Take a trip to New York City and experience all the Big Apple has to offer. You and your guest will enjoy an enchanting evening with a one-night stay at the New York Edition hotel in a deluxe room, breakfast included.

Enjoy complimentary tickets to a Broadway show of your choosing and 4 Golden Passes to the Museum of Natural History.

Available between June 30, 2025-June 30, 2026. Advanced reservations are required. Confirmed blackout dates for 2025: October-December.

Note: This item is part of the live auction that will take place during the Sailabration Gala on June 30th. If you are unable to attend and would like to submit a proxy bid, please send your highest bid to [email protected] by 12:00 p.m. on June 30.

A Dazzling Dinner Party for 12
Host a dazzling dinner party for twelve guests in the comfort of your own home. Kick off the evening with a wonderful array of hors d'oeuvres followed by a four-course dinner created together by the host and Chef Joe Cizynski.

Each course is thoughtfully paired with fabulous wines to complement the dining experience.

To ensure seamless service, a skilled waitperson will be on hand to attend to every detail throughout the evening. And, Chef Joe will provide guests with interesting notes about the food and its preparation for the various courses, while recounting some fun stories about his career in the culinary and wine businesses.

You and your guests are sure to enjoy a most memorable dining experience!

Note: This item is part of the live auction that will take place during the Sailabration Gala on June 30th. If you are unable to attend and would like to submit a proxy bid, please send your highest bid to [email protected] by 12:00 p.m. on June 30.

A Culinary Story-Telling Experience for 6: Hosted by Joseph Carr with Mystery Chef

Join Joseph Carr in his Dennis home for an unforgettable evening of exquisite dining and wine pairings. You and five guests will be greeted with a welcoming toast of Josh Cellars Prosecco Rose and gougeres.

Local mystery chef is preparing a taste of romance with a delectable watercress Vichyssoise soup, a blue cheese vinaigrette Bibb, endive and pear salad, warm baguettes of bread, followed by a classic French lamb stew, finishing with an extraordinary flourless chocolate cake and raspberry coulis.

Exceptional wine pairings to savor and an evening to be remembered!

The date is specific for this item, and the dinner will be held on Saturday, October 4th, at 6 p.m.

Note: This item is part of the live auction that will take place during the Sailabration Gala on June 30th. If you are unable to attend and would like to submit a proxy bid, please send your highest bid to [email protected] by 12:00 p.m. on June 30

Escape to seaside elegance with a two-night stay at the iconic Chatham Bars Inn. Enjoy beautifully appointed accommodations and wake each morning to a delicious breakfast for two. Whether you're strolling the beach or simply relaxing in luxury, this unforgettable Cape Cod getaway awaits.

Restrictions & Inclusions:

Non-refundable, non-transferrable, no cash value. Major Holidays excluded. Valid September 15th, 2025-June 15, 2026.

Note: This item is part of the live auction that will take place during the Sailabration Gala on June 30th. If you are unable to attend and would like to submit a proxy bid, please send your highest bid to [email protected] by 12:00 p.m. on June 30

Escape to seaside elegance with a two-night stay at the iconic Chatham Bars Inn. Enjoy beautifully appointed accommodations and wake each morning to a delicious breakfast for two. Whether you're strolling the beach or simply relaxing in luxury, this unforgettable Cape Cod getaway awaits.

Restrictions & Inclusions:

Non-refundable, non-transferrable, no cash value. Major Holidays excluded. Valid September 15th, 2025-June 15, 2026.

Note: This item is part of the live auction that will take place during the Sailabration Gala on June 30th. If you are unable to attend and would like to submit a proxy bid, please send your highest bid to [email protected] by 12:00 p.m. on June 30

You'll feel like a guest at your own party with this Cape Cod clambake for ten provided by Backside Bakes. You will be the perfect host without having to lift a single finger. Your delivered bake for ten will include a 1.5 lb. lobster, steamers, mussels, red potatoes, onions, linguica, and corn on the cob for each guest. There will also be meal options available for non-seafood lovers. Without question, you and your guests will be able to savor a fabulous Cape Cod dining tradition.

Clambake drop-off must take place on a mutually agreeable date to the location of your choosing on the Mid/Lower Cape.

Tee off in style at Eastward Ho!-one of the Cape's most scenic and exclusive golf courses.

You and two friends will join a member at Eastward Ho! for 18 holes that will challenge your game while enjoying breathtaking views, legendary greens and fairways where there are no flat lies!

