Martha’s Vineyard Retreat: A Vineyard Square Itinerary For Small Groups

All teams need a break from the great land of cubicles and water coolers once in a while, and if we may be so bold to say, sandy shores and ocean blues make for the best recess. From acclaimed eateries to island recreation, a Martha’s Vineyard retreat has all the getaway essentials to get the thumbs-up from each and every one of your team members.


A Martha's Vineyard retreat.
Photo: Massachusetts Office of Travel & Tourism / CC BY-ND 2.0.


Pick A Meeting Venue To Get The Job Done

Without a place to put down your papers and laptops, your team meeting would be quite the challenge. If you’re as big a fan of convenience as we are, have your meeting space at the same spot as your homebase. Our intimate meeting room at Vineyard Square makes an ideal spot to host small meetings and can be customized accordingly if this retreat is a little less business and a little more team building. We’re all for thinking beyond the boardroom, too — go ahead and make breakout spaces out of our many lounges and parlor suites, or choose to gather in the comfort of our courtyard.


Find Activities To Break The Ice…The Island Way!

Perhaps you’ve made a few new hires, or maybe you’re long overdue for good old-fashioned team bonding. Either way, Martha’s Vineyard attractions allow you to get far more creative than your standard set of icebreaker games (we can almost hear the groaning from here).


Your options include (but are far from limited to): embarking on a group culinary tour of island tastes with Farm.Field.Sea., soaking up the sun and tossing around frisbees at South Beach, or pushing some pedals over 44 miles of down-island Martha’s Vineyard bike trails, complete with glistening ocean views.


Save Seats For Your Squad At Island Restaurants

With their abundance of fresh flavors, island restaurants are a frontlining argument in favor of planning a Martha’s Vineyard retreat. Plan a private luncheon at the Atlantic Fish & ChopHouse before savoring a succulent lobster dinner with a view on The Seafood Shanty’s expansive deck. On at least one night, grab a plate from our on-site friends at Chesca’s Restaurant — hardly having to part from your quarters makes it perfect for a post-meeting meal. But of course, we’re hardly skimming the surface of the Edgartown dining scene.


It merits mention: don’t forget to make reservations well in advance for your island eatery of choice. Even a small group may take some extra preparation on the restaurant’s part, so preparing in advance is a surefire way to ensure that itinerary goes off without a hitch!


When You Need A Moment Alone…

Meeting Space at Vineyard Square, perfect for a small group Martha's Vineyard retreatLove ‘em or not, you can’t be around those colleagues 24/7. When the need for a little “me time” calls your name, you can count on several spots right here at the Square to help you recharge from the spa to the full fitness center. If some retail therapy helps you recharge, you’re in good hands with a number of boutique Edgartown shops just steps away from our doors. (Gotta pick up a keychain or lighthouse calendar for the folks back home, after all.)


To tinker your itinerary to the specific needs of your group, take some tips from the pros. Reach out to our staff as you start planning your Martha’s Vineyard retreat — we’ll be your go-to guides for a comfortable stay and for recommendations on which island attractions will be a hit for your crew.

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