upscale menu and friendly atmosphere at Chesca’s Restaurant, or venture into downtown Edgartown to quench seafood cravings over a waterfront meal at Atlantic Fish and Chop House. The island offers a plethora of delicious restaurant options, so take a vote on where you and your family would like to sit down and dig in (and don’t forget to make those reservations early)!

 

Getting to the Vineyard

When it comes to getting everyone to Martha’s Vineyard at the same time for your family reunion, the earlier you make travel arrangements, the better. The island is accessible by plane or by a 45-90 minute ferry ride. For more information on getting to Martha’s Vineyard, try our travel guide.

 

Moving The Crew

The Vineyard Transit Authority bus system will help you move your whole crew.If you’re venturing outside Edgartown, have your folks hop aboard the Vineyard Transit Authority bus system. Day passes are inexpensive, and shuttles run regularly from town to town all day during the summer. If Aunt Sally isn’t a fan of public transit, call the Stagecoach Taxi and peruse the Vineyard at your leisure.

 

Book Your Vineyard Family Reunion Directly With Your Hotel

When all that’s left on your family reunion planning list is to pick a place to rest your head at night, you’ll find the best rates when you book directly with your Martha’s Vineyard hotel rather than on a huge travel site. That’s because those sites charge an arm and a leg for something we know we can do better — helping you plan a top-notch family reunion on Martha’s Vineyard with Aunt Sally and the rest of the crew.

Visiting Martha’s Vineyard: How to Spend 48 Hours (or Less) on Our Island
The What, Where and How of the Martha’s Vineyard Craft Beer Festival
Take the Path Less Paved: Off Road Martha’s Vineyard Bike Trails
7 Essentials for Visiting Martha’s Vineyard: Your Island Travel Checklist
A Martha’s Vineyard Farmer’s Market Walkthrough: 7 Things To Expect
The Vineyard Cup Regatta: A Shipshape Addition to Your Summer Itinerary
Getting to Martha’s Vineyard: Fast Ferries and Flights
Plan a Girlfriend Getaway to Martha’s Vineyard in 5 Steps or Less

Whether it’s the thought of impending boredom or general angst, being stuck on an island with family is a nightmare-come-true for many teens. They’re too young for island nightlife, but too old to be caught enjoying time with their parents (or worse, younger siblings). We can’t help out with an aging potion, but there’s progress to be made in the family bonding area. Here are some tips on ways to survive a Martha’s Vineyard vacation with a teenager.

 

Knock ‘Em Down at the Barn Bowl Bistro 
Barn Bowl Bistro

The Barn Bowl Bistro has a cool factor that makes anyone glad to wear bowling shoes for a few hours. Yes, even your teen. This gem takes bowling night up a notch with Italian bistro dishes delivered right to the lane’s comfy couches as you play. Between the lanes, darts, and ping pong (plus a full bar for the grownups), it’s no wonder the alley’s website greets visitors with a “not your grandfather’s bowling alley” salute.

 

Lead the Way on an Island Bike Ride

One classic tactic to surviving a Martha’s Vineyard vacation with a teenager is simply to tire them out. With complimentary bikes from Vineyard Square, or rentals found in downtown Edgartown, this mission is easily accomplished. Pedal along one of the many island biking routes, or direct the wheels to a nearby beach for a dip in the water and a competitive game of frisbee.

 

See Where the Wind Will Take You on Mad Max

You won’t find Mel Gibson or Tom Hardy on board, but the whole family is still in for an adventure on this Mad Max ride. The catamaran sets sail right from Edgartown Harbor with afternoon or sunset sailing options. Marvel at views of whaling villages and the shores of Chappaquiddick Island before you’re completely surrounded by the deep blue sea. A word to the wise: resist the temptation to throw anyone overboard, no matter how teenager-y anyone gets.

 

Find Balance on a Stand Up Paddle Board

Another go-to tactic for surviving a Martha’s Vineyard vacation with a teenager is to distract them with a new challenge. Between learning how to maneuver the paddle and getting the courage to stand up without falling, a stand-up paddleboarding excursion is just the ticket. We’d suggest saving that Jaws night for later, though.