Having undergone a renovation directed by Kyle Franz in the off-season 2024-2025, the course promises new challenges amidst its classic Herbert Fowler links design. Afterwards, enjoy a round of drinks and polish your stories for friends!

Round must be scheduled with donor. Valid through June 2026

Take to the friendly skies with Stick 'n' Rudder for an unforgettable 60-minute scenic tour of Cape Cod in a classic Waco Biplane. Soar above the beautiful blue coastline and take in breathtaking views like never before, departing from CQX in Chatham.

To complete your adventure, enjoy breakfast for two with a gift certificate to Hangar B-an ideal way to start or end your flight experience.

Experience a luxurious one-night stay at the Wequassett Resort and Golf Club.

Wequassett invites you to enjoy one evening in a deluxe room, complete with a delicious breakfast. This stay will showcase the Cape's coastal elegance and impeccable service right on Pleasant Bay.

Reservations are required. Offer valid September-June.

Le Petite Day Spa invites you to experience and enjoy a complete mind, body, and soul makeover. Get pampered with this $100 gift certificate to book the service of your choosing.

Located right in the heart of Chatham, from the moment you enter Le Petite Day Spa, you will be impressed with the elegant surroundings and relaxing atmosphere. Get ready to leave feeling relaxed, rejuvenated, and restored.

Rest, relax, and repeat while at the South Cottage right here at Pleasant Bay Community Boating.

Spend one week during Fall or Spring in this 6-bedroom 3.5-bath home. It is a perfect setting for two families or multi-generations vacationing together. It includes a full kitchen, dining room, spacious living room, and has two master bedrooms with private baths located on opposite ends of the first floor.

Additionally, there are four bedrooms located on the second floor. All bedrooms have views of Pleasant Bay and beyond to the Atlantic.

Offer good for fall 2025 or spring 2026.

Enjoy an unforgettable matinee at the Boston Opera House with two tickets to a spectacular show during the 2025-2026 theater season. Experience the magic from premium seats in the second row, left center of the Dress Circle-offering an exceptional view of the stage.

Tickets are available for a show during the 2025-2026 Boston Opera House theater season and will be mailed to you electronically when tickets become available after Labor Day.

Featured shows are Mrs. Doubtfire on 9/21; The Sound of Music on 1/18; Some Like It Hot on 2/8; Suffs on 3/29; The Outsiders on 4/12; and Disney's Beauty & the Beast on 4/26.

Set sail with PBCB's Board President, John Dickson, on Pleasant Bay aboard a Sanderling Catboat for up to three guests.

Glide with the tide through scenic Hog Island Creek and perhaps explore around Strong Island, where the world (or Pleasant Bay) is truly your oyster.

You and a guest will join the Center for Coastal Studies staff and board members for a very special Sunset Whale Watch with the Dolphin Fleet of Provincetown.

Chat with CCS scientists, enjoy a picnic dinner with complimentary beer, wine, and soft beverages, and take in the spectacular marine wildlife of Cape Cod Bay and the Stellwagen Bank. This will be a most memorable time on the water.

Reservations for tickets must be made at least three weeks in advance of sailing date. Available 2025 dates are Friday, July 18, Saturday, August 2, and Saturday, August 23. All trips depart at 5:30 PM. Meet the Dolphin Fleet Boat at the MacMillan Pier in Provincetown.

Rowing lesson with USA Olympic & Harvard Rowing Coach Tom Siddall

Enjoy an exclusive one-hour private rowing lesson with Tom Siddall, acclaimed U.S. Paralympics and Harvard Rowing Coach.

Glide in perfect rhythm along the iconic Charles River, then step inside the historic Newell Boathouse for a behind-the-scenes tour of Harvard's legendary rowing facility.

Step into the Captain's Chair at the Massachusetts Maritime Academy, the full mission bridge simulator creates a mathematical model of a ship that behaves like its real-life counterpart. Cadets work together with classmates and experienced, licensed mariners to learn specialized skills and teamwork, preparing for the situations they will encounter in commercial shipping and navigation. Some of these situations include undocking a tanker in Japan, transiting the Strait of Gibraltar in heavy traffic, handling a ship in heavy weather, and returning to our own home port in Buzzards Bay. The goal is to give cadets the skills they need to function as effective bridge team members.

Enjoy this exclusive Mass Maritime Ship Simulator experience!