 

Enjoy Downtime with a MovieEdgartown Cinemas

If a vacation day turns rainy or everyone needs some rest, Martha’s Vineyard has a few terrific movie theatres to visit. If nothing on the marquee catches your teen’s interest, head back to Vineyard Square to pick from our collection of DVD’s and create your own movie night in the comfort of your room.

 

 

Planning a Martha’s Vineyard family vacation with a teenager in tow seems tricky, but our tiny island is packed with entertainment for all ages. Having the best of Edgartown just outside the door may even make them forget they’re on a family vacation.

 

Visiting Martha’s Vineyard: How to Spend 48 Hours (or Less) on Our Island
The What, Where and How of the Martha’s Vineyard Craft Beer Festival
Take the Path Less Paved: Off Road Martha’s Vineyard Bike Trails
7 Essentials for Visiting Martha’s Vineyard: Your Island Travel Checklist
A Martha’s Vineyard Farmer’s Market Walkthrough: 7 Things To Expect
The Vineyard Cup Regatta: A Shipshape Addition to Your Summer Itinerary
Getting to Martha’s Vineyard: Fast Ferries and Flights
Plan a Girlfriend Getaway to Martha’s Vineyard in 5 Steps or Less

Pet lovers, it’s crushing to get the “what about me?” look as you’re preparing to take off for vacation. Luckily, there’s no need to leave the dogs behind when you visit The Vineyard. From pet friendly accommodations to tail wagging beaches, here’s everything you need to know about traveling with pets to Martha’s Vineyard.

 

Ferries, and Buses, and Taxis, Oh My!

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All paws on deck! Get the sailor’s cap ready, because someone will officially become a sea dog on this getaway. Dogs are welcome aboard Martha’s Vineyard ferries free of charge as long as they are with their owner (leashed or in a pet carrier). Owners are responsible for cleaning up any messes and keeping paws off seats and tables. Aside from service animals, pets are not allowed to enter food service areas (let’s keep the drool to a minimum!).

 

Don’t be surprised if plain ol’ car rides become boring compared to getting around the island. Canines can tag along on cab rides and are even allowed to fetch the Edgartown trolley with their owners. Martha’s Vineyard buses are dog friendly too, but they do have a pet policy. If a passenger already on the bus objects to having a pet on board, then you and your pup will be asked to get the next bus (and vice versa). After all, pet dander and sniffles don’t make the best travel companions.

 

Pet Friendly Accommodation

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When hounds are hot on the scent of pet friendly hotels in Martha’s Vineyard, they end up at the dog friendly suites here at Vineyard Square Hotel. Reserved specifically for guests traveling with pets, these suites feature their own access from the Winter Street Entrance and are spaciously sized for dogs of all sizes. 

 

Yay or Nay on Doggy Beach Days?

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What do dogs and protected birds have in common? They both love Vineyard beaches. Depending on the time of year, Fido may have to share the turf on dog-friendly beaches in Martha’s Vineyard. In July, dogs could go on leashed beach walks before 9 a.m. or after 5 p.m., while in January it’s likely that no restrictions apply. Ask our front desk team for tips on where to bring your dog during your stay!

 

Let Loose at Trade Winds Preserve

For a barking good time, head to the Trade Winds Preserve in Oak Bluffs. This is the official dog park of Martha’s Vineyard and spans 71.8-acres with trails, meadows, and wooded areas. Designated off-leash areas give dogs the freedom to make friends and let loose, making this a stop on the travel agenda almost as good as a biscuit.

 

To Leash or Not to Leash?

Leash laws vary throughout the island. The Town of Tisbury, Mass., for instance, has a very specific leash law that does not permit dogs to roam free outside of the owner’s property. As a general rule, play it safe and keep pets on a leash in public. Remember, not everyone accepts a lick on the face as a warm welcome.

 

Pet Emergencies

Emergencies in unfamiliar territory are not the ideal travel plan, but Sparky’s habit of swallowing socks is one thing that can’t be left at home. It’s important to know where the nearest Martha’s Vineyard veterinarian is located. For Edgartown guests, Vineyard Veterinary Clinic is located less than 10 minutes from Vineyard Square Hotel.

 

Dining for Dogs

Didn’t pack enough puppy chow? Make a trip to Good Dog Goods in Oak Bluffs where dogs can do their own shopping. The pet-friendly store even has their own doggie bakery, in case treats didn’t make it into the travel bag either.

 

Dining with Dogs

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Once the kibble is settled, where can you stop to eat with a pet by your side? Many restaurants with outdoor seating, like Espresso Love in Edgartown, will welcome owners and well-behaved dogs to dine.

 

Why leave four-legged friends behind if they can tag along? From transportation to pet friendly accommodation, Martha’s Vineyard makes traveling with pets simple!

Visiting Martha’s Vineyard: How to Spend 48 Hours (or Less) on Our Island
The What, Where and How of the Martha’s Vineyard Craft Beer Festival
Take the Path Less Paved: Off Road Martha’s Vineyard Bike Trails
7 Essentials for Visiting Martha’s Vineyard: Your Island Travel Checklist
A Martha’s Vineyard Farmer’s Market Walkthrough: 7 Things To Expect
The Vineyard Cup Regatta: A Shipshape Addition to Your Summer Itinerary
Getting to Martha’s Vineyard: Fast Ferries and Flights
Plan a Girlfriend Getaway to Martha’s Vineyard in 5 Steps or Less

We know what you’re thinking. If Presidents of the United States have vacationed here, it can’t possibly be done on the cheap. Leave that logic on the mainland! All it takes to visit Martha’s Vineyard on a budget is a bit of planning and a pinch of compromise.

 

Fair Ferry Fares

Martha's Vineyard Steamship Authority
Photo: versageek via flickr / CC BY-SA 2.0

A round-trip ride on the Steamship Authority ferry is less than $20 for adults, though it gets pricey when a car is involved. Travelers may think they need a vehicle to get the best Martha’s Vineyard experience, but we’ll cover a better way to save on getting around the island. Leave the car behind and take the ferry for cheap!

 

Cheap Travel on the Island

Vineyard Square Hotel bikes

 

Pass on the expensive car rentals. Our trusty Vineyard Transit buses visit every town on the island. While one-way fares are $1.25 per town, passengers can save and ride around to their hearts content with a one- or three-day pass. It’s a great budget-friendly way to see the 100-square-mile island of Martha’s Vineyard on a budget.

 

An alternative way to get around the island is to pedal it! Vineyard Square Hotel guests have access to complimentary bikes, or we can point you to good local bike shops. Cycle your way to Oak Bluffs to see the famous Jaws bridge, or stick closer to town and point your bike in the direction of South Beach. If you choose this classic mode of transport, we’ve mapped out the best routes to take in our Martha’s Vineyard biking guide.

 

Save During the Shoulder Season

Vineyard Square Hotel Cozy Room

 

You don’t have to visit in the dead of winter (although that’s an option) to save on a Martha’s Vineyard vacation. Plan a trip during the shoulder season for the perfect compromise. It’s not quite peak, not quite off-season, and just right for travelers looking to save without sacrificing seasonal experiences. In fact, the months before and after summer are a favorite time to visit for many of us. Room rates dip between September and May, so you can enjoy a Cozy Room instead of packing a tent to camp in.

 

How to Dine on a Dime

Back Door Donuts

 

You don’t have to survive on PB&J from the grocery store, although a picnic lunch on the beach is a budget-friendly (and may we say, romantic) option. We do have some notable places for cheap eats on Martha’s Vineyard. If you stay at a hotel with complimentary breakfast, that’s one meal taken care of! Otherwise, a trip to Back Door Donuts in Oak Bluffs is worth an apple fritter. For affordable lunch or dinner, Sharky’s Mexican Cantina in Edgartown and Oak Bluffs boasts “50 items under $10” options.

 

What to See, What to Do

Flying Horses Carousel

 

There are many free or inexpensive ways to entertain yourself when visiting Martha’s Vineyard on a budget. For starters, we’re surrounded by beautiful beaches to sink your toes into. We also recommend marveling at the Aquinnah Cliffs or taking a spin on the Oldest Carousel in the World for just $2.50 a ride. Vineyard Square guests can even take their bikes on the ferry for plenty to see and explore (like a 14-acre zen garden) on the next-door island of Chappaquiddick.