Experience a different side of Provincetown with Art's Dune Tours. Starting in the chaos of Commercial Street, Provincetown you will hop into a large SUV and ease into the sand dunes of the National Seashore. You and a guest will take an hour tour of Pilgrim Lake nestled among the dunes and the famed artists' dune shacks.

Sure Catch Fishing Trip
Bob Masi is an avid recreational fisherman and Chatham resident, who would enjoy taking a group of up to four on a five-hour fishing excursion. You will enjoy hearing about his fishing expertise off Monomoy and hopefully land some fabulous striped bass and a few blues to take home for dinner. Of course, Bob is hoping to catch his first keeper! Just kidding... because if Bob's boat doesn't land at least the max allowable number of keepers, it's a lackluster day on the water. Plus, complimentary filleting is included! And, of course, Bob has the best Food & Beverage Director this side of Pleasant Bay to ensure you have your favorite beverages and munchies on board to keep your energy levels up to reel in your biggest keeper. Knowledgeable fisherman that he is, Bob recommends booking this trip in the first three weeks of July before the Cape waters warm up and many of our fish head up to Maine on vacation!

This is based on Bob's availability and when the weather is favorable and the fish are running.

Enjoy a private wine and spirit tasting for a party of six complemented by lunch from the Blackfish Food Truck at the Vineyards. Choose five of their hand-crafted wines or spirits to sample. Your tasting will be followed by a glass of wine or cocktail of your choice, while you are savoring a wonderful Blackfish lunch.

Valid July through September 2025.

Morning Kids Birthday Party at The Orpheum!
Be the coolest kid in town and host your own birthday party or another special occasion at the Chatham Orpheum Theater. This theater located right on Main Street holds 34 people and the show includes popcorn. The Joan Kent Dillon Theater features 4K high-definition projection and movies can be shown on both Blu-Ray & DVD. HDMI inputs are available in the theater for laptops and other media systems. You bring the media, we supply the theater! You and your party are sure to enjoy a most memorable show in your own private theater for the morning!

Please book your theater date at least two weeks in advance. The theater is available in the mornings before regularly scheduled showtimes.

Serve Up Some Fun with Tennis Pro Baysie Wightman!

Enjoy an exclusive tennis experience with the one and only Baysie Wightman at the beautiful Chatham Beach and Tennis Club! You and up to three friends will hit the court with Coach Baysie, creating a day filled with rallies, laughter, and unforgettable memories. After working up a sweat, kick back and relax with a delicious lunch included in this special day. A perfect playdate for tennis lovers-don't let this ace opportunity slip by!

Valid through 9/2/2025.

A Glorious Sail for Twelve on the Maria

Slide gracefully along the beautiful shores of Pleasant Bay and admire the spectacular scenery aboard Maria - one of Cape Cod's finest sailing vessels. Whether you're simply looking to sit back and relax or are a seasoned sailor who wants to take the helm, the captain will help ensure a most memorable experience for you and your party aboard this handsome 33' craft.

The Maria leaves from the Wequassett Resort & Golf Club's dock for this two-hour private cruise.

This sail is for a mid-week daytime charter on a mutually agreeable date between the Captain and the winning bidder to be used during the 2025 summer season.

Master the Art of Dumplings!

Join Chef Chris Rugg for an hour-long culinary adventure in the Chef's kitchen at Ukiyo Cape Cod in Brewster! You and up to 9 friends will learn to make dumplings filled with sesame port, ginger, and lemongrass. The class will be a hands-on cooking experience, focusing on the art of creating dumplings. Each participant will create dumplings to enjoy during the class and be able to take home a "dumpling kit" to make additional delicious dumplings after class. All ingredients will be provided by Chef Chris Rugg, and 10 Chef's Aprons are included!

Must be a mutually agreed upon date between September 1, 2025 and April 15, 2026.

Nestled in on a side street just off Route 28 in Harwich Port, the Cape Sea Grille will be perfect for you! Serving the finest in creative American cuisine, Chef and owner Douglas Ramler crafts an ever-changing menu featuring fresh local ingredients and native seafood-staying true to the heart of Cape Cod and New England.

Situated in a 19th-century sea captain's home just steps from the water's edge, the restaurant cultivates a relaxed, yet elegant atmosphere with white linens, warm candlelight, and fresh-cut flowers.

Stop by Cape Sea Grille and experience some if the finest fresh seafood around with a $100 gift card towards your meal.