 

Ditch the car for a ride on the bus, plan picnic lunches on the beach, and take in the best of the island without overwhelming your credit card. Planning a trip to Martha’s Vineyard on a budget isn’t as hard on the wallet as it seems.

Visiting Martha’s Vineyard: How to Spend 48 Hours (or Less) on Our Island
The What, Where and How of the Martha’s Vineyard Craft Beer Festival
Take the Path Less Paved: Off Road Martha’s Vineyard Bike Trails
7 Essentials for Visiting Martha’s Vineyard: Your Island Travel Checklist
A Martha’s Vineyard Farmer’s Market Walkthrough: 7 Things To Expect
The Vineyard Cup Regatta: A Shipshape Addition to Your Summer Itinerary
Getting to Martha’s Vineyard: Fast Ferries and Flights
Plan a Girlfriend Getaway to Martha’s Vineyard in 5 Steps or Less

Though we love our summers and the folks that they bring, winter weekends on Martha’s Vineyard have their own magic. The busy vibe is replaced with relaxation mode, and the peaceful crash of ocean waves isn’t muffled by the buzz of beach crowds. Compared to the summer, it’s like having the island to yourself! That’s why winter can be one of the best times to plan a romantic weekend.

 

How can you make the most of a short romantic jaunt this time of year? We have some suggestions to help you enjoy a winter weekend getaway in and around Edgartown.

 

Bundle Up and Get Outdoors

Edgartown Lighthouse
Enjoy private views of Edgartown Lighthouse.

There are miles of empty oceanside to explore during the winter. Take a romantic walk on the beach to enjoy sunset views or take a drive to Oak Bluffs to try and spot snowy owls. If you have a third wheel in the form of a four-legged friend, Lighthouse Beach in Edgartown also happens to be one of Martha’s Vineyard’s dog-friendly places to unleash your pup during the winter.

 

Get Pampered at the Spa

Sea Spa Salon Edgartown
Relax at the Sea Spa Salon in Edgartown

Winter temperatures are not kind to our skin, which is partially why we suggest heading to the spa for an afternoon of self-care. Our on-site friends at Sea Spa Salon will leave you feeling totally rejuvenated. The other reason we recommend a visit? No romantic winter weekend getaway to Martha’s Vineyard is complete without a couple’s massage!

 

Pair an Outing at the Museum with Dinner

Downtown Edgartown dining
Enjoy downtown Edgartown dining.

You can do dinner and a movie anywhere. When you’re spending a romantic winter weekend in Edgartown, go a slightly different route: a trip to the museum followed by dinner and drinks in town. The chillier season is the perfect time to take in the exhibits at Martha’s Vineyard Museum, where curious minds can find plenty of fun facts about the island’s history to discuss over a hot meal.  

 

Stay Tucked Away Indoors

Vineyard Square Hotel pet friendly suites
Bring furry friends along for a stay in one of our dog friendly suites!

Arguably the most important aspect of a successful romantic winter weekend getaway to Edgartown is having the right space to retreat to. When you want to trade the public for some privacy, our luxury suites are a great place to be. Leave the chill outside and come back to a spacious room where you can get cozy by your own gas fireplace. As for that furry third-wheel we mentioned earlier? Our pet friendly suites also remain open for winter getaways with your pup!

 

Come to Edgartown for a romantic winter weekend getaway and balance your time exploring the island with some sweet indoor escapes.

 

 

Visiting Martha’s Vineyard: How to Spend 48 Hours (or Less) on Our Island
The What, Where and How of the Martha’s Vineyard Craft Beer Festival
Take the Path Less Paved: Off Road Martha’s Vineyard Bike Trails
7 Essentials for Visiting Martha’s Vineyard: Your Island Travel Checklist
A Martha’s Vineyard Farmer’s Market Walkthrough: 7 Things To Expect
The Vineyard Cup Regatta: A Shipshape Addition to Your Summer Itinerary
Getting to Martha’s Vineyard: Fast Ferries and Flights
Plan a Girlfriend Getaway to Martha’s Vineyard in 5 Steps or Less